Cottages in Brewster, MA at the best prices

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Brewster, MA cottages
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62 Best cottages in Brewster, MA

Best family friendly Brewster, MA cottage rentals

Among the 62 accommodations in Brewster, MA, here are the 1 best family friendly cottage rentals

33 M² Cottage ∙ 1 Bedroom ∙ 4 Guests - Brewster, MA
10 1 review
Brewster, MA
04/08 – 08/08
$664/nighttotal: $2656 (4 )

33 M² Cottage ∙ 1 Bedroom ∙ 4 Guests

1 4
cottage , Yarmouth
Luckenbooth Cottage, a South Yarmouth self-catering studio, is a short walk from a private beach on Nantucket Sound, offering easy access to ferries for Nantucket and Martha's Vineyard.
This one-bedroom property sleeps four, features a well-equipped kitchen, Smart TV, Wi-Fi, and includes the Xplorie package providing free tickets to local attractions such as island cruises, whale watching, and golf at Cranberry Valley or Chequessett Golf Courses.

Best Brewster, MA cottages with a garden

Cozy Cottage Near Rock Harbor (2223) - Brewster, MA
9.0 13 reviews
Brewster, MA
22/06 – 27/06
$494/nighttotal: $2470 (5 )

Cozy Cottage Near Rock Harbor (2223)

2 2
cottage , Orleans
This Orleans marsh-side cottage offers a tranquil setting near Rock Harbour, the Cape Cod Rail Trail, and Orleans town centre; distances to these attractions are unspecified.
Sleeping five guests, this two-bedroom, one-bathroom holiday home features a full kitchen with fridge and microwave, air conditioning, a garden, parking for two cars, and an outdoor shower; a three-season porch and charcoal grill are also available.
New For 2026! 1/2 Mile To Swan Pond (2414) - Brewster, MA
Brewster, MA
04/08 – 08/08
$746/nighttotal: $2984 (4 )

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

2 4
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.
Screened Porch Overlooking Marsh, Spacious Yard, Patio, Fire Pit, And Close To Beach - Brewster, MA
Brewster, MA
04/08 – 08/08
$1469/nighttotal: $5876 (4 )

Screened Porch Overlooking Marsh, Spacious Yard, Patio, Fire Pit, And Close To Beach

2 4
cottage , Eastham
This holiday home is situated in North Eastham, a 5-minute drive or cycle from South Sunken Meadow Beach and close to the Cape Cod National Seashore.
This renovated 65 square meter cottage offers accommodation for four guests with two bedrooms, 1.5 bathrooms, a separate hangout cottage with a TV, an on-site laundry, and a patio with a fire pit, complemented by two outdoor showers and marsh views.
Mooncusser Cottage On Taylor's Pond! - Brewster, MA
Brewster, MA
18/07 – 25/07
$968/nighttotal: $6776 (7 )

Mooncusser Cottage On Taylor's Pond!

2 6
cottage , Chatham
Mooncusser Cottage, a two-bedroom holiday home in South Chatham, offers convenient access to Cape Cod beaches and attractions such as the Cape Cod Inflatable Park and Nauset Beach (distances unspecified).
This self-catering property sleeps six, features a fully equipped kitchen with dishwasher, in-cottage laundry, and a terrace; nearby activities include visits to Adventure Chatham and the Cape Cod Lavender Farm.

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?

Destinations nearby

Best Brewster, MA cottage rentals with jacuzzi

Among the 62 accommodations in Brewster, MA, here are the 1 best cottage rentals with a jacuzzi

The Coast: Cozy Cape Escape In Dennis Port - Brewster, MA
Brewster, MA
22/06 – 27/06
$702/nighttotal: $3510 (5 )

The Coast: Cozy Cape Escape In Dennis Port

2 2
cottage , Dennis
This holiday home is located in Dennis Port, less than 1 kilometre from Raycroft Beach and Sea Street Beach, and within walking distance of Seaview Park and Sunday School Ice Cream Parlor.
This 81 square meter holiday home accommodates up to four guests, featuring two bedrooms, one bathroom, air conditioning, Wi-Fi, and a kitchen equipped with a fridge, microwave, and dishwasher, alongside outdoor amenities such as a firepit and gas grill, and includes daily free tickets to local attractions through the Xplorie partnership.

Best pet friendly Brewster, MA cottage rentals

Among the 62 accommodations in Brewster, MA, here are the 2 best pet friendly cottage rentals

Charming Cape Cod Cottage Walking Distance To The Beach - Brewster, MA
Brewster, MA
18/07 – 25/07
$1490/nighttotal: $10430 (7 )

Charming Cape Cod Cottage Walking Distance To The Beach

4 6
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.
Cozy Cottage Near Rock Harbor (2223) - Brewster, MA
9.0 13 reviews
Brewster, MA
22/06 – 27/06
$494/nighttotal: $2470 (5 )

Cozy Cottage Near Rock Harbor (2223)

2 2
cottage , Orleans
This Orleans marsh-side cottage offers a tranquil setting near Rock Harbour, the Cape Cod Rail Trail, and Orleans town centre; distances to these attractions are unspecified.
Sleeping five guests, this two-bedroom, one-bathroom holiday home features a full kitchen with fridge and microwave, air conditioning, a garden, parking for two cars, and an outdoor shower; a three-season porch and charcoal grill are also available.
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