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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).

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
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
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
Peaceful Upgraded Condo Minutes from VH and Ferry/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, Property ID: 38371
Cozy West Chop Cottage, Walk or Bike to Beach & Woods, 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
Fabulous Contemporary With Steinway Piano & Tremendous Charm
2BR
1 bath
Sleeps 4

Winter rental monthly from Mid September to April 1, May 1 or June 1. $2500 Minimum 6 months. (Winter/Spring Year 2024-2025,

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
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
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