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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: 11

Vineyard Haven

Waterfront Cottage with Private Beach
4BR
2 baths
Sleeps 9

September through October and May and June. $2000 to $3000 per week. Long term rentals are available in the summer months as well. Contact owner for ...

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

Amazing Views Year-Round, Private Beach, Great for Kayaking
3BR
2 baths
Sleeps 6

Home is available for discounted multi-week and monthly rentals from November through April. Pricing including utilities starts at $1,200/week depend...

Contact: Tim Macy, Property ID: 29492

Hine's Point Waterfront
2BR
1 bath
Sleeps 6

Waterfront 2 bedroom ranch. Mid October 2023 thru Mid May 2024. $1900/month plus utilities. 6 month minimum.

Contact: Dan & Roseann Sheping, Property ID: 4482

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

winter rental 1-2 people Nov 1 - April 15 $1400 - $1600 per month

Contact: Darlene Webb, Property ID: 19399

Relax..You're on Island Time...A little piece of paradise..
2BR
1 bath
Sleeps 4

I rent my place for the winter months beginning in October until May for $2000 per month which includes all utilities.

Contact: Lynne Demond, Property ID: 7436

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

Year Round for $3500 per month plus utilities. Maximum 3 people. Winter rental monthly from October 1 to May 1 or June 1 for $2750. Minimum 6 month...

Contact: Barbara, Property ID: 16502

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

Property is available from October 1, 2024 to April 30, 2025 for $2800 per month plus utilities. * Special rate for September, 2024 and May and June...

Contact: Barbara, Property ID: 34386

Cozy Cottage in the Woods, Walk to Beach, Bike to Town
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-...

Contact: Maggie, Property ID: 38039

Peaceful Upgraded Condo Minutes from VH and Ferry/Pool
2BR
1 bath
Sleeps 4

Longer term rentals may be an option, including off season rental. Price range 4000 roughly per month. Contact for details and to discuss.

Contact: Tom, Property ID: 38371

Waterview of Vineyard Sound, sleeps 2.
1BR
1 bath
Sleeps 2

Winter Rental from Oct 1st to May 31st, $1,000 monthly. Contract Required.

Contact: Geri Cecilio, Property ID: 7718