Cottages in Brewster, MA at the best prices

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Brewster, MA cottages
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48 Best cottages in Brewster, MA

Best family friendly Brewster, MA cottage rentals

Among the 48 accommodations in Brewster, MA, here are the 2 best family friendly cottage rentals

81 M² Cottage ∙ 2 Bedrooms ∙ 4 Guests - Brewster, MA
No reviews

81 M² Cottage ∙ 2 Bedrooms ∙ 4 Guests

cottage, Dennis
This detached house is located on a quiet road in Dennis Port, under 1 kilometre from Raycroft Beach and Sea Street Beach, and within walking distance of Seaview Park and the Sunday School Ice Cream Parlour.
This 81 square metre property accommodates four guests in two bedrooms and features a well-equipped kitchen, air conditioning, parking, and complimentary linens, with included daily free tickets to local attractions via Xplorie.
81 M² Cottage ∙ 2 Bedrooms ∙ 4 Guests - Brewster, MA
No reviews

81 M² Cottage ∙ 2 Bedrooms ∙ 4 Guests

cottage, Dennis
This Cape-style holiday home is located at the end of a quiet road in Dennis Port, less than 1.6 kilometres from Raycroft Beach and Sea Street Beach, and within walking distance of Seaview Park, Sunday School Ice Cream Parlor and The Oyster Company.
This 81 square metre bungalow offers accommodation for four guests with two bedrooms and one bathroom, featuring air conditioning, Wi-Fi, a full kitchen, a firepit, an outdoor shower, and complimentary daily tickets to local attractions through Xplorie, including Island Cruises and Whale Watch tours.

Best Brewster, MA cottages with a garden

Walk To Private Beach, Central Air, Wifi, 3 Bedrooms. - Brewster, MA
9.8 56 reviews

Walk To Private Beach, Central Air, Wifi, 3 Bedrooms.

cottage, Chatham
This charming three-bedroom cottage is situated in South Chatham, just a 2.4km walk from Cape Cod Beaches and Forest Beach, and within 3.2km of Red River Beach and the Chatham Chamber of Commerce. The cottage has received excellent reviews from previous guests and is perfect for families or groups of up to six people.
The cottage offers 86 square metres of comfortable living space, with two bathrooms and a well-equipped kitchen. Guests can enjoy a private patio with a barbecue grill, a garden, and free parking, as well as access to the internet and air conditioning.
New For 2026! 1/2 Mile To Swan Pond (2414) - Brewster, MA
No reviews

New For 2026! 1/2 Mile To Swan Pond (2414)

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.

Frequently Asked Questions about cottages in Brewster, MA

  • What would be a good 1-day itinerary for visiting in and around Brewster, MA?

    You could start your day by visiting the Cape Cod Rail Trail, which runs right through Brewster. After a bike ride or walk, head to the Brewster Ladies' Library, a charming historic building. In the afternoon, relax on the beach at Breakwater Beach or Drummer's Lane Beach. For dinner, enjoy fresh seafood at the Lobster Claw Restaurant.
  • What are the best cottage rentals in Brewster, MA?

    Among the cottage rentals in Brewster, MA, The Drake Cottage - Brewster Beach Getaway, Private Woodland Cove Michael's Cottage and Daffodil Cottages #49 are the most popular ones.

  • What are the can't-miss sights in Brewster, MA?

    The Brewster Ladies' Library, a beautiful historic building, is a must-see. The Cape Cod Rail Trail, a scenic paved path that runs through Brewster, is perfect for a bike ride or walk. And, of course, no trip to Brewster would be complete without spending some time on the beach at Breakwater Beach or Drummer's Lane Beach.
  • What are the best cottage rentals with a pool in Brewster, MA?

  • Can you easily explore Brewster, MA on foot or by bike?

    Brewster is a very walkable town, especially the downtown area. The Cape Cod Rail Trail also runs through the town, providing a great way to explore the area by bike. There are also plenty of bike rental shops in town.
  • What are the best cottage rentals with a jacuzzi in Brewster, MA?

    Pondside Retreat With Hot Tub and Sprawling Brewster House+cottage W/hot Tub are the best cottage rentals with a jacuzzi in Brewster, MA.

  • What activities are available in and around Brewster, MA?

    Brewster offers a variety of activities, from swimming and sunbathing on the beaches to exploring the Cape Cod Rail Trail. You can also visit the Brewster Ladies' Library, go kayaking or paddleboarding in the bay, or play a round of golf at one of the local courses. There are also several shops and restaurants in town.
  • What are the best cottage rentals for families and kids in Brewster, MA?

    The best cottage rentals for families and kids in Brewster, MA are The Drake Cottage - Brewster Beach Getaway, Daffodil Cottages #49 and Daffodil Cottages #45.

  • What famous towns or cities are near to Brewster, MA?

    Brewster is located on Cape Cod, which is home to many charming towns and cities. Some of the nearby towns include Chatham, Orleans, and Provincetown. The city of Boston is about a 2-hour drive from Brewster.
  • What are the best pet friendly cottage rentals in Brewster, MA?

    The best pet friendly cottage rentals in Brewster, MA are Daffodil Cottages #49, Daffodil Cottages #43 and Daffodil Cottages #45.

  • What are the most common amenities in cottages in Brewster, MA?

    Cottages in Brewster typically offer amenities like a kitchen, bathroom, living area, and bedrooms. Many also have outdoor spaces like a patio or deck, and some may offer additional features like a fireplace, washer and dryer, or access to a pool.
  • What are the best cottage rentals with parking in Brewster, MA?

Popular destinations

Best Brewster, MA cottage rentals with jacuzzi

Among the 48 accommodations in Brewster, MA, here are the 1 best cottage rentals with a jacuzzi

Skaket Dream 2/10 Mile To Beach! - Brewster, MA
9.0 2 reviews

Skaket Dream 2/10 Mile To Beach!

cottage, Orleans
This Orleans holiday home, situated 0.32km from Skaket Beach and close to the Cape Cod Rail Trail and Orleans' town centre, offers a peaceful retreat at the end of a sandy lane with stunning tidal marsh views.
The three-bedroom property sleeps six, features a fully equipped kitchen with dishwasher and in-unit laundry, plus central air conditioning, a gas grill, Wi-Fi, cable TV (two TVs), and a garden with parking; nearby activities include biking on the Cape Cod Rail Trail and exploring Orleans' shops and restaurants.

Best pet friendly Brewster, MA cottage rentals

Among the 48 accommodations in Brewster, MA, here are the 4 best pet friendly cottage rentals

Renovated Chatham Cottage  Steps To Beach - Brewster, MA
8.6 24 reviews

Renovated Chatham Cottage Steps To Beach

cottage, Chatham
This newly renovated holiday home in South Chatham offers proximity to Nantucket Sound beaches, located just 150 metres away, and is within walking distance of South Chatham village, tennis courts, and the Cape Cod Rail Trail.
This 98 square metre property, accommodating up to 8 guests, features 3 bedrooms, 1 bathroom, air conditioning, Wi-Fi, a fully equipped kitchen with a dishwasher, and a private garden with a gas grill and patio.
Charming 2-bedroom Cottage In Fabulous Harwich With Wifi, Ac - Brewster, MA
9.0 6 reviews

Charming 2-bedroom Cottage In Fabulous Harwich With Wifi, Ac

cottage, Harwich
This two-bedroom Harwich holiday home is situated in Northwest Harwich, offering easy access to attractions such as Cape Cod Baseball & Bumper Boats and Cape Cod Lavender Farm (distances to these attractions require further clarification).
Sleeping up to 10 guests, the property features two bathrooms, Wi-Fi, air conditioning, and is pet-friendly; further details on proximity to Hyannis Harbour, West Dennis Beach, and Mayflower Beach (distances unspecified) are needed.
Charming Cape Cod Cottage Walking Distance To The Beach - Brewster, MA
No reviews

Charming Cape Cod Cottage Walking Distance To The Beach

cottage, Harwich
This Northwest Harwich holiday home is situated a short 1.9km walk from both Cape Cod Beaches and Pleasant Road Beach.
The self-catering property boasts four bedrooms, 1.5 bathrooms, a fully equipped kitchen including a dishwasher, and on-site parking, comfortably accommodating families or groups.
Cape Code Waterfront Cottage - Brewster, MA
9.6 47 reviews

Cape Code Waterfront Cottage

cottage, Dennis
This waterfront holiday home is located in Dennis, just 3.2 kilometres from the Cape Cod Theatre Company and Jericho House and Barn Museum, and 4.8 kilometres from Sea Street Beach and the Cape Cod Rail Trail. It has received excellent user ratings, making it a popular choice for travellers.
This 3-bedroom property offers 111 square metres of space and can comfortably accommodate up to 6 guests. The cottage features a fully equipped kitchen, a private garden with barbecue facilities, a swimming pool, a jacuzzi, a terrace, and free Wi-Fi, providing everything you need for a relaxing and enjoyable stay.
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