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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, 142 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!

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, 190 reviews

The Drake Cottage - Brewster Beach Getaway

Experience quintessential Cape Cod in The Drake Cottage located right on 6A in Brewster, Ma. The Drake Cottage is conveniently situated within a mile of Drummer Boy Park, The Cape Museum of Natural History, Paines Creek Beach and a 9 min drive from Oceans Edge. The 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.

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, 216 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, 189 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

The living area features a light-colored sofa complemented by two armchairs, arranged around a patterned rug. A piece of artwork depicting sailboats adorns the wall, while natural light enters through two windows, enhancing the inviting ambiance.

Home in Brewster

4.99 out of 5 average rating, 122 reviews

Perfect Cape Cod vacation home

SUPER LOCATION for biking & hiking! Quiet neighborhood with direct access to 31 mile Cape Cod Rail Trail, 1900 acre Nickerson State Park and local clam shack / ice cream shop. Easy walking / biking access to Linnell & Crosby Landing Cape Cod Bay beaches and Flax & Cliff Pond fresh water beaches. Easy drive to towns of Orleans, Chatham, Harwich & Dennis. Whether it's a quiet walk, an exhilarating bike ride, salt or fresh water beaches, or a comfortable place to relax, this house has it all!

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, 141 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

4.97 out of 5 average rating, 120 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 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, 102 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

4.88 out of 5 average rating, 280 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, 618 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, 314 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.

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, 282 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...

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A space thats all yours, with room for everyone

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Convenient locations with everyday essentials

Popular amenities for Brewster vacation rentals

Laptop-friendly workspace

Stay near Brewster's top sights

Skaket Beach89 locals recommend

Sesuit Harbor Cafe257 locals recommend

Nickerson State Park171 locals recommend

Brewster house rentals

A spacious dining area features a long white table adorned with a runner and decorative centerpiece. Overhead, a chandelier adds elegance, while large windows frame views of the water. Natural light brightens the room, complemented by charcoal slate flooring and a cozy seating arrangement nearby.

Home in Chatham

4.95 out of 5 average rating, 291 reviews

Slate House - a modern waterfront getaway

Home in Orleans

4.98 out of 5 average rating, 40 reviews

1850 Orleans Antique Home with Path to Arey’s Pond

Top guest favorite

A charming cottage exterior is visible, featuring a gray shingle facade and a red brick chimney. Lush green shrubs and blooming hydrangeas line the pathway, leading to a welcoming entrance. The sunroom is situated to the left, showcasing windows that enhance natural light.

Home in Chatham

5 out of 5 average rating, 170 reviews

Chatham Charmer

A charming Cape house is presented, featuring a green roof and inviting front porch. Lush greenery lines the landscaped yard, with a winding brick pathway leading to the front door. Sunlight filters through the trees, enhancing the natural surroundings.

Home in Brewster

4.93 out of 5 average rating, 86 reviews

Custom House w Central AC at the heart of the Cape

A spacious living room area features a large sectional sofa adorned with blue accent pillows. A coffee table sits in the center on polished hardwood floors. Natural light filters in through large windows, illuminating a simple mantel above the stone fireplace.

Home in Brewster

4.94 out of 5 average rating, 16 reviews

Brewster Beach House

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, 21 reviews

Family-Friendly Home with Expansive Backyard!

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

4.87 out of 5 average rating, 15 reviews

Old Cape Charmer

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

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, 117 reviews

#25 Seasonal Cottage is 200 feet from the Beach

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, 47 reviews

On the water/Dog Friendly/Sleeps 7/SeaDuction

The photo captures a collection of charming coastal cottages nestled along a sandy beach. A road runs parallel to the shoreline, lined with greenery and flowering plants. The sunny sky and natural landscape enhance the serene seaside setting.

Home in Wellfleet

4.83 out of 5 average rating, 6 reviews

Sandy beach cottage on Wellfleet Bay

Home in Barnstable

4.98 out of 5 average rating, 48 reviews

Private Lake Beach | Spectacular Views & Amenities

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

4.86 out of 5 average rating, 7 reviews

Huge Private Beach Fab Bay View

Top guest favorite

A charming beach house with shingle-style siding is displayed, set within a landscaped yard. Two large bushes frame the entryway, and the building features multiple rooflines and skylights. A brick pathway leads to the front door, with trees providing partial shade in the foreground.

Home in Chatham

4.98 out of 5 average rating, 87 reviews

Beachfront Charmer! Newly Renovated.

Top guest favorite

Aerial view of a beach house situated near the shoreline, showcasing a spacious lawn and landscaping. Calm waters and a sandy beach extend along the coast, with the property positioned for optimal water access. The nearby neighborhood is visible in the background.

Home in West Yarmouth

5 out of 5 average rating, 6 reviews

Sunset on Shore - Lewis Bay Waterfront

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, 135 reviews

Private Bay Beach and Sunset Views! Dog friendly.

Lakefront house rentals in Brewster

Top guest favorite

A wooden outdoor table and benches are positioned on a stone patio, overlooking a serene pond. Lush greenery lines the water's edge, and white flowers in a planter enhance the natural setting. The calm water reflects the surrounding trees and sky.

Home in West Yarmouth

5 out of 5 average rating, 324 reviews

gorgeous waterfront cottage w/4kayaks and 2 SUPs

A modern home with light grey siding is featured in the background, surrounded by landscaped gardens. A heated saltwater pool, with clear blue water, is framed by grey stone paving. Lounge chairs and shaded seating are situated beside the pool, enhancing the outdoor space.

Home in Popponesset

5 out of 5 average rating, 16 reviews

18 Menemsha Rd., Popponesset, Pool, 3-Beds, 4 bath

Top guest favorite

A private waterfront deck offers a serene view of Flax Pond, surrounded by lush greenery. Adirondack chairs are positioned for relaxation, providing a perfect spot to enjoy the tranquil waters and natural surroundings.

4.99 out of 5 average rating, 292 reviews

Stunning Waterfront with Serene Sunrise Views!

Top guest favorite

A bright screened-in porch offers views of the waterfront, furnished with comfortable seating and natural light. Overhead, a light fixture illuminates the space, surrounded by large windows revealing green grass and lake scenery beyond.

Home in Yarmouth Port

5 out of 5 average rating, 80 reviews

Beachfront· Sauna· Screened Patio· 2Kings· DogsYes

Top guest favorite

A waterfront hot tub is set against a natural backdrop of trees and calm waters. Inside, a dining area features a large window with views of the lake. A cozy living room displays comfortable seating, while an outdoor patio has seating for relaxation and enjoying the scenery.

Home in South Yarmouth

4.95 out of 5 average rating, 243 reviews

Waterfront Spa|Hot Tub+Cold Plunge in Lake| Pet ok

An aerial view captures a spacious lakefront home surrounded by lush greenery, with calm waters reflecting the sky. A vast lawn leads to the edge of Lawrence Pond, providing a serene backdrop to the property.

Home in Sandwich

4.97 out of 5 average rating, 100 reviews

Serene Lakefront home in Cape Cod, #onlawrencepond

Top guest favorite

A serene view of a freshwater pond is captured, with gentle ripples reflecting the clear blue sky. Leafless trees frame the scene, adding a touch of nature's beauty. Lush greenery can be seen in the distance, showcasing the peaceful surroundings.

Home in North Eastham

4.97 out of 5 average rating, 35 reviews

Cozy Cape Stay! bike path, beaches, water view!

An aerial view showcases the waterfront house surrounded by lush greenery, with Long Pond visible nearby. The property features a driveway and landscaped yard, emphasizing a serene, natural environment that invites relaxation.

Home in Yarmouth

5 out of 5 average rating, 3 reviews

Sunset Point on Long Pond- Large 4BR 3000 sqft

Quick stats about vacation rentals in Brewster

Total rentals
460 properties
Nightly prices starting at
G$12,536 GYD 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 East Brewster, and over 740 vacation rentals in Pleasant Lake.
Are there house rentals with a dedicated workspace in Brewster?
Yes! Work meets play with ease at over 150 house 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 house rentals in Brewster?
Four-legged friends are welcome in Brewster. Choose from more than 120 house 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.
Do house rentals in Brewster have wifi?
Absolutely! We offer over 300 house rentals with wifi 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.

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