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Long-Term Vacation Rentals in Vineyard Haven

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: 5

Vineyard Haven
Vineyard Haven Rental
Island Living New Bi Level Apartment
3BR
2 ½ baths
Sleeps 8

$7000 monthly starting October 5, 2026. Long term rental through May 31st.

Contact: KIM, ID: 41372
Vineyard Haven Rental
Pine Tree Cottage; Steps from the Beach, Close to Town
3BR
1 bath
Sleeps 6

Longer-term rentals are available from 32-60 days. Monthly rates range from $9,750 to $11,250. November through April are not available.

Contact: Nancy, ID: 40537
Vineyard Haven Rental
Charming West Chop Cottage, Walk or Bike to Town & Beach
2BR
2 baths
Sleeps 4

Available for 1-4 months off-season from January through April, and 1-3 months in season June through August. Off-season monthly rate: $7,000 In-se...

Contact: Maggie, ID: 38039
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 $3500 a month from Oct - May - Please inquire about specifics

Contact: KIM, ID: 41837