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Long-Term Vacation Rentals on Martha's Vineyard

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.

# of Rentals: 17

Chilmark

Chilmark Rental
Beetlebung Guest House/Access to Tennis Courts & Hiking
2BR
1 bath
Sleeps 4

Available for long term winter rental September through June 1 $2200-2400 winter rate.

Contact: Anne, ID: 40083

Edgartown

Edgartown Village Rental
Edgartown Village, Ideal Location-walk to town/bike to beach
3BR
1 ½ bath
Sleeps 6

Available from November 1 to May 1 $3400 per month + $85 internet + monthly electric bill

Contact: David Brady, ID: 11620

Edgartown Rental
Cozy Couples Hideaway - Contemporary
1BR
1 bath
Sleeps 4

Will rent during the off season for $2200. per month plus utilities.

Contact: Kathleen Collins, ID: 2937

Edgartown Rental
The Crow’s Nest: Spacious Modern One-Bedroom Apartment
1BR
1 bath
Sleeps 2

Monthly rentals considered. $2500-4000

Contact: Margaret, ID: 35154

Oak Bluffs

Oak Bluffs Rental
The “Summer Wind” House - Walk to the Beach!
5BR
3 baths
Sleeps 10

$20K per month off-season.

Contact: Wendy , ID: 35217

Oak Bluffs Rental
Spacious Oak Bluffs Farmhouse
4BR
2 ½ baths
Sleeps 8

Available as a long-term rental from approximately September-May (depending on bookings) for $3500/month.

Contact: Studio Realty, ID: 38312

Oak Bluffs Rental
Beachfront Oasis within Minutes from Downtown
4BR
1 ½ bath
Sleeps 8

April-October Summer 2026: Monthly price: $45,000- $60,000 Off Season 2026: Monthly price: $20,000- $30,000

Contact: Eric, ID: 39711

Oak Bluffs Rental
Classic waterfront Vict. cottage, walk to town; huge porch
4BR
2 baths
Sleeps 8

$6200 per month; discount for multiple months. Jan, Feb., March, April, available for a month or more. Great place to read, write, contemplate the cha...

Contact: Jamie, ID: 31304

Oak Bluffs Arts District Rental
The Loft at Ginsey
1BR
1 bath
Sleeps 3

Monthly rates, including utilities: 1 to 2 months: $2,200 per month, 3 to 5 months: $2,100 per month, 6 months or longer: $2,000 per month. Furn...

Contact: Frank, ID: 42077

Oak Bluffs Rental
CozyBluffs - Walk to Beach/Circuit Ave/OB ferries!
1BR
1 ½ bath
Sleeps 2

November 2026 - March 2027 will consider stays over 30 days. Price range 3,000-4,500 per month. See calendar & rates for more details.

Contact: Fran M., ID: 34909

Vineyard Haven

Vineyard Haven Rental
Vineyard Retreat |Winter Rental + 2 Prime Aug Weeks + Pool
4BR
2 ½ baths
Sleeps 7

The home is available monthly January - May. Priority will go to 3-4 month lease. $6,000-$7,500 including utilities

Contact: Nancy, ID: 42109

Vineyard Haven, Martha's Viney Rental
Charming Vineyard Haven 2-Bedroom Cottage Close to Main St
2BR
2 baths
Sleeps 6

Available September through May as a Long-Term Rental, for a maximum of 9 months. Monthly rate of $4500/month.

Contact: Latitude - Vacation Home Services, ID: 41740

Vineyard Haven Rental
Charming Bright Sunny Cape Home in Vineyard Haven
3BR
2 baths
Sleeps 4

available for winter rental October 1 - May 1. $2300 per month, heating additional. Internet included

Contact: Darlene Webb, ID: 19399

Tisbury Rental
Peaceful Upgraded Condo walk to VH w AC, deck, pool
2BR
1 bath
Sleeps 4

Medium term rentals (1-5 months) may be an option, including off season rental. Price range 3500-4000 roughly per month. Contact for details and to di...

Contact: Tom, ID: 38371

Vineyard Haven Rental
Blue Whale Cottages
1BR
1 bath
Sleeps 3

Available at $3000 a month from Oct - May - Please inquire

Contact: KIM, ID: 41837

West Tisbury

West Tisbury Rental
Lambert's Cove Home poss flex w/arrival dates!
3BR
3 baths
Sleeps 6

This outstanding, private setting is available for $4500 per month through May for a winter rental. No pets. Utilities not included. Please inquire fo...

Contact: Nancy Polucci, ID: 26305

West Tisbury Rental
Beautiful Island Home; Beach Pass to Lambert's Cove Beach
3BR
3 ½ baths
Sleeps 6

Depending on the renters and their needs. It would need to be negotiated. Would like to meet the renters prior to signing a contract if possible and h...

Contact: Angela, ID: 42195