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.
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
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
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
Considered upon request: $10,000-$15,000. Non-refundable deposit required to secure rental, fully refundable damage deposit also required.
Contact: Kathy, ID: 5527
Available for winter rental December - mid-May, $1900 per month plus utilities.
Contact: Jeanine, ID: 23036
Winter rental $1800/month. Minimum 5 month lease. No pets. Fabulous location in heart of historic Brewster! Must have great references.
Contact: Victoria Majewski, ID: 12130
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
Available for winter rental beginning January 2025 $3,500.00 per month includes utilities.
Contact: Marcia, ID: 35940
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
Open to longer terms rentals - $7,000-$8000/month
Contact: Bill, ID: 39756
October 2026 -May 20, 2027 $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
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
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
Oct 2026 - May 2027. 4 Bedroom furnished home $2500/ mo. Less than 7 months negotiable. I pay for internet & trash. You would be responsible for gas ...
Contact: Marsha A., ID: 23933
We will rent for 32 days subject to availability in June and July each summer season. The rent is $28,000 for June and $32,000 for July, plus two cle...
Contact: Lisa Fabian Lustigman, ID: 7160
September and October monthly rentals available for $6000. Please contact for more details.
Contact: Sheldon, ID: 29425
Long-term rental is available off-peak season. $3,500-$5,000/mo Please inquire
Contact: Sandra Callahan, ID: 40897
We have rented this cottage the past two Winters, September through May and will consider shorter stays than May. Winter rent is $2200 including, ele...
Contact: Michelle, ID: 39312
Open to consideration between November and April. Monthly rentals begin at $3500 and include utilities.
Contact: Christine Fiske, ID: 35643
Summer months $30,000 July and August. Winter months $4,500 October - May.
Contact: Sally, ID: 39873
We are happy to have winter renters. September -April 2750 a month
Contact: Nicholas, ID: 40071
Available Sept - Dec 2026 $3,000-4,000/mo negotiable
Contact: Kathy, ID: 40197
1 month or more: Available Oct 2026-April 2027: $4,000/month (minimum 2 months) or 1200/week (minimum 4 weeks). 4BR beach house, 3-4-min walk to shore...
Contact: Inna, ID: 41592
Long Term Rental Available by the Month of Season $12k to $24K
Contact: Sean Kearney, ID: 7091
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
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