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Long-Term Vacation Rentals in Brewster

Rental homes are available for an extended stay of a month or more at a time. 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). Monthly prices may vary depending on the number in your party and length of stay.

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

# of Rentals: 22

Brewster

Beautiful Home Close to Beaches, Sesuit Harbor & Golf
6BR
3 baths
Sleeps 13

'October to May for $3,000 per month, depending on party size and length of stay. Includes utilities.'

Contact: Gerry or Cindy, Property ID: 19604

Sheep Pond Escape - 5 bedroom with private beach
5BR
3 baths
Sleeps 12

1-week rate: $4,000 (includes cleaning fee) 2-week rate: $6,500 (includes cleaning fee) 4-week rate: $10,000 (includes cleaning fee)

Contact: Talia, Property ID: 34024

Renovated Brewster Beach House + Cottage
4BR
3 baths
Sleeps 12

Longer rentals of this newly renovated and private property in Brewster are available on a case-by-case basis. Please inquire for details. Generally...

Contact: Christine and Steve, Property ID: 33519

Gorgeous 4 Bedroom, 3.5 Bath Home w/AC in Brewster
4BR
3 ½ baths
Sleeps 12

We would be interested in a Long Term Winter tenant.

Contact: Kevin and Erin, Property ID: 33835

Sheep's Pond,Open Concept Family Home, Plenty of Fun
4BR
2 baths
Sleeps 10

Longer term renters are avaliable Oct through April.

Contact: Annmarie, Property ID: 30493

Stars Align Near Pleasant Bay
4BR
2 baths
Sleeps 10

Available January-March, $7000 a month +utilities

Contact: Elise Costa, Property ID: 36106

Brewster's Best Private Bay Beach Getaway - monthly rentals
3BR
2 baths
Sleeps 10

We would consider a winter rental if one was to be remodeling or relocating, must be out by May 1st

Contact: Roger Gallagher, Property ID: 19762

Charming Cottage and Glamping Bunkhouse Steps From The Beach
3BR
1 bath
Sleeps 10

The long term rental calendar is open for December 15 2022-April 15 2023.

Contact: Carole , Property ID: 31348

Private Beach Access, Great Family Get Away
4BR
2 baths
Sleeps 8

Some longer term rental is available. Please contact owner for specific information

Contact: Nick, Property ID: 30572

Family Friendly Home at Cobbs Pond/Cape Cod Bay in Brewster
4BR
3 baths
Sleeps 8

Long term can be done in off season

Contact: Jenn, Property ID: 19423

Renovated Coastal Farmhouse at Greenland Pond
3BR
2 baths
Sleeps 8

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

Contact: Christine and Steve, Property ID: 35643

The Mink Shell - 5 Min Walk to TWO Bay Beaches!!
3BR
2 baths
Sleeps 8

If looking to retire on the Cape or just wintering and you need a wonderful place to stay while you find your dream home, try ours for the season! Ava...

Contact: John, Martha, Elly and little Olivia, Property ID: 5843

Brewster Mountain Retreat (Blueberry Pond)
3BR
2 baths
Sleeps 8

Available from December - May for multi month rental. Price is $2,500/month.

Contact: Eric, Property ID: 33279

Luxury Waterfront Oasis on Private Sunset Beach
3BR
2 baths
Sleeps 8

$2500-$4000

Contact: James and Janet, Property ID: 33328

Escape to the Cape
3BR
3 baths
Sleeps 6

Long-term rental considered September 2021 - May 2022. Monthly rentals vary for the off season months starting at $4,000.

Contact: Margaret, Property ID: 34624

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, Property ID: 12150

Well-appointed Home Steps from Private Sunset Beach
3BR
1 ½ bath
Sleeps 6

$2500-$4000

Contact: James and Janet, Property ID: 25423

Lovely Beach Cottage, Grassy Yard, Walk to Bay!
3BR
1 ½ bath
Sleeps 6

For the right person or couple, we are open to discussing winter rentals from October 15, 2022 through May 31, 2023. We charge $1850.00 per month plus...

Contact: Liz, Property ID: 29262

Charming 2 Bedroom near Breakwater Beach
2BR
1 bath
Sleeps 6

September 15 to May 31

Contact: John , Property ID: 23175

Perfect Cape Cottage
2BR
1 bath
Sleeps 6

***WINTER RENTAL AVAILABLE 2022-2023*** SEPTEMBER - JUNE...HURRY! WON'T LAST LONG :)

Contact: Jacqueline , Property ID: 32667

Private Beachfront sunset cottage on bluff . Bay views
2BR
1 bath
Sleeps 4

Winter rental available starting in Nov. - April $7000 a month.

Contact: Bruce or Rina , Property ID: 30177

Charming Beach Cottage Retreat - Walk to Paines Creek Beach
2BR
1 bath
Sleeps 4

Long Term Rental both Summer and Winter is an option and can be discussed based on month and availability.

Contact: Lou, Property ID: 36330