Vacation rentals in Brewster

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Top-rated vacation rentals in Brewster

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite
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, 147 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!

Guest favorite
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, 197 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.

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
4.92 out of 5 average rating, 153 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 leather recliners & couch, Jøtul gas stove, 65” OLED TV Wooded yard - gas fire table, grill Ping Pong - (unfinished basement) Near 25-mile long Bike Trail, beaches, golf/mini-golf, tennis, boating Please, no smoking

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, 123 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!

Guest favorite
An outdoor seating area features a stone fire pit surrounded by five Adirondack chairs in various colors. The spacious yard is partially shaded, with a picnic table and grill visible in the background, leading to the home's exterior with large windows.
Home in Brewster
4.87 out of 5 average rating, 135 reviews

Sun filled single level retreat, outdoor shower

Wonderful 3 Bed, 2 full bath single floor home. Bedrooms on two separate wings. Fully stocked kitchen with center island and breakfast bar. Large living room, vaulted ceiling exposed beams, floor to ceiling windows overlooking private backyard. Central A/C, wifi, smart TVs, washer/dryer, outdoor seating/eating, fire-pit, outdoor shower. Very close to Cape Cod Rail bike path, restaurants, Beaches, Nickerson State Park, golfing, shopping. Dog allowed by request; $30 per night or $150 per week.

Top guest favorite
A charming cottage exterior is framed by blooming cherry blossom trees. A light-colored deck features a small café table with chairs, surrounded by various potted flowers. Large windows allow natural light to fill the interior, enhancing the welcoming ambiance of the outdoor space.
Guesthouse in Brewster
4.92 out of 5 average rating, 270 reviews

Charming Antique Cape Cod Cottage

Our cottage is situated in a lovely, landscaped yard with a private deck and back yard for our guests. We have a self check in that allows for privacy. While there is a feeling of privacy, you are close to stores and other conveniences. There are many walking trails nearby and beaches for outdoor activities. Perfect location for getting away or seeking adventure. Be sure to check out our fall and holiday specials. OCTOBER, NOVEMBER AND DECEMBER - BOOK 3 NIGHTS GET FOURTH NIGHT FREE!

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, 124 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.

Top guest favorite
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, 106 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.

Top guest favorite
Guesthouse in Brewster
4.96 out of 5 average rating, 135 reviews

Brand new, on a secret pond

Welcome to our chic guest house. This brand-new retreat includes a bedroom with king bed, a living room with a sofa bed, smart TV, sleek breakfast bar, and a contemporary bathroom with rainshower and a heated towel rail. Steps away the beach invites you to relax by the water of a semi-private pond next to the rail trail. Welcome to a retreat that strikes the perfect balance between contemporary luxury and the tranquility of nature – for those who appreciate the finer things in life.

Top guest favorite
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, 318 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.

Guest favorite
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, 337 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. TWO KING beds, along with pullout couch allows 6 to sleep comfortably. Linens are included!! Large kitchen with washer/ dryer, AC units and heat throughout the entire unit. Wifi and THREE 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 bright and airy interior space features a light wood table accompanied by two chairs. A comfortable gray sofa is positioned nearby, with decorative cushions adding a touch of color. Large windows allow natural light to fill the room, enhancing a cozy atmosphere.
Cottage in South Dennis
4.88 out of 5 average rating, 468 reviews

Waterfront Cottage on White Pond(Graham Cracker)

Our cottage (Graham Cracker House) sits steps from crystal clear White Pond. The cottage offers private access to the pond for swimming, fishing and boating. The large outdoor space is great for dining and relaxing by the pond. It is 1.5 miles to the Cape Cod rail trail (bike trail), close to many dining options and 3 miles to some of the best beaches Cape Cod has to offer. There is another cottage on the property for rent that sleep 4 guests. No sharks here!

Popular amenities for Brewster vacation rentals

When is the best time to visit Brewster?

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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 200 vacation rentals in East Brewster, over 720 vacation rentals in Pleasant Lake, and over 1,790 vacation rentals in East Harwich.

  • Are there vacation rentals with a dedicated workspace in Brewster?

    Yes! Work meets play with ease at over 220 vacation rentals in Brewster featuring dedicated workspaces. Stay connected and productive 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 170 vacation rentals for guests traveling with pets.

  • 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 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 self check-in?

    Absolutely! We offer over 90 house rentals with self check-in in Brewster. Enjoy a tailored experience with all the comforts you desire.

  • 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 270 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 90 homes with self check-in, over 150 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about vacation rentals in Brewster

  • Total vacation rentals

    Explore 440 vacation rentals in Brewster

  • Nightly prices starting at

    Brewster vacation rentals start at ﺩ.ﺇ184 per night before taxes and fees

  • Verified guest reviews

    Over 16,200 verified reviews to help you choose

  • Family-friendly vacation rentals

    350 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 170 rentals that welcome pets

  • Vacation rentals with a pool

    60 properties feature pools

  • Rentals with dedicated workspaces

    220 properties have a dedicated workspace

  • Wi-Fi availability

    430 of Brewster vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Self check-in, Beachfront, and Gym across Brewster rentals

  • 4.9 Average rating

    Brewster stays are highly rated by guests—averaging 4.9 out of 5!