Vacation rentals in South Chatham, MA with free parking

16670 - A Touch of Blue: Updated Beach House Deck Outdoor Shower! Nautical colors and floods of natural light welcome you to A Touch of Blue. Located in Chatham, this beach house is walking distance from immaculate Forrest Beach on Nantucket Sound. <br><br>With ample seating outside, and a private plot set back from the road, this home is a nice place to relax this Cape Cod summer. A sprawling outdoor deck, with a shade umbrella and great outdoor seating, welcomes you to your vacation home. Step through the patio, with additional seating, and into A Touch of Blue. <br><br>The open concept living room and kitchen house an exposed brick chimney and sun soaked sofas, with a dine-in island at the center of the kitchen. Head down the hallway towards the sleeping quarters of this home- two bedrooms, the primary bedroom with a queen bed, and the second bedroom with a full bed and a twin/ twin bunk bed. <br><br>Other amenities include a washer and dryer, a secluded backyard with hammock for relaxing, an outdoor shower and central A/C. Surround yourself with the joys of Chatham at A Touch of Blue. <br><br>Home Details:<br>-Dogs Welcomed (w/fee of $40/night per dog)<br>-Sleeps 6<br>-Single Floor<br>Bedrooms<br>-Total 2<br>-1st Floor Bedroom: 1 King Bed<br>-1st Floor Bedroom: 1 Full Bed + 1 Bunk Bed (2 Twins)<br>Bathrooms<br>-Total 1<br>-1st Floor Bathroom: Full Bathroom w/ Shower<br>Other Amenities<br>-Fully Equipped Kitchen<br>-Central A/C<br>-Smart Lock<br>-WiFi<br>-Smart TV/Streaming<br>-Washer/Dryer<br>-Covered Porch w/ Seating<br>-Deck w/ Outdoor Dining<br>-Propane Grill<br>-Outdoor Shower<br>-Fireplace- not for guest use<br>-Hammock<br>-Private Yard<br>-Parking for 2-3 Cars<br>-8 Minute Walk (0.4 mile) to Forest Beach on Nantucket Sound<br>-Sheets and Bath Towels Provided with Beds Made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>C0408470550

16622 - The Yachtsman: Newly Renovated Modern Pond Access! Fully updated and modernized, this vacation home offers the ideal balance of seclusion, convenience, and comfort. Located off a private road in South Chatham, our home is right around the corner from Main Street, where you will find some of the great dining, shopping, and entertainment options that Chatham has to offer. You will also be near the Cape Cod Rail Trail and within minutes of multiple beaches and ponds. Drive to Cockle Cove Beach in four minutes, Ridgevale Beach in five minutes, or Forest Beach in six minutes. Taylor’s Pond is close by, and with deeded access, you can enjoy swimming, kayaking, and fishing in this beautiful body of water. When you walk through the front door of our home you will find a bright and open living space, including kitchen with stone countertops, stainless steel appliances, and island seating, a dining room set, and living area with a sectional couch and large flat screen TV. Upstairs is another living area with a couch, flat screen TV and gas fireplace, as well as a full bathroom and two bedrooms, one with a twin trundle and the other with two full + twin bunk beds. The house has central air conditioning for constant comfort on even the hottest of summer days. Thoughtfully equipped for a relaxing stay, the home features a Smart TV, WiFi, a washer and dryer in the basement, and fresh sheets and towels provided upon arrival. After a day at the beach, rinse off in the outdoor shower, then challenge family and friends to a game of ping pong—perfect for friendly competition, rain or shine. Outside, fire up the gas grill and enjoy meals al fresco on the spacious deck with comfortable outdoor seating. Spend your next vacation in style and book this amazing vacation home now! Home Details: -Dogs Welcomed (w/fee of $40/night per dog) -Sleeps 8 -2 Floors -1st Floor Bedroom #1: King Bed -1st Floor Bedroom #2: Queen Bed -2nd Floor Bedroom #1: 2 Full/Twin Bunk Beds -2nd Floor Bedroom: Twin with Twin trundle Bathrooms -Total: 2 -1st Floor: Full Bath w/ Tub/Shower Combo -2nd Floor: Full Bath w/ Shower -Central A/C -SmartTV -WiFi -Washer/Dryer in Basement -Game Space -Ping Pong Table -Bathtub -Gas Fireplace -Outdoor Shower -Gas Grill -Fire Pit (wood) -Deeded Access to Taylor’s Pond -1 Minute to Main Street/Close to Beaches -Sheets and Bath Towels Provided with Beds Made Upon Arrival -Cleaned with Hospital Grade Disinfectant -C0426490550

16632 - Casa Al Mare: 15 Minute Walk to Pleasant Street Beach! Your perfect seaside getaway starts with this adorable home on Pleasant Street in South Chatham. Lovingly updated with comfortable coastal decor, spacious and incredibly clean. Just a 15 minute walk to Pleasant Street Beach (or very short drive), you’ll have no problem spending your days on the beach and soaking up the summer rays. <br>A short drive will bring you to a number of excellent dining options - for classic Italian fare try Bucca’s - just a mile away. For a more casual vibe, hope in the car and drive 10 minutes to downtown Chatham where shopping, dining, and good times await. Spend your evenings in the backyard, grilling up dinner or lounging under the stars. When you’re ready to retire for the night, there are four comfortable bedrooms to choose from, ensuring everyone can relax in comfort.<br><br>Whether you’re looking for a quick weekend getaway or a family summer vacation, Casa Al Mare is the perfect home to make your vacation dreams come true- don’t miss your chance to book today!<br><br>Home Details:<br>-No Dogs (fines remitted)<br>-Sleeps 8<br>Bedrooms<br>-Total 4<br>-1st Floor: Queen Bed<br>-1st Floor: 2 Twin Beds<br>-2nd Floor: 1 Full Bed<br>-2nd Floor: 2 Twin Beds<br>Bathrooms<br>-Total 2<br>-1st Floor Full Bath<br>-2nd Floor Full Bath<br>Cable TV<br>-WiFi<br>-Washer/Dryer <br>-Gas Grill<br>-Walk to the Water <br>-Sheets and Bath Towels Provided with Beds Made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>C0018510550

This home is professionally managed by Pretty Picky Properties Luxurious Chatham Home, Heated Saltwater Pool, Newly Renovated Rents Friday to Friday during peak season Linens Included. Beds made. Sleeps 12 Pool & Hot Tub open from Memorial Day to Columbus Day Be one of the first to stay in this masterfully renovated home with a brand-new saltwater pool under a mile (.7 mile) to Ridgevale Beach in Chatham. The 5-bedroom home plus bonus room has been totally updated from top to bottom and features brand new furniture throughout. The focal point of course is the custom saltwater pool with a built-in hot tub. The outdoor living space is stunning with an expansive travertine patio, plenty of lounge seating and an outdoor kitchen set up with a grill and granite counter. Don’t forget to use the outdoor shower after the beach! Inside, the attention to detail is evident from the coffered ceilings to custom local art on the walls. The main living area is open to the kitchen and dining area. The kitchen is of course fully equipped with all you’ll need to prepare any meal. The main level is also home to the primary bedroom with a King-sized bed and exquisite private bathroom. There are two additional bedrooms on the main level: one with a queen and one with 2 twins. There is a full bath for these rooms as well. Finally there is a second vaulted living area with additional lounge seating and a TV. Upstairs features a classic Cape set up with a full bathroom at the top of the stairs. There are bedrooms on either side. Both bedrooms feature custom ship-lapped walls and ceilings and have King beds with a twin trundle. Even more living space awaits on the fully finished lower level! There is another TV lounge area plus a workspace and an exercise area. There is a flex sleeping area down here which houses 2 queen beds. A brand-new full bath on the lower level completes the space. A 15 minute walk or a very short bike ride brings you down to one of Nantucket Sound’s most desirable beaches: Ridgevale Beach. Relax on the beach, have the little ones play in the creek flowing into the Sound and grab a bite to eat at the snack bar. A 6-8 minute drive brings you to both Chatham and Harwich Port Villages for pedestrian friendly shopping and dining. There are ample dining and shopping opportunities along Route 28 closer to the house as well. 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 3-night minimum outside of the peak season. 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 the Pretty Picky site for your best selection of prime vacation homes available for summer rental on Lower Cape Cod. It’s your vacation. Get Picky! ® Town of Chatham Registration #STR-562

16638 - The Flying Fish: Perfect for Group w/ Kids & Dogs w/ Hot Tub Are you searching for a recently renovated home with a hot tub and room for the whole family for your vacation? Look no further than The Flying Fish! New for the 2022 season was the hot tub on the back deck, the perfect place to take your vacation relaxation to the next level, whatever the season! Located in a quiet neighborhood within walking distance of Forest Beach this house is also a short drive away from some of the best restaurants and shops both Harwich Port and Downtown Chatham have to offer! Also new for the 2022 season was an interior redesign and renovation including new flooring, paint, appliances, fixtures, and countertops done in a sophisticated coastal style. The Flying Fish features an open concept eat-in kitchen and large living room. Also on the first floor is a bedroom with a Queen bed, half bath, and laundry room. On the second floor you’ll find two Queen bedrooms, one with an en-suite full bathroom. There is another full bathroom upstairs as well as the “bunk” room which has five bunk beds! The home is also equipped with WiFi, a YouTube TV streaming subscription, and A/C to make sure you spend your vacation in comfort.<br><br>On the outside, this home offers a large semi-fenced private yard with a gas and charcoal grill, an outdoor shower, and a welcoming deck with plenty of seating–a great spot from which to enjoy those beautiful summer evenings! Don’t forget that your pups are welcome to join in on the fun too! Up to 2 dogs are allowed at the Flying Fish (with an additional fee). <br>Under half a mile away, you will find Forest Beach–one of Chatham’s best-known and most beautiful bayside beaches. What could be better than taking a short walk to the beach just down the street?<br><br>The Flying Fish is also convenient to local favorite restaurants like The Talkative Pig, Bucca’s Tuscan Roadhouse, Brax Landing. If you are feeling adventurous the Freedom Ferry to Nantucket also departs from nearby Saquatucket Harbor. Home Details: -Dogs Welcomed (w/fee of $30/night per dog) -Sleeps 11 -2 Floors -2nd Floor Master Bedroom: 1 Queen Bed with en suite Full Bathroom -2nd Floor Bedroom #2: 1 Queen Bed -2nd Floor Bedroom #3: 5 Twin Beds -1st Floor Bedroom: 1 Queen Bed -A/C Units in Bedrooms -YouTube TV Streaming Subscription -WiFi -Washer/Dryer -Hot Tub -Outdoor Shower -Ping Pong Table -Foosball Table -Propane Grill -Sheets and Bath Towels Provided with Beds Made Upon Arrival -Cleaned with Hospital Grade Disinfectant C0416360550

16606 - Chatham Charmer: Game Room Walk to Nantucket Sound! Nestled between Harwich Port and Chatham Center, this charming Cape Cod retreat offers the perfect blend of relaxation and recreation for your family getaway. The home boasts two spacious family rooms and a large backyard, providing ample space for everyone to unwind. The expansive back deck, complete with a convenient outdoor shower, is the ideal spot for morning coffee in the sun or a delicious evening barbecue on the gas grill.<br><br>A short, leisurely 10 minute stroll takes you to two picturesque beaches—Forest and Pleasant Street—where you can soak up the sun and enjoy the coastal breeze. For more beach adventures, Ridgevale and Hardings Beach are just a quick drive away, perfect for family outings. If you’re in the mood for a scenic ride, the Old Colony bike trail is only a few blocks from your door, offering a delightful way to explore the area.<br><br>Inside, the home is equipped with modern comforts including central air conditioning, Wi-Fi, and three smart TVs, ensuring a comfortable and connected stay. You’ll enjoy a new dining room that seats ten and a lively game room in the basement—perfect for kids and active adults alike.<br><br>This dog-friendly haven welcomes your furry friends for an additional fee, making it a true family-friendly destination. With beds made upon arrival, fresh linens, and thorough cleaning with hospital-grade disinfectant, you can relax from the moment you step inside. Whether you’re here to create new memories or continue a cherished tradition, this home is the perfect base for your Cape Cod adventures.<br><br>Home Details:<br>-Dogs Welcomed (w/fee of $40/night per dog)<br>-Sleeps 10<br>Bedrooms:<br>-Total 4<br>-1st Floor Bedroom: 1 Full Bed<br>-1st Floor Bedroom: 1 Queen Bed<br>-2nd floor Bedroom: 1 Queen Bed<br>-2nd floor Bedroom: 1 Queen Bed and 1 Bunk Bed (2 Twins) <br>Bathrooms:<br>-Total 2 Full Baths, 2 Half Baths<br>-1st Floor: Half Bathroom<br>-1st Floor: Full Bathroom w/ Shower/Tub combo<br>-2nd Floor Half Bathroom<br>-2nd Floor: Full Bathroom w/ Shower/Tub combo<br>Other Amenities<br>-Gas Grill<br>-Smart TV<br>-WiFi<br>-Central A/C<br>-Private Yard<br>-Outdoor shower<br>-GAME ROOM!<br>-Sheets and Bath Towels Provided with Beds Made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>-C0424570550

17755 - Deer Run Hideaway: Minutes to Red River Beach, Dog Friendly! Welcome to Deer Run Hideaway, a contemporary Cape Cod gem perfectly situated near the stunning Red River Beach. Surrounded by a manicured lawn, this inviting home features a new outdoor patio and a private backyard, ideal for relaxing in the sun or enjoying al fresco dining.<br><br>Step inside to discover a spacious sunroom and a cozy living room, offering ample space for family gatherings or quiet moments with a favorite summertime novel. Bring your yard games to make the most of the expansive outdoor area, and gather around the fire pit in the evenings for s’mores and storytelling under the stars.<br><br>Nestled on a peaceful street and cul-de-sac, Deer Run Hideaway offers the perfect blend of beachside fun and tranquil family time. Spend your days basking in the sun or exploring the nearby shore, then return to the spacious family room for evening game nights, complete with comfortable seating and plenty of table space.<br><br>Conveniently located in the heart of Harwich, you’ll have easy access to a variety of attractions, including the Freedom Ferry to Nantucket, exciting seal tours, charming shops, delightful restaurants, and local bakeries. Venture into Chatham, just a short drive away, where you can catch a movie at the Orpheum, or enjoy Friday night concerts. Savor the local culinary scene at Buca’s Tuscan Roadhouse (Harwich) and Brax Landing (Harwich), both known for their delicious offerings.<br><br>Experience the perfect Cape Cod getaway at Deer Run Hideaway, where relaxation and adventure await!<br><br>Home Details:<br>-Dogs Welcomed (w/fee of $40/night per dog)<br>-Sleeps 6<br>Bedrooms<br>-Total 3<br>-1st Floor Bedroom: 1 King Bed, ensuite bathroom w/Shower<br>-1st Floor Bedroom: 1 Queen Bed<br>-1st Floor Bedroom: 2 Twin Beds<br>Bathrooms<br>-Total 2<br>-1st Floor: Shower (ensuite)<br>-1st Floor: Tub and Shower<br>Other Amenities <br>-Central A/C <br>-WiFi<br>-Smart TV<br>-Washer/Dryer <br>-Propane Gas Grill<br>-Fire pit<br>-Outdoor Shower<br>-Indoor Fireplaces are not for guest use(fines remitted)<br>-Please note outdoor amenities are available seasonally<br>-Please note there is a front door camera that faces outward and is turned off during the rentable period<br>-Please note there is a backyard camera that is turned off during the rentable period<br>-Sheets and Bath Towels Provided with Beds made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>-Parking for 3 cars maximum Please note there is a front door camera that faces outward and is turned off during the rentable period

16677 - Nautical Nest: 0.6 Miles to Beach Great for families! Seals swim off shore while you soak up the rays on the immaculate beaches of Chatham! Enjoy fine dining, outdoor concerts, saltwater and sunshine at your new favorite vacation destination, the Nautical Nest<br><br> Stepping up the covered front porch, enter into the home’s beautiful living room, with ceilings towering above and natural light flooding in from the skylight and patio doors at the rear of the home.<br><br>Adjacent to the living room, the home’s kitchen, complete with breakfast bar, is a wonderful place to whip up some treats before heading out to the beach. Past the kitchen, the dining room, complete with bay windows, even has beautiful framed instructions on how to prepare clams and other Cape Cod delicacies, as well as displays on the many types of animals you may see while exploring the Cape. <br><br>An additional TV room, with large sectional and flat screen tv, is a great place to unwind after a long day of exploring Chatham. <br><br>When it’s truly time to call it a night, choose from one of three bedrooms in this sleeps 8 home. Located on the first floor, the home’s primary bedroom, fittingly named the Captain’s Quarters, welcomes you in with a comfortable king bed. On the ground floor, the perfect escape for kids awaits, with a shark themed kids bedroom, and even a full playroom and private TV space to enjoy their own favorite flicks.<br><br>Outside, enjoy the Chatham sunshine on the back deck, or wander down to the patio, both complete with outdoor dining and lounging options. Minutes from your front door are countless beaches, including lovely Forest Beach, where you and the family can enjoy the wonders and natural beauty of Cape Cod. Your next vacation will have memories that will last a lifetime, why not flutter on down to the Nautical Nest! <br><br>Home Details:<br>-Sleeps 10 <br>-3 Floors (Ground Floor, 1st Floor + 2nd Floor)<br>-1,512 Sq Ft<br>Bedrooms<br>-Total 4<br>-Ground Floor Bedroom: 4 Twin Beds<br>-1st Floor Bedroom: 1 King Bed<br>-2nd Floor Bedroom: 1 King Bed<br>-2nd Floor Bedroom: Queen Bed<br>Bathrooms<br>-Total 3<br>-Ground Floor: Full Bathroom w/ Shower<br>-1st Floor: Full Bathroom w/ Shower<br>-2nd Floor: Full Bathroom w/ Tub/Shower Combo<br>Other Amenities <br>-Fully Equipped Kitchen with Dishwasher<br>-Smart Lock/Self Check-In<br>-WiFi<br>-Smart TV with Streaming and Cable <br>-Washer & Dryer (Ground Floor)<br>-Central A/C<br>-Deck & Patio with Outdoor Dining and Lounging<br>-Basement TV Room and Kids Play Space<br>-Propane Grill<br>-Fire Pit (wood)<br>-Outdoor Shower<br>-Private Yard<br>-NO PETS (fines remitted)<br>-0.6 Miles to Forest Beach<br>-Sheets and Bath Towels Provided with Beds Made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>C0414080550

16648 - Quail Trail: Fully Updated Home w/ Great Outdoor Space! This beautifully updated house in South Chatham is located at the end of a quiet neighborhood cul-de-sac and nestled in the scrub pines, just a ten-minute drive to nearby beaches. <br><br>This modern “smart home” has all the amenities with a large central smart TV and open floor plan including an eat-in kitchen, a cozy living room with a puzzle and game table, and a full bathroom. The kitchen sliders open to a deck with comfortable outdoor furniture, gas grill and outdoor shower and is the perfect spot to unwind after a day at the beach or a day of shopping and dining in town. Two bedrooms offer queen beds (one with an en-suite half bath, another with a work desk). Both have plenty of natural light, cell-phone charger stations, remote-controlled ceiling fans, central air, and reading lamps. <br><br>Enjoy coffee and sunbathing in the morning and cocktails in the evening on the deck, or ping pong and soft darts downstairs complete with a walk out basement- level patio and outdoor fire pit with seating for six. This home is a little off-the-beaten path, but perfect for getting away from the hustle and bustle of town! <br><br>Home Details:<br>-Sleeps 4<br>​​​​​​​-1 Floor + Basement<br>Bedrooms<br>-Total 2<br>-1st Floor Bedroom:1 Queen Bed w/ en suite Half Bathroom<br>-1st Floor Bedroom Queen Bed w/ Desk Area<br>Bathrooms<br>-Total 1.5<br>-1st Floor: Half Bathroom (en suite Queen Bedroom)<br>-1st Floor: Full Bathroom w/ Shower<br>Other Amenities<br>-Central A/C<br>-TV<br>-WiFi<br>-Washer/Dryer<br>-No pets allowed (fines remitted)<br>-Patio & Fire Pit<br>-Gas Grill<br>-Ping Pong Table<br>-Deck<br>-10 Minutes to Area Beaches and Towns<br>-Sheets and Bath Towels Provided with Beds Made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>CO453720550

Experience beachside bliss when you stay at this 3-bedroom, 3-bath South Chatham vacation rental! The home also features a large bonus room, conveniently located near one of the home's bathrooms, providing extra privacy for families or groups. Start your mornings with a workout in the exercise studio and coffee in the sunlit sunroom, then head just minutes away to Forest Beach for swimming, shell collecting, and seaside walks. Book today and start planning your breezy Cape Cod escape! -- THE PROPERTY -- Mass Tax Connect ID No. C0317590550 | Dog Friendly w/ Fee | Outdoor Shower | Game Room Bedroom 1: Queen Bed | Bedroom 2: Queen Bed | Bedroom 3: 2 Twin Beds | Bonus Room: Queen Bed INDOOR LIVING: 2 Smart TVs (YouTube TV provided), board games & books, dining table, ping pong table, fireplace (decorative) OUTDOOR LIVING: Deck, picnic table, outdoor seating, gas grill (propane provided), backyard KITCHEN: Dishwasher, refrigerator, stove/oven, microwave, Keurig/drip coffee maker, hot water kettle, Instant Pot, toaster oven, toaster, cooking basics, dishware & flatware, wine glasses, trash bags & paper towels GENERAL: Free WiFi, complimentary toiletries, hair dryer, towels & linens, yoga mats, weights, washer & dryer, central heating & A/C, keyless entry FAQ: Pet fee (paid pre-trip), 2 exterior security cameras (facing out) ACCESSIBILITY: Multi-level home, 3 steps to enter, 3 bedrooms & 2 bathrooms on main level PARKING: Driveway (3 vehicles) -- THE LOCATION -- BEACHES: Forest Beach (2 miles), Cockle Cove Beach (2 miles), Ridgevale Beach (2 miles), Red River Beach (3 miles), Hardings Beach (4 miles) GOLF: Wequassett Resort and Golf Club (3 miles), Eastward Ho! Country Club (4 miles), Cranberry Valley Golf Course (4 miles), Harwich Port Golf Club (5 miles), The Captains Golf Course (5 miles) OUTDOOR ACTIVITIES: Chatham Lighthouse (5 miles), Cape Cod National Seashore (17 miles), Sandy Neck Gate House (24 miles), Mashpee National Wildlife Refuge (30 miles) SHOPPING: Downtown Chatham (4 miles), Downtown Hyannis (17 miles), Cape Cod Mall (17 miles) AIRPORT: Boston Logan International Airport (86 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/ $50 fee (+ fees & taxes, 2 dogs max) - No events, parties, or large gatherings - Must be at least 21 years old to book - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: This multi-level home requires 3 steps to enter. There are 3 bedrooms and 2 full bathrooms located on the main level - NOTE: Your safety matters. This property features 2 doorbell devices with exterior security cameras. Camera 1 is located in the doorbell at the front door facing the front outdoor entry, and camera 2 is located in the doorbell at back door facing the back outdoor entry. The cameras are outward-facing and do not look into interior spaces. The cameras record video when activated by motion, but are not active when guests are in residence - NOTE: The fireplace is decorative only and not available for guest use Licence number: C0317590550

This property is professionally managed by Pretty Picky Properties Luxury Living in Chatham with Pool and Hot Tub Pool open for the season as of May 1st till Columbus weekend Sleeps 8 3 Bedrooms plus flex bonus room, 3.5 Bathrooms ​​​​Rents Friday to Friday during peak season Linens Included, Beds Made Small Dogs Considered Here’s your Chatham summer home --- for a week, a month or possibly all summer long! Built in 2020, 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 deck or travertine 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 handsome fire table for gazing at the stars. You’ll also find a handy outdoor shower plus a sizable pool cabana. Drive just four minutes to popular Oyster Pond Beach and 2 miles to Hardings Beach. Or leave the car at the house and take a short, easy walk up to Main Street – only six minutes to Mac’s Fish & Lobster. 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 living room with appealing, comfortable lounge seating and upscale appointments. This home has central air conditioning, high speed WiFi, cable, as well as smart TV and a Sonos® sound system – all brand new. The first of two primary room 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 king master suite, full bath included. Upper level guest room with a king size bed. A flex bonus room has a private balcony with water views equipped with twin beds in addition to the king. There are 3.5 baths in all at the house. 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 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 #675

This property is professionally managed by Pretty Picky Properties, Inc. Spectacular Harwich Port Waterfront Retreat on Nantucket Sound NEW Listing for 2026! Sleeps 14 in 5 bedrooms plus bonus sleeping area Linens included, beds made Pets considered (up to 25lbs) Rents Saturday to Saturday in the summer months Experience the ultimate Cape Cod escape at this extraordinary 5-bedroom, 6.5-bath waterfront estate in coveted Harwich Port. Set on expansive acreage with a private beach on Nantucket Sound, this newly constructed home offers sweeping water views, a peaceful setting, and effortless coastal elegance—just minutes from town. Designed for both comfort and entertaining, the open-concept main level showcases a sun-filled living area, spacious dining room, and beautifully appointed chef’s kitchen, all flowing seamlessly toward the water. Step outside to an expansive deck and screened porch overlooking the Sound, perfect for morning coffee, afternoon breezes, and unforgettable sunset gatherings. A main-level primary suite features a king bed and spa-like ensuite bath, offering serene privacy and convenience. Upstairs, four additional ensuite bedrooms provide luxurious accommodations for family and guests. One bedroom features a king bed plus a twin trundle, two bedrooms offer a queen bed, and the final bedroom upstairs includes two queens and two twins—ideal for groups traveling together. The walkout lower level extends the living space with a comfortable TV lounge, two additional twin beds, and a full bath—perfect for kids, teens, or overflow guests. Outside, the property unfolds into a sweeping lawn leading to your private sandy beach, creating an idyllic setting for swimming, sunbathing, paddleboarding, or simply relaxing to the sound of gentle waves. Despite its tranquil setting, this exceptional home is just a 5-minute drive to Harwich Port village and 10 minutes to Chatham, offering easy access to charming shops, acclaimed dining, and classic Cape Cod attractions. This is waterfront living at its finest—an unforgettable retreat where luxury, privacy, and natural beauty converge. 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 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! ®

17739 - Deja Blue: Heated Pool AC 1/2 Mile to Beach! Accommodations for twenty people, a heated pool, and a prime location? All this and more awaits in immaculate Harwich. All this and more awaits in immaculate Harwich… wait a minute, it’s Deja Blue all over again! Located in a calm neighborhood, this large home is perfect for families looking to escape to the peace and quiet of Cape Cod. <br><br>Upon arrival, you’ll walk towards the backyard and private heated pool, a highlight of your vacation before you even enter the home. Opening the door to this stunning complex, you’ll enter into a convent mudroom, keeping the beach sand outside and the indoors clean. Head to the right, and step into the modern kitchen, with ample counter space. Or, head left off of the mudroom and down into the dining area. Also located here are even two full sets of washer and dryers to keep everyone fresh all vacation long.<br><br>Passing back through the kitchen, you’ll find the large living room. With a sprawling sectional, the living room is a great place to relax, watch a movie, or play some board games on a summer night. Down the hall, the first of the home’s many bedrooms are located. This sleeps 20 home has plenty of space for the whole family, friends, and their family and friends, as well as two dogs! Sleeping arrangements include eight bedrooms, split between the first and second floor. On the first floor, the primary bedroom has a king size bed, while the second and third bedrooms each have a queen size bed. Head up the staircase, with a stunning unique banister, and to the left where you will find three bedrooms. One bedroom has two full size beds, a second bedroom has two twin size beds, and a third bedroom has a queen size bed. Down the hall to the right of the stairs, the remaining two bedrooms preside, one with three twin size beds and fun dog artwork on the walls, and the final bedroom with one twin size bed and one full size bed.<br><br>After a long night’s rest, be sure to relax under the sun on one of eight chaise lounges around the outdoor, heated pool. Or, step outside the pool’s gates to the spacious yard for some fun yard games and room for your pup to roam.<br><br>Other amenities include a roomy outdoor shower, a massive outdoor picnic-banquet table, pool toys and floats, and central A/C. Just down the street from Red River Beach, whether you want the privacy of your own heated pool, or the joy of the Cape Cod salt water, you have a variety of swimming options to choose from. Be sure to bring everyone along this vacation, you’ll be wanting to come back again and again, at Deja Blue.<br><br>Home Details:<br>-Dogs Welcomed (w/fee of $40/night per dog)<br>-Sleeps 20<br>-2 Floors<br>Bedrooms<br>-Total 8 <br>-1st Floor Bedroom: 1 Queen Bed<br>-1st Floor Bedroom: 1 Queen Bed<br>-1st Floor Bedroom: 1 King Bed<br>-2nd Floor Bedroom: 2 Full Beds<br>-2nd Floor Bedroom: 2 Twin Beds<br>-2nd Floor Bedroom: 1 Queen Bed<br>-2nd Floor Bedroom 1 Full Bed & 1 Twin Bed<br>-2nd Floor Bedroom: 3 Twin Beds<br>Bathrooms<br>-Total 2.5 <br>-1st Floor: Half Bathroom<br>-1st Floor: Shower<br>-2nd Floor: Shower/Tub combo<br>Other Amenities<br>-Fully Equipped Kitchen<br>-Central A/C<br>-Smart Lock/Self Check-In<br>-WiFi<br>-Cable TV<br>-2 Washing Machines + 2 Dryers (full size)<br>-Private Heated In-ground Pool (Pool Open from Memorial Day to Labor Day - may be longer but not guaranteed)<br>-Patio w/ Outdoor Seating & Lounging<br>-Propane Grill<br>-Outdoor Shower<br>-Large Private Yard<br>-Lawn Games<br>-Located South of Route 28<br>-Half Mile to Red River Beach<br>-Sheets and Bath Towels Provided with Beds Made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>C0371191260

16690 - Chatham Haven: Walk to Beach, Private Patio and Backyard! Discover the charm of Chatham at Chatham Haven, a delightful vacation home perfectly located in a private, wooded yard adorned with beautifully maintained gardens. <br><br>With Pleasant Street Beach just a short walk away, families can easily enjoy sun-soaked days by the shore, accessible for children of all ages. Forest Beach is also a short walk away, with the added bonus of if you decide to drive no beach sticker is required. The home accommodates multi-generational families with two comfortable first-floor bedrooms and a convenient shared bathroom.<br><br>Step outside to the brick patio, a serene oasis surrounded by lush gardens. With ample seating, a propane grill, and an outdoor shower, this space is perfect for dining al fresco or simply unwinding after a day at the beach. Plus, Red River Beach is only a mile away, offering even more opportunities for seaside fun<br><br>Chatham Haven is ideally situated near a variety of beloved local restaurants. Savor delicious meals at Brax Landing, indulge in Italian at Buca’s Tuscan Roadhouse, or grab a casual bite at Drifters—each just a short drive away.<br><br>Experience the perfect blend of relaxation and adventure at Chatham Haven, where cherished memories await in this beautiful coastal escape.<br><br>Home Details:<br>-Dogs Welcomed (w/fee of $40/night per dog)<br>-Sleeps 10<br>Bedrooms<br>-Total 4<br>-1st Floor Bedroom: 1 Queen Bed<br>-1st Floor Bedroom: 2 Twin Beds<br>-2nd Floor Bedroom: 1 Queen Bed<br>-2nd Floor Bedroom: 2 Bunk Beds - (four twins)<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>-Central A/C<br>-WiFi<br>-Cable TV<br>-Washer/Dryer <br>-Propane Gas Grill<br>-Fire Pit (wood)<br>-Outdoor Shower<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 3 cars maximum<br>

You’ll be able to hear the crashing waves from every corner of this Chatham, MA, vacation rental. This 3-bedroom, 2-bathroom home sits just a short walk from Harding’s Beach and a quick drive from all of Cape Cod’s top attractions! Spend some time at the beach, then rinse off in the outdoor shower before relaxing in the sunroom. Head out to shop the day’s catch at Chatham Pier Fish Market, go on a cranberry bog tour, or take the family for a day of fun at Whydah Pirate Museum. -- THE PROPERTY -- C0395230550 | Outdoor Shower | RV/Trailer Parking (30’ Max) | Fireplace | 1,700 Sq Ft Bedroom 1: King Bed | Bedroom 2: King Bed (New Photos Coming Soon) | Bedroom 3: 2 Twin Beds INDOOR LIVING: Flat-screen TV, DVD player, board games, books, dining table, walk-in closet OUTDOOR LIVING: Private yard, deck KITCHEN: Cooking basics, dishware/flatware, dishwasher, refrigerator, stove, microwave, coffee maker, coffee grinder, kettle, toaster, garbage disposal GENERAL: Free WiFi, keyless entry, central A/C, ceiling fans, complimentary toiletries, linens/towels, washer/dryer, laundry detergent, hangers, hair dryer, trash bags/paper towels SUITABILITY: Stairs required to access, bedroom/full bathroom on 1st floor PARKING: Driveway (3 vehicles), street (first-come, first-served) -- THE LOCATION -- SUN & SAND: Harding’s Beach (0.2 miles), Ridgevale Beach (3 miles), Cape Cod National Seashore (5 miles) COASTAL LIVING: Chatham Lighthouse (4 miles), Chatham Pier Fish Market (4 miles), Shark Center Chatham (4 miles) FAMILY FUN: Pirate's Cove Adventure Golf (14 miles), Whydah Pirate Museum (15 miles), Cape Codder Water Park (23 miles) AIRPORT: Cape Cod Gateway Airport (20 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 - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: The property requires stairs to access Licence number: C0395230550

Welcome to a classic coastal getaway at this charming Chatham vacation rental. Located 1 mile from the shore and steps from Goose Pond, this 3-bedroom, 2-bath plus basement den is the perfect home base! The best of the Mid-Cape is at your fingertips; it's just 3 miles to downtown Chatham shopping and restaurants and minutes from trails, including direct access to the Old Colony Rail Trail. There’s plenty to do at the rental, too, like grilling, roasting s’mores, and relaxing by Goose Pond. -- THE PROPERTY -- MassTaxConnect ID C0447510550 | Dog Friendly w/ Fee | Fenced-In Backyard | Outdoor Dining Area | EV Charger | Unwind Fireside Bedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: King Bed | Basement Living Room: 2 Twin Beds INDOOR LIVING: 65” Smart TV, wood-burning fireplace, board games, dining table & breakfast bar OUTDOOR LIVING: Furnished deck, gas grill, bocce ball, fire pit w/ seating, outdoor shower, beach chairs & towels, Goose Pond access, 4 Trek Bikes, 2 paddleboards, Old Colony Rail Trail/CCRT access KITCHEN: Dishwasher, stove/oven, refrigerator, microwave, cooking basics, dishware & flatware, coffee maker, toaster, trash bags & paper towels GENERAL: Free WiFi, central heating, mini split A/C units (1 on each floor), complimentary toiletries, linens & towels, in-home laundry, hair dryer, hangers, iron & board, keyless entry, 1 small, 1 medium, 2 large & 2 extra-large dog crates w/ cushioned beds, 2 soft Yeti coolers FAQ: Stairs required for access, 1st-floor bedroom & bathroom, pet fee (paid pre-trip) PARKING: Driveway (4 vehicles), free street parking, RV/trailer parking allowed on-site, EV charger -- THE LOCATION -- SUN & SAND: Goose Pond (beach access, walking distance), Ridgevale Beach (1 mile), Hardings Beach (2 miles), Cape Cod National Seashore (4 miles) LOCAL LIVING: Marion's Pie Shop (0.6 miles), Mac's Chatham Fish & Lobster (2 miles), Main Street (3 miles), Chatham Pier Fish Market (4 miles), Chatham Lighthouse (5 miles), Cape Cod Lavender Farm (5 miles), Cranberry Bog Tours (8 miles) FAMILY FUN: Old Colony Rail Trail (0.2 miles), Historic Downtown Chatham (3 miles), Wharfinger Chatham Fish Pier (3 miles), Cape Cod National Seashore Salt Pond Visitor Center (12 miles) AIRPORT: Cape Cod Gateway Airport (17 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/ $150 fee (+ fees & taxes, dogs only) - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: This property requires stairs for access

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

This property is professionally managed by Pretty Picky Properties Magnificent Harwich Port Estate, Heated Pool, Walk to Wychmere Harbor and Village Sleeps 20 Linens Included, beds made Rents Friday to Friday during peak season Pets considered Pool is open Memorial Day weekend through Columbus Day weekend Just across the street from picturesque Wychmere Harbor, “Wychmere Heights” offers unique and private accommodations in the heart of Harwich Port. The 6800+ square foot property is located on a large acre lot and features tremendous indoor and outdoor living spaces for your group of up to 20. Featuring 9 bedrooms, 7 full baths, and 2 half baths there is ample room for groups to spread out and have their own space inside. Outside your focus will no doubt be the heated 20x40 saltwater pool and surrounding spacious patio. The property also has a lush, irrigated lawn for recreation or relaxation. Interior Living Space The property’s main level is comprised of a spacious living and dining room. There is seating for 18-20 at two dining tables. The living room has a TV, ample seating and has a slider out to the pool area. The updated kitchen is adjacent to the dining rooms and features new appliances, 2 full size refrigerators, 2 ovens, 2 dishwashers, a waterfall granite counter, and a spacious bar area. The roomy kitchen area is ideal for entertaining and has a slider to the pool area. There are two primary bedroom suites on this level as well. Both rooms have private baths and king-size beds. Finally, there is a private wing off the other side of the kitchen that has a small den, two bedrooms with a queen bed in each plus a full bath. This area may be ideal for a young family or anyone who may need some extra privacy from the rest of the group. In all, the main level has four bedrooms. The lower level is set up with a King bedroom suite with a spa-like private bath, a secondary TV lounge plus a game room. There is also a half bath down here. Upstairs, you’ll find 4 additional bedrooms. There are two primary suites (Orleans Room & Brewster Room) each with a king size bed. The Dennis Room features a double bed plus a twin. The final bedroom upstairs is the "bunk room" and in here you will find 3 XL twin beds plus a queen size bed. There is a full bath in the hallway up here as well. Outdoor Space The heated pool is surrounded by a spacious patio with plentiful lounging and seating. The dining area has seating for up to 18-20 and features chaise lounges to soak up the sun. The pool includes an auto safety cover that can be closed with a flick of a switch. This keeps the pool safe for any young ones and also helps to keep debris out and heat in the pool. You will also find a stand alone hot tub and a gas firepit. There is a playset on the side yard for the kids to enjoy. Harwich Port From the house, you can head west into Harwich Port Village, about a 7-minute walk. The village has several dining and bar options to choose from. There’s also ice cream, boutiques, and art studios to browse. It’s a charming village center that features Port Summer Nights on Wednesdays in the summer. The streets are closed to vehicle traffic and the area is festive with live music, food trucks and other attractions. Saquatucket Harbor You can also head just east to Saquatucket Harbor. There are waterfront dining options here as well as a great selection of charter boats on which to get out on the water with a rod and reel. Or, head out to Nantucket for the day! The Freedom Ferry will have you over to the island in just over an hour. Don’t forget the beach! You can walk across the street and down Snow Inn Road to Merkel Beach, about a 10-minute walk from the house (half a mile). Here you have an expansive Nantucket Sound beach with the calm warm waters of the sound massaging the shoreline. Wychmere Harbor Wychmere Harbor is a stone’s throw from the property and is one of the most photographed vistas on the Cape. Wychmere is also home to the Wychmere Beach Club. The club is private but is very popular for weddings and events. “Wychmere Heights” is uniquely set up to welcome guests of events for long weekends in the shoulder seasons. Though large events are not permitted at “Wychmere Heights”, modest dinner gatherings or the like are considered with approval. Experience the best of Cape Cod at “Wychmere Heights” with all your favorite people! Please enter in 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 3-night minimum stay outside of the peak season. 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 rental on Cape Cod. It’s your vacation. Get Picky! ®

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

16636 - Canoe Club: Pond Front Home w/ Game Room Dog Friendly! Awake to water views and enjoy your morning coffee on the back deck as you take in the landscape of the pond and let the kids (dog included!) run in the fenced-in yard below. Spend your day canoeing, paddle boarding or kayaking in Mill Pond or head to one of the various area beaches for a day spent with your toes in the sand. Return home to our impeccably clean and cheerful home to cool down in the air conditioning, and whip up some favorite summertime snacks in the brand new kitchen. On the first floor of this home, you will find two bedrooms, one with a king bed, and one with two Twin beds. You’ll also find the kitchen, living room and full bathroom. Upstairs there’s a Queen bedroom, full bathroom and private sitting area with a Chess Board and other table game classics! The finished basement has a bedroom with 2 sets of bunk beds (4 twin beds) and a half bath -- AND a pool table, ping pong table, foosball table, and other fun amenities for kids of all ages. Enjoy warm evenings grilling on the back deck -- maybe before heading out to the famous weekly Chatham Band Concert or taking in a movie at the deluxe Orpheum theater downtown. Other Chatham favorites not to be missed are Chatham Corner Store (for fast and fresh Mexican food), Hangar B Eatery (for the best breakfast of your life), and Mac’s Chatham Fish & Lobster (delicious local seafood). This home offers something for everyone in your party - the chef, the water sport enthusiast, the gamer, and even the dog! Don’t miss out on your opportunity to make great Chatham memories! <br><br> Home Details:<br> -Dogs Welcomed (w/fee of $30/night per dog)<br> -Sleeps 10<br> -2nd Floor Master Bedroom: 1 Queen Bed -1st Floor Bedroom #1: 1 King Bed -1st Floor Bedroom #2: 2 Twin Beds -Ground Level Bedroom: 4 Twin Beds (2 sets of twin over twin bunk beds) -Central A/C -Window A/C in Upstairs Bedrooms -Cable TV -WiFi -Washer/Dryer -Outdoor Shower -Foosball Table -Ping Pong Table -Pool Table -Chess Board -Table Games -Gas Grill -Water Views -Waterfront -Walk to Water -Parking is available in the driveway for a maximum of 2 cars. There is no street parking available or allowed. -Sheets and Bath Towels Provided with Beds Made Upon Arrival -Cleaned with Hospital Grade Disinfectant -C0406140550

This property is professionally managed by Pretty Picky Properties Chatham Landmark Estate, Awesome Barn/Guest House, Pool Sleeps 18 8 Bedrooms, 7.5 Bathrooms Rents Friday to Friday during peak season Linens included, beds made Pets Considered Pool is open from Memorial Day through Columbus Day weekend. As you roll up the extended driveway and catch your first glimpse of the homes, you realize the impressive individuality of this property. From the Federalist style side gambrel roof on the expanded Colonial main house to the thoroughly exposed wood posts, beams and rafters inside, this place retains the unique charm demanded by its original sea captain owner 220 years ago. First, soak in the location and setting. Here you have 1.61 acres of artfully landscaped privacy, abutting the upscale Eastward Ho! private golf course, with beautiful Pleasant Bay beyond. The carefully kept, expansive lawns make a wonderful and safe play space for children. Note the line of grape arbors leading to an unexpected wishing well. Your private, heated pool is a large one, complete with its own freestanding and well equipped cabana. When you need some beach time, it’s only a two-minute drive over to Jackknife Cove Beach on Pleasant Bay. Or go in the opposite direction for a minute more and discover Strong Island Landing Beach. Inside the two story main manor house, centuries’ old charm mingles perfectly with thoughtful renovation for the best of beauty, function and comfort. The completely updated and outfitted kitchen adjoins a handy breakfast nook and flows into one of the most impressive dining rooms you’ll ever experience. There are three separate lounge and gathering places on the main level, a living room, sitting room and family room. Two of the main house’s six bedrooms and 2.5 of its baths are located here as well. The upper level provides another four bedrooms, including two primary suite bedrooms with ensuite baths and two other bedrooms, one with two queens and one with king size bed. There is also another full bath upstairs. Enter the nearby Guest House/Barn, and it’s hard not to gape at the expanse and sheer visual impact of the great room, so aptly named. It’s positively gigantic in every way, accentuated by the soaring ceiling with its dramatic exposed beams and rafters. The rest of the Guest House includes a second fully equipped kitchen, two more bedrooms and two more full baths. ** Please note that the Guest House (Barn) is fully winterized (closed) from Mid-October through April for off-season stays each year. As a result the property only has 6 bedrooms and 5.5 bathrooms sleeping a maximum of 14 guests. ** The 4,350 square feet of the Main House and Guest House combined are centrally air conditioned or serviced by high efficiency split units. There is also high speed Wi-Fi, as well as several smart flat screen TVs with cable. NOTE: the main part of the barn is not air conditioned, just the bedrooms and the kitchen/living room area. 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 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 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 #584

This property is professionally managed by Pretty Picky Properties Stunning Newly Built Custom Compound in Chatham with a Resort-Style Ambiance NEW Listing for 2026! Rents Friday to Friday during peak season Linens Included, Beds Made Sleeps 12 Pool & Hot Tub open from Memorial Day to Columbus Day Welcome to Three Buoys, a stunning multi-structure home located in picturesque North Chatham, MA. This spacious retreat is perfect for families or groups, comfortably accommodating up to 12 guests across its five beautifully appointed bedrooms and 7.5 bathrooms. With a serene pool view, this property offers a perfect blend of luxury and relaxation. Step inside to discover a chef-inspired kitchen that is fully equipped with modern appliances, including a gas stove, refrigerator, and dishwasher, making meal preparation a delight. The dining area is perfect for gathering around delicious meals, while the living room invites you to unwind with its cozy ambiance and gas fireplace. The outdoor space is a true highlight, featuring a heated private pool, hot tub, and a fire pit, ideal for evening gatherings under the stars. Enjoy the fresh air on the patio, or challenge your friends to a game of pool in the game room. Each bedroom is designed for comfort, with multiple en suite options, including four king beds and three twin singles, ensuring everyone has their own space to relax. Additional amenities include air conditioning, free WiFi, and 2 sets of washers/dryers for your convenience. Located near beautiful beaches and bike trails, Three Buoys is the perfect base for exploring the charming attractions of Chatham. Whether you’re looking to relax by the pool, enjoy a family barbecue, or explore the local area, this property has it all. Book your stay today and create unforgettable memories! 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%. 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 #1212

This property is professionally managed by Pretty Picky Properties Luxurious Chatham Home with Expansive Water Views Sleeps 10 in 4 bedrooms, 4.5 baths Rents Friday to Friday during peak season Linens included, beds made Location Water views from almost every room! Walk to two beaches and a shared dock! Located in one of Chatham’s most picturesque neighborhoods, this newly renovated and expanded residence has undergone an amazing transformation that now highlights stunning water views of saltwater Crow’s Pond. Indoor Space Upon entry, you are greeted by an impressive foyer that welcomes you to both the common and private areas of this nearly 4,000 square foot home. Built in 1985 and remodeled in 2023, the open floor plan of this 4-bedroom home is enhanced by gorgeous white oak flooring and professional interior design. The home features a state-of-the-art kitchen with top-of-the-line custom cabinetry, Thermador® appliances, weathered Quartzite® countertops, and custom tile work. A pillar flanked sunroom with skylights and bank of windows perfectly frames westerly views of the water. The living room is adjacent and features more cozy seating with a TV over the fireplace. There’s also a spacious office on the first floor. The main level also presents a laundry room with two washers and two dryers, a powder room, and a California Closet® pantry. The lower level provides a bright family room with custom built-ins, wet bar and billiard table. Outdoor Space Professionally landscaped, the home features an artistic blend of brick walkways, natural stone steps, and native plantings. The home has an enclosed outdoor shower and has easy access to a shared deep-water dock across the street, as well as to two private beaches on Pleasant Bay (8-minute walk) and on Crow’s Pond (across the street). Sleeping Accommodations On the main level you’ll find one of two primary suites with a four poster King bed, offering captivating water views and a spa-like bathroom with high-end fixtures. On the second level there is an additional King bed primary suite showcasing glass sliders leading to a private balcony with wonderful water views. You’ll be delighted by the luxurious, private bathroom with soaking tub and double vanity. The primary suite also has two walk-in closets. Additionally on the second level, another loft area greets you at the landing with views of Crow’s Pond. There is a second bedroom up here with a King bed and an exceptionally appointed full bathroom. There is also a bedroom on the lower level with two twin-over-full bunk beds. There is a full bathroom on this level as well. 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 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! ® Town of Chatham Registration #956

This property is professionally managed by Pretty Picky Properties Luxurious Estate by the Bay in Brewster: Sleeps 20 with Expansive New Pool, Walk to Beach, Walk to Town Rents Saturday to Saturday in Peak Summer Off-Season Weekends and Partial Weeks Available Choose this vacation headquarters and give your group of up to 20 the best of all options. A main house plus separate guest house on nearly an acre and a half of level yard for play space. A stunning new 20’ X 60’ heated saltwater pool with large stone patio. A three-minute walk to Brewster’s Breakwater Beach. And an eight-minute walk to the iconic Brewster Store and Main Street/Route 6A, where you’ll discover some excellent restaurant choices. The main house, just completed in 2020, offers elegance without pretense, centered on its spacious, thoughtfully outfitted chef’s kitchen. Here you’ll appreciate the large center island with high boy seating, beautiful granite and tile, as well as abundant counter space bathed in natural light. The kitchen opens to a TV lounge, which walks out to the expansive patio and pool. There is also a good-sized dining room here, as well as a handy half bath and laundry. The main house has sleeping for up to 12 in five bedrooms, two of which are king masters, one on the main level, the other upstairs. Each master has its own private full bath en suite. The separate guest house offers single level living and sleeps up to eight in three bedrooms with a full bath. You have a full eat-in kitchen here, as well as a TV lounge. Your outdoor summer living is optimized on the oversized patio which envelops the big pool. There’s also a hot tub, a large gas grill, a fire pit and an enclosed outdoor shower. Each house is centrally air conditioned, has cable TV, a SONOS Sound system and high speed Wi-Fi. 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%. 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! ®