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Long-Term Vacation Rentals in Brewster

A long-term rental is considered to be an extended stay of more than 31 days. While some rentals by owner will be available for long-term stays during the summer or year-round, majority are available during the off-season (fall, winter and spring). Massachusetts Landlord Tenant Laws will apply.

Rentals are listed by location, sleeping capacity, and number of bedrooms.

# of Rentals: 9

Brewster
Brewster Rental
Renovated Brewster Beach House + Cottage Near Bay Beaches
4BR
3 baths
Sleeps 12

Case-by-case basis. Monthly rentals begin at $3500 and vary by month. Please inquire for details.

Contact: Christine Fiske, ID: 33519
At Greenland Pond Rental
Renovated Coastal Farmhouse at Greenland Pond
3BR
2 baths
Sleeps 9

Open to consideration between November and April. Monthly rentals begin at $3500 and include utilities.

Contact: Christine Fiske, ID: 35643
Brewster Rental
Family Friendly Home at Cobbs Pond/Cape Cod Bay in Brewster
4BR
3 baths
Sleeps 8

Starting early January 2026, this property is available for long term rental around 3200 per month!

Contact: Allan and Jenn Peterson, ID: 19423
Brewster Rental
Single Level, Sun Filled, Family Retreat - 4 Seasons
3BR
2 baths
Sleeps 8

Long term rental available September - May. 4 month min. $3000-$4000 a month plus utilities.

Contact: Elizabeth, ID: 33496
Brewster Rental
Private Retreat on 2 Acres; Walk/Bike to 3 Brewster Beaches
3BR
2 baths
Sleeps 8

Available Sept - Dec 2026 $3,000-4,000/mo negotiable

Contact: Kathy, ID: 40197
Brewster Rental
Charming Cottage, Walk/Cycle to Beach/Shops/Cafes
3BR
1 bath
Sleeps 6

Winter rental $1800/month WITH SIX MONTH lease. We do not rent by the month for the winter. The price is $1800 plus utilities. But you must commit to ...

Contact: Victoria Majewski, ID: 12130
East Brewster Rental
Birdwatcher's Delight
3BR
1 ½ bath
Sleeps 6

Available upon request. For two months or more, monthly rent is $2,400 in the winter months (December, January, February, March); $3,800 / month in sp...

Contact: Mary, ID: 12150
Brewster Rental
Charming Historic Home, Walk to the Beach
3BR
1 bath
Sleeps 5

Available for long term rental September - May. $3000-$4000 per month.

Contact: Elizabeth, ID: 41823
West Brewster Rental
Cranberry Cottage: Cozy, Convenient, Charming, and Cool!
2BR
1 bath
Sleeps 4

Contact owner for long-term rental. Monthly rate ranges from $2,000-$10,000 depending on season.

Contact: Christy Johnson, ID: 41031