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.
Wellfleet
4BR
2 baths
Sleeps 8Considered upon request: $10,000-$15,000. Non-refundable deposit required to secure rental, fully refundable damage deposit also required.
Contact: Kathy, ID: 5527
Orleans
3BR2 bathsSleeps 8We would love to open our home for a winter rental of 1-8 months. Rental rate ranges from $2000-$4000 per month plus utilities, depending on how many …
Contact: Carrie and Tim, ID: 29389
Truro
3BR2 bathsSleeps 6October through April is $2700. per month plus utilities.
Contact: Irene, ID: 30595
Yarmouth
2BR2 bathsSleeps 4Long Term rental is available from November 2026 - May 2026. $2000 per month plus utilities.
Contact: David, ID: 35363
Sandwich
4BR2 bathsSleeps 8Property available for long term rental from mid-September to May. Price ranges from $3,500 to $4,500 depending on utilities included and length of s…
Contact: Marcia, ID: 7487
Sandwich
3BR2 bathsSleeps 8September - May Rental $2900 - $3300 - Please ask for details.
Contact: Robbi Laak, ID: 4699
Falmouth
3BR2 bathsSleeps 6Available for monthly rental in the off-season $2,700 - $3,200, depending on utilities and/or timing.
Contact: Kevin, ID: 23333
Falmouth
3BR2 bathsSleeps 6October 2026 -May 20, 2027 $4000- $6000/month includes All utilities and wifi
Contact: Mary, ID: 39927
Harwich
2BR1 bathSleeps 4Off Season Monthly Rental - $2150 + Utilities - Great Location Near the Rail Trail. One floor living with basement laundry.
Contact: Melissa, ID: 40670
Eastham
3BR2 bathsSleeps 6Winter rental available mid October until the end of May, but dates are flexible. A full winter rental price is $1900 a month. Summer long term rental…
Contact: Jen, ID: 41836
Harwich
4BR2 bathsSleeps 10Open to longer terms rentals - $7,000-$8000/month
Contact: Bill, ID: 39756
Eastham
2BR1 bathSleeps 4Winter Rental from November to Mid June. 2500/month fully furnished, utilities, wifi, laundry on site included. Responsible for trash and light winte…
Contact: Lisa & Brian Hoag, ID: 38403
Dennis
4BR3 bathsSleeps 103 month minimum. $3500/mo, utilities not included. Our home is primarily a summer rental but is also available for long-term rental from December 1, 2…
Contact: Billy Hartmann, ID: 38985
Plymouth
2BR1 bathSleeps 6We 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
Falmouth
4BR2 bathsSleeps 11Prices 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
Barnstable
3BR1 bathSleeps 8Summer months $30,000 July and August. Winter months $4,500 October - May.
Contact: Sally, ID: 39873
Dennis
4BR1 bathSleeps 812/2026 - 5/2027: Four-bedroom furnished home $2400/mo. Dogs considered. I pay for internet & trash. You would be responsible for gas & electric. Par…
Contact: Marsha A., ID: 23933
Harwich
4BR4 bathsSleeps 10Quiet vacations in the winter, monthly rates $8000.
Contact: Greg Stone, ID: 13970
Wellfleet
1BR1 bathSleeps 4Nov-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
Yarmouth
2BR1 bathSleeps 6MONTHLY 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
Wellfleet
3BR3 bathsSleeps 8Nov-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
Wellfleet
3BR2 bathsSleeps 6September and October monthly rentals available for $6000. Please contact for more details.
Contact: Sheldon, ID: 29425
Provincetown
4BR2 bathsSleeps 8We 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
Plymouth
4BR2 bathsSleeps 10Bargain winter rental for only $2,300/month for a large 4 bedroom waterfront home. November 1st until May 1st view the ocean and walk the beach. Celeb…
Contact: Candace Nattie, ID: 6521
Dennis
6BR3 bathsSleeps 15Available 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
Bourne
4BR2 bathsSleeps 10Available November 2026 - May 2027. $4,000 - $6,000/mo including utilities.
Contact: Jennifer Moore, ID: 40321
Dennis
3BR1 bathSleeps 6Available off-season 2026-2027, $1,800.00/mo, with a $250 gas/electric usage cap - monthly availability November 2026 through May 2027 with First and …
Contact: Rich, ID: 38206
Truro
3BR2 bathsSleeps 8This home is available at $4,000-$5,000/mo for the months of November, December, January, February, March, and April.
Contact: Xia, ID: 41918
Duxbury
4BR4 bathsSleeps 13Available September 3- June 15 2026 for $6,000/mo plus utilities
Contact: Shari, ID: 26427
Brewster
3BR1 bathSleeps 6Available 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
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