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Vacation rentals in Brewster

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Top-rated vacation rentals in Brewster

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The living area features wooden cathedral ceilings and a cozy seating arrangement with two grey sofas, adorned with colorful pillows. A wooden coffee table is centered on a patterned rug, with a fully equipped kitchen visible in the background.

Home in Brewster

4.93 out of 5 average rating, 140 reviews

Shop, Swim, Hike, Bike in Historic Brewster

Spacious, sunny, A/C'd, one floor cottage! Centrally located: 1.3 mi to beach, .5 mi walk to the charming Brewster Store, Brewster Scoop & Route 6A. The bike trail is 1 min bike ride. Sheeps Pond is 1.3 mi; you can swim, kayak, canoe, fish. Newer mattresses/pillows, bunk bed for kids. Laundry facilities, kitchen composting, Britta filter, Linen option. Big backyard, outdoor picnic table and hot shower! BBQ and Adirondack chairs around fire pit. Bike shed, beach chairs, umbrellas, toys. Parking!

A wooden dock extends into a serene freshwater pond, surrounded by lush green foliage. The calm water reflects the clear blue sky and distant tree line, creating a tranquil setting for relaxation and outdoor activities.

Home in Brewster

4.87 out of 5 average rating, 213 reviews

Water Front Pond House - 3 acre Cape Cod Sanctuary

Extraordinary pondfront sanctuary on Cape Cod. 1300 sq.ft. home sleeps 8 in 3 bedrooms and 1 bath. Private dock and beach area. House is on the Pond and sited on 3 pristine acres - this property offers exceptional privacy with full water recreation opportunities while also being close to everything "Cape Cod". Centrally located in laid-back Brewster, 5 minutes to Bayside beaches, 10 mins to Chatham, Harwich Port, and Orleans. Local owners have 22 years of online vacation rental experience.

A welcoming entryway is observed, featuring a rustic 'WELCOME' sign on the wall. Light wood flooring extends into a cozy living and dining space, illuminated by natural light. A dining table is visible in the background, surrounded by comfortable chairs.

Condo in Brewster

4.97 out of 5 average rating, 184 reviews

Ocean Edge Resort-Pool Access-End Unit-2 bdr/2 bth

2nd floor Ocean Edge end unit condo located in the heart of Brewster with access to OE resort amenities: pools, gyms, tennis courts, as well as access to resort activities (fees apply). Easy access to Cape Cod Rail Trail for bicycles. Scenic route 6A offers arts & crafts galleries and local shops. A 10 minute car ride to a 36 hole Captains Golf course. Short ride to 10 Brewster bay beaches famous for tidal flats. A 30 minute ride to Cape Cod National Sea Shore. Welcome to your Happy Place!

Top guest favorite

A charming two-story home is nestled among the trees, featuring a gray exterior and a welcoming red front door. Lush green shrubbery and blooming flowers are visible near the entrance, enhancing the natural setting.

Home in Brewster

4.91 out of 5 average rating, 138 reviews

4BR/3B | Pond | BikePth | W/D | FireTbl | AC |Deck

Updated, spacious, peaceful Mid-Cape home Private road, private beach/pond (5 min walk) Silent central AC 4 BR/3 full bth: > Ground floor: 2 BR + 2 bth - sleeps 4 > Upstairs: 2 BR + 1 bth - sleeps 4 Hardwood Floors Large, screened porch Large living room: 2 recliners, leather couch, Jøtul gas stove, Roku TV Wooded yard - gas fire table, grill Ping Pong - (in unfinished basement) Near 25-mile long Bike Trail, beaches, golf/mini-golf, tennis, boating Please, no smoking

Top guest favorite

A charming studio cottage with wooden shingles is nestled among trees, featuring a private deck and gas grill. Colorful flowers line the pathway leading to the entrance. A lush green lawn surrounds the building, creating a tranquil outdoor setting.

Apartment in Brewster

4.96 out of 5 average rating, 114 reviews

Songbird Studio- Secluded but close to everything!

Bright, sunny, secluded, green 600 sqft studio apartment at rear of Antique home in the heart of Brewster, Northside of Rt 6A. Private entrance. Private backyard with lawn & gardens. Small private deck, gas grill. Bird and small animal life abounds outside. Tons of stars at night.. salt air on the wind. Walking distance to coffee shop, convenience store, multiple restaurants, Bike Trail. Short car ride to bay beaches, easy drive to Ocean beaches. Gas "woodstove" for heat, AC for cooling.

The exterior of The Drake Cottage is surrounded by lush greenery and a well-landscaped yard. The charming two-story structure features a mix of wood and stone siding, complemented by a gravel driveway leading to the entrance. Natural stones and native plants are arranged in the gardens.

Home in Brewster

4.83 out of 5 average rating, 188 reviews

The Drake Cottage - Brewster Beach Getaway

Come and experience quintessential Cape Cod in The Drake Cottage located right on 6A in Brewster, Ma. The Drake Cottage is conveniently situated within about a mile of Drummer Boy Park, The Cape Cod Museum of Natural History and Paines Creek Beach. The Drake Cottage offers an expansive private back yard with an acre of land. Enjoy a newly extended patio complete with fire pit, 10 person picnic table and BBQ grill. Our newly updated interior provides our guests with many modern amenities.

The exterior of a charming cottage is visible, featuring natural cedar shingles and a welcoming porch. Lush flower beds, including vibrant blue hydrangeas, frame the entrance, while a white picket fence adds to the quaint appeal. A well-maintained lawn enhances the home's inviting presence.

Home in Brewster

4.92 out of 5 average rating, 101 reviews

Antique Cape Home With Modern Conveniences

The Elisha Howland Saltbox provides your opportunity to experience the unmatched essence of a true 'Olde Cape Cod' home. We offer a restored antique Saltbox with 2 bedrooms and 2 bathrooms. For an additional charge, there is a detached cottage which can accommodate two more guests. PLEASE NOTE: we accept ONLY FULL WEEK RENTALS from mid-June to mid-September, but we welcome shorter or much longer stays during the rest of the year. Our home is a lovely place to spend a winter on Cape Cod.

The exterior view presents a two-story condo unit with a stairway leading to the entrance. Lush greenery surrounds the path, while well-maintained shrubs complement the soft landscaping. The balcony above offers additional outdoor space, enhancing the overall appeal of the building.

Condo in Brewster

4.87 out of 5 average rating, 270 reviews

Shining Sea Condo

Ocean Edge condo with cathedral ceilings! Beautiful private deck located on the 5th hole of the Ocean Edge golf course! Located within Eaton village. One king bed and one queen, along with pullout couch allows 6 to sleep comfortably. Linens are included!! Large kitchen with washer/ dryer, AC in living room and heat throughout the unit. Wifi and two smart TVs with ROKU devices. Flexible dates allows guests to stay whatever length they would like instead of a mandatory week. Come enjoy!

Top guest favorite

A spacious backyard features a well-maintained lawn, surrounded by lush greenery. A wooden deck with seating overlooks the area, complemented by colorful flower pots. A hammock is nestled between trees, inviting relaxation. Comfortable chairs are arranged for outdoor enjoyment.

Guest suite in Harwich

4.99 out of 5 average rating, 614 reviews

Romantic getaway suite

GENEROUS DISCOUNT FOR LONG TERM OFF SEASON STAYS. ( February, March, November, and December) Contact direct. Ten year old private one bedroom lavish suite over two car attached garage with private entrance, deck, and parking in a quiet neighborhood central to all the Cape has to offer. Beautifully furnished with central air, gas fireplace, hardwood floors, double slipper clawfoot soaking tub, separate subway tiled shower, wireless internet and Sony 49 inch 4KUHD edge -lit streaming TV.

The cottage showcases a classic Cape Cod design, framed by greenery and a gravel pathway. A standalone structure is visible with a sloped roof and a front door lined with dark shutters. Sunlight casts a warm glow on the exterior against a clear blue sky.

Home in East Dennis

4.93 out of 5 average rating, 305 reviews

Cape Cod Cottage by the Bay!

Classic, beautifully crafted, newer cottage by Cape Cod Bay. All amenities. Stainless steel kitchen, Cathedral ceilings, Wide plank wood floors, water view. 2 min walk to one of the best beaches on the Cape! Quiet locale in the historic village of Quivet Neck, within East Dennis. 35 miles to Provincetown. I do not allow pets. I have family members with severe allergies who use the cottage. There is no AC at this cottage. I have 15 windows, 4 fans and an ocean breeze.

The bathroom features a freestanding white soaking tub with a wooden shelf holding toiletries and a glass of wine. A textured blue throw is draped over the side, and a light blue mat with the word 'PEACH' adds a touch of color.

Apartment in Brewster

4.96 out of 5 average rating, 165 reviews

Sophisticated, Private Cape Cod living

LOCATION: 3/4 mile off main road (unpaved road). Located on the town line of Brewster and Orleans with less than 5 minutes to Chatham or Harwich by car. Nauset and Skaket beaches are less than 3 miles away. Nickerson state park less than 1 mile away. Cape Cod National seashore is located within 7.2 miles of our property. Shopping on Main Street in Chatham is 15 minutes. Enjoy a nice, tranquil walk, listen to the birds or feast your eyes on the surrounding conservation land.

A charming two-story structure features dark wooden siding and a welcoming entryway. Surrounding greenery includes tall trees and well-maintained shrubs, providing a serene outdoor setting. A grassy area leads up to the building, emphasized by a clear blue sky overhead.

Home in Brewster

4.92 out of 5 average rating, 273 reviews

Privacy with Cape Cod charm

This lovely, private one bedroom apartment is located above the unused garage on the grounds of our classic half cape house, just a 3 minute walk to our private beach on the bay. It sleeps 2 with a double bed and has a full kitchen and bathroom, along with an outdoor shower, grill, fire pit and picnic table located in private yard. Linens will be provided. Coffee maker and coffee will be waiting for you...

Vacation rentals for every style

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Apartments

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A space thats all yours, with room for everyone

Villas

Luxurious estates for the ultimate escape

Popular amenities for Brewster vacation rentals

Laptop-friendly workspace

Stay near Brewster's top sights

Skaket Beach32 locals recommend

Sesuit Harbor Cafe87 locals recommend

Nickerson State Park56 locals recommend

Brewster house rentals

This charming home features a light-colored exterior with blue shutters and a welcoming door. A manicured lawn surrounds the property, showcasing lush green shrubs and colorful flower beds. Tall trees provide a natural backdrop, creating a peaceful and inviting setting.

Home in Harwich

4.94 out of 5 average rating, 17 reviews

Charming Cape Cod Retreat–Walk to Long Pond Beach!

Top guest favorite

An outdoor dining setting features a table with a plate of salad and wine glasses, accompanied by a bottle of white wine. In the background, a charming shed displays ‘Cape Away’ signage, surrounded by well-maintained greenery and a cozy lounge area.

Home in South Yarmouth

5 out of 5 average rating, 162 reviews

Relax w/ Amenities | King Beds * Sauna * Bar Shed

A spacious heated saltwater pool is surrounded by a large deck featuring colorful lounge chairs and an umbrella. The attractive two-story house stands in the background, framed by lush greenery and trees, creating a peaceful outdoor setting.

Home in Brewster

4.97 out of 5 average rating, 36 reviews

Modern Cape, Private Salt Water Pool, Beaches-Golf

A single-story house is surrounded by lush greenery and colorful shrubbery under a clear blue sky. The structure features a light blue exterior with white trim, a front door, and a single-car garage. Sunlight illuminates the well-maintained lawn and garden area.

Home in Brewster

4.95 out of 5 average rating, 19 reviews

Family-Friendly Home with Expansive Backyard!

A sandy pathway is framed by lush green bushes, leading toward a coastal view. Calm waters stretch into the distance, reflecting the soft blue sky with scattered clouds. The tranquil beach setting invites exploration and relaxation.

Home in Brewster

4.92 out of 5 average rating, 93 reviews

Brewster Bay Getaway; walk to private & pub. beach

A cozy living room features a plush sofa with decorative pillows and a comfortable armchair. A dark wood coffee table rests on soft carpeting, with natural light illuminating the space through windows. Wall art adds character, while a modern television is mounted above a classic fireplace.

Home in Brewster

4.85 out of 5 average rating, 13 reviews

Old Cape Charmer

The exterior of a single-story home is presented, featuring white siding with blue shutters. A pathway of stone pavers leads to the front door, framed by landscaped greenery and a well-maintained yard under clear blue skies.

Home in Harwich

5 out of 5 average rating, 15 reviews

Newly Renovated in Harwich: After Dune Delight

The sunlit living area features vaulted ceilings and exposed wooden beams. Two cozy sofas are arranged around a central coffee table on a decorative rug. Light flows through large windows, enhancing the inviting atmosphere. A small dining table is positioned in the background for additional seating.

Home in Brewster

5 out of 5 average rating, 6 reviews

NEW! Water Views + Dog Friendly Cape Cod Retreat

Brewster beach vacation rentals

Top guest favorite

The beach house is set against a backdrop of lush greenery, featuring a wraparound porch with white railings. Light-colored siding and windows create a bright appearance, while a sandy path leads up to the entrance. A seated area and natural landscaping enhance the outdoor surroundings.

Bungalow in Cotuit

4.98 out of 5 average rating, 59 reviews

Cozy Cape Cod Beach House Bungalow

The vintage beach cottage is depicted with a light blue exterior, settled near the edge of a sandy beach. Waves gently crash against the shoreline while a lush green area surrounds the cottage, providing a serene coastal setting. A single vehicle is parked near the entrance.

Cottage in East Sandwich

4.86 out of 5 average rating, 410 reviews

Oceanfront Cottage w/Private Beach ~ Lil’ Sea Sass

Top guest favorite

A charming entrance features a dark blue door adorned with a shell-themed wreath. Next to the door, a wooden oar is displayed, and the adjacent wall showcases a large number '4'. Soft lighting is provided by a wall-mounted fixture.

Cottage in Cummaquid

4.98 out of 5 average rating, 100 reviews

Private Beach-Barnstable Harbor Beachside Cottage

A charming cottage exterior is surrounded by lush greenery and blooming rose bushes, with a white picket fence enclosing the front yard. The gabled roof and shingle siding complement the tranquil landscape, offering a welcoming first impression.

Cottage in New Seabury

4.91 out of 5 average rating, 169 reviews

Quaint Cape Cod Cottage on a Private Beach!

The cottage, surrounded by mature landscaping, is located near a private beach. A sandy expanse is visible in the background, highlighting the close proximity to the shore. Nearby structures exhibit a rustic charm, contributing to the serene beach environment.

Cottage in East Sandwich

4.92 out of 5 average rating, 275 reviews

Hideout at Water's Edge, 131 North Shore Blvd, #4

Top guest favorite

A serene beach scene is captured, featuring calm waters reflecting a clear blue sky. Grass and low vegetation frame the foreground, leading to gently sloping sandy shores. In the distance, the outline of an island is visible against the horizon, contributing to the tranquil atmosphere.

Bungalow in Wellfleet

4.96 out of 5 average rating, 124 reviews

Beach Bungalow - Cape Cod Classic

An open-concept living area features a spacious blue sectional sofa and a flat-screen TV mounted on the wall. Natural light floods the room through large windows, offering views of the surrounding greenery. A decorative plant and a textured area rug add warmth to the space.

Condo in Chatham

4.86 out of 5 average rating, 109 reviews

Steps to Private Beach in Chatham

A quaint cottage is nestled among lush greenery, with vibrant shrubs and trees providing natural coverage. A set of wooden stairs leads from a sandy path to the inviting entrance of the home, framed by bright blue skies.

Cottage in North Eastham

5 out of 5 average rating, 11 reviews

Quaint beachfront cottage

Beach house rentals in Brewster

A sandy beach area is captured, featuring soft dunes and gentle ridges formed by the wind. A building with a distinctive cupola is visible in the distance, surrounded by wooden walkways. Clear blue skies complement the serene coastal setting.

Home in Centerville

4.89 out of 5 average rating, 114 reviews

#25 Seasonal Cottage is 200 feet from the Beach

Top guest favorite

A bright living area features a comfortable sofa adorned with decorative cushions. Large windows provide a view of the water, allowing natural light to fill the space. A small coffee table and a stylish lamp are included, creating a relaxing atmosphere.

Home in Harwich

4.94 out of 5 average rating, 50 reviews

Waterfront★ Pvt Beach ★ On Bike Path ★Bikes★Kayaks

A charming beach house is nestled on a sandy shoreline, surrounded by sparse vegetation. Large windows and a welcoming deck provide unobstructed views of the bay. A set of stairs leads down to the rocky beach area, offering easy access to the water.

Home in North Eastham

5 out of 5 average rating, 46 reviews

On the water/Dog Friendly/Sleeps 7/SeaDuction

Top guest favorite

Home in Barnstable

4.98 out of 5 average rating, 45 reviews

Private Lake Beach | Spectacular Views & Amenities

Top guest favorite

Home in Yarmouth Port

5 out of 5 average rating, 73 reviews

Beachfront· Sauna· Screened Patio· 2Kings· DogsYes

A well-appointed kitchen featuring a stainless steel sink beneath a large window, allowing natural light to illuminate the space. A potted plant with vibrant flowers adds a touch of color, while a banana rest on the countertop enhances the functional atmosphere.

Home in Brewster

5 out of 5 average rating, 6 reviews

Huge Private Beach Fab Bay View

Top guest favorite

A sandy beach is lined with beachgoers enjoying the sun, and colorful umbrellas provide shade. Gentle waves ripple in the water under a clear blue sky, while grassy dunes frame the scene, highlighting the natural beauty of the coastal location.

Home in North Eastham

4.98 out of 5 average rating, 133 reviews

Private Bay Beach and Sunset Views! Dog friendly.

A charming cottage is surrounded by lush greenery and soft landscaping. The exterior features a light wood shingle design with a welcoming porch and a shaded deck area. Outdoor seating is present, inviting relaxation under the clear blue sky.

Home in Hyannis Port

4.88 out of 5 average rating, 172 reviews

Cottage with private beach in Hyannis Port

Quick stats about vacation rentals in Brewster

Total rentals
460 properties
Nightly prices starting at
R1,079 ZAR before taxes and fees
Total number of reviews
15K reviews
Family-friendly rentals
370 properties are a good fit for families
Pet-friendly rentals
160 properties allow pets
Rentals with a pool
60 properties have a pool

Frequently Asked Questions

Where should I stay in Brewster?
Make yourself at home in Brewster by choosing from our most frequently booked neighborhoods. We have over 1,860 vacation rentals in East Harwich, over 200 vacation rentals in West Brewster, over 200 vacation rentals in East Brewster, and over 740 vacation rentals in Pleasant Lake.
Are there vacation rentals with a dedicated workspace in Brewster?
Yes! Work meets play with ease at over 210 vacation rentals in Brewster featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in house rentals in Brewster?
Experience the best of Brewster with our house rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly vacation rentals in Brewster?
Four-legged friends are welcome in Brewster. Choose from more than 160 vacation rentals for guests traveling with pets.
Do house rentals in Brewster have self check-in?
Absolutely! We offer over 100 house rentals with self check-in in Brewster. Enjoy a tailored experience with all the comforts you desire.
Are there Brewster house rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 20 house rentals with pools in Brewster, available on Airbnb. Make a splash and soak up the sun in style!
Do house rentals in Brewster have a bbq area?
Absolutely! We offer over 150 house rentals with a bbq area in Brewster. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Brewster have a gym?
Absolutely! We offer over 20 house rentals with a gym in Brewster. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Brewster?
Brewster has more than 290 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for House Rentals in Brewster?
Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with a gym, over 150 homes with a bbq area, over 100 homes with self check-in, and more. Indulge in the ultimate retreat, tailored to your preferences.

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