Chatham, MA Vacation Rentals

This property is professionally managed by Pretty Picky Properties Alluring Chatham in-town home with pool, walk to it all Sleeps 10 Rents Friday to Friday during peak season Linens included, beds made Pool & Hot Tub open from Memorial Day to Columbus Day Here you’re close to everything that counts in Chatham. Walk 0.4 mile (8 minutes) to popular Oyster Pond Beach. Walk five minutes to the unique shops, restaurants and galleries of Main Street. You can order amazing take-out sushi from Blue Fins and be home with it before the edamame cools off! Consider your outdoor living options at this property. When you’re not splashing with the kids in the large, heated in-ground pool, you’ll be lounging in the shade of several large poolside umbrellas. Or serving appetizers and drinks on the superb screened porch, cooled by a perfectly placed ceiling fan. Maybe you’ll fire up the gas grill, after rinsing off the beach sand and salt in the outdoor shower. Or jump in the hot tub and enjoy the starry evening. It’s amazing how much privacy you have in these outdoor spaces, given your location in the heart of Chatham. Inside, this home provides 2,800 square feet of the most upscale, yet unpretentious accommodations you could ever hope for in a summer vacation home. The well-outfitted chef’s kitchen is big and bright with custom cabinets, stainless steel and granite throughout. There’s highboy seating at the large center island, encouraging a pleasantly social meal prep experience. The kitchen flows into the elegant dining room, embraced by two walls almost entirely comprised of oversized windows, adding to the cheery ambience. The dining area, in turn, flows into the living room and TV lounge with its comfy seating and large flat screen smart TV. There’s one bedroom on the main level. It’s roomy with a generous king size bed. You’ll find a full bath with a combination tub/shower directly across the hall. The rest of the main level is allocated to a mud room back entry, laundry and a second stairway that leads up to a huge primary bedroom over the garage. The primary has a king size bed plus a twin bed with trundle underneath. There’s a luxurious full bath en suite, offering a twin sink vanity and step-in shower. Another second level bedroom has a queen size bed plus a twin with trundle. Down the hall you’ll find a bedroom with two twins, each with a trundle. There is also a loft at the top of the main stairway which features a desk, for those zoom calls, and a queen size sleep sofa. For those days when the weather doesn’t cooperate there is a wonderful game room for kids of all ages in the lower level. Down there you’ll find a foosball table, air hockey, a pop-a-shot hoops game plus comfy seating and a large flat screen TV! There’s even a table for playing cards or board games. Overall the home has four bedrooms and three full baths. It sleeps up to 10. It has central air conditioning, high speed Wi-Fi and cable/smart TVs. Please enter your travel dates for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $245.00. In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%. This property offers a three-night minimum stay during select weeks in May – June & September – November. Guests are charged a cleaning fee for all stays less than seven nights. Stay seven nights or more and the cleaning fee is waived. Be sure to search this site for your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ® Town of Chatham Registration #151

16658 - Home Base: Centrally Located Home w/ Patio Fire Pit! Conveniently situated in the middle of Chatham Village, a mere 3 minute (.2 mile) walk from downtown Chatham, is Home Base--the perfect location for your next Cape Cod getaway! Enjoy all that Chatham has to offer within easy reach of this house’s convenient central location. This unique home features a comfortable front patio and side deck with plenty of room to make the most of beautiful Cape Cod weather Chatham’s downtown area has a variety of dining, bars, shopping and even a movie theatre all within easy walking distance. The charming downtown area is sure to captivate you like so many others who have fallen in love with Chatham. You don’t even need to go downtown for a delicious meal though! Home Base is directly across the street from the Chatham Filling Station which is a favorite breakfast and lunch destination of locals and visitors alike. <br><br>Only a 100 feet away from the private front patio of Home Base sits Veteran’s Field which is home field of the Cape Cod Baseball League’s Chatham Anglers. Catching an Anglers game is the perfect way to spend a warm summer night enjoying a slice of small town America reminiscent of a simpler time. If relaxing under the stars instead of the lights of Veteran’s Field is more your style, don’t worry! There is a side deck at Home Base with a propane grill for barbequing and a fire pit for relaxing with a cocktail or making s’mores with the kids.<br><br>Upon entering Home Base you are greeted by a spacious and well equipped kitchen and beautiful wood floors which run throughout the home. Through the dining room you will find a hallway leading to a bathroom, laundry, and master bedroom with Queen size bed and private bathroom. Walking in the other direction through the living room leads you to the upstairs of the house. <br><br>Upstairs there are three bedrooms, two with a queen size bed and one with a bunk bed that is a twin on top and a full on the bottom. There is also a beautifully refinished bathroom with tasteful subway tile for a sleek and modern look. Between the central location, spacious accommodation and unique charm we are confident Home Base will be a Grand Slam when it comes to a location for your next Cape Vacation.<br><br>*NOTE - This is an antique home and stairs to second-floor bedrooms are steep (not appropriate for young children or elderly adults)!<br><br>​​​​​​Home Details:<br>-Dogs Welcomed (w/fee of $40/night per dog)<br>-Sleeps 9<br>-2 Floors<br>-1st Floor Master Bedroom: 1 Queen Bed<br>-2nd Floor Bedroom #2: 1 Queen Bed<br>-2nd Floor Bedroom #3: 1 Queen Bed<br>-2nd Floor Bedroom #4: 1 Full bed & 1 Twin Bed (Bunk)<br>-Central A/C<br>-WiFi<br>-Cable TV<br>-Washer/Dryer <br>-Gas Grill <br>-Outdoor Shower<br>-Firepit<br>-Deck with Furniture<br>-Patio with Furniture<br>-Sheets and Bath Towels Provided with Beds made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>C0422690550

This home is professionally managed by Pretty Picky Properties Gorgeous Chatham Estate with heated pool, walk to Town or Beach Sleeps 15 7 bedrooms, 5.5 baths Rents Friday to Friday during peak season Linens Included, beds made Pool is open from Memorial Day through Columbus Day weekend If you appreciate the timeless charm of a meticulously preserved, spacious home circa 1848, but insist on all the modern comforts and conveniences, your group of up to 15 will be thrilled to spend your Chatham vacation at this property. Here, wood floors with various width planks, Federalist period glass doorknobs and randomly exposed brick from the original home blend appealingly with today’s tile, granite and stainless steel. It’s hard to find a better location anywhere in Chatham. It’s only a 0.3 mile, five minute walk to Oyster Pond Beach (Children’s Beach) for swimming with the kids. Or go the other way and your walk to the shops, restaurants and all the fun of Main Street, Chatham is only 0.4 mile or eight minutes. Even closer to the house: quaint little Chase Park with its Godfrey Windmill and the challenging Chatham Labyrinth. And every time you head out, you’re strolling safely on sidewalks through one of Chatham’s most beautiful, upscale neighborhoods. This property offers the joys of warm weather outdoor living in a variety of spaces. There’s a large covered porch on one side of the house with an adjacent patio with a dining table and chairs. On the opposite side of the house, there’s a small brick patio where you’ll find the large gas grill and outdoor shower. No doubt, the majority of your outdoor time will be spent on the new patio and in the heated pool at the rear of the property. Here you’ll also enjoy soaking in the hot tub and later, star gazing as you gather your group around the gas fire pit. All of these outdoor spaces are hidden from a curb view for your private enjoyment. What about the kids? When they’re not splashing in the pool, they’ll love the game room over the garage with its ping pong, foosball, arcade game and TV lounge all their own. Inside this extraordinary home you’ll be delighted with all 4,500 square feet of comfy upscale living space. Start with the large chef’s kitchen, fully equipped with topline appliances and everything else you’ll need to operate in style. There’s a large kitchen dining table with seating for eight, with the even larger primary dining table in the adjacent dining room. The main level also has multiple lounges, several smart/cable TVs, and a half bath off the kitchen. One of three primary suites is located on this level as well. It offers a king size bed and private full bath ensuite. There are two stairways up to the second level, which makes sense with so much second level to access. There are a total of six bedrooms upstairs. First, there’s the primary suite, unusually spacious with a king size bed and full private bath and views of the pool. The home’s third king primary suite with private full bath is located on the second level as well. Then you will find a king bedroom that shares a full bath with a bedroom that has a pair of comfy twins. Then there are two bedrooms with bunk beds, each with a full size double on the bottom, one with a pull out trundle under the bottom bed. The washer and dryer are upstairs as well. The home has central air conditioning and high speed Wi-Fi. Please enter your travel dates in the top right corner of this page for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $245.00 In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%. Be sure to search the Pretty Picky site for your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ® Town of Chatham Registration #153

This property is professionally managed by Pretty Picky Properties New Luxury Home in Chatham with Pool & Hot Tub, Walk to Town Sleeps 8 4 Bedrooms, 3 Bathrooms, 2 Half Bathrooms Rents Friday to Friday during peak season Linens Included, Beds Made Pool is open from Memorial Day through Columbus Day weekend It’s difficult to find a property with all the attributes of “Stepping Stones Sanctuary” completed in 2022, everything here is fresh, new and top of the line. Outdoor warm weather living doesn’t get any better. Whether you’re lounging on the expansive flagstone patio watching the kids splash in the heated saltwater pool or firing up the built-in gas grill with granite counters to enjoy a perfect dinner al fresco. Later on, you’ll want to gather around the custom outdoor fireplace for gazing at the stars. There’s also a hot tub for unwinding at the end of an active day. Here, too, you’ll find the obligatory Cape Cod enclosed outdoor shower. Inside this home you’ll be charmed by the open floor plan with all brand-new high-end furnishings, appliances and appointments. The sparkling chef’s kitchen is right out of a magazine feature story, where practical functionality and beautiful design join forces to create a meal preparation experience you will long treasure. The adjacent dining area elevates the cheery, open impression still more, as does the large vaulted ceiling living room with appealing, comfortable lounge seating and upscale appointments. This home has central air conditioning, high speed Wi-Fi, cable, as well as smart TV’s– all brand new. There are also two convenient half baths on the main level. The first of two master bedroom suites is on the main level. It is spacious and luxurious with a new king size bed. There’s a roomy private full bath en suite. The upper level serves up the other master suite, this one with a king size bed and full bath included. Two more upper level bedrooms are located up a second staircase, one with a 2 queen size beds, and the other with 2 queen size beds. There is a shared full bath in this area. There are three full baths along with two half baths in all. If you do choose to venture from the property you are about a half mile from the Chatham Anglers baseball field and under a mile to downtown Chatham with plentiful options for entertainment, shopping and dining. You are also under a mile to Oyster Pond where Children’s Beach awaits. “Stepping Stones Sanctuary” offers a refined living experience, all within a mile of one of the most idyllic villages on Cape Cod and a short walk to Chatham’s bike trails and the Chatham Bakery! Please enter your travel dates for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $ 245.00 In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%. This property offers a three-night minimum stay during select weeks in September – November. Guests are charged a cleaning fee for all stays less than seven nights. Stay seven nights or more and the cleaning fee is waived. ​​​​​​​Be sure to search this site for other Pretty Picky Properties - your best selection of prime vacation rental properties on Cape Cod. It’s your vacation. Get Picky! ® Town of Chatham Registration #1208

This property is professionally managed by Pretty Picky Properties Sleeps 16 Eight Bedrooms, Nine Baths Rents Friday to Friday during Peak Season Linens Included, beds made Pool is open from Memorial Day through Columbus Day weekend This totally renovated former Bed & Breakfast, known as the Chatham Gables Inn, brings a new level of luxury and comfort to a Chatham vacation for your group of up to 16. Not that you will ever feel the need to leave the property, but should you choose to venture out, it’s good to know you’re close to everything you love about Chatham. Bring or rent bikes! That’s all you’ll need with so much, so close. Bike five minutes to Lighthouse Beach, Chatham’s biggest and best. Or ride two minutes to Oyster Pond Beach (aka Children’s Beach), a smaller, more sheltered beach. Or walk down to the Chatham Pier Fish Market, where you can take home the catch of the day, fresh off the boat. And it’s only a few-minutes’ walk to Main Street, Chatham Village, for shops, restaurants, galleries, concerts, Cape League baseball, playground, tennis courts, ice cream parlors and much more. The 4,200+ square foot house presents the perfect intersection of classic New England charm and leading-edge creature comforts and convenience. Exposed beam ceilings, heated wide plank wood floors and tasteful choices of furnishings, fabrics, paint and wallpaper all combine to create a one-of-a-kind living experience. The home’s centerpiece is the gleaming white farmhouse kitchen with its expansive center island with second sink. All appliances are new and commercial grade. The kitchen flows into the charming conservatory, which in turn, opens to the patio beyond. Your outdoor living will, of course, center on the beautiful, heated pool and adjacent hot tub. There is also a gas fueled fire pit, so your outdoor pleasure extends beyond sunset. The gas grill lives out here, as well, and you’re likely to prepare and serve most meals using the outdoor kitchen-area and patio dining table and chairs. This home offers multiple inviting lounge areas, each as comfortable and appealing as the next. Sleeping accommodations include eight bedrooms, each with its own name such as “Surfside,” “Nantucket” or “Great Point.’ Each has bedding for two. There are five kings, one queen and two bedrooms each with two twins. Each bedroom has its own private full bath en suite, and each has a smart TV. The lower level includes an oversized laundry with two washers and two dryers plus an additional refrigerator. And to complete its resort-like amenities, there is a game room down here as well. There is cable/smart TV and high-speed Wi-Fi, of course. The home is cooled via an ultra quiet system, which allows customized climate control for each bedroom. It also features Lutron Lighting® allowing guests to automatically or manually adjust the level and even the color of the LED light to create the ideal environment for any living space. Please enter your travel dates in the top right corner of this page for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $245.00. In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%. Be sure to search this site for your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ® Town of Chatham Registration #152

16620 - A Step Above: Full Renovation! Amazing Spot with Views! Our completely renovated and newly furnished condo, located directly in the center of town on Main Street in Chatham, is the perfect vacation spot for your next trip to Cape Cod. You will be a short walk away from many great restaurants, including Impudent Oyster, Chatham Squire, Bluefins Sushi & Sake Bar, and Wild Goose Tavern, as well as a variety of local shops, galleries, a movie theater, and plenty of other entertainment options. In addition to offering a central Main Street location, our condo is just a short drive from a number of desirable Chatham beaches; Lighthouse Beach and Oyster Pond Beach are each just a three minute drive away!<br> <br>Enter our thoughtfully-decorated second story condo to find a welcoming bright, open, and clean kitchen and living area with modern decor. Some features include new appliances, island seating, a large flat screen TV with sectional couch seating, central A/C, a washer/dryer, deck with gas grill, and two bedrooms on opposite sides of the condo, providing a level of privacy for each guest. Want to go shopping for shoes - just downstairs on the 1st floor of our condo building is the ultra-chic If The Shoe Fits boutique. Grab something new for your evening or beach outings. Such an amazing location with all the amenities you will need, in addition to being dog friendly, makes this vacation rental one that you won’t want to miss out on!<br><br>Home Details:<br>-Dogs Welcomed (w/fee of $40/night per dog)<br>-Sleeps 4<br>-Single Floor (2nd story walkup)<br>-Bedroom #1: 1 King Bed<br>-Bedroom #2: 1 Full Bed<br>-Central A/C<br>-Cable TV<br>-WiFi<br>-Washer/Dryer<br>-Deck<br>-Gas Grill<br>-Located on Main Street<br>-Minutes to the Beach<br>-Sheets and Bath Towels Provided with Beds Made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>C0427480550

This property is professionally managed by Pretty Picky Properties. Spacious Custom Chatham Home w/Pool, Guest Cottage & Water Views Sleeps 12 Heated salt-water pool, outdoor kitchen and spa! Linens included, beds made Rents Friday to Friday in peak season To view a slide show with captions, click on icon in upper right corner of the photo. Pool is open from Memorial Day through Columbus Day weekend This immaculate custom home features three primary en suite bedrooms and is close to everything to love about Chatham. The property is centrally located just 0.75 miles from the popular restaurants, shops and live entertainment of Chatham Village. The Cape Cod Rail Trail is a scant 0.3 miles up the road. The location is close to several fan-favorite beaches as well. Set on scenic Perch Pond, the outdoor living and dining space is superb. With a large deck, heated salt-water pool with built in spa, gas grill and outdoor kitchen all overlooking the pond for relaxing days and amazing sunsets. The deck table can seat 12 for relaxing meals while viewing the wildlife that calls Perch Pond home. The ever changing sounds and mix of birds makes for a relaxing environment. Featuring plenty of private yard area to enjoy outdoor lawn games there is even an official sized bocce court for extended outdoor fun. In total, the 3,300+ sq. ft. home, plus separate cottage, has at total of five bedrooms and 4.5 baths and includes all the modern amenities including central air conditioning. The main level of the house offers a generous, bright and cheerful open-plan living space with a fully loaded kitchen, seating and dining area, breakfast room, and one of four lounge areas in the house. The main level also features a primary bedroom suite, including a comfy king size bed and a private luxury bath. There’s also a cozy TV lounge area just off the kitchen as well as a half bath/laundry room. On the upper level, you’ll find a second primary suite with a king bed and en suite bathroom. This primary bedroom has a small adjacent room that can serve as extra sleeping space for young children or a quiet getaway for reading and relaxing. Also on the second level, there is a bedroom with a queen size bed and a bunk room with four twin size beds. Those two bedrooms share a full bath. The unfinished basement includes a small workout area with exercise flooring, yoga mats, hand weights, a TV for casting your workouts and a Peleton (please bring your own shoes and subscription). You can also play a rousing game of ping pong or darts in case the weather isn’t cooperating! Finally, there is a bonus living area over the garage that is accessed by a separate stairway. Here you’ll find a large TV with surround sound, ample lounge seating and a card/game table. Just out the back door of the main house is the freestanding, very well-appointed separate guest cottage with a queen bed, TV/sitting area, coffee bar, full bath with shower and a wraparound deck overlooking the pond. The deck at the "Perch Pond Yacht Club", as the cottage is named, is a perfect place to relax with morning coffee or a glass of wine while enjoying the sunsets. The house is close to Chatham Bars Inn and Wequassett for those attending events or simply eager for an extraordinary dining experience. The home is ideally suited for summer or off-season relaxation. Please enter your travel dates in the top right corner of this page for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $245.00. In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%. This property offers a 3-night minimum stay during select weeks in May – June & September – November. Guests are charged a cleaning fee for all stays less than 7-nights. Stay 7-nights or more and the cleaning fee is waived. Be sure to search this site for your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ® Town of Chatham Registration #155

8 Bedrooms- 5.5 Bathrooms- Sleeps 18 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many of our homes offer flexible stays with a 3 night minimum in the off season - ask our Reservation Specialists for more details. Complimentary Linens Service Provided: This includes bedsheets, bath, beach, and dish towels for total home occupancy We offer a 4pm Check-In and 10am Check-Out Updated, Central A/C, dog-friendly, located in the most sought after in-town Chatham location - perfect for a large family or group! The Priscilla House was built by a Sea Captain for his daughter Priscilla and this popular large vacation home is nestled on Main Street. Our Guests love that they can walk to restaurants, unique local retail shops - our favorite bagel bakery is right next door! Close by are popular beaches - Lighthouse Beach, Andrew Harding’s Beach, and Oyster Pond. This exquisite home sleeping up to 18 people is ideal for family reunions, holidays, and special occasions. Gas fire pit, expansive outdoor living space with a great porch to sip your favorite beverage and enjoy the view! Free Wifi too. **Ask us about 3-night packages during the off-season*** Owners Share Why I Love My Home: This home is uniquely located right in the center of town while maintaining a private and quiet vibe. The house is set back just enough off of Main Street making the front porch a perfect place to enjoy morning coffee as morning walkers whisk by. Coffee is even available across the street or next door if you don’t feel like making your own! When stepping out the backdoor into the perfectly poised backyard, you feel as if you are miles away from the hustle and bustle of town as you relax by the fire pit or grill dinner and play frisbee. Inside, the oversized kitchen island provides the perfect spot for casual morning breakfasts while prepping lunches for a day at the beach. This is such a special home to share with family and friends for the perfect getaway. Let Us Tell You About This Home: This large luxury style coastal vacation home has been thoroughly updated to provide you with all the modern conveniences and comfortable accommodations in a relaxed setting. Everything is included – bed linens, bath towels, outdoor barbeque grills, beach chairs, wagons to cart to the beach. An excellent base for exploring Cape Cod, just step out the front door and walk to great shops, restaurants, ice cream parlors, art galleries, beaches, concerts, and local theaters with plays changing weekly. When you enter the home through the East entrance, you will be in the State of the Art kitchen with all stainless appliances. This is a entertainers delight! Large center Quartz island lends you to create wonderful family meals with ease. The quartz countertops are sure to delight the baker in your group as well. Off the kitchen is a laundry room offering a full size washer and dryer. There is also a half bath just beyond the laundry area. Straight ahead you will find yourself in the living area with a sectional couch offering plenty of comfortable seating and a large flat screen television. Enjoy the ease of outdoor grilling with the wall to wall sliders to the outdoor patio area. Across from the kitchen is the Butlers pantry with Wet bar, the perfect place for the mixologist in your group, to create that iconic Cape Codder! Chill your favorite wine and beer in the mini fridge and an additional dishwasher to handle those extra glasses! On the left side of the home is the dining room with a large dining table that seats 12-16, gather here for great conversation over a family dinner. To the right the dining room opens up to the den which offers a coastal seating area and another large flat screen television. Past the den and to the left , is a covered porch offering seating, a special spot to sit back with a book or just people watch as families come and go to the beach and downtown shopping village. To the right of the den, at the front of the home, you will find The Stage Harbor Room , Bedroom #1 This master Suite offers a King Bed and a Full bath with shower and is conveniently located on the 1st floor. Head up to the 2nd floor- Up these stairs and to the right are the following bedrooms all off the East Hallway: The Oyster Room Bedroom #2, with a Queen Bed. Down the hall on the left is Bathroom #2, a full bath with a shower and tub. Continue past the staircase and on your left is The Sand Dollar Room Bedroom #3, with 1 Queen bed. The Starfish Room Bedroom #4, with 2 twin beds is at the end of the East Hallway To the right of the beginning of the hallway is the entry to the West Hallway. Immediately to the right of the West Hallway is The Chatham Light Room Bedroom #5, which offers a King Bed with en suite with full bath that offers a shower. Continue down the hallway and on your right is Bathroom #3 a full bathroom with a tub and shower. Further down the hallway on the right is: The Scallop Room Bedroom #6, offering 1 Queen bed. The South Beach Room Bedroom #7,with a two twin beds is at the end of the hallway. Back at the beginning of the West hallway, to the left is the staircase that leads to the Upper level of the home. The North Beach Suites. At the top of the stairs is a small seating area. Through the French doors and to the right is Bathroom #4, a full bathroom offering a shower (no tub). Straight ahead is The North Beach Suites. At the top of the stairs is a small seating area. Through the French doors and to the right is Bathroom #4, a full bathroom offering a shower (no tub). Straight ahead is North Beach Room #1 and 2, Bedrooms #8 and 9 , this room has 4 Twin beds and a separate private room off the sitting area with a queen bed. The backyard of this home has high hedges and is mostly fenced in offering you privacy. You are in the heart of Chatham but still have your own area to sit back and relax with your favorite libation on the back deck as the sun sets. Enjoy a dinner prepared on the gas grill and gather around any of the 2 picnic tables or dining table on the deck. While waiting grab your favorite libation and relax around the fire pit! There is even a fully enclosed outdoor shower with hot and cold water for washing away a day well spent in the sun at any of the area’s beaches - a true Cape Cod tradition. A special home to experience the most iconic area on the Cape - Chatham. Leave the car at the Priscilla House and walk to a variety of restaurants from casual sandwich shops to the famous Chatham Bars Inn. Beaches are a short stroll away - the most photographed lighthouse is just around the corner! **Ask us about 3-night packages during the off season*** Free Tickets and Complimentary Activities! Create unforgettable memories and experience Cape Cod like a local! Enjoy $750 worth of daily exclusive free tickets to exciting local attractions through our partnership with Xplorie. Your amenities include activities such as Island Cruises, Whale Watch, Bike Rentals and admission to Whydah Pirate Museum. When you’re not soaking up the sun on the beach, enjoy daily rounds of golf at Cranberry Valley or Chequessett Golf Courses and mini-golf for family fun. With all NEVR properties, we think of the little things to make your vacation special. Our Guest Welcome Bag, compliments of the homeowner, contains starter quantities of kitchen and bathroom essentials, with a few locally sourced snacks as well (subject to change based marketplace availability). This home offers Keyless Entry for your convenience. NO SMOKING of anything containing tobacco, any other substance, and e-cigarettes, inside or outside of the home. PET FRIENDLY HOMES are for a DOG only. This home allows 1 dog for $25 per night. A Pet Registration form must be completed upon reservation confirmation. Max parking of cars at property: 6 No parking on lawn anytime. Additional Information to Assist You: Departure cleaning is included with your reservation at no additional charge. Simply follow our basic check-out instructions at your departure. State and local taxes are charged if applicable. For Reservations made over 60 days away, you will make two payments - 50% initial payment with reservation and the final balance will be auto billed to your credit card 60 days prior to arrival. We accept Mastercard and Visa for payments. A confirmed reservation is non refundable--please consider purchasing trip cancellation insurance. Ask our guest specialist for more details regarding cancel options and trip insurance. You must be 25+ years old unless accompanied by a parent or guardian to book one of our Vacation Rental Homes. An ID must be furnished upon request. Area Info: *Mileage is approximate Priscilla House – Walking Distance to the Best of Chatham! Just 2 tenths of a mile to The Impudent Oyster, Chatham Candy Manor, and The Chatham Squire! Only 4 tenths of a mile to Andrew Hardings Lane Beach! A quick 10 minute walk to the famous Chatham Lighthouse and Lighthouse Beach. Stop next door at JoMama’s for bagels, coffees, and sandwiches at this convenient cafe. Priscilla House of Chatham is located in town and is just a short walk to amazing destinations including pristine beaches, shopping, dining, and more. The town of Chatham is an ideal base from which to explore the natural beauty of Cape Cod. Walk to beaches – Andrew Hardings Beach just a half mile away - Lighthouse beach 0.6 mile away- a short stroll down Chatham Bars Ave- just .3 tenths of a mile to Claflin Landing - a short stroll to Oyster Pond! Shopping Chatham’s town center boasts a mile of fun and unique shops including nautical antiques, jewelry, clothing, gifts, novelties and specialty stores. Main Street alone has a dozen Galleries with works by local artists, in watercolor, oil, sculpture, scrimshaw, pottery, weaving and more. Dining Whether you are in the mood for fine dining, traditional Cape Cod fare, or scrumptious take-out, Chatham’s restaurants, tearooms, and bakeries provide you with a wide variety of selections. Beaches Chatham is renowned for its miles of pristine white sand beaches. Build sand castles, swim, fish, or just soak up the sun. The beaches are but a short walk from Priscilla House. Entertainment Walk to Kate Gould Park with your folding chair and blankets and enjoy the concerts on Friday evenings during the summer. ​​​​​​​Take in a movie at the Chatham Orpheum Theater Performing Arts: Monomoy Theatre- Live Theatre! Nature Bike Chatham’s beautiful paths, roads and off the beaten paths. Explore Monomoy National Wildlife Refuge. Hike Chatham Conservation Foundation’s Trails. Book a cruise on a ferry or boat tour. Sports Bring your clubs and play challenging golf courses overlooking the Atlantic Ocean. Take in a Chatham Anglers (Chatham A’s) baseball game. Chatham offers many opportunities for the sport fisherman, boater, rower or sailor. Museums Caleb Nickerson House –Experience colonial life in this restored home of an American Revolutionary War veteran built in 1772 Visit Chatham’s Old Grist Mill built in 1797 by Col. Benjamin Godfrey to grind corn using only wind power. Chatham Marconi Maritime Center preserves and interprets the history of maritime wireless communication. Mayo House – an excellent example of a traditional Cape Cod house built in 1820. The Old Atwood House Museum is one of the oldest in Chatham – erected in 1752 when the men who engineered the job were all subjects of His Majesty, King George the III of England. The Chatham Railroad Museum features a relic of the first commercial railroad in the U.S. in 1826, and includes hundreds of factors of historical significance in the railroad field. Licence number: C0030860550

This property is professionally managed by Pretty Picky Properties Chatham Waterfront with Pool, Stunning Views of Oyster Pond, Chatham Villa Sleeps Eight Four Bedrooms, Four Baths Rents Friday to Friday during Peak Season Linens Included Pool operational from Memorial Day to Columbus Day ​​​​​​​ The pool is great, the house is lovable, but what truly sets this property apart is its location directly on picturesque Oyster Pond. Sit back in your lounge chair overlooking the pool and marvel at the sails in the foreground, with the one-of-kind view of Chatham Village beyond. Bring your kayak and take a tour of the pond and river. Another nice thing you’ll notice when you’re hanging out at the pool: it’s quiet and very private, because you’re at the end of a neighborhood road with no outlet and next to no traffic. The large new deck provides another special outdoor living space with water views, especially thanks to its built-in fire pit where you’ll gather when the sun goes down for gazing at the stars. There’s also a good sized dining table here that seats eight for meals al fresco, and an awning to provide shade when needed. Inside, you’ll quickly discover that the floorplan was created with the water views in mind, especially noteworthy from the dining table which seats eight. The open kitchen is spacious, very social and nicely equipped (including a Nespresso Machine!). The living room provides plenty of comfy lounge seating, and there’s a bathroom here where you’ll find a small washer and dryer. There’s another full bath just off the pool deck which essentially serves as an outdoor shower. Sleeping quarters on the main level include one bedroom with a queen size bed and another with twin beds. Walk upstairs to discover a second, lounge area with a large TV. There are two more bedrooms on this level, including the spacious master suite with a King size bed, full bath en suite and amazing elevated views of the water. The home’s fourth bedroom provides a queen size bed. There’s another full bath off the upstairs hall that’s used by the occupants of the queen bedroom and has been recently upgraded. You’ll also find another laundry here with a full-size washer and dryer. The home has central air-conditioning, high-speed Wi-Fi and cable/smart TV. Please enter your travel dates in the top right corner of this page for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $245.00 In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%. Be sure to search this site for more Pretty Picky Properties - your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ® Town of Chatham Registration #778

16688: Sand Bar - Walk to Downtown Chatham, Steps to Beach! Introducing Sand Bar: Your Private Haven by the Sea<br><br>Just off the iconic Shore Road and a short walk from the tranquil Aunt Lydias Cove in Chatham, Sand Bar presents a destination of relaxation and convenience. Privately ensconced behind verdant hedges, this spacious 4-bedroom retreat offers the perfect blend of seclusion and accessibility.<br><br>Step into a world of leisure where two decks beckon for al fresco dining amidst the serene Chatham breezes. A BBQ area with ample seating provides an ideal spot for savoring culinary delights while soaking in the harbor views. Rain or shine, the TV room, and adjacent formal living room offer cozy retreats for moments of relaxation or afternoon naps on plush seating.<br><br>For beach lovers and adventurers, Sand Bar offers convenient access to sandy shores for a relaxing day in the sun or a launching point for kayaking adventures (kayaks available for rent locally). At just 0.9 miles from Chatham Lighthouse, a beacon of the town’s rich maritime heritage, and a mere 0.4 miles from the vibrant Chatham Squire, where live music and delectable dining await, every moment promises unforgettable experiences. You are also in convenient proximity to Chatham Bars Inn, which has five restaurants open to the public for you dining pleasure. <br><br>Explore the enchanting Chatham Main Street, where treasures like Chatham Candy Manor and Bluefins Sushi Bar await, alongside a plethora of charming boutiques offering souvenirs to immortalize your cherished memories of Chatham.<br><br>Experience the epitome of coastal living at Sand Bar, in this idyllic Chatham getaway.<br><br>Home Details:<br>-Dogs Welcomed (w/fee of $40/night per dog) <br>-Sleeps 8<br>Bedrooms<br>-Total 4<br>-Ground Floor Bedroom: 1 King Bed<br>-Ground Floor Bedroom: 4 Twin Beds (2 Bunks)<br>-1st Floor Bedroom: 1 Queen Bed<br>-2nd Floor Bedroom: 1 King Bed<br>Bathrooms<br>-Total 3<br>-Ground Floor: Shower<br>-1st Floor: Tub/Shower Combo<br>-2nd Floor: Tub and Shower<br>Other Amenities <br>-Window A/C<br>-WiFi<br>-Smart TV<br>-Cable TV<br>-Washer/Dryer <br>-Propane Grill<br>-Indoor Fireplaces are not for guest use(fines remitted)<br>-Please note outdoor amenities are available seasonally<br>-Sheets and Bath Towels Provided with Beds made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>-Parking for 2 cars maximum<br>-Detached Garage is not available for guest use

16655 - Riptide: 1 Mile from Downtown Chatham Walk to Pier One of the many perks of staying at this four-bedroom home is its great location within walking distance to the Chatham fish pier and the downtown area. A favorite pastime of residents and visitors alike is watching commercial fishing boats unload their haul for the day at the fish pier (a half mile away). Downtown Chatham is less than a mile from the home. Here you’ll find restaurants (The Chatham Squire, Impudent Oyster, Bluefins Saki & Sushi Bar) and plenty of shopping. There are also many attractions within a mile, including Cape Cod Baseball League games at Veterans Field, films at the historic Chatham Orpheum; Oyster Pond Beach for swimming; and fun exhibits at the Shark Center, where you can learn all about Atlantic White Sharks.<br><br>Other perks include a spacious backyard with a deck and a dining table for six, an outdoor shower, fire pit, plus a picnic table for eight set on a well-manicured lawn, as well as a ping pong table in the basement.<br><br>The first floor of the home has an open and airy living room with comfortable seating, Smart TV, and direct access to the deck and the private backyard; a half bath; full kitchen with countertop seating for three; a formal dining room — great for board games and entertaining; and the master bedroom with a TV and en suite bathroom.<br><br>The second floor features a full bathroom with three additional bedrooms — one with a king bed; a second room with two queen beds, a couch, TV and DVD player; and a third bedroom with a king bed and its own private entrance.<br><br>Home Details<br><br>-Sleeps 10<br>-2 Floors<br>-1st Floor Master Bedroom: 1 Queen Bed w/ en suite Full Bathroom<br>-2nd Floor Bedroom #1: 1 King Bed<br>-2nd Floor Bedroom #2: 2 Queen Beds<br>-2nd Floor Bedroom #3: 1 King Bed<br>-Central A/C<br>-WiFi<br>-Smart TV<br>-DVD Player<br>-Ping Pong Table (Basement)<br>-Washer/ Dryer (Half Bathroom)<br>-Spacious Outdoor Living Area<br>-Deck with Furnishings<br>-Outdoor Shower<br>-Fire Pit<br>-Weber Gas Grill<br>-1 Mile to Downtown Chatham<br>-Half Mile to Fish Pier<br>-NO pets fines remitted<br>-Sheets and Bath Towels Provided with Beds Made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>C0071810550

This property is professionally managed by Pretty Picky Properties. Renovated Chatham Village Farmhouse, Pool, Walk to Beach and Town Sleeps 10 Rents Friday to Friday during peak season Pets Considered Linens Included, beds made Pool open from Memorial Day to Columbus Day Charm, privacy, style, comfort and convenience -- it’s all yours in this one-of-a-kind Chatham in-town farmhouse. The location is ideal. Sandy Lighthouse Beach is a short walk across Main Street. Walk the other way on Main Street for 10 minutes to find the shops, restaurants, movie theatre, galleries and feel-good vibe of Chatham Village town center. Not to mention the Chatham Anglers of the Cape Cod Baseball League. Back at the farmhouse, the secluded, half acre includes a beautiful grassy yard, a large in-ground heated pool, a comfy seating area with umbrella shaded tables, a built-in grill and gas firepit as well. The pool area includes a freestanding pool house where you’ll find a bedroom, private bath and a sitting area. And the garage has been converted into a game room with a flat screen smart TV, couch, extra refrigerator, and ping pong table. Walk into the expansive kitchen and dining area, and you realize that the special allure of this home is its flawless blend of 19th century charm and modern furnishings and features. Contrast the exposed beam ceiling here with the totally cutting edge kitchen with its island seating and Miele appliances. But keep in mind that as an older home, the ceilings are lower in some places than those of a more recently built home. The main level also includes a comfortable living room with a smart TV, den, half bath and laundry. And there is an enclosed outdoor shower. No Cape vacation is complete without an outdoor shower! Upstairs you’ll find a total of three bedrooms, the king primary bedroom with full bath en suite. There is also a queen bedroom upstairs with peaks of the water at Lighthouse Beach. You’ll also find the “bunk room” that houses a bunk bed plus two twin beds. There is another full bath located on the second level. This home has split unit air conditioning and a couple of window units, which effectively cools its 2,400 square feet of living space and allows individual temperatures to be set. There’s also a SONOS sound system and high-speed Wi-Fi, of course. It’s unusual to find a spacious family compound such as this in the heart of Chatham Village, so close to everything that makes Chatham the vacation destination of choice for so many families. Please enter your travel dates in the top right corner of this page for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $245.00. In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%. This property offers a three-night minimum stay during select weeks in May – June and September – November. Guests are charged a cleaning fee for all stays less than seven nights. Stay seven nights or more and the cleaning fee is waived. Be sure to search this site for your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ®

This property is professionally managed by Pretty Picky Properties Updated Chatham Family Compound, Heated Pool with Hot Tub, Walk to Town/Beach Rents Friday to Friday in Peak Season Linens Included, Beds Made Pets Under 25 Pounds Considered Pool is open from Memorial Day to Columbus Day weekend If you relish the charm of Chatham but love modern amenities, here’s the resort style vacation destination for your group. The acre-plus property provides two separate structures with sleeping for up to 10. The in-ground heated pool is the focus of summer outdoor living here, further embellished by the hot tub. The property’s location is ideal. You can walk or bike to the restaurants, shops and entertainment unique to Chatham Village. Or slip into your swimsuit, grab a towel and head to nearby Oyster Pond Beach or famous Lighthouse Beach, your choice. Each less than a 15-minute walk. The larger main house features a big covered outdoor patio with a dining table, plenty of seating and a gas grill. The patio overlooks the pool house and pool less than 100 feet away. The pool house adjoins the surprisingly large pool, surrounded by a roomy stone deck with a dining table, plenty of lounge and other seating, an outdoor shower, gas grill and beverage center, fire table and, of course, the tempting spa. Inside the main house, you’ll be delighted by the fully outfitted, renovated kitchen with granite counters and a center island with built-in gas range top. The kitchen walks out to the patio for convenient serving when you dine outside. You’ll also find a handy half bath just off the kitchen. There’s a good sized dining room with a patio view. The large, comfortable living room adjoins the dining room and offers a flat screen TV. The main level also has a small den/office with a another TV seating area for the kids to watch shows/movies. The home has high speed Wi-Fi, a SONOS system, and is centrally air conditioned. The primary bedroom suite is also on the main level and includes a big king size bed and a remodeled full bath en suite. There is also a flat screen TV. On the upper level of the main house, there are two bedrooms, one with a king size bed. The other bedroom has four twins. These two bedrooms share a roomy full bath. The pool house offers rustic, lodge-like charm with exposed beams and vaulted ceiling in the full kitchen and adjoining family room/TV lounge. The kitchen is fully equipped and includes a round dining table and chairs. The pool house has a main level bunk room with four twins. There is also a ping pong table on the main level and a full bath. The upstairs sleeping area has a small lounge area with another TV and a step-up section with a comfortable king size bed. That upper level walks out to a second level deck overlooking a natural vista of undeveloped woodlands. Please enter your travel dates in the top right corner of this page for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $245.00. In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%. This property offers a 3-night minimum stay during select weeks in May – June & September – November. Guests are charged a cleaning fee for all stays less than 7-nights. Stay 7-nights or more and the cleaning fee is waived. Be sure to search this site for your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ® Town of Chatham Registration #286

16682 - Nob Hill: Quintessential Cape directly on the Cape Cod Rail, Dog Friendly! In this Quintessential Cape, your vacation dreams become a reality, offering a blend of outdoor adventures, and vibrant local culture. Nestled in the heart of Chatham, this charming vacation rental is your gateway to relaxation. A direct path from the home to the rail trail was recently cleared. Chatham Pier and Chatham Lighthouse Beach, both just a short drive away at 1.6 miles and 2.5 miles respectively, beckon with their coastal beauty, promising unforgettable experiences. <br>This home embodies the natural Cape spirit, bathed in light with bright, cheerful colors that infuse every corner with warmth and vibrancy. An open layout welcomes you, inviting you to unwind and savor the moments of your vacation, or weekend getaway! <br><br>Nature enthusiasts and dog lovers will find their haven right in the backyard, where the Old Colony Rail Trail awaits. Whether you prefer a leisurely stroll or an exhilarating bike ride, this scenic path promises unforgettable adventures.<br><br>Step outside to your private outdoor patio space, equipped with propane grill, a perfect spot for al fresco dining and making cherished memories under the open sky. As the sun settles below the horizon rejuvenate yourself in the outdoor shower and cool down before your evening plans. When you’re ready to wind down for the evening, Inside are 4 spacious bedrooms with comfort amenities for the whole family. <br><br>When it’s time to savor local flavors, head to the beloved Chatham Squire, a mere 1.4 miles away on Main Street. Delight in dinner and drinks, and after your meal, explore the charming shops and candy stores that line Main Street, adding a touch of whimsy to your Cape Cod evenings. Secure your stay today and immerse yourself in the Cape’s timeless charm.<br><br>Home Details:<br>-Dogs Welcomed (w/fee of $40/night per dog)<br>-Sleeps 8<br>-2 Floors<br>Bedrooms<br>-Total 4<br>-1st Floor Bedroom: 1 Queen<br>-1st Floor Bedroom: 2 Twin Beds<br>-2nd Floor Bedroom: 1 King Bed<br>-2nd Floor Bedroom: 2 Twin Beds<br>Bathrooms<br>-Total 2<br>-1st Floor: Full Bathroom w/ Shower/Tub Combo<br>-2nd Floor: Full Bathroom w/ Shower/Tub Combo<br>Other Amenities <br>-Central AC<br>-WiFi<br>-TV<br>-Washer/Dryer<br>-Propane Grill <br>-Outdoor Shower<br>-Please note outdoor amenities are available seasonally<br>-Sheets and Bath Towels Provided with Beds made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>C0417190550

Your next Cape Cod adventure awaits at this cozy Chatham vacation rental. Perfect for a memorable family getaway on the coast, this 3-bedroom, 2-bath house sits in a convenient location for exploring top area attractions. Head to a number of nearby sandy beaches for some fun outdoors before visiting shops and restaurants around downtown. Or, opt to stay closer to home, with spots like the Old Colony Rail Trail and White's Pond Swimming Beach just a short walk away! -- THE PROPERTY -- Mass Tax Connect ID No. C0340950550 | In-Unit Laundry | Private Deck | 1 Mi to Downtown Chatham Bedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: 2 Twin Beds INDOOR LIVING: Smart TV, fireplace, dining table, ceiling fans OUTDOOR LIVING: Outdoor shower, spacious yard KITCHEN: Refrigerator, Keurig & drip coffee makers, stove/oven, microwave, dishwasher, toaster, dishware & flatware, cooking basics GENERAL: Self-check-in, free WiFi, central A/C, washer & dryer, iron/board, towels/linens, trash bags/paper towels, complimentary toiletries, hair dryer ACCESSIBILITY: Single-story house w/ basement, 4 steps required to enter FAQ: Pet fee (paid pre-trip) PARKING: Driveway (6 vehicles), free street parking -- THE LOCATION -- OUTDOOR FUN: Old Colony Rail Trail Access (on-site), Monomoy RMS Park - tennis, pickleball & basketball courts (0.3 miles), White's Pond Public Swimming Area (0.5 miles), Monomoy National Wildlife Refuge (4 miles) NEARBY BEACHES: Lighthouse Beach (2 miles), Ridgevale Beach (3 miles), Hardings Beach (3 miles) AREA ATTRACTIONS: Downtown Chatham - local restaurants, shops, entertainment (~1 mile), Chatham Lighthouse (2 miles), Atwood Museum (2 miles) GOLF COURSES: Eastward Ho! Golf Course (3 miles), The Captains Golf Course (6 miles), Cranberry Valley Golf Course (6 miles) AIRPORTS: Chatham Municipal Airport (1 mile), Boston Logan International Airport (88 miles) -- REST EASY WITH US -- Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - Pet friendly w/ $75 fee (+ fees & taxes, dogs only, 1 max) - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: This single-story house requires 4 exterior steps to enter. While all of the home’s bedrooms and 1 full bathroom are accessible on the main floor, there is a full bathroom in the basement

16665 - Summer Breeze: Lovely Home Near Bike Path Dog Welcome! This lovely four bedroom vacation home, located on a large lot in the beautiful seaside town of Chatham, is just the place to bring the whole family, including the dog, for an unforgettable Cape Cod vacation! <br><br>Hop on your bicycles and head down the street to the Old Colony Rail Trail, where you can journey through this completely paved eight mile former railroad trail running from Chatham to Harwich before connecting to the Cape Cod Rail Trail. From the property, you can hop in the car and drive just a few minutes to Chatham’s beautiful, pedestrian-friendly Main Street, where you will find some of the best seafood around, not to mention the many fine shops and galleries that make downtown Chatham so unique. Spend a day at nearby Chatham Lighthouse Beach, located only half a mile from downtown or two miles from the property, where you can relax on the beach, enjoying the sun, sand, and ocean, or try climbing to the peak of the lighthouse to be treated to breathtaking panoramic views of the beach and surrounding scenery. <br><br>Back at the property, you will enjoy a large grassy yard; perfect for running around with the kids (and dog) and playing yard games. There is a nice deck area with a picnic table, where you can enjoy family meals outside under the blue skies, and you can fire up the gas grill for a nice BBQ as often as you’d like, as full propane tanks will be supplied. Enjoy taking morning showers in the enclosed outdoor shower.<br><br>Inside the home, you will find a living room with hardwood floors and a flat screen TV; a great space for relaxing and enjoying movie nights with the family. The fully equipped kitchen features stone countertops, bar seating, and stainless steel appliances, with a six seat dining area adjacent. Also on the main floor are two bedrooms, one with a queen size bed and the other with a twin single and twin trundle, as well as a full bathroom with a tub/shower combo. Walk up the stairs to the second floor to find the other two bedrooms, including the master with a queen size bed and en suite full bathroom with a tub/shower combo, and the last bedroom with three twin singles. Other amenities include a smart lock for easy self check-in, window A/C units in the bedrooms, a washer and dryer in the basement, and sheets and bath towels provided to all guests at no extra cost with beds made upon arrival.<br><br>Home Details:<br>-Dogs Welcomed (w/fee of $40/night per dog)<br>-Sleeps 8<br>-2 Floors<br>-1,680 Sq Ft<br>Bedrooms<br>-Total 4<br>-1st Floor Bedroom: 1 Queen Bed<br>-1st Floor Bedroom: 1 Twin Bed w/ Trundle (2 twins total)<br>-2nd Floor Bedroom: 1 Queen Bed w/ en suite Full Bathroom<br>-2nd Floor Bedroom: 3 Twin Beds<br>Bathrooms<br>-Total 2<br>-1st Floor: Tub/Shower Combo<br>-2nd Floor: Full Bath w/ Tub/Shower Combo (en suite Queen bedroom)<br>Other Amenities<br>-Fully Equipped Eat-In Kitchen w/ Bar Seating & Dishwasher<br>-Window A/C Units in Bedrooms<br>​​​​​​​-Fireplace NOT for guest use<br>-WiFi<br>-TV<br>-Smart Lock/Self Check-In<br>-Driveway Parking for 3 Cars<br>-Washer/Dryer (basement)<br>-Outdoor Shower<br>-Deck w/ Furniture<br>-Gas Grill<br>-Large Private Yard<br>-Next to Old Colony Rail Trail<br>-1 Mile to Downtown Chatham<br>-2 Miles to Chatham Lighthouse<br>-Sheets and Bath Towels Provided with Beds Made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant

16656 - Decked Out Oyster: Steps to Oyster Pond Private Dock! Calling all water enthusiasts! This stunning home has water views and a floating dock just down the street! Enjoy a swim off of your own personal dock or take one of the home’s paddle boards or inflatable boats for a spin! The perfect place to entertain, this home comes fully equipped for ten people, boasting two balconies, a spacious backyard deck, outdoor grill, fire pit and a large well-manicured lawn. But, the fun does not stop there! The home also has croquet and bocce ball sets, an outdoor ping pong table, and air hockey table in the basement.<br><br>The home’s coastal-inspired interior features sun-drenched living areas and plenty of space. On the first floor there is a formal living room with large sofas and a fireplace; a contemporary kitchen with countertop seating as well as a formal dining area; a master bedroom with a king bed and a full, en suite bath; a second bedroom with a queen bed; plus, a third bedroom with a queen bed and office space perfect for working remotely.<br><br>On the second floor, there is a family room with a smart TV, board games and a deck for sunset and water viewing; a bedroom with a twin bunk bed; and another bedroom with two double beds and a private deck, as well as a Jack-and-Jill bathroom with jacuzzi tub (and upstairs washer/dryer) shared between both the upstairs bedrooms.<br><br>Chatham Main Street is only a 20-minute walk or a 3-minute drive away from the home; here, you’ll find a fabulous selection of local restaurants and one-of-a-kind stores. Some popular places to dine are The Impudent Oyster, Bluefins Saki and Sushi Bar and The Wild Goose Tavern. Nearby attractions also include movies at the historic Chatham Orpheum; guided tours of Chatham Lighthouse and learning about the Atlantic White Sharks at the Chatham Shark Center. <br><br>Home Details:<br>-Dogs Welcomed (w/fee of $30/night per dog)<br>-Sleeps 10<br>-2 Livable Floors <br>-1st Floor Master Bedroom: 1 King Bed w/ en suite Full Bathroom (walk-in shower)<br>-1st Floor Bedroom #2: 1 Queen Bed -1st Floor Bedroom #3: 1 Queen Bed -2nd Floor Bedroom #4: 2 Full Beds -2nd Floor Bedroom #5: 2 Twin Beds (bunk beds) -Central Heat & A/C -Smart TV w/ Cable -DVD Player -WiFi -Washer/Dryer (Basement) -Air Hockey (Basement) -Outdoor Ping Pong Table -Spa Tub in 2nd Floor Bathroom -1st Floor Gas Fireplace (Living Room) for guest use -2nd Floor Gas Fireplace (Not for Guest Use) -Fire Pit -Private Yard -Lawn Games -Propane Grill -Paddle Boards & Inflatable Rafts -Steps to Oyster Pond with a Private Floating Dock -Sheets and Bath Towels Provided with Beds Made Upon Arrival -Cleaned with Hospital Grade Disinfectant

16619 - Chatham Cruiser: On the Chatham Loop - 1 Min to the Beach! Chatham Cruiser is the perfect mix of modern comfort and historic charm, offering a classic Cape Cod summer experience. <br><br>Start your day in the beautiful kitchen, and once breakfast is ready, sit down in the sun-soaked breakfast nook for the most important meal of the day. Relax in the bright living room before heading on a nice stroll through the gorgeous Chatham neighborhood to get to Oyster Pond Beach - the perfect place to take the kids for the day. Main Street is also just down the road, where you will find plenty of options for dining, shopping, and entertainment. <br> <br>Return home to the patio in the back, under the shade of the Japanese cherry tree. Serve up BBQ and evening cocktails, with the large, fenced-in yard being a great space to play lawn games, entertain, and regroup to go out and enjoy some evening fun at the many beaches or restaurants close by. Retire for the evening to one of the five bedrooms, all with air conditioning to beat the summer heat. The primary bedroom has a queen bed, with another queen bed on the second floor, twin beds in bedrooms 3 and 4, and two twin beds in the final, fifth bedroom. <br><br>Other amenities include an outdoor shower, propane grill, washer/dryer, multiple TVs with cable, and numerous indoor and outdoor dining options. Staying at Chatham Cruiser, you will feel the stories this home has experienced, and can excitedly add to the rich history of this Cape gem. <br><br>Home Details:<br>-No Pets(Fines Remitted)<br>-Sleeps 8<br>-2 Floors<br>Bedrooms<br>-Total 5<br>-1st Floor Bedroom: 1 Queen Bed<br>-1st Floor Bedroom: 1 Twin Bed<br>-2nd Floor Bedroom: 1 Queen Bed<br>-2nd Floor Bedroom: 1 Twin Bed<br>-2nd Floor Bedroom: 2 Twin Beds<br>Bathrooms<br>-Total 2<br>-1st Floor: Full Bathroom w/ Shower/Tub combo<br>-2nd Floor: Full Bathroom w/ Shower<br>Other Amenities<br>-Fully Equipped Eat-In Kitchen<br>-4 Mini-Split A/C Units + 2 Window A/C Units<br>-Smart Lock<br>-TV<br>-WiFi<br>-Washer/Dryer (1st floor)<br>-Patio w/ Outdoor Dining<br>-Propane Grill<br>-Outdoor Shower<br>-Private Fenced-In Yard<br>-NO Pets (fines remitted)<br>-Located on the Chatham Loop<br>-Minutes to Oyster Pond Beach & Main Street<br>-Sheets and Bath Towels Provided with Beds Made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>C0409890550

16617 - Skipping Stone: Located on Rail Trail By Beach & Downtown! This beautifully updated home is a great place to enjoy a family vacation on Cape Cod! Beautiful downtown Chatham is less than a mile away, so all the best restaurants, shopping, and entertainment are just around the corner. Not only are Lighthouse beach and Jackknife Cove just a couple miles away, this home is surrounded by ponds that are within walking distance. Emery Pond, White Pond, Perch Pond, and Lover’s Lake are all half a mile or less from the house, and the Chatham Airport is just a few minutes away. The home itself is well-updated with modern appliances and plenty of room for 8 guests. The 1st floor of the home offers a living room, large sunroom, eat-in kitchen, two bedrooms, and a full bathroom. One of the first floor bedrooms offers a queen bed, while the other bedroom offers two twin beds. Upstairs there are two additional bedrooms; one has a king size bed and a crib, and the other has two twin beds. A brand new central A/C system will be sure to keep you cool on those hot summer days. The outdoor area is beautiful and offers a small deck with a gas grill and a dining area. The deck leads down into a great grassy backyard - perfect for kids and your dog to play or to relax and soak up the sun. This is a great location to experience Chatham and the surrounding areas of Cape Cod. Don’t wait to book this awesome vacation home!<br> <br> <br>Home Details:<br>-Dogs Welcomed (w/fee of $40/night per dog)<br>-Sleeps 8<br>-Bedroom 1: 1st floor, 1 queen bed<br>-Bedroom 2: 1st floor, 2 twin beds<br>-Bedroom 3: 2nd floor, 1 king bed + crib<br>-Bedroom 4: 2nd floor, 2 twin beds<br>Bathrooms<br>-Total: 2<br>-1st Floor: Full Bath w/ Tub/Shower Combo<br>-2nd Floor: Full Bath w/ Shower<br><br>-Central A/C<br>-Window Units/Floor Unit A/C in each bedroom<br>-Smart TV<br>-WIFI<br>-Washer and Dryer<br>-Outdoor Shower<br>-Private yard<br>-Gas Grill<br>-Located on the Old Colony Rail Trail<br>-Sheets and Bath Towels Provided with Beds Made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>C0409420550

3 Bedroom (2 Primary) - Loft - 5.5 Bathroom - Sleeps 8 During Peak Summer Season Until Labor Day - a 7-night Friday-to-Friday rental reservation is required Complimentary Linens Service Provided: This includes bedsheets, bath, beach, and dish towels for total home occupancy We offer a 4 PM Check-In and 10 AM Check-Out Experience Sandpiper! Pet-friendly home with coveted location walking distance to Town and Lighthouse Beach. Recently renovated and refreshed, this entire 3 bedroom, 5.5 bath vacation rental located in the heart of Chatham’s historic village, has an ocean view, central AC, private bathrooms in every bedroom, large loft room with additional sleeping area, entertainment/media level with a full bar and pool table, bonus/multi-purpose room, hot tub, outdoor dining, Solo stove fire pit, WIFI, 8 HDTVs with streaming services, Sonos System, and lots of private spaces for relaxing or enjoying quiet time. ​​​​​​​Bonus: Complimentary items including linens, beach towels, and beach chairs. Beds will be made! Owners supply starter paper products, kitchen and laundry detergents, paper goods, and cleaning supplies. Bonus: Complimentary items including linens, beach towels, and beach chairs. Owners supply starter paper products, kitchen and laundry detergents, paper goods, and cleaning supplies. Owners Share Why They Love Their Home: Our home offers complete relaxation and escape for all ages. Put away your car keys - with the beach just across the street and shops and restaurants within walking distance. No need to pack up for a long day at the beach. The short walk into town means no hassling with parking and a pleasant walk any time of day or evening. With 3 large private bedrooms, each with its own bathroom and a large upstairs loft with with additional beds and bathroom, the house is perfect for families with kids of any age, 2 families or multiple couples. We love to entertain and this home is just perfect for everyone! The cook’s kitchen includes everything you need to prepare a meal at home and the large dining area and open living room and wet bar make all your guests comfortable. The entertainment/media level provides great space to relax in the evenings. We had rented this house previously and when it came on the market, we enjoyed it so much we decided to purchase it. We immediately invested in updating and refreshing the house to improve the experience for our guests. The minute you walk in the door you sense you are on vacation. Let Us Tell You About This Home: FIRST FLOOR As you open the door you will find a spacious living room with stone fireplace, HDTV, wet bar, and plenty of comfortable seating. The newly refreshed modern coastal decor will add to your experience of staying at the beach. Recently added SONOS system with speakers throughout the main floor lets everyone join in on the entertainment whether relaxing, dining or cooking together. An open dining/kitchen area with a large dining table along with a breakfast bar is great for large family dinners or easy entertaining. The kitchen is complete with Subzero refrigerator. a wine fridge and Wolf appliances as well as all the small appliances you need to complete your stay including a Keurig and KitchenAid mixer. The kitchen is fully stocked with everything you need to prepare meals. Make sure to take in the views of the Atlantic Ocean just across the street while you dine. For your convenience, just off the kitchen is a large mudroom, half bath, laundry and side entry perfect for entering after a day on the beach. Outdoors. The home includes a newly expanded private patio with new upgraded furniture and is perfect for outdoor dining. The outdoor space also includes an outdoor shower, a hot tub for relaxing, a new Weber gas grill, and a Solo Stove fire pit and seating for relaxing outside after a day at the beach. Main Floor Primary Just off the large open-air living space is the main floor Primary Bedroom with a king bed, HDTV and an ensuite bathroom with shower. The Bedroom has been completely updated and refreshed with new linens and décor. There is a large closet complete with shelving and plenty of storage. SECOND FLOOR The Second Floor Primary with ocean views has a king bed, a newly renovated (Spring 2024) ensuite bathroom, a sitting area for a quiet escape, a desk workspace, a new 50" HDTV, a large walk-in closet with plenty of storage and two large dressers. The room has been completely refreshed and updated. Bedroom 3. This large peaceful room has a view of the ocean and includes two queen beds and a completely renovated (Spring 2023) ensuite bathroom (double vanity, shower with shower seat) and HDTV. The room includes a walk-in closet with lots of storage space and a second closet with lots of shelving and has been completely refreshed with new beds and new bedding. Loft. The loft has a 40" HDTV and a desk area for anyone needing to get some screen tome or work done. There is also a newly constructed (Spring 2033) private bathroom with shower, and an additional sleeping area with two twin beds. LOWER LEVEL When you are ready for the entertainment to begin, head to the lower level where you will find a full wet bar with a keg tap, sink, dishwasher, full refrigerator and seating for eight, a pool table and media seating area featuring a new 96" HDTV. The large living area also includes a small table for cards and puzzle making. The lower level also includes a newly renovated multi-purpose room which includes light weights, exercise bands, yoga mats and an HDTV perfect for a workout. The room is quite large (14 x 18) and can be used for rainy day activities or quiet space to escape. There is also a 5th full bath with shower on the lower level. Free Tickets and Complimentary Activities! Create unforgettable memories and experience Cape Cod like a local! Enjoy $750 worth of daily exclusive free tickets to exciting local attractions through our partnership with Xplorie. Your amenities include activities such as Island Cruises, Whale Watch, Bike Rentals and admission to Whydah Pirate Museum. When you’re not soaking up the sun on the beach, enjoy daily rounds of golf at Cranberry Valley or Chequessett Golf Courses and mini-golf for family fun. This home offers Keyless Entry for your convenience. NO SMOKING of anything containing tobacco, any other substance, or e-cigarettes, inside or outside of the home. PET FRIENDLY HOME for one DOG only. A Pet Registration form must be completed upon reservation. LINENS: All bed linens and towels are included including beach towels BEACH CHAIRS, UMBRELLA, BEACH CART AND COOLERS all available for guests use. COMPLIMENTARY ITEMS include a starting supply of paper products, kitchen and laundry detergents, sponges, trash bags, cleaning supplies and some pantry items MAX PARKING: 4 cars at property. No parking on lawn anytime. Town of Chatham Rental Certificate: STR-388 **Hot Tub is generally open from May thru October, but please confirm exact dates with NE Vacation Rentals** Additional Information to Assist You: Booking direct with New England Vacation Rentals offers the best rate guarantee on the web. Our calendars are updated in real-time and are accurate. Departure cleaning is included with your reservation at no additional charge. Simply follow our basic check-out instructions at your departure. State and local taxes are charged if applicable. For Reservations made over 60 days away, you will make two payments - 50% initial payment with reservation and the final balance will be auto billed to your credit card 60 days prior to arrival. We accept Mastercard and Visa for payments. A confirmed reservation is non refundable--please consider purchasing trip cancellation insurance. Ask our guest specialist for more details regarding cancel options and trip insurance. You must be 25+ years old unless accompanied by a parent or guardian to book one of our Vacation Rental Homes. An ID must be furnished upon request. Area Info: *Mileage is approximate Across the street to the north end f beautiful Lighthouse Beach 0.2 mile to main entrance of Lighthouse Beach 0.6 mile to Kate Gould Park where you can enjoy a bandstand concert on Friday nights 0.6 mile to historic Chatham Bars Inn offering a beach bar, a full service spa, and fine dining all open to the public 0.8 mile to Chatham Seaside Golf Links 0.8 mile to the Chatham Fish Pier where you can eat fresh seafood and watch the fishing boats come in 1.2 mile to the bike path - More info on The Rail Trail can be found here: Info on Cape Cod bike trails Only a half mile to downtown Chatham where you will find : ​​​​​​​Shopping Spas and massage Restaurants Friday night Band stand concerts The Orpheum Theater for movies –make sure to check out “Jaws” on the big screen The Monomoy Theater – for live theater Playground Public Tennis Chatham A’s Baseball Licence number: C0264800550

6 bedrooms- 6.5 Bathrooms- Sleeps 14 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many of our homes offer flexible stays with a 3 night minimum in the off season - ask our Reservation Specialists for more details. Complimentary Linens Service Provided: This includes bedsheets, bath, beach, and dish towels for every bed home sleeps and total home occupancy. We offer a 4 pm Check-In and 10 am Check-Out Welcome to Sand Simeon - a luxury Coastal Cape Cod home with a Pool, in the sought after and charming town of Chatham! We invite you to enjoy Complimentary Linens, A/C , WIFI, and more at this Dog-Friendly home, only .2 miles from Lighthouse beach and a short stroll to town. This home has everything needed for a special vacation! Owners Share Why I Love My Home: This home is truly special. It’s not just the perfect beach house - it’s a comfortable spot year round. It’s the ideal layout for groups of any age - teens can be watching a movie or playing pool in the basement while adults enjoy dinner at the large dining room table and drinks by the firepit, all the while little ones can be sleeping upstairs. In the summer the pool is a fun respite from the gorgeous beach - which is just steps away. With so much space to enjoy the house both indoors and outdoors you really don’t need to leave, but for the occasional dinner in town, Main Street is just a short stroll away. Let Us Tell You About This Home: This luxury home is pet friendly with a private pool, central ac, linens (in summer season), WIFI, and more. In historic village of Chatham and 0.2 mile to Lighthouse Beach. This restored and completely updated home has even earned a preservation award! Escape from the outside world as soon as you enter the foyer and find yourself surrounded by the comfort of the coastal accommodations. On the first floor you will find the gourmet kitchen with professional appliances (2 dishwashers, subzero refrigerator, dual Wolf ovens & cook top, and granite counter tops) which opens up to the dining area with seating for 12. As you enter into the large living area you will find several comfy couches and cozy chairs along with a fireplace, 42’’ HDTV, and wet bar. Just off of the dining/living area, you will walk through the sliders onto the wrap-around patio with outdoor seating, fire-pit, and gas grill. There is a master suite on the first floor with a King bed, fireplace, flat screen TV, full bathroom with whirlpool tub, and sliders out to the balcony that overlooks the pool. Just down the hall is another bedroom with a Queen bed and full en suite bathroom. The second floor boasts a second King master suite with fireplace, flat screen TV, & full en suite bathroom with whirlpool tub at the end of the hall. The 4th and 5th bedrooms on the second floor also have flat screen TV’s and full en suite bathrooms with showers. One of the bedrooms offers a King bed and the other has 2 twins. The entertainment and resort like amenities can be found on the lower level of the home! There are 2 large flat screen TVs, pool table, media area, and second kitchen/bar area which leads out to the outdoor pool, shower, & additional patio area for entertaining. Every amenity is at your fingertips including: A built-in stereo system with DVD players, iPod docking stations, wireless high-speed internet to keep you connected, and central air to keep you cool and comfortable. The bunk room with 4 twins, flat screen TV, and en suite bathroom with a shower is also located on the lower level. There are 2 laundry areas, one on the first floor and one on the lower level! Need extra sleeping space? There’s a double blow up mattress in the closet. Thinking of a family reunion? Leave your worries behind, escape to the Cape, and enjoy all this luxury vacation rental has to offer you! **Most NEVR Pools/Hot Tubs are open from Memorial Day Weekend thru Labor Day Weekend. Please feel free to check with NE Vacation Rentals and the home info -- to confirm exact dates when the pool and/or hot tub is opened or closed for the season** Gas fireplaces are off in the summer The pool is heated and open June 1 - Oct 1 Free Tickets and Complimentary Activities! Create unforgettable memories and experience Cape Cod like a local! Enjoy $750 worth of daily exclusive free tickets to exciting local attractions through our partnership with Xplorie. Your amenities include activities such as Island Cruises, Whale Watch, Bike Rentals and admission to Whydah Pirate Museum. When you’re not soaking up the sun on the beach, enjoy daily rounds of golf at Cranberry Valley or Chequessett Golf Courses and mini-golf for family fun. With all NEVR properties, we think of the little things to make your vacation special. Our Guest Welcome Bag, compliments of the homeowner, contains starter quantities of kitchen and bathroom essentials, with a few locally sourced snacks as well (subject to change based marketplace availability). This home offers Keyless Entry for your convenience with. NO SMOKING of anything containing tobacco, any other substance, and e-cigarettes, inside or outside of the home. DOG FRIENDLY HOMES are for a DOG only. This home allows 1 dog for $25 per night. With owner approval, a second dog may be considered for an additional $25 nightly fee. A Pet Registration form must be completed upon reservation confirmation. Max parking of cars at property: 5. No parking on lawn anytime. Additional Information to Assist You: Our calendars are updated in real-time and are accurate. Departure cleaning is included with your reservation at no additional charge. Simply follow our basic check out instructions carefully and there will be no extra charges. State and local taxes are charged if applicable. For Reservations made over 60 days away-you can make 2 payments-50% deposit with reservation and the final balance will be auto billed to your credit card 60 days prior to arrival. We accept Mastercard and Visa for Payments. A confirmed reservation is non refundable--please consider purchasing trip cancellation insurance. Ask our guest specialist for more details regarding cancel options and trip insurance. NEVR complies with the directives listed on the Mass.gov website. Please be aware that information may be updated and the details of your reservation may also be required to change, potentially without much notice. If the MA Governor issues a MA Rental Ban for MA Vacation Rental Homes, we will allow you to move your reservation to a future date, or provide a refund. Please note, any other reasons to cancel would follow our normal cancellation policy. Our NEVR Homes come with mattress covers, pillows and a bed cover such as blanket, quilt, bedspread etc. Linens - bed sheets, bath/dish/beach towels and bath mats can be rented at time of booking or at a later date through our linen/concierge services if not included with your rental home. Please ask our guest specialist for details. You must be 25+ years old unless accompanied by a parent or guardian to book one of our Vacation Rental Homes. Area Info: .2 mile to beautiful Lighthouse Beach .5 mile to Monomoy Coffee Company .6 mile to Kate Gould Park where you can enjoy a bandstand concert on Friday nights .7 mile to historic Chatham Bars Inn offering a beach bar, a full service spa, and fine dining all open to the public 1 mile to the Chatham Fish Pier where you can eat fresh seafood and watch the fishing boats come in 1.6 mile to the bike path at Crowell Road - More info on The Rail Trail can be found here: Info on Cape Cod bike trails Only a half mile to downtown Chatham where you will find : Seal tours Shopping Spas and massage Restaurants Friday night Band stand concerts The Orpheum Theater for movies –make sure to check out “Jaws” on the big screen The Monomoy Theater – for live theater Playground Public Tennis Chatham A’s Baseball *Mileage is approximate Licence number: C0274210550