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62 Best cottages in Brewster, MA
Brewster, MA
08/04 – 08/08
$590/nighttotal: $2360 (4 )
Charming Cape Cottage In Dennis Port
2 4
cottage , Dennis
This Cape-style cottage is located in Dennis Port, 0.7 miles from Raycroft Beach and 0.9 miles from Sea Street Beach, with Sunday School Ice Cream Parlor 0.2 miles away. This 870 sq ft dwelling accommodates up to 4 guests in 2 bedrooms and 1 bathroom, featuring air conditioning, Wi-Fi, a full kitchen, keyless entry, a doorbell security camera, and includes $750 of daily Xplorie tickets for local attractions.
Brewster, MA
06/20 – 06/27
$1036/nighttotal: $7252 (7 )
Little Queen - 3 Bedroom Renovated Cottage In Chatham
3 2
cottage , Chatham
This renovated 1860 cottage in South Chatham is located less than a mile from Goose Pond and within walking distance to the Corner Store, offering convenient access to downtown Chatham and Harwichport. This 3-bedroom, 2-bathroom cottage accommodates up to 7 guests and features a chef's kitchen with a Breville espresso maker, organic cotton linens, a soaking tub, and ample outdoor living spaces including a private outdoor shower.
Brewster, MA
06/20 – 06/27
$478/nighttotal: $3346 (7 )
The Coast: Cozy Cape Escape In Dennis Port
2 2
cottage , Dennis
This Dennis Port cottage is located on a quiet road, less than a mile from Raycroft Beach and Sea Street Beach, and within walking distance of Seaview Park and Sunday School Ice Cream Parlor. This 870 sq ft rental accommodates four guests with two bedrooms, one bathroom, and features a full kitchen, air conditioning, and includes $750 of daily free tickets to local attractions through the Xplorie partnership.
Brewster, MA
06/22 – 06/27
$445/nighttotal: $2225 (5 )
New For 2026! 1/2 Mile To Swan Pond (2414)
2 2
cottage , Dennis
This Dennis Port seaside cottage offers stunning ocean views and is an 8-minute drive from both Cape Cod Beaches and Sea Street Beach. The 820-square-foot house features two bedrooms, one bathroom, sleeps four, and includes a fully equipped kitchen, in-unit laundry, Wi-Fi, air conditioning, a garden, and parking.
Brewster, MA
06/20 – 06/27
$500/nighttotal: $3500 (7 )
Peaceful Waterfront Cottage Escape
2 2
cottage , Eastham
This Eastham cottage is located directly on Town Cove with private dock access, situated 2 miles from Rock Harbor Beach and 1.5 miles from the Cape Cod Rail Trail. This 1300 sq ft rental accommodates up to 4 guests with 2 bedrooms and 2 bathrooms, offering amenities like air conditioning, Wi-Fi, a full kitchen, and complimentary daily tickets through Xplorie for local activities.
9.4 34 reviews
Brewster, MA
06/27 – 07/11
$307/nighttotal: $4298 (14 )
Great Location, Beach 4 Minutes Walk, Large Patio And Parking For One Vehicle.
1 2
cottage , Dennis
This studio cottage in Dennis Port is a 4-minute walk to Depot St Beach and very close to local dining like Wee Packet and Sundae School Ice Cream. This 280 square foot dwelling sleeps 3 adults and features a kitchenette, a 3/4 bath, a private backyard with a patio and gas grill, outdoor shower, wireless internet, and both heat and air conditioning.
9.2 25 reviews
Brewster, MA
06/22 – 06/27
$401/nighttotal: $2005 (5 )
Cozy Cape Cottage
1 2
cottage , Brewster
This Brewster cottage rental is conveniently located less than 2 kilometers from Nickerson State Park, Linnell Landing Beach, and Ocean Edge Golf Club, offering easy access to Cape Cod's beaches and attractions. This 500-square-foot vacation home features two bedrooms, one bathroom, and accommodates three guests, complete with a fully equipped kitchen, air conditioning, a patio, and on-site parking.
Brewster, MA
08/04 – 08/08
$864/nighttotal: $3456 (4 )
Catch A Cape Escape At The Tin Lobster
1 4
cottage , Yarmouth
The Tin Lobster cottage, located in South Yarmouth's Bass River district, offers easy access to Nantucket Sound and is a short walk from Pirate's Cove Mini Golf and Bass River Sports World, with convenient proximity to ferries for day trips to Nantucket and Martha's Vineyard. This one-bedroom, one-bathroom vacation home sleeps four guests comfortably with a queen bed and queen sofa bed, a fully equipped kitchen, fireplace, Smart TV, shared BBQ area, and includes $750 in Xplorie tickets for local attractions.
10 1 review
Brewster, MA
08/04 – 08/08
$475/nighttotal: $1900 (4 )
33 M² Cottage ∙ 1 Bedroom ∙ 4 Guests
1 4
cottage , Yarmouth
Luckenbooth Cottage, a South Yarmouth studio, offers a short walk to a private Nantucket Sound beach and convenient access to ferries for Nantucket and Martha's Vineyard day trips. This one-bedroom, one-bathroom unit sleeps four, features a full kitchen with stove, oven, microwave, and fridge, includes a Smart TV and WiFi, and provides access to $750 worth of Xplorie tickets for local attractions.
10 24 reviews
Brewster, MA
06/20 – 06/27
$300/nighttotal: $2100 (7 )
Clean And Cute Brewster Cottage
2 2
cottage , Brewster
This Brewster cottage is located just a tenth of a mile from the Cape Cod Rail Trail and a mile from Brewster's beaches, offering easy access to both scenic bike paths and the beautiful coastline. The 530-square-foot cottage features two bedrooms, one bathroom, and can comfortably accommodate four guests, with amenities including central air conditioning, a full kitchen, and an outdoor shower.
Brewster, MA
06/20 – 06/27
$336/nighttotal: $2352 (7 )
Cozy 1 Bedroom Cottage In Beautiful Orleans With Ac. A Perfect Spot To Get Away.
1 2
cottage , Orleans
This cottage in South Orleans is located near Cape Cod Beaches and Mayflower Beach, a short walk to Orleans Bowling Center and Edward Penniman House and Barn. This 1-bedroom, 1-bathroom cottage accommodates up to 4 guests and offers a microwave oven, air conditioning, parking, and internet, with nearby opportunities for kayaking, motor boating, and fishing.
Brewster, MA
08/04 – 08/08
$587/nighttotal: $2348 (4 )
Luckenbooth Seas The Day By The Sound
1 4
cottage , Yarmouth
This cottage is located in the Bass River neighborhood of South Yarmouth, a short walk from Nantucket Sound and its private beach, with Main Street and Bass River Lighthouse nearby. This 360 square foot rental accommodates up to four guests with a queen bed and a sofa bed, featuring a kitchenette with a fridge and stove, and offering complimentary tickets worth $750 for local attractions like Island Cruises and Whale Watch.
Best Family-Friendly Cottages in Brewster, MA
Kid-friendly cottages in Brewster, MA with room for the whole family to spread out make vacations a breeze.
10 1 review
Brewster, MA
08/04 – 08/08
$475/nighttotal: $1900 (4 )
33 M² Cottage ∙ 1 Bedroom ∙ 4 Guests
1 4
cottage , Yarmouth
Luckenbooth Cottage, a South Yarmouth studio, offers a short walk to a private Nantucket Sound beach and convenient access to ferries for Nantucket and Martha's Vineyard day trips. This one-bedroom, one-bathroom unit sleeps four, features a full kitchen with stove, oven, microwave, and fridge, includes a Smart TV and WiFi, and provides access to $750 worth of Xplorie tickets for local attractions.
9.2 25 reviews
Brewster, MA
06/22 – 06/27
$401/nighttotal: $2005 (5 )
Cozy Cape Cottage
1 2
cottage , Brewster
This Brewster cottage rental is conveniently located less than 2 kilometers from Nickerson State Park, Linnell Landing Beach, and Ocean Edge Golf Club, offering easy access to Cape Cod's beaches and attractions. This 500-square-foot vacation home features two bedrooms, one bathroom, and accommodates three guests, complete with a fully equipped kitchen, air conditioning, a patio, and on-site parking.
Best Brewster, MA cottages with a garden
Brewster, MA
08/04 – 08/08
$439/nighttotal: $1756 (4 )
Yarmouth Cottage Steps To Water Park & Near Beach
1 4
cottage , Yarmouth
This West Yarmouth cottage offers unbeatable proximity to the Cape Cod Inflatable Park, located just steps away, and is minutes from multiple Cape Cod beaches and a 10-minute drive to downtown Hyannis shops, restaurants, and harbor. This 1-bedroom, 1-bathroom rental accommodates up to 4 guests and features a full kitchen, Smart TV, air conditioning, a garden with seating and a fire pit, an outdoor shower, and includes four beach chairs and parking for two vehicles.
8.4 15 reviews
Brewster, MA
06/20 – 06/27
$399/nighttotal: $2793 (7 )
Pets Welcome Near Town & Bike Trail (1471)
3 2
cottage , Orleans
This Orleans, Massachusetts cottage near Cedar Pond offers easy access to Main Street (under 0.5 miles), the Cape Cod Rail Trail (under 0.5 miles), and Skaket Beach (1 mile). This three-bedroom, one-bathroom house sleeps six, features a fully equipped kitchen, a renovated bathroom, a deck with a gas grill, and an enclosed outdoor shower; pets are welcome.
Brewster, MA
08/04 – 08/08
$435/nighttotal: $1740 (4 )
Sweet Memories- Cozy 2 Bedroom Cottage In West Yarmouth
2 4
cottage , Yarmouth
This cottage is located in West Yarmouth, 4 miles from Hyannis and 5 miles from the Cape Cod Mall, with close proximity to a water park and beaches. This 2-bedroom, 1-bathroom vacation rental accommodates up to 4 guests and features a full kitchen, air conditioning, internet, a garden, a spa, and parking, with kayaking, motor boating, and fishing opportunities nearby.
Brewster, MA
08/04 – 08/08
$1051/nighttotal: $4204 (4 )
Screened Porch Overlooking Marsh, Spacious Yard, Patio, Fire Pit, And Close To Beach
2 4
cottage , Eastham
This vacation rental, a cottage in North Eastham, is located 5 miles from South Sunken Meadow Beach and close to the Cape Cod National Seashore. This 700 square foot dwelling accommodates up to 4 guests in 2 bedrooms and features 2 bathrooms, air conditioning, a full kitchen, and on-site laundry, with opportunities for birdwatching and kayaking nearby.
Frequently Asked Questions about cottages in Brewster, MA
What would be a good 1-day itinerary for visiting in and around Brewster, MA?
Start your day with a walk along the beautiful Brewster Beach, then head to the Cape Cod Rail Trail for a bike ride. In the afternoon, visit the Brewster Historical Society Museum to learn about the area's history. You can end your day by enjoying a delicious seafood dinner at one of the many restaurants in town.
You definitely want to see the Brewster Lighthouse, which is a classic Cape Cod landmark. Another must-see is the Cape Cod Rail Trail, a great place for walking, biking, and enjoying the natural beauty of the area. Don't forget to check out the Brewster Historical Society Museum, which has a lot of interesting exhibits about the town's history.
What are the best cottages with a pool in Brewster, MA?
Can you easily explore Brewster, MA on foot or by bike?
Brewster is a pretty walkable town, especially the downtown area. You can easily explore the shops and restaurants on foot. The Cape Cod Rail Trail runs right through town, making it a great place to explore by bike. You can rent bikes at several places in town.
What are the best cottages with a jacuzzi in Brewster, MA?
What activities are available in and around Brewster, MA?
Besides the beach, Brewster offers a lot of activities. You can go kayaking or paddleboarding on the bay, play golf at one of the local courses, or visit the Cape Cod National Seashore. The town also has a number of art galleries and shops to explore.
What are the best cottages for families and kids in Brewster, MA?
What famous towns or cities are near to Brewster, MA?
Brewster is located on Cape Cod, so you're close to a lot of other towns and cities. Provincetown is a popular destination for its art scene and history. Chatham is known for its beautiful beaches and quaint shops. And you're just a short drive from the city of Hyannis.
What are the best pet friendly cottages in Brewster, MA?
What are the most common amenities in cottages in Brewster, MA?
Most cottages in Brewster have basic amenities like a kitchen, bathroom, and bedrooms. Many also have outdoor spaces like decks or patios. Some cottages might also have features like fireplaces, hot tubs, or private pools.
What are the best cottages with parking in Brewster, MA?
Guest-Favorite Cottages with Jacuzzi in Brewster, MA
A private hot tub at your cottage makes every trip to Brewster, MA truly unforgettable after a day by the water.
Brewster, MA
08/04 – 08/08
$864/nighttotal: $3456 (4 )
Ocean Breezes Await At The Paradise On The Sound
1 4
cottage , Yarmouth
Paradise on the Sound Cottage, located in Bass River, South Yarmouth, offers direct access to a private Nantucket Sound beach and proximity to Hyannis Harbor and West Dennis Beach. This one-bedroom vacation rental sleeps four with a queen and two twin beds, a kitchenette, free Wi-Fi, a Smart TV, and includes a $750 Xplorie package for local attractions.
Neighborhoods and points of interest in Brewster, MA
Browse Pet-Friendly Cottages in Brewster, MA
These dog-friendly cottages in Brewster, MA ensure your pet loves the vacation as much as you do.
9.0 13 reviews
Brewster, MA
06/20 – 06/27
$318/nighttotal: $2226 (7 )
Cozy Cottage Near Rock Harbor (2223)
2 2
cottage , Orleans
This Orleans marsh-side cottage offers stunning views and is conveniently located near Rock Harbor, the Cape Cod Rail Trail, and Orleans town center, though precise distances aren't specified. This pet-friendly (fee applies) two-bedroom, one-bathroom home sleeps five and features a full kitchen, microwave, outdoor shower, three-season porch, grill, air conditioning, internet access, and parking for two cars.
Brewster, MA
06/20 – 06/27
$498/nighttotal: $3486 (7 )
Relaxing Eastham Retreat With Waterfront Views
2 2
cottage , Eastham
This Eastham rental cottage offers direct waterfront access on Town Cove with a private dock, located within 2 miles of Rock Harbor Beach and the Cape Cod Rail Trail. This 550 sq ft cottage sleeps 4 guests, features 2 bedrooms and 1 bathroom, includes complimentary bed and bath linens, and provides daily free tickets to local attractions through Xplorie, such as Island Cruises and Whale Watch.