Large group vacation rentals in Brewer, ME

Free WiFi (900 Mbps) | Remote-Work Friendly | Pet Welcome w/ Fee Immerse yourself in the coastal beauty and historic charm of Cape Cod when you visit this modern 2-bedroom, 2-bath vacation rental in Brewster — known as the ‘Sea Captain’s Town.’ Featuring a full kitchen, 3 Smart TVs, and a large yard with a fire pit, this cottage offers a seaside haven like no other! Walk to Breakwater Beach, explore Nickerson State Park, or visit the nearby lighthouses. -- THE PROPERTY -- Permit: MassTaxID C0318350410 SLEEPING ARRANGEMENTS - Bedroom 1: 1 queen bed - Bedroom 2: 2 twin beds - Office: 1 queen sleeper sofa OUTDOOR LIVING - Grill, outdoor dining area - Backyard, deck, fire pit - Outdoor shower, string lights - Bike path nearby - Beach gear INDOOR LIVING - 3 Smart TVs w/ cable, DVD player - Board games, books - Fireplace (decorative only) - Farmhouse dining table - Roll-in shower, shower/tub combo - Vaulted ceilings KITCHEN - Fully equipped w/ cooking basics - Keurig coffee maker, dishware/flatware GENERAL - Central air conditioning/heating - Keyless entry - Washer/dryer, linens/towels, iron/board - Hair dryer, hangers, trash bags/paper towels ACCESSIBILITY - 1 step to enter, single-story home - 2 steps down back deck FAQ - Loft is hazardous for small children - Pet fee (paid pre-trip) PARKING - Driveway (6 vehicles), free street parking -- THE LOCATION -- - Walking distance to Main Street - 0.6 miles to Breakwater Beach - 1 mile to Harbor Lights Mini Golf - 2 miles to Ocean Edge Resort & Golf Club - 2 miles to Cape Cod Museum of Natural History - 86 miles to Boston Logan International Airport -- 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 inside or outside - Pet friendly w/ $200 fee (+ fees & taxes, max 2 pets) - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in ADDITIONAL INFORMATION - The loft area may be hazardous for small children and should not be used as a sleeping area - The fireplace is not available for guest use

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! ®

18826 - Brewster by the Bay: Close to Bayside Beaches w/ Pool Table, Fire Pit Centrally located in the heart of Brewster, with secluded outdoor areas and plenty of space to relax, you’ll be sure to have a calming vacation at Brewster by the Bay. Walking up the winding brick path, the unique lamppost out front will be sure to catch your eye before entering this two-story home. Once inside, guests will be greeted by the large open concept kitchen and dining room. Natural light spills onto the fun white and blue rug in the living room, with blue couches to match. Passing through the dining room and to the great outdoors, a bright red umbrella brings shade and a splash of color to the back deck, complete with propane grill and an outdoor dining table. Down the steps to the back yard, you can spend the night under the stars, huddled by the warmth of the fire pit out back. <br><br>Return indoors and retire for the night in one of the four bedrooms. The primary bedroom, located on the first floor, is complete with a queen bed, while a second queen bed bedroom is also located on this floor. Upstairs, two bedrooms with a total of five twin beds is the perfect spot for the kids to crash for the night. <br><br>Other amenities include a washer/ dryer and an outdoor shower. Even your competitive side can come along on vacation, with a pool table and Pop-a-Shot basketball hoop in the basement game room. Just over a mile from numerous bayside beaches, whether you choose to spend your time soaking in the sun on the sand, or relaxing indoors all vacation long, you’ll be happy with whatever you choose with Brewster by the Bay.<br><br>Home Details:<br>-Dogs Welcomed (w/fee of $45/night per dog)<br><br>-Sleeps 9<br>-2 Floors + Basement<br>-4 Bedrooms<br>-Bedroom #1: 1 Queen Bed, 1st Floor<br>-Bedroom #2: 1 Queen Bed, 1st Floor<br>-Bedroom #3: 3 Twin Beds, 2nd Floor<br>-Bedroom #4: 2 Twin Beds, 2nd Floor<br>-2 Bathrooms<br>-Bathroom #1: Full Bath w/ Tub/Shower Combo, 1st Floor<br>-Bathroom #2: Full Bath w/ Shower, 2nd Floor<br>-Fully Equipped Kitchen<br>-Portable (floor) & Window A/C Units<br>-Smart Lock/Self Check-In<br>-WiFi<br>-Smart TV/Streaming<br>-Washer/Dryer (basement)<br>-Pool Table & Basketball (basement)<br>-Deck w/ Outdoor Dining<br>-Propane Grill<br>-Fire Pit<br>-Outdoor Shower<br>-Private Yard<br>-Corn Hole Set<br>-1.2 Miles to Point of Rocks Beach<br>-1.5 Miles to Breakwater Beach<br>-Easy Access to Route 6A<br>-Sheets and Bath Towels Provided with Beds Made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>C0373920410

18813 - Days Ease: Pond Front Home with Private Dock! Claim your own piece of paradise this season with a stay at Days Ease! Set in a quiet neighborhood, this four-bedroom home overlooks Schoolhouse Pond and is an easy, half-mile stroll along the sidewalk to Brewster Village Marketplace for sandwiches and Brewster Ladies Library for the latest summer beach read. Less than a mile away, stock up on souvenirs at the historic Brewster General Store and amble next door for an ice cream sundae at The Brewster Scoop. You could spend the whole day beach-going, biking, walking, and visiting nearby attractions, including the Cape Cod Museum of Natural History, the Stony Brook Grist Mill and Museum, and the herring run. Or, you could kick back and relax at the house. The home features three bedrooms and two bathrooms on the first floor: a room with two twin beds, another with a queen bed, and the master suite with a queen bed, en suite bath and its own entrance to the backyard deck. The fourth bedroom is located in the basement and has two twin beds and a private entrance that leads to a backyard patio area and an outdoor shower. &lt;br&gt;&lt;br&gt;A short walk down a wooded pathway will bring you to the home’s private dock on Schoolhouse Pond, where you can launch your kayak or canoe rentals. Lounge lawnside in a hammock, play board games in the living room, or foosball in the basement. But, don’t forget to end your day with a sunset dinner on the large backyard deck. You are also within biking distance to bayside Paine’s Creek Beach (2 miles), Sheep Pond (3 miles) and the Cape Cod Rail Trail on Underpass Road (2 miles).&lt;br&gt;&lt;br&gt;Home Details:&lt;br&gt;-Dogs Welcomed (w/fee of $40/night per dog)&lt;br&gt;-Sleeps 8&lt;br&gt;-2 Floors&lt;br&gt;Bedrooms&lt;br&gt;-Total 4&lt;br&gt;-1st Floor Master Bedroom: 1 Queen Bed w/ en suite Full Bathroom&lt;<br&gt;-1st Floor Bedroom #2: 1 Queen Bed&lt;br&gt;-1st Floor Bedroom #3: 2 Twin Beds&lt;br&gt;-Ground Floor Bedroom #4: 2 Twin Beds&lt;br&gt;Bathrooms&lt;br&gt;-Total 2&lt;br&gt;-1st Floor: Full Bath w/ shower/tub combo&lt;br&gt;-1st Floor: Full Bath w/ shower/tub combo&lt;br&gt;Other Amenities&lt;br&gt;-Central A/C&lt;br&gt;-WiFi&lt;br&gt;-TV&lt;br&gt;-Washer/Dryer&lt;br&gt;-Gas Grill&lt;br&gt;-Deck w/ Furniture&lt;br&gt;-Kayak&lt;br&gt;-Canoe&lt;br&gt;-Private Yard&lt;br&gt;-Pond Views&lt;br&gt;-Walk to Brewster Ladies Library&lt;br&gt;-Bike to Sheep Pond and Paine’s Creek Beach&lt;br&gt;-Outdoor Shower&lt;br&gt;-Basement Foosball Set&lt;br&gt;-Private Dock on Schoolhouse Pond&lt;br&gt;-Sheets and Bath Towels Provided with Beds Made Upon Arrival&lt;br&gt;-Cleaned with Hospital Grade Disinfectant&lt;br&gt;C0281930410

This property is professionally managed by Pretty Picky Properties Magnificent Mansion, Privacy, Pool, Water Views in Brewster Come for July 4th! Arrive on Thursday July 2 or Friday July 3rd and enjoy the holiday! Sleeps 22 in 10 Bedrooms, 9.5 Baths Linens and Bed Making Included The newly constructed Quivett Compound is the perfect summer retreat for your discerning group of up to 22. The property is secluded on seven-plus acres and set far back from the historic Old King’s Highway in beautiful West Brewster by the bay, the property serves up sweeping views of Quivett Creek and Cape Cod Bay beyond. Launch an owner-provided kayak or canoe and explore the creek. Watch the kids frolic in the in-ground heated pool, which provides continuous entertainment when they come off the nearby bay side beaches in both Brewster and Dennis. You’ll spend a lot of time on the expansive shaded deck or outdoor patio with its built-in gas grill, fire pit and large dining table. Set up the net provided and organize a volley ball or badminton tournament. You certainly have plenty of space to do it! Inside, you’ll roam through 6,300 square feet of modern luxury, exquisitely designed and superbly furnished and appointed. The main level common living space includes an immense living room with two seating areas, one with a large flat screen, wall mounted TV. There is also a separate TV lounge with wet bar upstairs. The kitchen is big, bright and totally social. It is equipped with everything you could ask for, including two dishwashers, a beverage center and a Keurig coffee maker. The adjacent dining room offers a great place to gather inside, although you’ll likely choose to eat outside most summer days on the deck and patio. The lower level has a very cool game room, ready for action with a pool table, ping pong table, air hockey, video games and more. Then, it’s show time in the home theater, with its huge movie screen and comfy recliner chair seating. The laundry lives on this level, as well, with not one but two new washers and dryers. The ten bedrooms break down as follows: six kings, three queens, one full size double and two twins. The 9.5 baths sort out this way: one half bath on the main level, six bedrooms with en suite baths plus two full baths on the lower level. Finally, there is a room above the detached garage withe a King bed and a full bath. Of course, the home is centrally air conditioned and has high-speed Wi-Fi and Cable TV. **Please note that the bedroom and bathroom over the garage is fully winterized from 11/1 - 5/1 each year. As a result the property only has 9 bedrooms and 7.5 baths from November through April sleeping a maximum of 20 guests*** *** Pool is open and heated from Memorial Day (late May) through Columbus Day (early October)*** ****The Quivett Creek Compound does consider small events (with a maximum of 50 attendees including guests staying at the property) on site on a case by case basis in May, June, September and October. There are no events allowed in July and August. Please contact us for more details.**** 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 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! ®

18821 - Cozy Cape: Less Than 1 Mile to Beach with Custom Fire Pit! The peace and quiet of Brewster can’t be matched, with the salt air and sunshine just waiting for your next vacation. Located just .6 miles from the beach, get ready to cozy up and relax, at the Cozy Cape. Upon arriving at this beautiful home, you enter through the kitchen, past the breakfast bar, and into the living room, with vaulted ceilings reaching high overhead. &lt;br&gt;&lt;br&gt;One of the bedrooms has a queen size bed and the other has two twin bunk beds as well as an additional twin trundle bed, perfect for children!&lt;br&gt;&lt;br&gt;Outside this lovely home, you will find plenty to add to your vacation experience. You can rinse off a day of sun and sand in the spacious outdoor shower. Enjoy a meal outdoors on the side deck of the house or an evening under the stars around the custom stone fire pit and patio.&lt;br&gt;&lt;br&gt;Whether you are looking to explore all the Cape has to offer, or hunkering down for a relaxing vacation, you will find everything you need at the Cozy Cape. &lt;br&gt;&lt;br&gt;Please note the loft area is not for guest use.&lt;br&gt;&lt;br&gt;Home Details:&lt;br&gt;-No Pets(Fines Remitted)&lt;br&gt;-Sleeps 5&lt;br&gt;-Single Story Home&lt;br&gt;Bedrooms&lt;br&gt;-Total 2&lt;br&gt;-1st Floor Bedroom: 1 Queen Bed&lt;br&gt;-1st Floor Bedroom: 1 Twin Bunk Bed with Twin Trundle (3 Twin Beds Total)&lt;br&gt;Bathroom&lt;br&gt;-Total 1&lt;br&gt;-1st Floor: Full Bathroom w/ Shower&lt;br&gt;Other Amenities&lt;br&gt;-Full Kitchen w/ Dishwasher&lt;br&gt;-Mini split units&lt;br&gt;-WiFi&lt;br&gt;-Cable TV &lt;br&gt;-Washer/Dryer &lt;br&gt;-Gas Grill&lt;br&gt;-Fire Pit&lt;br&gt;-Deck with Furniture&lt;br&gt;-Outdoor Shower&lt;br&gt;-NO pets (fines remitted)&lt;br&gt;-Loft area NOT for guest use&lt;br&gt;-0.6 Miles to Saints Landing Beach&lt;br&gt;-1 Mile to Brewster General Store&lt;br&gt;-Sheets and Bath Towels Provided with Beds made Upon Arrival&lt;br&gt;-Cleaned with Hospital Grade Disinfectant&lt;br&gt;C0404060410

18803 - Kat’s Place: Huge Deck Outdoor Shower Dog Friendly! This charming Cape Cod home, located minutes from several Brewster bayside beaches, is the perfect place to bring the whole family for your next vacation! &lt;br&gt;&lt;br&gt;Situated in a quiet neighborhood on the desirable bayside, this vacation home is just 3 minutes from Paine’s Creek, 3 minutes from Saint’s Landing, and 4 minutes from Robbins Hill Beach (Mants Landing). Take a stroll down the street in this beautiful area of Brewster to a variety of places, including The Cape House, Luke’s Liquor, Dunkin’ Donuts, Cape Cod Museum of Natural History, and a variety of lovely shops. &lt;br&gt;&lt;br&gt;Return home from your activities and relax with a cocktail on the huge deck in our private back yard (plenty of seating for everyone), or let the hammock rock you to sleep. This home can sleep 8 guests in four bedrooms, two upstairs and two downstairs. The primary bedroom on the first floor has a king bed and across the hall is a twin w/trundle next to a full bathroom. Each of the second floor bedrooms has two twin beds. &lt;br&gt;&lt;br&gt;Other features include a large outdoor shower, gas grill, full kitchen, TV, WiFi, washer/dryer, and central AC. This vacation rental has everything your family will need to have an amazing vacation, and is also pet friendly - so bring the dog along too!&lt;br&gt;&lt;br&gt;Home Details:&lt;br&gt;-Dogs Welcomed (w/fee of $40/night per dog)&lt;br&gt;-Sleeps 8&lt;br&gt;-2 Floors&lt;br&gt;Bedrooms&lt;br&gt;-Total 4&lt;br&gt;-1st Floor Primary Bedroom: 1 King Bed&lt;br&gt;-1st Floor Bedroom: 1 Twin Bed w/ Trundle (2 Twins)&lt;br&gt;-2nd Floor Bedroom: 2 Twin Beds&lt;br&gt;-2nd Floor Bedroom: 2 Twin Beds&lt;br&gt;Bathrooms&lt;br&gt;-Total 1&lt;br&gt;-1st Floor: Full Bathroom w/ Shower/Tub combo&lt;br&gt;Other Amenities&lt;br&gt;-Central A/C&lt;br&gt;-TV&lt;br&gt;-WiFi&lt;br&gt;-Washer/Dryer&lt;br&gt;-Outdoor Shower&lt;br&gt;-Large Private Yard&lt;br&gt;-Huge Deck w/ Furniture&lt;br&gt;-Gas Grill&lt;br&gt;-Minutes From Bayside Beaches&lt;br&gt;-Linens and Bath Towels Provided with Beds Made Upon Arrival&lt;br&gt;-Cleaned with Hospital Grade Disinfectant&lt;br&gt;C0405190410

This home is professionally managed by Pretty Picky Properties Luxury Brewster Estate – Pool, Hot Tub, Steps to Bike Trail "Brewster Barefoot Bliss" 3447-BMH Rents Saturday to Saturday in Peak Season Linens Included, Beds Made Six bedrooms, Seven Full Baths Sleeps Twelve Pets Considered **Additional separate two bedroom cottage available to rent next door, total occupancy of sixteen possible** Discover the perfect blend of classic Cape Cod charm and modern luxury at this stunning six bedroom vacation home in Brewster. With four private bedroom suites and space to sleep 12 guests, this expansive retreat is designed for relaxation and adventure alike for groups of any size. Location Nature lovers will appreciate the home’s prime location—adjacent to the popular Cape Cod Rail Trail bike path and just across the street from Nickerson State Park. Spend your days exploring the park’s scenic trails or take a short stroll (under a mile) to Crosby Landing Beach, considered Brewster’s best by many. You can be in downtown in Orleans in about two miles via the bike path. Outside Living Space No doubt most of your lounging and living will be done out on the spacious pool patio with a covered cabana area, gorgeous outdoor kitchen, a large dining table and chairs, a full bathroom and, of course, the heated pool. There’s also a hot tub and gas fire pit, ideal for gathering under the stars. You can whip up a feast in the cabana’s completely outfitted outdoor kitchen. The large, manicured yard is bordered by a tasteful variety of flowering plantings and makes a perfect place to throw a Frisbee ® or whack a Whiffleball ® And here’s an unusual extra amenity: your own private hockey rink! The special synthetic surface accommodates both roller blades and ice skates. Inside Living Space This home seamlessly blends classic coastal elegance with modern finishes, offering stylish and comfortable living spaces. The main level consists of a spacious and elegant kitchen, complete with everything you’ll need to prepare any meal and entertain any group. There’s seating for 12+ at the main dining table and adjacent round table plus there’s additional counter seating at the immense kitchen island. This part of the main level includes a wet bar, pantry and parlor. Fitness enthusiasts will appreciate the fully equipped gym. Then there’s the “Great Room,” which is nothing short of awe inspiring. Original to the structure, this room with soaring ceilings exudes old world charm in stunning fashion. The wood paneled walls are from a French chateau, the circular stairs from a British ship. Sleeping Accommodations The main level rounds out with two bedrooms, one with a queen, the other with a pair of twins, plus a full bath and a half bath. There are three, count ’em, three sets of stairs to the second level bedrooms. The first is off the small parlor and features a vintage narrow staircase to a queen bedroom with a private full bath. The second, more modern staircase leads to a second level area with two queen-bedroom suites, each with a private full bath. The final upstairs area is the most recent renovation and is essentially a self-contained apartment with a living area, kitchenette, king bedroom and a luxurious bathroom with a step-in shower, soaking tub and dual vanity. For a summary of bedrooms and bed configurations, use the Room Details tab above. Amenities This home has high speed WiFi, a Sonos® Sound System and central air conditioning. For a complete list of amenities, please click on the Amenities tab above. The owners reside in a smaller home on the grounds. so you can be sure that any issues that may arise will be quickly addressed. But you won’t see them unless you need them. Book now and experience the best of Brewster in this extraordinary vacation retreat. 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 vacation rental on Cape Cod. It’s your vacation. Get Picky! ®

18827 - Turquoise Treasure: Walk to Pond, Amazing Backyard! Beach volleyball, the beauty of Brewster, and Blueberry Pond? These treasures are just a trip away, to the Turquoise Treasure. &lt;br&gt;&lt;br&gt;Walk up the brick pathway and step up through the front door into this beautiful three story home. The seafoam green walls of the front hallway welcome you in before stepping into the cozy living room to your right. The exposed brick and beach decor accompany you as you watch your favorite movie on the wall mounted TV. Through the living room, an elegant dining room awaits vacation meals and nighttime drinks, with access to the stunning back deck through the sliding glass doors. Entering into the kitchen, you’ll notice the rich blue walls adorning this beautiful room. The breakfast bar is the perfect place for morning coffee, and with ample counter space, you’re sure to bake up some delicious treats to bring to the beach. &lt;br&gt;&lt;br&gt;After a long vacation day, you’ll be sure to rest and recharge in one of the home’s four bedrooms. Located on the second floor, the home’s primary bedroom houses a queen size bed and calming decor. A second bedroom has a queen size bed, with the third bedroom fitting two sets of bunk beds, totaling four twin size mattresses. A finished ground floor has an additional seating area with wall-mounted TV, as well as the home’s final bedroom, with a queen size bed and sliding glass door to the gorgeous backyard. &lt;br&gt;&lt;br&gt;Perhaps as exciting as the home itself is the incredible yard it sits above. A sprawling backyard slopes down to your own private beach volleyball court, where you’re sure to play a few sets before eating some s’mores at the fire pit. Watch the volleyball unfold below from the home’s large back deck, complete with pergola, outdoor lounging, and numerous outdoor dining options to fill your vacation with outdoor fun. &lt;br&gt;&lt;br&gt;Other amenities include a washer and dryer, a propane grill, and an outdoor shower. There’s even more adventures just down the road at Blueberry Pond, with private access at the Millstone Village Association Beach. An almost hidden gem of Cape Cod, the town of Brewster will bring peace and relaxation to your next vacation- It’s time to stay at the Turquoise Treasure.&lt;br&gt;&lt;br&gt;Home Details:&lt;br&gt;-Dogs Welcomed (w/fee of $40/night per dog)&lt;br&gt;-Sleeps 10&lt;br&gt;-3 Floors (Ground Floor + 1st Floor + 2nd Floor)&lt;br&gt;-1,568 sq. ft.&lt;br&gt;Bedrooms&lt;br&gt;-Total 4&lt;br&gt;-2nd Floor Bedroom: 1 Queen Bed&lt;br&gt;-2nd Floor Bedroom: 1 Queen Bed&lt;br&gt;-2nd Floor Bedroom: 2 Twin/Twin Bunk Beds (4 twins total)&lt;br&gt;-Ground Floor Bedroom: 1 Queen Bed w/ en suite Full Bathroom&lt;br&gt;Bathrooms&lt;br&gt;-Total 2.5&lt;br&gt;-1st Floor: Half Bath&lt;br&gt;-2nd Floor: Full Bath w/ Tub/Shower Combo&lt;br&gt;-Ground Floor: Full Bath w/ Shower (en suite Queen Bedroom)&lt;br&gt;Other Amenities&lt;br&gt;-Fully Equipped Kitchen w/ Dishwasher&lt;br&gt;-Window A/C Units in Bedrooms&lt;br&gt;-Fireplace NOT for guest use&lt;br&gt;-Smart Lock/Self Check-In&lt;br&gt;-WiFi&lt;br&gt;-Smart TV&lt;br&gt;-Washer/Dryer (ground floor)&lt;br&gt;-Deck w/ Pergola & Outdoor Dining&lt;br&gt;-Propane Grill&lt;br&gt;-Outdoor Shower&lt;br&gt;-Private Yard&lt;br&gt;-Fire Pit&lt;br&gt;-Full Sand Volleyball Court&lt;br&gt;-Walk 6 Minutes (0.3 mile) to Beach on Blueberry Pond&lt;br&gt;-Sheets and Bath Towels Provided with Beds Made Upon Arrival&lt;br&gt;-Cleaned with Hospital Grade Disinfectant&lt;br&gt;C0375530410

18811 - Pond Launch: Steps to Freshwater Beach Kayaks Sauna! Just before you turn the corner into the driveway, you’ll see the pristine Sheep Pond, perhaps one of the best bodies of freshwater on Cape Cod. The water is clear and clean, and fish are abundant, hence the name of the beach area - Fisherman’s landing. The sunsets here are amazing too, and the home is just steps away from this picturesque pond beach. The home itself is perched on a small grassy plateau, with a beautiful flat yard with fire pit and seating, and plenty of outdoor space that feels remote and private. If you’re a dog lover, bring two furry friends along to enjoy the great yard this home has.&lt;br&gt; &lt;br&gt; Inside the home, you’ll be greeted by the warmth of wood walls, bright open space, and a modern beach cottage/log cabin vibe that is perfect for the location; it feels like a vacation as soon as you enter. The property has two structures, very close together. In the main house an expansive kitchen and dining area connect to an equally large living space, which provides plenty of space for relaxation, as well as space to prepare delicious meals in the fully updated kitchen. The living area opens up to a large deck, providing options for outdoor living. This floor features the master bedroom, with a king size bed, and full ensuite bathroom. At the other end of the first floor is another bedroom with a queen bed. Downstairs, things get more casual, with a large playroom for the kids with foosball and movie area, and a sauna for adults to relax and unwind after a hard day of vacationing. In addition to the shared spaces downstairs, there are also two additional bedrooms, one with two twin beds and a queen bed, and another with three twin beds. The detached structure of the home offers an in-law suite, which has its own full eat-in kitchen, full bathroom, and a studio style living/bedroom area with a king bed. The detached studio also has its own deck, offering more private outdoor space.&lt;br&gt;&lt;br&gt;We provide two kayaks for you and your guests to use, along with portage carts for easy transportation. While the location beside Sheep Pond is amazing, don’t forget that just a few miles down the road is Breakwater Beach, with unbelievable sunsets, and tidal ebbs that leave miles of beach to explore. Just before the beach, is Brewsters Downtown strip, where driving along you’ll find many good spots to eat, like The Brewster Fish house, Guapo’s, or the Island Blue Crab. Whether you are spending time on site next to Sheep Pond, or adventuring across the Cape, this home offers an amazing place to rest and relax, and experience the beauty of Cape Cod!&lt;br&gt;&lt;br&gt;Home Details:&lt;br&gt;-Dogs Welcomed (w/fee of $40/night per dog)&lt;br&gt;-Sleeps 11&lt;br&gt;-2 Floors&lt;br&gt;-1st Floor Master Bedroom: 1 King Bed w/ en suite Full Bathroom&lt;br&gt;-1st Floor Bedroom #2: 1 Queen Bed&lt;br&gt;-Ground Floor Bedroom #1: 1 Queen Bed & 2 Twin Beds&lt;br&gt;-Ground Floor Bedroom #2: 3 Twin Beds&lt;br&gt;-Detached Studio Bedroom: 1 Queen Bed&lt;br&gt;-A/C in All Bedrooms (mini-splits & wall units)&lt;br&gt;-WiFi&lt;br&gt;-Cable TV&lt;br&gt;-Washer/Dryer &lt;br&gt;-Gas Grill&lt;br&gt;-Fire Pit&lt;br&gt;-Deck w/ Furniture&lt;br&gt;-Private Yard&lt;br&gt;-Walk to Sheep Pond&lt;br&gt;​​​​​​​-Outdoor Shower&lt;br&gt;-Kids Playroom w/ Foosball Table (supervision required)&lt;br&gt;-Sauna (adult use only)&lt;br&gt;-2 Kayaks w/ Oars & Portage Carts&lt;br&gt;-Sheets and Bath Towels Provided with Beds Made Upon Arrival&lt;br&gt;-Cleaned with Hospital Grade Disinfectant&lt;br&gt;C0068110410

18810 - Indigo Path: Beautiful Home Close to Ponds and Beach! From your doorstep, a short walk down a quiet dirt road leads down to beautiful Sheep Pond, a perfect place to kayak, swim, fish, and enjoy the beautiful natural environment of Cape Cod. The pond access here is for the neighborhood only, and offers the use of private beach space. Inside the home, tall ceilings in the dining area lead to sliding doors onto the deck, giving the home a nice airy feeling, and a perfect way to enjoy both indoor and outdoor space while together.&lt;br&gt;&lt;br&gt;A large finely updated kitchen with stainless appliances is adjacent to the living room in this semi-open floor plan, and a den behind the living room offers even more common space to relax, and a great spot to watch movies. Upstairs, you’ll find your sleeping quarters. The primary bedroom offers a king bed, the 2nd bedroom has a queen, and the third bedroom has two bunk beds - perfect for a kids room. A bathroom upstairs provides easy access for all three bedrooms.&lt;br&gt;&lt;br&gt;Outside, you’ll find yourself perched atop a hill, with a nicely shaded deck overlooking the neighborhood towards the pond. An outdoor shower provides a great place to rinse off after enjoying the beach or pond, and a small yard offers a place to stretch out in the sun. Head down to Breakwater beach around sunset, at low tide, and you’ll see absolutely amazing views. JT’s, Stone L’oven pizza, and several other great restaurants are close by, and don’t forget a pitstop at Deepwater Dogs along Long Pond Rd on your way to the beach. Or, take a right and keep going for tacos and cervezas at Guapos Tortilla Shack with great outdoor seating options; either way you can’t go wrong. When you return back to the home, relax with a glass of wine on the back deck under the pine tree, and soak in everything wonderful about this house on the pond.&lt;br&gt;&lt;br&gt;Home Details:&lt;br&gt;-Dogs Welcomed (w/fee of $40/night per dog)&lt;br&gt;-Sleeps 8&lt;br&gt;-2 Floors&lt;br&gt;Bedrooms&lt;br&gt;-Total 3&lt;br&gt;-2nd Floor Primary Bedroom: 1 King Bed&lt;br&gt;-2nd Floor Bedroom: 1 Queen Bed&lt;br&gt;-2nd Floor Bedroom: 2 Bunk Beds (4 twin beds)&lt;br&gt;Bathrooms&lt;br&gt;-Total 2&lt;br&gt;-1st Floor: Full Bathroom w/ Shower/Tub Combo&lt;br&gt;-2nd Floor: Full Bathroom w/ Shower/Tub Combo&lt;br&gt;Other Amenities&lt;br&gt;-Central AC&lt;br&gt;-WiFi&lt;br&gt;-TV&lt;br&gt;-Washer/Dryer&lt;br&gt;-Deck with Furniture&lt;br&gt;-Outdoor Shower&lt;br&gt;-Wood Fire Pit&lt;br&gt;-Indoor fireplaces NOT for guest use (fines remitted)&lt;br&gt;&lt;br&gt;-Pond Access&lt;br&gt;-Sheets and Bath Towels Provided with Beds made Upon Arrival&lt;br&gt;-Cleaned with Hospital Grade Disinfectant&lt;br&gt;C0409850410

Waterfront on Black Pond and Long Pond! Two bedrooms plus sleeping loft cottage. Inside you will find the charm of Cape Cod from the moment you open the door. Nautically inspired interior design with a focus on maximized use of space, this vacation home is a dream come true. The living room is bright and tastefully accented with colorful rugs, whimsical art and comfy furnishings (sofa is a pull-out bed). The remodeled kitchen is fully equipped and ready for the catch of the day. An attached dining area affords the option of dining inside or out on the pond-side patio. Also on the main level is Bedroom 1 with a full size bed and Bedroom 2 with full sized sofa bed and TV, a 3/4 bath with shower. There is also a sweet little nook with a day bed, books and a view of Black Pond. Climb the stairs to the upstairs loft with 2 twin bed trundle and sitting area. Air conditioning throughout will keep you cool during the hot summer days. The outdoor shower is a soothing place to end a full day. This cottage is cute as can be but this home is built on a little piece of Heaven and the many joys of summer on Cape Cod are steps away. Just .3 miles to the Cape Cod Rail Trail. Come and visit Brewster, the ponds, the shops, the summer baseball, the parks and beaches, all are close at hand and waiting for you to enjoy. **Blankets and Pillows are provided, but you will need to bring or rent sheets and towels** **Please note property has dryer only. Tight Tank Septic system restricts owner from having a washer**

18829 - Cape Escape: In-Ground Plunge Pool Dog Friendly! 18829 - Cape Escape: Amazing Home with In-Ground Plunge Pool, Dog Friendly! Fun for the Whole Family! &lt;br&gt;&lt;br&gt;Your beautiful Brewster vacation could include everything from an in-ground pool, family fun and games, relaxation and peace and quiet. You can even bring your dog along so they can experience the natural wonders of the Cape all vacation long with you. All you have to do is take a Cape Escape!&lt;<br&gt;&lt;br&gt;Pulling down a private road, turn down the stone driveway to the roundabout at the end, all while taking in the beauty of this two story home as you arrive at your vacation escape. Step up on the front porch and enter into the stunning living room with vaulted ceilings, and natural light flooding in from the skylights and windows throughout. A large sectional and wall-mounted TV awaits your favorite movies, while the upstairs loft area overlooking the living room and dining room is the perfect spot for a family game night. The dining room is adjacent to the living room with a bay window looking out onto the pool. A sprawling kitchen with breakfast bar, beautiful countertops and dark cabinetry is next to the dining room, ready for whatever you’ll need to cook up this vacation. &lt;br&gt;&lt;br&gt;Down the hallway next to the kitchen, you’ll pass a game table and bedroom to your left with a fun nautical theme and two sets of twin bunk beds. Further down the hall to the right is the home’s first half bathroom with access to the large outdoor shower. Continuing down the hall, you’ll find the home’s primary bedroom suite, with towering ceilings, desk area, built-in cabinetry, and en suite bathroom with a gorgeous stand-up shower with multiple shower heads. Upstairs is the home’s final bedroom, with wall mounted TV and a king bed plus daybed, just off of the additional seating area with another fun game table.&lt;br&gt;&lt;br&gt;Outdoors, the entertainment options are seemingly never ending. A wrap-around deck provides multiple lounging options, an outdoor dining table, and access to the private in-ground plunge pool, perfect for wading in and cooling off in the Cape Cod sun. When the cool summer breeze blows in, warm up at the fire pit next to the pool. Surrounding the pool is a grass yard and embankment, where you can play a round of corn hole and watch your pup run around before taking a rest in the hammock outback.&lt;br&gt;&lt;br&gt;Other amenities include a washer and dryer, ping pong table, game console, and full finished game room for some more gaming fun, and a propane grill. If you can pull yourself away from this incredible home, head over to Upper Mill Pond or any of the breathtaking bayside beaches, less than a few miles down the road. Natural beauty, family memories and vacation excitement are waiting for your next trip, why not make it a Cape Escape!&lt;br&gt;&lt;br&gt;Home Details:&lt;br&gt;-Dogs Welcomed (w/fee of $40/night per dog)&lt;br&gt;-Sleeps 9&lt;br&gt;-3 Floors (1st Floor + 2nd Floor + Basement)&lt;br&gt;-2,013 Sq Ft&lt;br&gt;-3 Bedrooms&lt;br&gt;-Bedroom #1: 1 King Bed w/ en suite Full Bathroom, 1st Floor&lt;br&gt;-Bedroom #2: 2 Twin/Twin Bunk Beds (4 twins total), 1st Floor&lt;br&gt;-Bedroom #3: 1 King Bed and 1 Twin Bed w/ en suite Full Bathroom, 2nd Floor&lt;br&gt;-2.5 Bathrooms&lt;br&gt;-Bathroom #1: Full Bath w/ Shower, en suite, 1st Floor&lt;br&gt;-Bathroom #2: Full Bath w/ Tub/Shower Combo, en suite, 2nd Floor&lt;br&gt;-Bathroom #3: Half Bath, 1st Floor&lt;br&gt;-Fully Equipped Remodeled Kitchen w/ Stainless Steel Appliances&lt;br&gt;-Window A/C&lt;br&gt;-Fireplace NOT for guest use&lt;br&gt;-Smart Lock/Self Check-In&lt;br&gt;-WiFi&lt;br&gt;-Smart TV w/ Streaming&lt;br&gt;-Stacked Washer/Dryer (1st floor)&lt;br&gt;-Game Room&lt;br&gt;-Air hockey&lt;br&gt;-Game Console&lt;br&gt;-Screened-In Porch w/ Dining & Seating&lt;br&gt;-Private Unheated In-Ground Pool (Pool Open from Memorial Day to Labor Day - may be longer but not guaranteed)&lt;br&gt;-Patio w/ Outdoor Dining & Lounging&lt;br&gt;-Propane Grill&lt;br&gt;-Outdoor Fire Pit&lt;br&gt;-Hammock&lt;br&gt;-Outdoor Shower&lt;br&gt;-Private Yard&lt;br&gt;-1.9 Miles to Upper Mill Pond&lt;br&gt;-Less Than 3 Miles to Bayside Beaches&lt;br&gt;-Sheets and Bath Towels Provided with Beds Made Upon Arrival&lt;br&gt;-Cleaned with Hospital Grade Disinfectant&lt;br&gt;C0408670410

18809 - Brewster Break: Hot Tub 1 Mile to Swimming on Long Pond! This home has been fully updated, and feels brand new inside; a large open living room and dining area greets you as you walk in, and high ceilings and plenty of light make this the perfect spacious beach house. Shiplap walls and tasteful nautical decor will have you feeling “vacation mode” right away!&lt;br&gt;&lt;br&gt;This amazing new kitchen with updated appliances is an ideal place to prepare a family vacation feast. The left side of the first floor offers two bedrooms, one with a queen bed, and ensuite half bathroom, and the other, a perfect kids room, with a bunk bed consisting of a full on the bottom and twin on top, plus another twin trundle and separate twin single. A full bathroom rounds out the first floor, and upstairs you’ll discover a private master suite, which is the only room on this floor. The upstairs master bedroom also has a full en suite bathroom. In the basement, there is a game room with a pool/ping pong table, and a perfect space for a movie night, with a large flatscreen TV and a massive comfy sofa to cozy up on.&lt;br&gt;&lt;br&gt;Outside the home, a large backyard with a deck, outdoor shower, and grill make this a perfect place to relax after a fun beach day, or a day exploring the Cape. Nearby, you’ll find Cahoon Pond Beach, a perfect spot to take a dip in pristine Long Pond. Head north just a few minutes and you’ll arrive at the downtown area of Brewster, which has many restaurants and shops. Grab some seafood at the Brewster Fish house, or some tacos at Guapos Tortilla shack. Just beyond this area lies Breakwater Beach, where you can be sure to catch one of the best sunsets of your life. Whether it’s the spacious updated interior filled with sun, or the amazing location close to great restaurants and beaches, this home is sure to become your next go-to spot for a spectacular family trip!&lt;br&gt;&lt;br&gt;Home Details:&lt;br&gt;-Dogs Welcomed (w/fee of $40/night per dog)&lt;br&gt;-Sleeps 8&lt;br&gt;-2 Floors&lt;br&gt;Bedrooms&lt;br&gt;-Total 3&lt;br&gt;-1st Floor Bedroom: 1 Queen Bed w/ en suite Half Bathroom&lt;br&gt;-1st Floor Bedroom: 1 Bunk Bed (Twin over Full w/ Twin Trundle), 1 Twin Bed (total 3 Twins & 1 Full)&lt;br&gt;-2nd Floor Master Bedroom: 1 King Bed w/ en suite Full Bathroom&lt;br&gt;Bathrooms&lt;br&gt;-Total: 2&lt;br&gt;-1st Floor: 1/2 Bath (en suite Queen Bedroom)&lt;br&gt;-1st Floor: Full Bath w Tub/Shower Combo&lt;br&gt;-2nd Floor: Full Bath w/ Shower (en suite King Bedroom)&lt;br&gt;Other Amenities &lt;br&gt;-Mini-Split A/C System&lt;br&gt;-Smart TV&lt;br&gt;-WiFi&lt;br&gt;-Washer/Dryer &lt;br&gt;-Gas Grill&lt;br&gt;-Deck w/ Furniture&lt;br&gt;-Private Yard&lt;br&gt;​​​​​​​-Hot Tub&lt;br&gt;-Outdoor Shower&lt;br&gt;-Game Room w/ Pool & Ping Pong&lt;br&gt;-Finished Basement w/ Sectional & Large Flatscreen TV, Peloton, & Weights&lt;br&gt;-1 Mile to Swimming at Long Pond&lt;br&gt;-Sheets and Bath Towels Provided with Beds made Upon Arrival&lt;br&gt;-Cleaned with Hospital Grade Disinfectant&lt;br&gt;C0422050410

18839 - The Homestead: Spacious home with deck and fire pit! Discover the charm of The Homestead, your ideal getaway located just 0.6 miles to Brewster Crosby Landing Beach. This delightful vacation home offers a generous yard perfect for outdoor activities and cozy evenings around a crackling fire pit. Inside, you’ll find a spacious kitchen that’s a dream for culinary enthusiasts, as well as a large living room designed for relaxation and shared moments. Enjoy family meals together in the inviting dining area, or take advantage of the home’s proximity to Nickerson State Park and the picturesque Cape Cod Rail Trail for outdoor adventures. Don’t miss the chance to savor a meal at the nearby Cobie’s, a local favorite. Whether you’re lounging by the fire or exploring the natural beauty of the region, The Homestead provides a perfect blend of comfort and convenience for a memorable Cape Cod retreat.&lt;br&gt;&lt;br&gt;Home Details:&lt;br&gt;-Dogs Welcomed (w/fee of $40/night per dog)&lt;br&gt;-Sleeps 10&lt;br&gt;Bedrooms&lt;br&gt;-Total 4&lt;br&gt;-1st Floor Bedroom: 1 King Bed (w/ Ensuite Bath)&lt;br&gt;-2nd Floor Bedroom: 1 Queen Bed&lt;br&gt;-2nd Floor Bedroom: 1 Queen Bed&lt;br&gt;-2nd Floor Bedroom: 4 Twin Beds&lt;br&gt;Bathrooms&lt;br&gt;-Total 2.5&lt;br&gt;-1st Floor: ½ Bath&lt;br&gt;-1st Floor: Ensuite bathroom w/ Jacuzzi and Shower&lt;br&gt;-2nd Floor: Shower/tub combo&lt;br&gt;Other Amenities &lt;br&gt;-Central Air&lt;br&gt;- Central Heat&lt;br&gt;-Gas Fireplace&lt;br&gt;-WiFi&lt;br&gt;-Smart TV&lt;br&gt;-Cable TV and Streaming&lt;br&gt;-Washer/Dryer &lt;br&gt;-Propane Grill&lt;br&gt;-Fire pit (wood)&lt;br&gt;-Outdoor Shower&lt;br&gt;-Please note outdoor amenities are available seasonally&lt;br&gt;-Sheets and Bath Towels Provided with Beds made Upon Arrival&lt;br&gt;-Cleaned with Hospital Grade Disinfectant&lt;br&gt;-Parking for 4 cars maximum

Exquisite in East Orleans, Heated Pool, Fire pit, Gym! Linens Included, Beds Made Pets Considered Rents Friday to Friday in Peak Summer Off-Season Weekends and Partial Weeks Available Pool & Hot Tub open from Memorial Day to Columbus Day Welcome to The Breakaway, a stunning vacation home nestled in the picturesque Tonset Area of Orleans, Massachusetts. This luxurious property offers a perfect blend of comfort and elegance, making it an ideal retreat for families or groups seeking a memorable getaway. With 5 spacious bedrooms and 5.5 bathrooms, this home comfortably accommodates up to 14 guests, ensuring everyone has their own space to relax and unwind. As you step inside, you’ll be greeted by a beautifully designed interior featuring a gas fireplace that adds warmth and charm to the living area. The central air conditioning throughout the home ensures a cool and comfortable atmosphere, even on the warmest summer days. The fully equipped kitchen is a chef’s dream, complete with modern appliances, ample counter space, and a dining area perfect for family meals. The outdoor space is truly a highlight, boasting a heated private pool and a hot tub, perfect for soaking up the sun or enjoying a relaxing evening under the stars. The fenced yard provides a safe space for children and pets to play, while the outdoor seating areas and fire pit create an inviting atmosphere for gatherings. For those looking to stay active, the property features a gym and a game room equipped with a pool table and entertainment options, ensuring fun for all ages. Each bedroom is thoughtfully appointed, with the master suites offering TVs and sound systems for added convenience. Located just a short walk from the beach and near various attractions, including local Breweries and outdoor adventures, The Breakaway is the perfect base for exploring all that Cape Cod has to offer. Don’t miss out on this exceptional property—book your stay today and create unforgettable memories! Please enter in your travel dates in 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! ®

This home is professionally managed by Pretty Picky Properties Grand Villa Overlooks Nauset Beach & the Atlantic, Heated Pool, Hot Tub & Gas Fire-pit! Rents Friday to Friday Off-season partial weeks available. Sleeps 14 Linens Included/Beds Made Pool and hot tub are open Memorial Day - Columbus Day Your group of up to 14 will vacation in style at this superb ocean side manor house at famous Nauset Beach in East Orleans. The stunning location provides panoramic views of the beach and ocean from both levels of the house. And you have a very short walk to the beach. The property also features a 36’x18’ heated pool, hot tub and gas fire pit!! The spacious, social, fully loaded kitchen anchors the main level and includes a breakfast bar with high boy seating for four. A few steps away, the large dining room easily seats 10 and can accommodate more. Relax in the exquisite living room with lounge seating and a large flat screen TV. This home has Sonos sound system off the back deck and in the lower level living space. It is centrally air conditioned and has hi-speed Wi-Fi and cable TV. A large, covered patio is just off the living room, with a dining table and chairs, plenty of lounge seating and views of the Atlantic. A separate lounge/bar room offers a wet bar with fridge, another TV, and bar seating for three. Walk out from there to a beautiful, hexagonal screened porch which leads to the pool deck. There is one bedroom on the main level, a roomy primary suite with a King size bed and full bath en suite with a walk in shower. The main level also includes a half bath and quiet den/study to serve as your work station, if necessary. On the upper level, you’ll first encounter another lounge area, which walks out to the upper deck that presents 180-degree breathtaking views of Nauset Beach and ocean. Comfy lounge seating here too, including a king-size super comfy sleeper sofa. On this level, you’ll find four more bedrooms. There’s a second, oversized primary suite, with a king size bed plus twin day bed with a twin trundle below. There is a full bath en suite, of course. Another bedroom suite features a King size bed and private full bath. Bedrooms #4 and #5 can be closed off to create a two-bedroom suite. Both bedrooms feature a queen size bed with a standard twin bed and twin trundle bed. The two bedrooms share a full bath between, Jack & Jill style. The lower level of the home houses an extraordinary full home theater with a projector, 10-foot screen and luxurious lounge seats with cup holders for up to 12, plus giant bean bag seating for more. What an amazing place should the weather not cooperate or for your evening entertainment. Also on this level: a workout room, a ping pong table, and a half bath. There are four full and two half baths in all. The yard and grounds provide plenty of space for kids to play safely. There is also a gas grill and horseshoe pits to keep everyone entertained. Consider planning your summer vacation at this truly remarkable property in one of Cape Cod’s most coveted locations. Please enter in your travel dates in 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 17.45%. 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! ®

18835 - Coastin Time: Wow! Private Pool, Game Room, and Fire Pit! Discover the epitome of Cape Cod living at this fun and inviting vacation destination, just 2.5 miles from the shores of Cliff Pond in Brewster. A timeless classic, the exterior mirrors the iconic Cape style, while the interior unfolds with a layout that seamlessly marries modernity and comfort. Immerse yourself in the coastal charm as tasteful decor creates a serene atmosphere. The generously sized rooms cater to both adults and kids, providing ample space for everyone to unwind and relish the vacation experience, creating lasting memories.&lt;br&gt;&lt;br&gt;Indulge in friendly competition within the finished basement game room, where a pool table and inviting lounge area beckon for memorable gatherings. For respite from the summer sun, the private in-ground pool in the backyard awaits, enclosed by a safety fence for peace of mind. After a refreshing swim, cleanse the day away in the outdoor shower, or savor a moment on the deck with cocktails as the grill heats up for a delicious dinner. As night falls, let the magic of Cape Cod envelop you under the starlit sky. Gather around a warm campfire with loved ones, creating lasting memories and relishing the tranquility of the moment. &lt;br&gt;&lt;br&gt;The property’s prime location offers easy access to the coastal wonders, with Paines Creek Landing Beach and Ellis Landing Beach just a scenic 10-15 minute drive away. Captains Golf Course is just a few minute drive down the road! Convenience meets culinary delight, with dining options like, The Kitchen Cafe, and JT’s Seafood just 3.5 miles away. If you’re looking for an outing with your furry friends, hop on over to the Brewster Dog Park also about 3 miles away. &lt;br&gt;&lt;br&gt;Your Cape Cod retreat beckons, promising an idyllic blend of relaxation and exploration for an unforgettable vacation experience.&lt;br&gt;&lt;br&gt;Home Details:&lt;br&gt;-Dogs Welcomed (w/fee of $40/night per dog)&lt;br&gt;-Sleeps 12&lt;br&gt;Bedrooms&lt;br&gt;-Total 4&lt;br&gt;-1st Floor: 1 Queen Bed&lt;br&gt;-2nd Floor: 1 King Bed&lt;br&gt;-2nd Floor: 1 Queen Bed&lt;br&gt;-2nd Floor: 2 Bunk Beds (Twin over Full)&lt;br&gt;Bathrooms&lt;br&gt;-Total 2.5&lt;br&gt;-1st Floor: ½ Bath&lt;br&gt;-2nd Floor: Tub/Shower Combo&lt;br&gt;-2nd Floor: Tub/Shower Combo&lt;br&gt;Other Amenities &lt;br&gt;-Private Unheated Pool (Pool Open from Memorial Day to Labor Day - may be longer but not guaranteed)&lt;br&gt;-Game Room w/Pool Table&lt;br&gt;-Wood Burning Fire Pit (Source wood locally)&lt;br&gt;-Central AC&lt;br&gt;-WiFi&lt;br&gt;-Smart TV&lt;br&gt;-Washer/Dryer &lt;br&gt;-Propane Grill &lt;br&gt;-Outdoor Shower&lt;br&gt;-Please note outdoor amenities are available seasonally&lt;br&gt;-Sheets and Bath Towels Provided with Beds made Upon Arrival&lt;br&gt;-Cleaned with Hospital Grade Disinfectant&lt;br&gt;-Parking for 4 cars maximum&lt;br&gt;C0354370410

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 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

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. "Second Wind" - An Orleans Estate with large heated pool, spa, on Town Cove Sleeps up to 24 in three dwellings Linens and bed making included Pets Considered up to 25 lbs. Weddings not permitted on property Pool is open Memorial Day - Columbus Day This Orleans Estate is located in the heart of Orleans Village on picturesque Town Cove. Bring the whole family and leave the cars in the driveway for the week. You’ll spend countless hours around the pool and spa at the Main House. There’s plenty of room for everyone to gather around the fire pit and cook out poolside at the outdoor kitchen. You can walk to everything in Orleans Center, including some of the best restaurants in town, village shops and of course, ice cream. There are four ice cream shops within walking distance! The mid-century homes have been recently updated with all the modern conveniences while retaining much of the original charm. The large 1.3 acre lot is waterfront on Town Cove and has a heated pool and spa (open Memorial Day - Columbus Day). The large lot provides plenty of recreation space on the gently sloping lawn. Hold your own version of the Whiffle Ball World Series. Town Cove is a great place to drop an owner-provided kayak or SUP and explore the in-land waterways of Nauset Cove and Nauset Marsh. Bring your boat and use the adjacent town boat ramp to motor your way to Nauset Beach by boat! The Main House underwent a full remodel in 2023, you have an updated kitchen with granite counters and new appliances, including a huge side-by-side refrigerator and two dishwashers. There are two dining areas along the back of the house so that large groups can dine together. There is also an enclosed porch overlooking the lawn, pool and cove beyond. The house is great for bringing family together but you have enough space to spread out as well. There are 3 large seating areas in the Main and Carriage Houses that are great spots to watch a ball game or for the kids to watch their shows/movies. The Main House has 5 bedrooms, 5 full baths and 1 half bath. You’ll find one of three primary suites on the main level of the Main House with a king size bed, sitting area and beautiful ensuite bath. There is also a powder room on the main level and living room with separate card-table room. Upstairs in the Main House, there are 3 bedrooms: the second primary suite with a king bed and a private full bath, the third primary suite features a king size bed and ensuite bath, and the third bedroom has a queen size bed with a twin bunk above. There is a full bath for guests of this room in the hallway with a tub/shower combination. In the lower level, you’ll find an extra sleeping area with 2 twin beds for overflow sleeping. Plus a wonderful new media room, laundry room and there is a full bath down here as well plus an outdoor shower not far away. Next door in the Carriage House, you’ll find a second full kitchen, a dining area, a powder room, a primary suite with king size bed and a private full bath on the main level. Upstairs in the Carriage House, you’ll encounter a loft space with a TV and cozy couch. There is a full bath and a bedroom with a queen sized bed plus 2 twins. The third structure, the Guest House has been fully remodeled – brand new kitchen with stainless steel appliances and granite counters. On the main level is a queen bedroom with full bath while upstairs you have a kid’s room with a bunk bed (full under a twin) and another twin with trundle bed with an en suite bath. The primary suite upstairs features a king size bed and stunning views of Town Cove with a wonderful en suite bath. The shower feels like an outdoor shower! In addition, the Guest House has an outdoor shower and 6-person hot tub overlooking the Cove. All three homes have AC, WIFI and cable TV. If you feel like leaving your own private resort, good news – two world famous beaches are less than 5 minutes’ drive away, Nauset Beach on the Atlantic or Skaket Beach on Cape Cod Bay. There is nothing that is overlooked at this ideal vacation property for larger groups. 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 Luxurious 5- Bedroom Retreat with Heated Pool & Hot Tub – Walk to Water! 5 bedrooms sleeps 12 Linens included, beds made Rents Friday to Friday in Peak Season Pets Considered (Small dog) Please note: pool and hot tub are open Memorial Day - Columbus Day. Escape to the heart of Lower Cape Cod in this newly renovated, luxury vacation home in East Orleans! Perfect for families and groups, this spacious 5-bedroom retreat offers the perfect blend of modern comfort and classic coastal charm. Inside, you’ll find a fully equipped, modern kitchen with everything you need to prepare gourmet meals, plus a large dining room with seating for 10 -- perfect for gathering after a day at the beach. The main level features two elegant bedrooms, both with a queens, each with new, spa-like private baths. Upstairs, two additional bedrooms. One has a spacious King and the other with a queen plus a twin with a trundle. There is a luxurious full bath upstairs as well. New for 2026: 5th bedroom as primary bedroom and private en-suite. Step outside and experience your private Cape Cod oasis -- a heated saltwater pool, relaxing hot tub, gas fire pit and a fully equipped outdoor kitchen make entertaining a breeze. Lounge in the poolside cabana, fire up the grill, or unwind under the stars after a day of exploring. Nature lovers will love the short walk to a nearby saltwater river, perfect for kayaking and paddleboarding. Plus, you’re just under a mile to Orleans Center for shopping and dining, and a 5-minute drive to both Nauset Beach and Skaket Beach—giving you the best of both the Atlantic Ocean and Cape Cod Bay. This stunning getaway has everything you need for an unforgettable Cape Cod vacation. 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%. 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! ®

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