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Long-Term Vacation Rentals on Martha's Vineyard

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: 52

Chilmark

Very Charming, Roomy Three Bedroom Home
3BR
2 baths
Sleeps 8

All in the town of Chilmark.

Contact: John and Caroline Moore., Property ID: 15956

Chilmark Casita - New Listing! Newly Renovated w/Central AC!
2BR
2 baths
Sleeps 5

February, March, and April are available for $1,500-$2,500 a week.

Contact: Jo, Property ID: 34169

On Upper Chilmark Pond overlooking Lucy Vincent Beach
2BR
1 bath
Sleeps 4

Available in Town of Chilmark.

Contact: John and Caroline Moore., Property ID: 13169

Quiet, Secluded Chilmark Cottage
2BR
1 bath
Sleeps 4

None

Contact: Brian & Caroline Giles, Property ID: 22294

Storybook Cottage in Chilmark
1BR
1 bath
Sleeps 2

Long and short term winter rental available.

Contact: Alyson at Karen M. Overtoom Real Estate, Property ID: 31847

Edgartown

Captain Morse House - Edgartown Village Living at its Finest
12BR
7 baths
Sleeps 25

We would consider it for the right tenant. Please contact me if interested.

Contact: Platt Johnson, Property ID: 18084

Classic Vineyard Beach House near Long Point
5BR
3 baths
Sleeps 10

Long Point Area. Monthly off-season & winter rentals available October - May. Warm (new gas heat ), quiet house with great meadow views off Edgartow...

Contact: Marty or Craig, Property ID: 7335

Relaxing Contemporary Home
4BR
2 baths
Sleeps 10

$1,000 - $1,500 per month. Terms and specifics negotiable.

Contact: Scott, Property ID: 13243

Relaxing Contemporary Cape with access to private tennis
3BR
2 baths
Sleeps 10

House is available for an off-season renter beginning on October 15th and ending on May 1st. Rent is $2450 per month which includes utilities (electr...

Contact: Joshua Finn, Property ID: 21009

Beautiful Edgartown Home with Water Views
3BR
2 baths
Sleeps 10

Long-term rental available in the off-season! Rates ranging from $3500-$4500 per month. Utilities included! Please contact us for more information.

Contact: Kristen, Property ID: 34614

Major Renovation - Everything New! Short Walk To Town
4BR
3 ½ baths
Sleeps 8

Home may be rented for off-season weekends or long-term winter rentals --available from October to end of April each year. Please inquire.

Contact: Barbara, Property ID: 2395

Felix Domus It's Location! Edgartown Home Top of Main Street
3BR
1 ½ bath
Sleeps 8

Long term rental starting 10/15/2019. Ideal for a professional couple. Walking distance to Edgartown School, Court House, Downtown. No pets, plus se...

Contact: John Topham, Property ID: 7825

A Little Piece of Heaven: Main House Plus Separate Guest Apt
3BR
2 ½ baths
Sleeps 8

cottage apartment available. Call for information and pricing

Contact: Donna, Property ID: 29862

Convenient , Ideal Location-walk to town/bike to beach
3BR
1 bath
Sleeps 7

Available from September thru June for school teachers or other professionals looking for long term rental. $1200-1400 per month.

Contact: David Brady, Property ID: 11620

Homestead: Enclosed Pet Yard, Near Trails, Near Downtown A/C
3BR
2 baths
Sleeps 6

WINTER RENTAL AT AN ABOVE-AVERAGE RENTAL HOME Sep/Oct to May/June. For a 7-8 month rental, price is only $2,000/mo plus utilities, based occupancy of ...

Contact: Ellen, Property ID: 9776

Cozy Couples Hideaway - Contemporary
1BR
1 bath
Sleeps 4

Will rent during the off season to no more than two persons for $1000. per month plus utilities.

Contact: Kathleen Collins, Property ID: 2937

Oak Bluffs

Oceanfront Family Compound, Walk to Everything!
5BR
3 ½ baths
Sleeps 14

Yes, longer term (shoulder season especially).

Contact: Laurie, Property ID: 31591

AKWAABA (''Welcome'') House Walk to Circuit Ave & Beach
5BR
3 baths
Sleeps 10

The house is available for rent during all four seasons. House is heated.

Contact: Deirdre, Property ID: 33204

Beautiful 4 BR/2 Bath w/AC. Walk to Park, Beach, & Downtown!
4BR
2 baths
Sleeps 10

N/A

Contact: David, Property ID: 33937

Steps to Beach! Updated OB Cottage, Walk to Town/Ferries, AC
4BR
2 baths
Sleeps 10

Long-term monthly rentals available this summer (June to September). Pricing starting at $8,000 per month depending on desired rental period. Please c...

Contact: Mike and Dana, Property ID: 31349

In-Town Victorian near Niantic Park
4BR
1 ½ bath
Sleeps 9

Long Term Rentals considered. $5500 monthly.

Contact: Leslie, Property ID: 34089

Now booking for Summer 2021! Classic, 4-bed,4-bath MV home
4BR
4 baths
Sleeps 9

Ask about monthly rental rates.

Contact: Carrington, Property ID: 33074

Ocean View East Chop Victorian Cottage - 6 Bedrooms Sleeps 8
6BR
1 ½ bath
Sleeps 8

Ask about long term spring and fall rentals, and August Monthly rentals. The house is not rented in the winter.

Contact: Ted Meleney, Property ID: 5746

Cozy home...walk to Oak Bluffs Marina & Gingerbread Houses
4BR
2 baths
Sleeps 8

n/a

Contact: Susan , Property ID: 29717

Renovated Victorian Home - 2 Blocks to Beach, Town & Parks
4BR
2 baths
Sleeps 8

Available October thru May $1,200-$1,800/month (depending on number of people)

Contact: Greg Ehrman, Property ID: 19178

3 Bedroom, 2 Bath Home for Rent Now in Oak Bluffs
3BR
2 baths
Sleeps 8

Monthly rentals and prices are posted. Prices vary by month, from 1700 to 3500.

Contact: Donna Drottar, Property ID: 19425

Enjoy Spring on the Vineyard and flexible check-in dates!
3BR
4 ½ baths
Sleeps 8

Monthly winter rentals available. Negotiable pricing beginning at $1000 per week.

Contact: Carol, Property ID: 29775

Perfect! 7 houses from the Beach-Walk to Ferry & Town!
3BR
2 ½ baths
Sleeps 7

Our year ‘round house is fully heated and available off-season for monthly or weekly rentals. Monthly Off-season rentals: $5000 to $8000 Thanksgivin...

Contact: Nancy, Property ID: 28831

Charming, Cute 3 Bedroom Summer Cottage
3BR
2 baths
Sleeps 7

Long-term winter rental available from 9/1/2021 to 6/01/2022. Price ranges from $2800 to $2900/month which includes electricity, heat, tv, cable and l...

Contact: Patricia , Property ID: 8278

Cozy, REMODELED Vineyard home. 10-min walk to Downtown OB.
3BR
2 ½ baths
Sleeps 7

Ask about monthly rental rates.

Contact: Carrington, Property ID: 33063

Newly Renovated East Chop Home. Walk to beach and town!
3BR
2 baths
Sleeps 6

Winter rental available monthly beginning September 15th to May 15th. $2500 + utilities. Perfect for travelling nurses as we are close to the hospit...

Contact: Debra Moran, Property ID: 32946

Waterfront Cottage on Oak Bluffs Harbor w/ Small Beach!
3BR
2 baths
Sleeps 6

N/A

Contact: Laurie Welch, Property ID: 9098

Walk To Everything Oak Bluffs! 3+bedrms, 2bath A/C, Pets
3BR
2 baths
Sleeps 6

Cozy three bedroom Oak Bluffs Home available in the off-season 2021. Perfect for the contractor looking for a place while working on a winter project,...

Contact: Christine Rose, Property ID: 28871

Rear half of duplex
2BR
1 bath
Sleeps 5

Winter rental available October through May.Price range 1500-2500. Contact owner by e-mail for more details.

Contact: Mary, Property ID: 29465

2 SUMMER WEEKS LEFT: JULY 3-10 and AUG 21-28.
2BR
1 bath
Sleeps 4

Off-season rental with multi-month lease considered. Please inquire regarding current availability and rates.

Contact: Inkwell Rental, Property ID: 30504

Guest House, Steps to Beach, Water Views!
1BR
1 bath
Sleeps 3

For the shoulder seasons (up until Thanksgiving and then from April to June) $3000 - $5000/month, utilities included. Not available for full-season (...

Contact: Laurie, Property ID: 32208

East Chop Perfect Hide-Away
1BR
1 bath
Sleeps 3

September - $2800; October - $2200: add gas and electric

Contact: Jim, Property ID: 17396

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

West Tisbury

''Moonlit'' - Beautiful Main Hse & Separate Guest House
4BR
3 baths
Sleeps 9

winter rental is available january until april $2700 a month plus utiities

Contact: Melissa Dribben, Property ID: 23921

Vineyard Meadow and Pond Views
4BR
3 baths
Sleeps 8

Monthly rental November - May @ 3,000 plus utilities

Contact: Bill, Property ID: 18138

Camp Cottage in the Woods
3BR
1 bath
Sleeps 6

No winter rental.

Contact: Susan Osmers, Property ID: 25563

Indian Hill Home on 6 Acres w/Flexible Arr/Dep Dates!
3BR
3 baths
Sleeps 6

$2500 per month

Contact: Nancy Polucci, Property ID: 26305

West Tisbury Country Home
3BR
2 baths
Sleeps 6

winter rental from November through April. $2500 per month.

Contact: Rich, Property ID: 21460

Custom-Designed West Tisbury Contemporary
2BR
1 ½ bath
Sleeps 5

Off-season weekly, monthly and long weekends available, with price to be determined based on length of stay and time of year.

Contact: Bruce or Deb, Property ID: 8615

Vineyard Gem
1BR
1 bath
Sleeps 2

Monthly rentals are available from November 1 to June 1. The monthly off-season rate is $2,000 including utilities.

Contact: Edward, Property ID: 34455