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Long-Term Vacation Rentals in Vineyard Haven

Rental homes are available for an extended stay of a month or more at a time. 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). Monthly prices may vary depending on the number in your party and length of stay.

Rentals are listed by location, sleeping capacity, and number of bedrooms.

# of Rentals: 8

Vineyard Haven

Amazing Views Year-Round, Private Beach, Great for Kayaking
5BR
2 baths
Sleeps 10

Home is available year-round for discounted multi-week and monthly rentals from November through April. Price with all utilities starts at $1,000/week...

Contact: Tim Macy, Property ID: 29492

Waterfront Cottage with Private Beach
4BR
2 baths
Sleeps 9

Long term rentals are available in the summer months as well. Contact owner for pricing. Shoulder seasons are beautiful. September through October an...

Contact: Dee Dice, Property ID: 18566

Renovated W Chop Home Near Beach. Flexible Arr/Dep Dates!
3BR
1 bath
Sleeps 6

October through May to be negotiated. November to mid-May $1500 per month

Contact: Lucy Myers, Property ID: 15230

Hine's Point Waterfront
2BR
1 bath
Sleeps 6

Waterfront 2 bedroom ranch. October 1, 2021 thru Mid May 2022. $1500/month plus utilities. 6 month minimum.

Contact: Dan & Roseann Sheping, Property ID: 4482

Fabulous Contemporary With Steinway Piano & Tremendous Charm
2BR
1 bath
Sleeps 4

Winter rental may be available from early to mid September, 2021 to Early to Mid-May, 2022. Efficient new Renai propane monitor heater. Fall 2020. Ren...

Contact: Barbara, Property ID: 16502

Architect Designed Two Bedroom Refuge w/Shared Private Beach
2BR
2 baths
Sleeps 4

Winter rental available. Please inquire.

Contact: Barbara, Property ID: 34386

Immaculate Couples Retreat
2BR
2 baths
Sleeps 4

November through May at $2200 per month

Contact: James, Property ID: 34417

Waterview of Vineyard Sound, sleeps 4.
1BR
1 bath
Sleeps 4

Winter Rental from Oct 1st to May 31st, $800 monthly. Contract Required.

Contact: Geri Cecilio, Property ID: 7718