Find short term rentals in Brewster, MA at the best prices
795 available short term rental offers
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating
Best Short term and Weekly rentals in Brewster, MA
9.1 327 reviews
Brewster, MA
04/08 – 08/08
$1191/nighttotal: $4764 (4 )
By The Sea Guests Bed & Breakfast And Suites
2 4
B&B , Dennis
By The Sea Guests is a charming bed and breakfast located in Dennis Port, Massachusetts, just a stone's throw from the beach. The property enjoys excellent ratings for location, cleanliness, and overall experience. The bed and breakfast offers a variety of rooms with comfortable amenities, including a private bathroom, mini-fridge, and cable TV. Guests can enjoy a range of features, such as a swimming pool, a terrace, a garden, and a bar, as well as a private beach area, a gas fire pit, and a gas grill.
Brewster, MA
06/08 – 10/08
$746/nighttotal: $2984 (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.
9.4 8 reviews
Brewster, MA
18/07 – 25/07
$665/nighttotal: $4655 (7 )
Spacious Harwich Haven Near Round Cove (1116)
3 6
apartment , Harwich
This detached house in Harwich is located on a quiet cul-de-sac, 800 metres from Round Cove on Pleasant Bay, offering convenient access to Chatham and Orleans. The property features four bedrooms accommodating up to eight guests, a well-equipped kitchen, a TV room, a large living room with deck access, a garden with an enclosed outdoor shower, and a gas barbecue, with nearby activities including sailing, surfing, fishing, and cycling.
9.9 26 reviews
Brewster, MA
26/06 – 29/06
$1504/nighttotal: $4512 (3 )
Close To Town And Nauset Beach, Ev Charger, Air Conditioning, Outdoor Shower.
4 6
apartment , Orleans
This apartment is located in Orleans, just a short walk from Baker's Pond and Nickerson State Park, and within easy reach of Nauset and Skaket Beaches. It enjoys a tranquil wooded setting, close to nature and popular beaches, and has received excellent ratings for its location, cleanliness, and overall experience. The property offers 279 square metres of space, comfortably accommodating up to 10 guests across multiple bedrooms. Enjoy modern amenities including central air conditioning, a well-equipped kitchen, a spacious patio with an outdoor shower and fire pit, and a shared landscaped yard.
Brewster, MA
04/08 – 08/08
$1208/nighttotal: $4832 (4 )
Ocean Breezes Await At The Paradise On The Sound
1 4
cottage , Yarmouth
This Yarmouth self-catering property, Paradise on the Sound Cottage, is located in South Yarmouth's Bass River district, a short walk from a private beach and near attractions such as Hyannis Harbour and various Cape Cod beaches. Sleeping up to four guests in one bedroom with a queen and two twin beds, the cottage includes a kitchenette, free Wi-Fi, a Smart TV, access to shared BBQ facilities and beach loungers, and free Xplorie tickets for local discounts.
9.9 15 reviews
Brewster, MA
18/07 – 25/07
$1082/nighttotal: $7574 (7 )
Beautiful Chatham Ma
3 6
apartment , Chatham
This Ryder's Cove property in Chatham, Massachusetts is situated 0.8 km from Jack Knife Beach, 1.6 km from the Wequassett Resort, 4 km from the Chatham Bars Inn, and 4.8 km from Chatham Centre. This three-bedroom house, plus a separate one-bedroom apartment, sleeps six guests and boasts modern amenities including a dishwasher, air conditioning, high-speed internet, smart TVs, solar power, and a backup generator; enjoy the garden and deck, ideally located for exploring Chatham's beaches and resorts.
Brewster, MA
04/08 – 08/08
$824/nighttotal: $3296 (4 )
Charming Cape Cottage In Dennis Port
2 4
cottage , Dennis
This Cape-style house is situated at the end of a quiet road in Dennis Port, less than 1 kilometre from Raycroft Beach and Sea Street Beach, and within walking distance of local shops, dining, and Seaview Park. This 81 square metre dwelling accommodates up to four guests in two bedrooms and offers amenities such as air conditioning, Wi-Fi, a fully equipped kitchen, an outdoor shower, a firepit, and complimentary daily tickets to local attractions through Xplorie, including Island Cruises and Whale Watch.
8.6 18 reviews
Brewster, MA
04/08 – 08/08
$1087/nighttotal: $4348 (4 )
Sunrise And Sunset From Private Beach In Dennis Port! (2132)
2 4
apartment , Dennis
This Dennis Port waterfront flat, approximately 0.03km from Nantucket Sound and a short distance from Old Wharf Village's private beach, offers easy access to the mid-Cape's attractions. The two-bedroom, two-bathroom apartment sleeps four, boasts a well-equipped kitchen including a dishwasher, air conditioning throughout, parking for two cars, and enjoys excellent guest reviews.
Brewster, MA
18/07 – 25/07
$1264/nighttotal: $8848 (7 )
Condo ∙ 3 Bedrooms ∙ 6 Guests
3 6
apartment , Brewster
This three-bedroom, three-bathroom flat within the Ocean Edge Resort in Brewster offers peaceful views of a golf course tee box and is conveniently located within 2 kilometres of local beaches and the Cape Cod Rail Trail. This family-friendly accommodation for six guests includes a fully updated kitchen with stainless steel appliances, air conditioning in all rooms, a swimming pool, garden, tennis court, and parking, with complimentary daily tickets to activities such as golfing, bike and kayak rentals, whale watching, and trips to Martha's Vineyard and Nantucket.
10 15 reviews
Brewster, MA
04/08 – 08/08
$1007/nighttotal: $4028 (4 )
Brand New Custom Built Year Round Cape House
1 4
apartment , Dennis
This Dennis, Massachusetts house is conveniently located near Routes 134 and 6, placing it within a few kilometres of beaches, shops, and restaurants. The four-bedroom, two-bathroom property sleeps eight guests and boasts a fully equipped kitchen with freezer and microwave, air conditioning, garden, parking, and excellent guest reviews; nearby activities include exploring Cape Cod's attractions.
9.9 28 reviews
Brewster, MA
18/07 – 25/07
$668/nighttotal: $4676 (7 )
Minutes To Beach, Bike Trail, Nickerson, & Orleans
1 6
apartment , Brewster
This Brewster, Cape Cod house, located in the Blueberry Pond neighbourhood, is a short walk from Blueberry Pond and its sandy beach, 0.8 km from the Cape Cod Rail Trail and Nickerson State Park, and 2.4 km from Brewster's bay beaches. This three-bedroom, two-bathroom property sleeps up to ten guests and boasts a fully equipped kitchen, a spacious living area, a quiet den, and outdoor amenities including a covered porch, gas grill, and outdoor shower; nearby attractions include the Ocean Edge Resort.
Brewster, MA
26/06 – 29/06
$1088/nighttotal: $3264 (3 )
Dog-friendly Pleasant Lake Cottage In Harwich
3 6
apartment , Harwich
This Harwich holiday cottage is located less than 400 metres from the Cape Cod Rail Trail and within 800 metres of Long Pond, Hinckley's Pond, and Seymour's Pond, with Pizza Shark and a general store nearby. This 153 square metre dwelling accommodates up to six guests and features three bedrooms, one bathroom, a three-season porch, an outdoor shower, a gas grill, central air conditioning, and complimentary daily tickets to local attractions through Xplorie.
Best family friendly Brewster, MA Short term rentals
Among the 795 accommodations in Brewster, MA, here are the 4 best family friendly rentals
8.0 1 review
Brewster, MA
27/06 – 11/07
$491/nighttotal: $6874 (14 )
99 M² Condo ∙ 2 Bedrooms ∙ 5 Guests
2 2
apartment , Brewster
This Ocean Edge townhouse in Brewster, Massachusetts, is conveniently located between Route 6A and Route 137, offering easy access to nautical shops and restaurants, and proximity to attractions such as the Cape Cod Rail Trail and Nickerson State Park. This two-bedroom, two-bathroom holiday home boasts 98 square metres of living space, featuring a remodelled kitchen with granite countertops, updated bathrooms, a patio with a gas grill, and sleeps up to five guests with three twin beds in a loft area and a queen-sized bed in a downstairs bedroom.
10 2 reviews
Brewster, MA
26/06 – 29/06
$1274/nighttotal: $3822 (3 )
Cape Cod Playhouse: Deck, Hot Tub & Games
3 6
apartment , Brewster
This Brewster flat is located in a desirable, quiet neighbourhood, just a few minutes' walk from Linnell Landing Beach, local shops, restaurants, and the Cape Cod Rail Trail. This family-friendly property sleeps up to eight guests across three bedrooms and three bathrooms, featuring a modern kitchen, a bonus room with air hockey and bunk beds, a private hot tub, a fenced garden with a deck and grill, an outdoor shower, and dedicated office space.
Brewster, MA
27/06 – 11/07
$572/nighttotal: $8008 (14 )
Condo ∙ 2 Bedrooms ∙ 6 Guests
2 2
apartment , Brewster
This two-bedroom townhouse is located in the Howland Village at Ocean Edge Resort, Brewster, offering a peaceful resort atmosphere with complimentary weekly activities valued up to £597. Sleeping up to four guests, this property features air conditioning, a kitchen equipped with a fridge, microwave oven, and dishwasher, and access to resort amenities including tennis and pickleball courts.
10 6 reviews
Brewster, MA
27/06 – 11/07
$830/nighttotal: $11620 (14 )
139 M² Condo ∙ 2 Bedrooms ∙ 7 Guests
2 2
apartment , Brewster
This Edinborough Village condo in Ocean Edge, Brewster, offers easy access to Route 6A/Main Street and Route 137, being within walking distance of The Linx Tavern and the Arbor pool complex. This 139 square metre (1,496 square feet) self-catering property sleeps seven guests across two bedrooms and two bathrooms, featuring a modern kitchen, private decks, and access to Ocean Edge Resort amenities (pool passes purchased separately).
Best Brewster, MA lodging with a balcony
9.4 12 reviews
Brewster, MA
26/06 – 29/06
$1861/nighttotal: $5583 (3 )
Renovated Classic Cape W/ Guest House, Game Room!
7 6
apartment , Dennis
This spacious Cape Cod-style holiday home is located in central Dennis Port, a short walk to downtown shops and restaurants and less than 1.1 kilometres from sandy beaches such as Inman Road Beach and West Dennis Beach. This pet-friendly property offers 297 square meters of accommodation across a main house and a separate guest house, sleeping up to 14 guests, and features a dedicated game barn and a large, fenced garden perfect for outdoor activities.
9.6 8 reviews
Brewster, MA
26/06 – 29/06
$2441/nighttotal: $7323 (3 )
Waterfront, Incredible Views And Private Dock!
6 6
apartment , Yarmouth
This South Yarmouth waterfront property offers direct Bass River access with a private dock, close to Wilbur Park and Blue Rock Golf Course. The 271-square-metre (2920 sq ft) holiday home boasts a spacious open-plan layout, sleeps up to 14 guests in six bedrooms and four bathrooms, and includes amenities such as a private dock, propane grill, and Wi-Fi.
10 1 review
Brewster, MA
18/07 – 25/07
$1031/nighttotal: $7217 (7 )
Waterfront Home With Lovely Lake Views, Great Deck, Sun Porch & Fireplace
3 6
apartment , Chatham
This waterfront property in South Chatham offers direct access to Mill Pond with scenic views, and is located 6 kilometres east of downtown Chatham, 1.6 kilometres from Hawksnest State Park, 3.2 kilometres from the Old Colony Rail Trail, and 4.8 kilometres from Forest Beach and Ridgevale Beach. This spacious 193 square metre residence, ideal for up to 10 guests, features an open layout, a sun porch, an eat-in kitchen, a living room with a 60-inch HDTV, three bedrooms, central air conditioning, a washer/dryer, complimentary WiFi, and a lake-facing deck with a gas grill.
9.6 17 reviews
Brewster, MA
26/06 – 29/06
$1165/nighttotal: $3495 (3 )
Beach & Town Walkable:family Friendly Cape Getaway
4 6
apartment , Eastham
This Eastham holiday home is situated within 3.2km of Campground Beach and Thumpertown Beach, offering easy access to Cape Cod's coastline. The four-bedroom, four-bathroom property sleeps eight guests and boasts a fully equipped kitchen, private balcony, garden, free Wi-Fi, and parking; limited housekeeping is provided.
Frequently Asked Questions about short term rentals in Brewster, MA
What are the best short term rentals in Brewster, MA?
Nautical-themed, Light And Bright Townhouse In Ocean Edge Resort's Howland Village!
2 2
apartment , Brewster
This townhouse is located in Brewster, within Ocean Edge Resort's Howland Village, offering proximity to Cape Cod Beaches and the Cape Cod National Seashore. This nautical-themed holiday home sleeps six, featuring two bedrooms, two bathrooms, a remodelled kitchen with a dining area for six, a furnished patio with a grill, and complimentary weekly activities including golf and ferry tickets to Martha's Vineyard & Nantucket.
10 1 review
Brewster, MA
26/06 – 29/06
$940/nighttotal: $2820 (3 )
Roomy 3 Bedroom Home - Perfect For Families!
3 6
apartment , Dennis
This three-bedroom flat in Dennis offers excellent proximity to local attractions and outdoor pursuits. This spacious accommodation for six guests includes central air conditioning, two living areas, a large garden with a deck and private outdoor shower, a BBQ grill, and complimentary daily tickets for attractions like Island Cruises and Whale Watch through Xplorie, alongside golf and mini-golf.
Brewster, MA
18/07 – 25/07
$682/nighttotal: $4774 (7 )
99 M² Condo ∙ 2 Bedrooms ∙ 6 Guests
2 6
apartment , Brewster
This Ocean Edge Resort condominium in Brewster offers convenient access to bay beaches, Nickerson State Park located 1.6 kilometres away, and the Cape Cod Rail Trail. This 98 square metre apartment sleeps up to six guests across two bedrooms and two bathrooms, featuring a private patio with a gas grill, a loft with an Xbox, and complimentary daily tickets for activities such as golf, bike and kayak rentals, and whale watching cruises.
9.6 39 reviews
Brewster, MA
04/08 – 08/08
$747/nighttotal: $2988 (4 )
We Still Have Some Great Weeks Open Plus Aug 4 For A 4 Day Rental Which Is Rare
2 4
apartment , Dennis
This East Dennis house, situated on a double lot 2.2 kilometres from Cold Storage Beach, Sesuit Harbour, and Corporation Beach, offers easy access to Route 6A and local attractions. The 111 square metre single-storey property sleeps up to 8 (owner prefers 6), boasts two bedrooms, two bathrooms, a garden, spa, and parking, plus amenities including a wood stove, fire pits, and a gas grill.
Best Brewster, MA lodging with laundry available
9.9 124 reviews
Brewster, MA
06/08 – 10/08
$888/nighttotal: $3552 (4 )
Walk To West Dennis Beach-fire Pit-outdoor Shower
1 3
apartment , Dennis
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
$753/nighttotal: $5271 (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.
10 3 reviews
Brewster, MA
04/08 – 08/08
$1303/nighttotal: $5212 (4 )
Coastal Haven In West Dennis
3 4
apartment , Dennis
This West Dennis waterfront apartment, a 5-10 minute walk (0.8-1.6km) from the beach, offers easy access to West Dennis Beach, the Cape Cod Rail Trail, and Bass River Golf Course. The 140 square metre property boasts three bedrooms, one bathroom, sleeps six, and includes a fully equipped kitchen with dishwasher, air conditioning, a terrace, garden, parking, and internet access.
Brewster, MA
27/06 – 11/07
$377/nighttotal: $5278 (14 )
52 M² Condo ∙ 1 Bedroom ∙ 4 Guests
1 2
apartment , Brewster
This Fletcher condominium in Brewster offers a recently refurbished one-bedroom, one-bathroom unit with modern kitchen appliances, a queen-size bed, and a Murphy bed in the living area, providing peaceful golf course views and convenient access to bay beaches, local shops, Nickerson State Park, and the Cape Cod Rail Trail. This 52 square meter flat sleeps up to four guests, featuring air conditioning, a fully equipped kitchen with a dishwasher, and on-site parking, making it ideal for families exploring the area's outdoor pursuits like kayaking and cycling.