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.
Average $3900/month, October through May. Be a local -- the off season is magical!
Contact: Natalie, ID: 36944
Winter months are 2600. plus utilities.
Contact: Irene , ID: 30595
Winter rental $1800/month. Wifi & Utilities included. Minimum 3 month lease. No pets. Fabulous location in heart of historic Brewster! Must have great...
Contact: Victoria Majewski, ID: 12130
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
Starting early January 2026, this property is available for long term rental around 3200 per month!
Contact: Allan and Jenn Peterson, ID: 19423
October 2025 to May 2026 monthly rentals available. $3000 - $4000/mo.
Contact: Ruth, ID: 20703
MONTHLY WINTER RENTAL **$1800-$2000 monthly** Renter's costs: Utilities which are Gas & Electric, and trash pick-up. (Owner will keep bill in the...
Contact: Tammie, ID: 30995
Monthly rental available from September to May $2600 to $4000. Untilities are not included with the long term rental.For more information please reach...
Contact: Deena, ID: 35403
February 16th 2026 - May 19th 2026 is available for $2500/month!
Contact: Valerie Bono-Bunker, ID: 35549
Prices range from $3000-$3500/mo depending on length of stay. Typical long-term availability runs from October through early April (with some flexibil...
Contact: Steve, ID: 37347
October 2025 thru April 2026 - $3000 per month plus utilities.
Contact: Nancy, ID: 38692
Available for Long-term winter rentals - Cottage is NOT included since it is not winterized Price range from $3,400 to 4,000
Contact: Kim, ID: 18302
December 2025 -May 20, 2026 $4000- $6000/month includes All utilities and wifi
Contact: Mary, ID: 39927
Off-season (October-March) available as long-term rental (generally monthly or longer). $4,500-$7,500/month depending on which utilities are included...
Contact: Jay, ID: 40479
Summer months $30,000 July and August. Winter months $4,500 October - May.
Contact: Sally, ID: 39873
Available off-season. Price range for Nov 1 2025 to May 1st 2026 is $5,000-5,500 per month
Contact: Katerina, ID: 40029
Monthly rental available - October 2025 through May 2026. $3600-$3,800/mo. Please inquire
Contact: Jeff, ID: 39358
Open to longer terms rentals - $7,000-$8000/month
Contact: Bill, ID: 39756
Available November 2025 - April 2026. $2,500-3,000/mo - please inquire
Contact: Amy, ID: 40755
Special pricing available upon request $3,500-$4,000/mo negotiable
Contact: Jen, ID: 40898
Contact owner for long-term rental. Monthly rate ranges from $2,000-$10,000 depending on season.
Contact: Christy Johnson, ID: 41031
We are happy to negotiate a long-term rental of 1-3 months. Rates are $12000/month July & August $10000/month June, September, October $6000 Nove...
Contact: Laura, ID: 41591
From Mid September 2025 to May 31st 2026. Price range from $3,500 to $5,200 depending on month, length of stay and if utilities are included.
Contact: Marcia, ID: 7487
Available as a winter rental end of October 2025 to mid May 2026. $1200-1500/ month plus utilities and security deposit.
Contact: Bob Sneden, ID: 23722
Sept 12 2026 to May 1 2026 $2,500 plus utility or $2,700 including utility
Contact: Anthony , ID: 31330
Nov-April, $4,000/month utilities included (FYI - Rentals over 31 days are exempt from the 17.45% short-term rental tax)
Contact: Bill & Joy O'Connor, ID: 32564
Nov-April, $2,500/month utilities included (FYI - Rentals over 31 days are exempt from the 17.45% short-term rental tax)
Contact: Bill & Joy O'Connor, ID: 33217
Available for winter rental beginning January 2025 $3,500.00 per month includes utilities.
Contact: Marcia, ID: 35940
Available for monthly rental in the off-season $2,700 - $3,200, depending on utilities and/or timing.
Contact: Kevin, ID: 23333
September and October monthly rentals available for $6000. Please contact for more details.
Contact: Sheldon, ID: 29425
Available November 2025 - April 2026 for $2,500 to $3,000 per month, including utilities, depending on length of stay. Minimum 32 day rentals from De...
Contact: Jim or Ellen, ID: 10025
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