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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: 26

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

Family Home On Cobbs Pond With Bay Beach Rights
5BR
1 ½ bath
Sleeps 12

N/A

Contact: Karen, Property ID: 29007

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

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

The price range is $3000-4000+/mo for the main house. November - March

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

Charming 4 Bedroom Home near Breakwater Beach
4BR
2 baths
Sleeps 10

Off season rental at $2300 per month October-May plus utilities.

Contact: John , Property ID: 23161

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

We offer long term winter rentals.

Contact: Carole , Property ID: 31348

Fabulous Air Conditioned 4BR, Great Views, Steps to Beach
4BR
2 baths
Sleeps 8

Available 6 October 2021 to 4 June 2022 at $1800 per month. Tenant pays utilities: natural gas, electricity and internet/cable TV. Tenant is respon...

Contact: James McGinnis, Property ID: 34056

Winslow Homestead - Spacious 1700s home, A/C, near Bay beach
4BR
1 ½ bath
Sleeps 8

Available September to June; price range $2,500 - $4,000 per month depending on month(s) and length of stay. Please inquire for more information.

Contact: Christy Johnson, Property ID: 12721

Walk to Sheep's Pond, Hot Tub, WIFI, A/C, Year Around Home
4BR
2 baths
Sleeps 8

winter rental considered

Contact: Annmarie ( all e-mails returned promptly ), Property ID: 16642

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

Long term winter rental available. Please contact owner for specific information

Contact: Nick, Property ID: 30572

Perfect vacation home, just off the bike path & bay beaches
3BR
2 baths
Sleeps 8

not available

Contact: Fred , Property ID: 29599

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

Great location, walk to Bay beach.
3BR
2 ½ baths
Sleeps 8

Available October - May (Contact us for further details if interested).

Contact: Leah Slye, Property ID: 11108

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

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

$2500-$4000

Contact: James and Janet, Property ID: 33328

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

$2500-$4000

Contact: James and Janet, Property ID: 25423

Charming Cottage, Great Location for Walking/Bike Riding!
3BR
1 bath
Sleeps 6

Winter Rental Available for 2021

Contact: Victoria Majewski, Property ID: 12130

Birdwatcher's Delight
3BR
1 ½ bath
Sleeps 6

Available upon request. For two months or more, monthly rent is $1800 in the winter months (December, January, February, March) and $2400 / month in s...

Contact: Mary, Property ID: 12150

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

We have booked a long-term rental for October 2020 through May 2021.

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

See calendar. Reduced rates for multiple weeks.

Contact: Jacqueline , Property ID: 32667

Lovely Ocean Edge Resort Condo (Pool Access, WiFi, A/C)
2BR
2 baths
Sleeps 4

Full month rentals are possible for April, October, and November only.

Contact: Lori , Property ID: 32101

Private Beachfront 2 BR Waterfront sunset cottage on bluff
2BR
1 bath
Sleeps 4

Winter rental available starting in Nov. $6850 a month for Nov - April.

Contact: Bruce or Rina , Property ID: 30177

Wright Studio by the Bay (Sunday to Sunday rental)
1BR
1 bath
Sleeps 2

$900/month off-season Nov-Mar

Contact: Kimlyn Wright, Property ID: 2932