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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: 12

Vineyard Haven

Reunion House - Car, Privacy and Character
5BR
4 ½ baths
Sleeps 11

Available in off-season on a monthly basis, negotiated for longer periods of time: $20,000/month. Use of garbage disposal included.

Contact: Andrew Monroe Storch, Property ID: 35577

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

Perfect Vineyard Vacay with Central AC, 4 Bedrooms, 2.5 Bath
4BR
2 ½ baths
Sleeps 8

RENT ALL OF JULY 32 DAYS and pay NOTAX

Contact: Matt and Karen, Property ID: 29569

Charming Bright Sunny Cape Home in Vineyard Haven
3BR
2 baths
Sleeps 6

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

Contact: Darlene Webb, Property ID: 19399

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

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 15, 2022 thru Mid May 2023. $1600/month plus utilities. 6 month minimum.

Contact: Dan & Roseann Sheping, Property ID: 4482

Commanding Lagoon Waterfront, Private Beach: 180° View
2BR
1 ½ bath
Sleeps 6

Happy to have you for a longer term. 32 nights or more gives you full tax exemption. Please inquire for dates!

Contact: Barbara, Property ID: 33283

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

Winter rental available, from mid/end September. Please inquire.

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

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

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