House vacation rentals in Brewster

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.

4.93 out of 5 average rating, 150 reviews

Shop, Swim, Hike, Bike in Historic Brewster

Sunny, air-conditioned, single-floor cottage on 3/4 private wooded acre — a rare combination of seclusion and location on Cape Cod. Breakwater Beach and Sheeps Pond, each 1.3 miles away: ocean one day calm freshwater the next. The Cape Cod Rail Trail is a one-minute bike ride; Brewster Store and the Scoop are a half-mile stroll. Gather around the fire pit, rinse at the outdoor shower, and sleep well on newer mattresses. Beach chairs and toys included. Ample parking. Note Airbnb increased price.

LocationValueCheck-in

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.

4.83 out of 5 average rating, 206 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.

LocationValueLong stay

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.

4.87 out of 5 average rating, 245 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.

ValueLocationComfort

The exterior of the single-floor home is showcased, featuring a gabled roof and large floor-to-ceiling windows. A private deck extends from the house, with outdoor seating visible. Lush greenery surrounds the home, creating a serene, park-like atmosphere.

4.87 out of 5 average rating, 139 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.

ValueFamilyAir conditioning

Superhost

A modern kitchen features butcher block counters and a spacious island. Black cabinets and white cabinetry provide a clean contrast. A dual range with a double oven is present. Multiple windows allow natural light, and artwork adorns the walls. Dining areas with tables and black chairs are visible.

4.91 out of 5 average rating, 91 reviews

Brewster Hideaway

Sunny, modern, open concept home with sunken living room and kitchen. Location affords privacy and natural, mature landscaping abutting conservation wetland. Chef's kitchen includes butcher block counters, 48 inch induction and gas range with double oven. Bike path access 1/4 mile down the road. Breakwater Beach on the bay side is a short 1.5 miles, Fisherman's Landing for freshwater swimming at Sheep Pond is 1.1 miles. Central location provides access to many restaurant and shopping options.

ValueLocationLayout

The backyard deck features a hot tub, surrounded by a spacious area for outdoor dining. A large table with multiple chairs is positioned on the deck, creating an inviting space for relaxation. Lush greenery and trees provide a natural backdrop.

5.0 out of 5 average rating, 96 reviews

Retreat by the Hot Tub & Fire Pit, Dog-Friendly!

This prime location is just over a mile from Main Street Brewster, Ocean Edge Resort & Golf Course, and Cape Cod Bay for the family-friendly Brewster Flats beaches. Bike down to the Cape Cod Rail Trail, or go on a hike at Nickerson State Park just around the corner. A 10-minute drive takes you to the closest grocery store in Dennis, Harwich, or Orleans, and beaches along the National Seashore. At home, enjoy wonderful amenities like the hot tub, fire pit, full kitchen, movie, and game nights!

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A modern kitchen features sleek white cabinets and stainless steel appliances, including a double door refrigerator. A spacious island with seating for four is highlighted, while a wooden dining table accommodates additional guests. Natural light filters through multiple windows, illuminating the light wood flooring.

5.0 out of 5 average rating, 70 reviews

Renovated Beach House, Central AC, Private Ponds

Renovated Cape Cod vacation home, centrally located in Brewster near beaches, abutting conservation land in a quiet private neighborhood. Steps from scenic Greenland Pond, Long Pond, and close to Cape Cod Rail Trail, downtown Brewster, and mid-Cape attractions. Enjoy stunning sunsets and swimming at nearby ponds and visit local beaches. Enjoy newer furnishings, fast WiFi, stocked kitchen, 2 smart TVs, comfy beds, workspace, finished basement, patio with fire pit and outdoor furniture.

LocationFamilyDecor

A spacious, modern kitchen area features a large island with a dark base and white countertops, accented by pendant lights above. To the side, an open concept living space includes a comfortable seating arrangement and dining area, with natural light streaming in through large windows.

4.99 out of 5 average rating, 135 reviews

Spacious cottage beach Wychmere < 4 min Central AC

Entire spacious newly renovated modern cottage in Harwich Port. Open concept living room with a large kitchen island. Great space for families ! Bank street Beach and Wychmere Beach Club wedding venue are 4 min drive from us ! We’re very close to Harwich Port downtown with great restaurants. We’re centrally located, close to Chatham, Brewster and Dennis. Freedom Cruise Line ferry to Nantucket at the end of our street. Enjoy the bike trail nearby with rental location if needed.

LocationFamilySleep quality

A bright living area features large windows overlooking a scenic marshland and ocean view. A cozy cream-colored couch and an armchair are positioned near a glass coffee table, inviting relaxation. Natural light fills the space, enhancing the tranquil ambiance.

4.97 out of 5 average rating, 177 reviews

The Osprey Nest - Beach house with stunning views

The Osprey Nest is a classic Cape Cod beach house just steps to the ocean with panoramic views across the protected marsh. A cozy and timeless retreat, with modern amenities and spacious and light-filled rooms. This home has been in my family since the 1960’s and you will feel the warmth and charm the minute you step in the door. The location is perfect for nature lovers but within 10 minutes of stores, restaurants, and charming towns. A perfect base for Cape Cod sightseeing.

LocationFamilyCheck-in

4.93 out of 5 average rating, 164 reviews

4BR/3B | Walk2Pond | Screened Porch | FireTbl | AC

Relax at this spacious mid-Cape retreat on a quiet private road, just a 5-minute walk to a private swimming beach and pond. Canoe included! Sleeps 8 with 4 bedrooms (2 on the main level, 2 upstairs) and 3 full baths with bidets. Enjoy central A/C, hardwood floors, a screened porch, 65" OLED TV, gas stove, gas fire table and grill, ping pong, and wooded yard. Convenient main-level washer/dryer. Near the Cape Cod Rail Trail, beaches, golf, tennis, boating.

ValueFamilyWalkability

4.93 out of 5 average rating, 339 reviews

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

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.

ValueFamilyComfort

An inviting living area features a comfortable seating arrangement with a grey sofa and an accent chair. A dining table is visible, accompanied by floral arrangements. Warm light filters through large windows, illuminating the space, while a fireplace and decorative elements enhance the cozy atmosphere.

4.99 out of 5 average rating, 216 reviews

SeaPeace Cottage-East Brewster Deck,Firepit,W/D AC

• Fully equipped + stocked kitchen • Driveway parking for 3 vehicle + boat • Outdoor fire pit + hammock • Enclosed outdoor hot shower + sink • Access to private Blueberry Pond • Private deck Weber gas grill Cape Cod corn Hole yard game • Onsite washer + dryer • 15min drive to Chatham • 10min drive to Orleans Stroll to Nickerson State Park 6 Adirondack chairs Sea Peace Cottage-East Brewster

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Popular amenities for Brewster house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.96 out of 5 average rating, 145 reviews

The expansive pool, surrounded by a landscaped yard, features a vibrant blue surface reflecting the clear sky. Comfortable lounge chairs are positioned alongside, inviting relaxation. A floating inflatable adds a playful touch to the tranquil setting.

Home in Cotuit

Private Pool, near beaches, 3 BR/3 BA, Central Air

FamilyLocationNearby

4.98 out of 5 average rating, 54 reviews

Modern Cape, Private Heated Pool, Beach, Golf

FamilyValueOutdoor spaces

4.92 out of 5 average rating, 52 reviews

A spacious outdoor area is highlighted by a seasonal heated pool surrounded by a wooden deck. Multiple blue lounge chairs are arranged around the pool, and a fire pit table is situated at the center. A large checkers board and garden beds add to the inviting atmosphere.

Home in Yarmouth Port

Winslow Acres [heated] Pool Escape; pool May-Oct

LocationFamilySleep quality

5.0 out of 5 average rating, 5 reviews

Home in West Yarmouth

Coastal Luxury Oasis - Ag2 Luxury Home

LocationFamilyGrill

A spacious backyard is featured, highlighting a refreshing oval pool surrounded by a textured patio. Lounge chairs are positioned for relaxation under the sun. Lush greenery and trees provide a natural border, while a well-kept lawn enhances the inviting outdoor space.

5.0 out of 5 average rating, 14 reviews

Pool. Hot Tub. Game Room. Walk to Beach. Luxury!

ValueFamilyCheck-in

An aerial view showcases a tranquil swimming pool surrounded by a spacious lawn. Adjacent seating areas, including sun loungers and a fire pit with chairs, are positioned within the private fenced yard. Lush greenery and garden beds enhance the outdoor space.

5.0 out of 5 average rating, 42 reviews

Harwich Haven: Pool & Fire Pit

LocationValueBeach

An inviting outdoor space showcases a rectangular pool surrounded by a spacious patio. Lounge chairs are placed for relaxation, and an umbrella provides shade near the water. Lush greenery frames the area, enhancing the natural setting of the home.

4.95 out of 5 average rating, 62 reviews

Amazing Chatham Pool/patio/deck, 5 BR 4 1/2 Bath

FamilyLocationSleep quality

5.0 out of 5 average rating, 11 reviews

Home in East Dennis

Charming Cape Escape with Pool, Hot Tub & Fire Pit

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Weekly house rentals

A charming exterior of a Cape Cod house is framed by verdant trees and a gravel driveway. The structure features a pitched roof, large windows, and a welcoming front porch with seating arrangements. Lush greenery surrounds the property, enhancing its serene rural setting.

4.94 out of 5 average rating, 64 reviews

Bayside retreat - Brewster flats

ValueLocationBeach

An outdoor seating area is presented with plush, striped furniture and a large firepit at the center. A bright turquoise umbrella provides shade, while the tranquil waterfront view showcases shimmering water and greenery. Potted flowers add a touch of color to the serene setting.

4.96 out of 5 average rating, 84 reviews

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

ValueLocationSleep quality

A vibrant garden displays blooming red roses and a variety of colorful flowers. An earthenware pot adds earthy tones, complementing the lush greenery. A rustic shed with wooden shutters serves as a backdrop to this lively scene, offering a glimpse of tranquility.

4.99 out of 5 average rating, 91 reviews

“Rooster Cottage and Gardens” Entire Private Home

LocationFamilyLaundry

5.0 out of 5 average rating, 30 reviews

The Brewster Pearl Brewster 3 bed 2 bath

LocationValueCheckout

4.98 out of 5 average rating, 52 reviews

Beautiful 4 bed/3 bath in Brewster, MA

FamilyLocationSleep quality

5.0 out of 5 average rating, 29 reviews

The Roost with path to beach

FamilyLocationParks

4.83 out of 5 average rating, 6 reviews

Your Home Away From Home!

FamilyLocationComfort

4.97 out of 5 average rating, 60 reviews

Cheerful and spacious 3BR, indoor fireplace

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Private house rentals

A cozy sleeping area showcases a patterned bedspread with floral designs, complemented by matching pillows and a neatly arranged stack of towels. A bedside table holds a lamp and a small bouquet, while a striking floral wallpaper adds warmth to the room.

4.96 out of 5 average rating, 84 reviews

Luxury Beach House! Firepit&PetoK&2Kingbeds

FamilyLocationCondition

5.0 out of 5 average rating, 5 reviews

Blueberry Pond Sanctuary by Cape Cod Rail Trail

FamilyLocationBiking

Outdoor lounge seating is arranged on a patio with a neutral rug. Cushions adorned with colorful patterns add a touch of comfort. Lush greenery surrounds the area, creating a serene atmosphere, while sunlight filters through the trees, enhancing the inviting setting.

4.94 out of 5 average rating, 18 reviews

Stunning Renovated Home Near Chatham & Beaches

FamilyLocationKitchen

5.0 out of 5 average rating, 7 reviews

3BR Pond Views | Private Beach & Kayaks

FamilyLocationParking

5.0 out of 5 average rating, 18 reviews

Home in Eastham

10 min walk to Beach - Amazing View & Huge Deck

FamilyLocationAccuracy

A sandy beach area is shown, populated with visitors enjoying the sun and water activities. Small boats are visible in the distance, while people are seen wearing casual summer attire. Beach chairs and umbrellas are scattered throughout the shoreline.

5.0 out of 5 average rating, 29 reviews

The Chatham Bars White Foam House Steps From Beach

FamilyLocationNearby

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.

4.97 out of 5 average rating, 34 reviews

Charming Cape Cod Retreat–Walk to Long Pond Beach!

ValueFamilyAccuracy

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.