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 favourite
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, 237 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.

Top guest favourite
A spacious sleeping area is highlighted by a king-sized bed adorned with white linens and accented with yellow pillows. A vintage-style claw-foot tub is positioned nearby against a backdrop of richly textured green tiles. Natural light floods the room through a window, complemented by decorative plants.
Guesthouse in Brewster
4.96 out of 5 average rating, 24 reviews

Claw Foot Tub & King Bed at Club Tanuki Cottage

Glorious gardens and bay breezes! King-sized Casper bed in romantic antique Cape Cod studio cottage with private entrance & patio, in-room double-slipper claw foot tub, luxe bath amenities, Brooklinen sheets. Just renovated soup-to-nuts! Marble & antique wooden floors, decorated with rotating collection of antiques, original local art & great light. Nestled along historic route 6A (Main Street) near other galleries, museums, walking trails, ponds and beaches; 90 seconds to closest beach.

Top guest favourite
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, 127 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 favourite
The exterior of the Brewster Farmhouse is showcased, featuring a charming stone facade with green trim. A well-maintained yard surrounds the house, adorned with autumn foliage. The entryway includes two large windows framed by shrubs, with a welcoming double door at the center.
Home in Brewster
4.98 out of 5 average rating, 101 reviews

Cape Cod Farmhouse: Walk to the Beach in Brewster!

Defined by understated furnishings throughout, The Brewster Farmhouse is a serene beach retreat, right across the street from Ocean Edge Resort and a 10 minute walk to Ellis Landing Beach. Total of 3 bedrooms and 4 full bathrooms, with central AC and heating. All bedrooms have queen-sized beds, and their own private, en-suite bathrooms. Right next door to cute antique shops, art galleries, and boutique farms. Close walk or drive to all of the best restaurants and cafes in Brewster!

Top guest favourite
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, 320 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 favourite
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, 182 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.

Guest favourite
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
4.89 out of 5 average rating, 349 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!

Guest favourite
The cottage's exterior features a light blue door, framed by multiple windows with green shutters. A walkway leads to the entrance, bordered by low greenery and natural landscaping, creating an inviting and serene environment. A tall tree provides shade to the front yard.
Home in Brewster
5 out of 5 average rating, 16 reviews

The Getaweigh: Walk to private beach & town!

Our newly renovated beach cottage is in the Pineland Park private community and is a short 5 minute walk to a beautiful private community beach available to you! The cottage features a spacious open concept living area with sky lights and a brand new kitchen, bathroom, living space and central air. Outdoors space has an oversized deck, grill and shower. Walk to locally owned bookstore, restaurants and Cape Cod Rail Trail. Sheets and towels are not provided.

Guest favourite
An open living area features a comfortable gray sofa facing a round dining table and chairs. A full kitchen is equipped with modern appliances, including a stainless steel refrigerator. Natural light brightens the space through large windows, complemented by light-colored wooden flooring.
Cottage in South Dennis
4.86 out of 5 average rating, 585 reviews

Beachfront Cottage on White Pond (Marshmallow)

Our Cottage sits directly on White Pond tucked away on acres of private property. Our cottage offers a private beach, deck, outdoor shower, outdoor dining area all while enjoying Cape Cod. White Pond is ideal for swimming, boating and fishing. The bike path and well known beaches are less than 2 miles and near to many delicious restaurants. There is another cottage on this property that sleeps four if you have other guest wanting to join

Guest favourite
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, 285 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...

Top guest favourite
Guesthouse in Brewster
4.9 out of 5 average rating, 51 reviews

Cape Cod beach inspired “Makondo” Suit Apartment!

Private, beach-inspired suite perfect for couples or small families. Makondo is fully independent with its own entrance, outdoor space, and parking. Relax in a bright coastal interior with full kitchen, washer/dryer, AC, and comfy sleeping options. Minutes to Cape Cod beaches, walking trails, and local attractions. Peaceful, clean, and thoughtfully designed for a relaxing getaway. Pet friendly (fee applies).

Top guest favourite
A quaint tiny home is framed by lush greenery, featuring large windows that allow natural light to fill the interior. The exterior includes a spacious deck surrounded by trees and stone pathways, enhancing the connection to nature.
Tiny homes in Brewster
4.97 out of 5 average rating, 126 reviews

Waterfront Romantic get away Nest

Prepare to be swept away by breathtaking panoramic views and bountiful wildlife. This is a secluded romantic getaway that is tucked back in the corner on our historic 9 acre cranberry bog and adjacent pond. Enjoy private pond access. Boats and fishing gear available for your enjoyment. The Nest tiny home is built Eco-Friendly and compliments the natural environment to give you and immersive feel.

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 750 vacation rentals in Pleasant Lake, and over 1,860 vacation rentals in East Harwich.

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

    Yes! Work meets play with ease at over 230 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 160 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 80 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 280 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 80 homes with self check-in, over 20 homes with a gym, 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 470 vacation rentals in Brewster

  • Nightly prices starting at

    Brewster vacation rentals start at $84 CAD per night before taxes and fees

  • Verified guest reviews

    Over 16,110 verified reviews to help you choose

  • Family-friendly vacation rentals

    380 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 160 rentals that welcome pets

  • Vacation rentals with a pool

    70 properties feature pools

  • Rentals with dedicated workspaces

    230 properties have a dedicated workspace

  • Wifi availability

    460 of Brewster vacation rentals include wifi 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!