House holiday 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, 146 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!

4.98 out of 5 average rating, 106 reviews

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.

Home in Harwich Port

Spacious Modern Cottage, beach& Wychmere <1.4mile

Entire spacious newly renovated modern cottage in Harwich Port. Sun filled open concept living room with a large kitchen island. Great for families ! Less than 4 min drive to Red River beach and Bank street Beach. 3 min drive to Wychmere Beach Club wedding venue. Close to Harwich Port downtown. Centrally located, close to Chatham, Brewster and Dennis. Freedom Cruise Line ferry to Nantucket at the end of our street. Enjoy a hike to Harwich Thompson's field Conservation area. Close to bike trail

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, 195 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.

4.86 out of 5 average rating, 219 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.

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.

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!

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.

4.92 out of 5 average rating, 148 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

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.

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.

4.96 out of 5 average rating, 214 reviews

A tranquil scene captures a couple seated on a dock, surrounded by tall green grasses. The calm water reflects soft hues of pink and blue from the sunset, creating a serene backdrop of trees across the pond.

Home in Dennis Port

Lakefront House/Private Dock/Year Round Hot Tub/AC

Beautiful cottage nestled on a half-acre of waterfront property on Swan Pond. The dock offers direct water access. Available are two kayaks, a canoe and two paddleboards. The kitchen offers beautiful views of the water while you enjoy your morning coffee. Local beaches are just minutes away. Enjoy the hammock, swings, hot tub, grill, outdoor fire pits and cocktails on the deck. Wanderers' Rest is located close to bike trails, boat rentals, movie theaters, restaurants, and bars.

4.97 out of 5 average rating, 152 reviews

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.

Home in Chatham

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.

4.93 out of 5 average rating, 318 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. 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.

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...

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, 201 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

Popular amenities for Brewster house rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.9 out of 5 average rating, 29 reviews

A private pool area is highlighted, featuring a rectangular pool surrounded by lounge chairs and umbrellas. Lush greenery and a white fence provide a serene backdrop, while the sun casts a warm glow over the inviting space.

Home in Chatham

Walk 2Beach, Pool, Hot Tub, GameRoom, PetsOK

5 out of 5 average rating, 32 reviews

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.

Home in Harwich Center

Harwich Haven: Pool & Fire Pit

5 out of 5 average rating, 43 reviews

An aerial view captures the estate's expansive layout, featuring two charming buildings, a central saltwater pool, and a clay tennis court. Surrounded by greenery, the property showcases landscaped areas and pathways, creating an inviting outdoor space suitable for various activities.

Home in East Sandwich

XL Estate: 2 Homes-Pool-Tennis-Game Barn - 20 ppl

5 out of 5 average rating, 18 reviews

Home in East Dennis

Sleeps 12 near beach. Hot tub game room

4.81 out of 5 average rating, 31 reviews

An inviting outdoor space is depicted, featuring a spacious in-ground pool surrounded by lounge chairs. String lights are strung across the pool area, illuminating the backyard. A pool house and umbrellas provide additional amenities, while the home's facade is visible in the background.

Home in Barnstable

Stunning Cape Home - Inground Pool, 5 Min To Beach

4.91 out of 5 average rating, 33 reviews

The backyard features an inground pool illuminated at night, surrounded by wooden decking. Nearby, a shed with white shutters enhances the outdoor space, while lush greenery provides a serene backdrop.

Home in Orleans

5-bedroom Cape with a pool and yard games.

5 out of 5 average rating, 8 reviews

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.

Home in Chatham

Heated Pool. Hot Tub. Game Room. Beach Nearby!

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.

4.98 out of 5 average rating, 42 reviews

Modern Cape, Private Salt Water Pool, Beaches-Golf

Weekly house rentals

The exterior of a traditional Cape style home is surrounded by lush greenery and blooming flowers. A pathway leads to the welcoming front porch, with large windows allowing natural light to illuminate the interior. Soft sunlight filters through the trees overhead, enhancing the serene landscape.

5 out of 5 average rating, 31 reviews

Brewster Cape House

4.95 out of 5 average rating, 22 reviews

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

Charming Cape Cod Retreat–Walk to Long Pond Beach!

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.

4.9 out of 5 average rating, 83 reviews

Brewster Hideaway

5 out of 5 average rating, 18 reviews

A bright and inviting living area showcases a cozy seating arrangement with plush, white sofas surrounding a light wooden coffee table. A brick fireplace adds warmth, complemented by a large wall-mounted television above. Soft lighting enhances the space, creating a welcoming atmosphere for relaxation.

Home in Harwich Center

Luxury 4 BR 1780s Cape, Near Wychmere, 3 King Beds

5 out of 5 average rating, 55 reviews

A comfortable living area features two light gray sofas adorned with red nautical-patterned pillows, positioned around a dark coffee table. A flat-screen TV is mounted above a brick fireplace. To the side, a dining area with a black table and two chairs is visible.

Home in South Dennis

Family Retreat in the Heart of Cape Cod!

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.

4.93 out of 5 average rating, 97 reviews

Brewster Bay Getaway; walk to private & pub. beach

An open-concept kitchen and dining area is highlighted by large windows providing natural light. A wooden dining table with six chairs is centered on a patterned rug. The kitchen features modern appliances and a view of the upper loft area, enhancing the spacious feel.

4.98 out of 5 average rating, 49 reviews

Cheerful and spacious 3BR, indoor fireplace

4.96 out of 5 average rating, 28 reviews

Walk to Beach from Sea Salt Cottage

Private house rentals

5 out of 5 average rating, 6 reviews

A warm bedroom features vaulted wooden ceilings with exposed beams. A spacious bed is adorned with light-colored bedding, and a fireplace is located nearby. A desk with a chair is positioned beside a sliding glass door that opens to a balcony, allowing for natural light and scenic views.

Home in Harwich

Lakeside Retreat in Pleasant Lake

5 out of 5 average rating, 24 reviews

Home in South Yarmouth

Villa Costa

A well-lit kitchen area features a wooden dining table with six chairs, adorned with a floral centerpiece. Open cabinetry displays kitchen essentials, and modern appliances are visible. Natural light streams through multiple windows, illuminating the polished wooden floor and creating an inviting atmosphere.

5 out of 5 average rating, 15 reviews

Cape Escape -Rare Peak Season 2 night Minimum

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, 50 reviews

Bayside retreat - Brewster flats

5 out of 5 average rating, 11 reviews

NEW! Water Views + Dog Friendly Cape Cod Retreat

A bright living area features vaulted ceilings with skylights, enhancing natural light throughout the space. A comfortable couch and modern armchair are positioned around a rustic coffee table. A dining area with seating and views of the pond can be seen through large glass doors.

5 out of 5 average rating, 9 reviews

The Pond House - Brewster

4.97 out of 5 average rating, 37 reviews

A sunlit sun porch features large windows framing views of greenery. A white sofa is adorned with striped and patterned cushions, accompanied by two green chairs. A small table with decorative items is positioned in the center, enhancing the relaxed ambiance of the space.

Home in Harwich

Sun filled home ready for you to enjoy!