This West Dennis, Massachusetts holiday home is a seven-minute walk (approximately 0.6km) from West Dennis Beach and 91 metres from Kelley's Pond, ideal for kayaking and fishing. The self-catering property sleeps six guests in two spacious bedrooms plus a sunroom/third bedroom, boasting a fully equipped kitchen, Roku TV, outdoor shower, fire pit, and deck; firewood is provided (guests need to bring kindling).
Brewster, MA
18/07 – 25/07
A$813/nighttotal: A$5691 (7 )
115 M² House ∙ 3 Bedrooms ∙ 8 Guests
3 6
house , Brewster
This dog-friendly cottage in Brewster, Massachusetts, is situated 2.9 kilometres from Crosby Landing Beach and 2.9 kilometres from Nickerson State Park, offering convenient access to local attractions. This 114 square metre holiday home accommodates up to eight guests across three bedrooms and features a fully equipped kitchen, air conditioning throughout, and an outdoor space with a fire pit, with complimentary daily activities such as golf and bike rentals available.
9.6 5 reviews
Brewster, MA
18/07 – 25/07
A$1156/nighttotal: A$8092 (7 )
111 M² Condo ∙ 2 Bedrooms ∙ 6 Guests
2 6
apartment , Brewster
This family-friendly apartment is situated at Ocean Edge Resort on Susanna Drive, Brewster, adjacent to the 15th tee of the Jack Nicklaus-designed golf course and within a 500-meter walk of Route 6A. This spacious 102-square-meter residence offers 2 bedrooms, 2 bathrooms, and accommodates up to 6 guests with an additional 46-square-meter enclosed lofted area featuring two full-size beds, plus complimentary weekly activities including golf and ferry tickets to Martha's Vineyard & Nantucket.
9.8 27 reviews
Brewster, MA
27/06 – 11/07
A$671/nighttotal: A$9394 (14 )
Beautifully Remodeled Classic Beach Home On Cape Cod Rail Trail
4 2
apartment , Orleans
This four-bedroom, two-bathroom residence in Namskaket, Orleans offers excellent proximity to the Cape Cod Rail Trail, just 200 metres away, and Skaket Beach, less than 1.6 kilometres distant. This spacious 151 square metre flat accommodates up to eight guests with its four bedrooms and bonus sleeping area, featuring a fully-stocked kitchen, air conditioning, a terrace, garden with a stone patio and gas grill, complimentary Wi-Fi, and parking for four cars.
Brewster, MA
06/08 – 10/08
A$759/nighttotal: A$3036 (4 )
New For 2026! 1/2 Mile To Swan Pond (2414)
2 3
cottage , Dennis
This Dennis Port seaside cottage, an 8-minute (approximately 13 km) drive from Cape Cod Beaches and Sea Street Beach, offers stunning ocean views. The 76 square metre property sleeps four guests in two bedrooms and one bathroom, boasting a fully equipped kitchen, in-unit laundry, a garden with barbecue, free parking, Wi-Fi, and air conditioning.
Brewster, MA
18/07 – 25/07
A$766/nighttotal: A$5362 (7 )
Condo ∙ 2 Bedrooms ∙ 6 Guests
2 6
apartment , Brewster
This two-bedroom townhouse in Brewster's Billington Village offers a peaceful escape, situated a few hundred metres from the Cape Cod Rail Trail and close to Cape Cod Bay beaches. This family-friendly apartment sleeps six and features a separate living/dining area with a half-bath, two bedrooms and a full bathroom upstairs, air conditioning, Wi-Fi, a swimming pool, and complimentary daily activities including bike and kayak rentals.
Brewster, MA
18/07 – 25/07
A$907/nighttotal: A$6349 (7 )
230 M² House ∙ 3 Bedrooms ∙ 8 Guests
3 6
house , Brewster
This four-bedroom detached house is situated on a quiet cul-de-sac in Brewster, offering convenient access to Sheep Pond, the Cape Cod Rail Trail, and the Brewster Flats. This 214 square meter property accommodates up to eight guests, featuring a modern kitchen, a main-floor den with a sofa bed, a primary queen suite with an en-suite bathroom, and two separate staircases for privacy, with complimentary daily activities including golf, bike and kayak rentals, whale watching, and trips to Martha's Vineyard and Nantucket.
9.4 24 reviews
Brewster, MA
26/06 – 29/06
A$1104/nighttotal: A$3312 (3 )
Areys Pond Point
4 6
house , Orleans
This Orleans beachfront property, Areys Pond Point, boasts stunning ocean views and is situated 14 kilometres from Nauset Lighthouse and 24 kilometres from Wellfleet Bay Wildlife Sanctuary. This four-bedroom, two-bathroom house offers 128 square metres of living space, complete with a fully equipped kitchen, private patio, free Wi-Fi, and parking, comfortably accommodating families or groups.
9.6 10 reviews
Brewster, MA
27/06 – 11/07
A$354/nighttotal: A$4956 (14 )
Eastham Cottage With Ac And Private Back Yard (2217)
2 2
cottage , Eastham
This Eastham seaside holiday home is situated within 3.2km of the Edward Penniman House and Barn, Jonathan Young Windmill, and Eastham Windmill, and under 4.8km from Cape Cod National Seashore and Cape Cod Beaches. The 46 square metre property sleeps four guests in two bedrooms and one bathroom, offering a fully equipped kitchen, including oven, hob, microwave, and fridge, plus outdoor charcoal grills, a TV with DVD player, and a smoke-free environment.
Brewster, MA
18/07 – 25/07
A$773/nighttotal: A$5411 (7 )
House ∙ 3 Bedrooms ∙ 6 Guests
3 6
house , Brewster
This dog-friendly, three-bedroom ranch bungalow in Brewster, Massachusetts, is located in a peaceful residential area bordering Punkhorn Parklands and is just 483 metres from Upper Mill Pond. This property accommodates six guests and features a fully equipped eat-in kitchen, a three-season sun porch overlooking the private garden, and outdoor amenities including a gas grill and an outdoor shower, with complimentary weekly activities such as golf, bike and kayak rentals, whale watching, and trips to Martha's Vineyard and Nantucket included.
Brewster, MA
18/07 – 25/07
A$1202/nighttotal: A$8414 (7 )
Slate & Salt | Beach Walk · Fire Pit & Kids Ready
1 6
apartment , Brewster
This renovated Brewster cape, located less than 1 kilometre from Point of Rocks Beach and Cape Cod Bay, offers convenient access to the Cape Cod Rail Trail and Nickerson State Park. This family-friendly, single-storey holiday home sleeps up to nine guests and features three bedrooms, two bathrooms, a fully equipped kitchen, air conditioning, a private garden with a fire pit and gas grill, and parking for seven cars.
8.8 34 reviews
Brewster, MA
06/08 – 10/08
A$492/nighttotal: A$1968 (4 )
Off Season Rate Of $209/nite For Oct-may
4 3
apartment , Yarmouth
This South Yarmouth waterfront property boasts private beach access to Lily Pond, ideal for swimming, fishing and canoeing, and is within walking distance of Bass River Golf Course, with another course just 0.5 km away and ocean beaches 5 km distant. The four-bedroom, three-bathroom house, sleeping eight, offers a finished basement with family room and office, a garden, parking, air conditioning, Wi-Fi, and child-friendly amenities including a play area; handicapped accessibility is provided throughout.
Best family friendly Brewster, MA holiday rentals
Among the 946 accommodations in Brewster, MA, here are the 4 best family friendly rentals
10 4 reviews
Brewster, MA
27/06 – 11/07
A$814/nighttotal: A$11396 (14 )
111 M² Condo ∙ 2 Bedrooms ∙ 6 Guests
2 2
apartment , Brewster
This Susanna Village patio home in Brewster, Massachusetts offers easy access to Route 6A and Route 137, placing you near Brewster's shops and restaurants. This 110 square metre (1184 square feet) two-bedroom, two-bathroom property sleeps six, boasting a remodeled kitchen, private patio with gas grill, in-unit laundry, free Wi-Fi, and access to the Ocean Edge Resort Golf Club pool (fees apply).
Brewster, MA
06/08 – 10/08
A$713/nighttotal: A$2852 (4 )
28 M² Apartment ∙ 1 Bedroom ∙ 4 Guests
1 3
apartment , Yarmouth
This South Yarmouth studio cottage, part of the Coastal Haven complex, offers exclusive access to a private Nantucket Sound beach and is a short walk from ferries to Nantucket and Martha's Vineyard. Sleeping four in two queen beds, the self-catering property includes a microwave, air conditioning, parking, and free access to local attractions via the Xplorie package (worth £600), plus free golf at Cranberry Valley or Chequessett Golf Courses.
Brewster, MA
18/07 – 25/07
A$920/nighttotal: A$6440 (7 )
149 M² Condo ∙ 3 Bedrooms ∙ 7 Guests
3 6
apartment , Brewster
This premier end-unit villa, located in Endicott Village at Ocean Edge Resort in Brewster, offers private deck views of the 9th green and is a short walk from the Arbor Pool, with proximity to the Cape Cod Rail Trail and Route 6A. This 148 square meter holiday home accommodates up to 7 guests with 3 bedrooms and 3 bathrooms, featuring a fully equipped kitchen with granite countertops, air conditioning, Wi-Fi, and includes a Sports Membership for resort amenities, plus complimentary daily activities for stays up to 27 nights.
9.0 301 reviews
Brewster, MA
26/06 – 29/06
A$812/nighttotal: A$2436 (3 )
Riverview Resort
1 6
resort , Yarmouth
Riverview Resort, A Vri Resort, is located on Cape Cod, just under 3 kilometres from Yarmouth's beaches and a 5-minute walk from restaurants and Pirates Cove Adventure Golf. This family-friendly resort has consistently received excellent ratings for its location, cleanliness, and overall experience. The resort offers modern suites with amenities like HD cable TV, free Wi-Fi, DVD players, kitchenettes, and sleeper sofas. Guests can enjoy a range of on-site facilities, including an indoor pool, hot tub, fitness centre, spa, bar, and room service.
Best Brewster, MA holiday rentals with a pool
Among the 946 accommodations in Brewster, MA, here are the 4 best rentals with a pool
10 6 reviews
Brewster, MA
18/07 – 25/07
A$4970/nighttotal: A$34790 (7 )
Exclusive Harwich Haven: Pool, Spa And More Rpam068
4 6
apartment , Harwich
This spacious four-bedroom holiday home is located just a short drive from the beautiful Cape Cod Beaches and the popular Captains Golf Club, making it an ideal base for exploring the area. The surrounding area is known for its peaceful atmosphere and stunning natural beauty. The property offers ample space for families and groups, with a capacity of up to 10 guests. It features a fully equipped kitchen, a comfortable living area, and a private pool and hot tub, ensuring a relaxing and enjoyable stay.
8.2 1395 reviews
Brewster, MA
06/08 – 10/08
A$1028/nighttotal: A$4112 (4 )
Riviera Beach Resort
1 3
resort , Yarmouth
The Riviera Beach Resort is located on a private beach in Yarmouth, Cape Cod, with stunning views of Nantucket Sound and easy access to the Blue Rock Golf Course. The resort has received very good user ratings, an excellent location rating and a good cleanliness rating. The resort offers a range of amenities for a comfortable stay. Guests can enjoy a swimming pool, a jacuzzi, a spa, a restaurant, a bar, a fitness centre, room service, valet parking and a private beach.
8.3 2767 reviews
Brewster, MA
27/06 – 11/07
A$958/nighttotal: A$13412 (14 )
The Mansion At Ocean Edge Resort & Golf Club
1 2
resort , Brewster
The Mansion at Ocean Edge Resort and Golf Club is located in Brewster, a short drive from the Cape Cod Museum of Natural History and the Wellfleet Drive-In Theater & Cinemas. It has consistently received very good ratings for location, cleanliness, and overall user experience. The resort offers a range of accommodation options, including guest rooms with patios or balconies and villas with full kitchens and living rooms. Guests can enjoy a private beach, two swimming pools, a spa, a fitness centre, tennis courts, and a variety of dining options, including a pub, a tavern, and a seasonal terrace.
Brewster, MA
18/07 – 25/07
A$2511/nighttotal: A$17577 (7 )
Private Pool, Game Room & Tons Of Fun In Harwich Rpam118
4 6
apartment , Harwich
This Harwich holiday home offers a central location within 1.5 kilometres of Harwich Port, Dennis Port, and Nantucket Sound beaches, with shops and dining a short walk away. This 256 square metre detached house sleeps up to 8 guests across four bedrooms, featuring a private heated saltwater pool, a games room with shuffleboard and arcade machines, and complimentary beach gear.
Frequently asked questions about holiday rentals in Brewster, MA
What are the local dishes in Brewster, MA region?
The local cuisine in Brewster is all about fresh seafood. You'll find plenty of restaurants serving up classic dishes like clam chowder, lobster rolls, and fried clams. Don't miss the opportunity to try some local specialties, such as Cape Cod oysters and fresh-caught fish. You'll also find plenty of restaurants serving up other types of cuisines, from Italian to Asian.
What are the best Airbnb and holiday rentals in Brewster, MA?
This West Dennis, Massachusetts property is a short 0.8-1.6 km walk from West Dennis beaches. The 140 square metre house sleeps six, boasting three bedrooms, one bathroom, a fully equipped kitchen, and a spa, plus parking and internet access; nearby attractions include restaurants and shops.
9.9 35 reviews
Brewster, MA
18/07 – 25/07
A$1104/nighttotal: A$7728 (7 )
Beautiful Home W/ Artistic Flair!
3 6
apartment , Chatham
This charming house is located near the sea in Chatham, within easy reach of the Chatham Chamber of Commerce, Cape Cod Beaches, Forest Beach and Cockle Cove Beach. It has consistently received excellent ratings for its location, cleanliness and overall experience. This three-bedroom, three-bathroom property offers 143 square metres of space and can comfortably accommodate up to seven guests. The house features a garden, barbecue grills, a fireplace, a fully equipped kitchen with a fridge, microwave, and washing machine, and a TV in the living area.
Brewster, MA
27/06 – 11/07
A$1237/nighttotal: A$17318 (14 )
1 Mile To Red River Beach, Game Room, Central Ac!
4 2
apartment , Harwich
This Harwich Port property is situated 1.6 kilometres from Red River Beach and 1.4 kilometres from Brax Landing and Saquatucket Harbour, offering easy access to maritime activities and local amenities. This spacious 184 square metre detached house accommodates up to 10 guests with 4 bedrooms and 3 bathrooms, featuring a private garden with BBQ, a game room with ping pong, and a gas fireplace, with sheets and towels provided.
8.9 643 reviews
Brewster, MA
06/08 – 10/08
A$1180/nighttotal: A$4720 (4 )
Red Jacket Beach Resort
1 3
resort , Yarmouth
The Red Jacket Beach Resort is located on Cape Cod's Nantucket Sound in South Yarmouth, Massachusetts, just a short drive from the popular tourist destination of Hyannis. The resort has received very good ratings for its cleanliness and overall experience, and an excellent rating for its location. The hotel has a range of facilities for guests to enjoy, including private beach access, outdoor and indoor pools, a spa, and a concierge service. Guests can also take advantage of on-site dining, tennis and shuffleboard courts, and a fitness centre.
Best Brewster, MA holiday rentals with parking
Brewster, MA
27/06 – 11/07
A$1459/nighttotal: A$20426 (14 )
Coastal Retreat
4 2
house , Brewster
This Coastal Retreat in Brewster is a detached house located a 13-minute walk from Crosby Landing Beach, 16 kilometres from Nauset Lighthouse, 18 kilometres from Wellfleet Bay Wildlife Sanctuary, and 19 kilometres from Cape Cod National Seashore. This detached house offers 289 square metres of living space, accommodating up to 15 guests with 4 bedrooms and 3 bathrooms, and includes complimentary Wi-Fi and private parking, with a strict no-smoking and no-party policy for a peaceful stay.
Brewster, MA
26/06 – 29/06
A$1044/nighttotal: A$3132 (3 )
Wellfleet Retreat Near The Drive In
3 6
apartment , Wellfleet
This Wellfleet flat is located rurally, providing straightforward access to Cape Cod Beaches and Cape Cod National Seashore, with Ocean Edge Golf Club a short drive away. This accommodation offers three bedrooms accommodating six guests, featuring a fully equipped kitchen, air conditioning, a terrace, garden with a grill and fire pit, and on-site laundry facilities, with opportunities for jet skiing, windsurfing, cycling, and hiking nearby.
Brewster, MA
26/06 – 29/06
A$1097/nighttotal: A$3291 (3 )
Bright & Cozy Harwich Getaway Near Beach & Trails
3 6
apartment , Harwich
This Harwich Port holiday home, situated in a peaceful cul-de-sac, is 3.2km from Red River Beach, 4km from Harwich Port's shops and restaurants, and 1km from Thompson's Field. The 187 square metre property boasts three bedrooms, three bathrooms, two living rooms, a sun-drenched deck with BBQ, and accommodates up to six guests, offering a fully equipped kitchen, in-unit laundry, and parking; pets are welcome (maximum two, small fee applies).
9.7 3 reviews
Brewster, MA
26/06 – 29/06
A$1238/nighttotal: A$3714 (3 )
4 Bedroom Home By Leavetown Vacations
4 6
house , Eastham
This Eastham holiday home is conveniently located a short walk from Campground Beach and within a few kilometres of Kingsbury Beach, Nauset Lighthouse, and Cape Cod National Seashore. This spacious 209 square metre property boasts four bedrooms, three bathrooms, and can comfortably accommodate fifteen guests, featuring a fully equipped kitchen, air conditioning, private balcony, and free Wi-Fi.