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Long-Term Vacation Rentals on Martha's Vineyard

A long-term rental is considered to be an extended stay of more than 31 days. 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). Massachusetts Landlord Tenant Laws will apply.

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

# of Rentals: 35

Chilmark

Chilmark Rental
Beetlebung Guest House/Access to Tennis Courts & Hiking
2BR
1 bath
Sleeps 4

Long term rental ranges from $1800 to $2000 per month. This property is available for Fall/Winter rental from mid September until June. It is availabl...

Contact: Anne, ID: 40083

Edgartown

Edgartown Rental
New Custom Built Home with a Pool
5BR
5 baths
Sleeps 12

My monthly range for winter is Oct to May with a range of 9,000 to 15,000 plus utilities.

Contact: Matt, ID: 35180

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

House is available for an off-season renter beginning in September and ending mid June. Rent is $3000 per month which includes all utilities (electri...

Contact: Joshua Finn, ID: 21009

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

Winter rental available! Please inquire! Monthly rate $4500-$6500 per month plus utilities.

Contact: Barbara, ID: 2395

Edgartown Village Rental
Edgartown Village, Ideal Location-walk to town/bike to beach
3BR
1 ½ bath
Sleeps 7

Available from November thru April for school teachers or other professionals looking for long term rental. $2950 per month. Includes Electric, Heat,...

Contact: David Brady, ID: 11620

Edgartown Rental
Perfect Edgartown Retreat
3BR
2 ½ baths
Sleeps 6

Available for long term rental starting 11/1/25 until 6/1/26. Price $3,750-$4,000/month plus utilities - depending on length of stay.

Contact: Alex Kogan, ID: 17438

Edgartown Rental
Charming Edgartown Village Cottage - Walk to everything!
3BR
2 ½ baths
Sleeps 6

October- May $3,000/week, utilities not included.

Contact: Eunice, ID: 3985

Edgartown Rental
Lovely Contemporary Home-Sengekontacket Pond at end of road
3BR
2 baths
Sleeps 6

I can do a month rental, fee would include utilities. $ 2,500.

Contact: Kim , ID: 9612

Edgartown Rental
Gorgeous Edgartown Homestead,Near Trails,Enclosed Play Yard
3BR
2 baths
Sleeps 6

REDUCED -$300/mo. Now only $2,700/mo (was $3,000). Plus utilities. Above-par rental. Excellent landlord seeks excellent renters. Sept/Oct 2025 to May/...

Contact: Ellen, ID: 9776

Edgartown Rental
Cozy Couples Hideaway - Contemporary
1BR
1 bath
Sleeps 4

Will rent during the off season for $2200. per month plus utilities.

Contact: Kathleen Collins, ID: 2937

Edgartown Rental
The Crow’s Nest: Spacious Modern One-Bedroom Apartment
1BR
1 bath
Sleeps 2

Monthly rentals considered. $2500-4000

Contact: Margaret, ID: 35154

Oak Bluffs

Oak Bluffs Rental
Island Escape with Water-Views; Lap Pool & Guest House
6BR
4 baths
Sleeps 15

Long term rentals considered! October - March $6,000/mo

Contact: Jack, ID: 39526

Oak Bluffs Rental
Ideal Coastal Home Close to Circuit Ave
4BR
3 ½ baths
Sleeps 12

Available November - March 31 $7,500 - $10,000 negotiable

Contact: Keisha, ID: 38638

East Chop Rental
Dempster Park of East Chop: Walk to Beach & Town!
4BR
3 baths
Sleeps 11

Long-term rentals available from October-Mid May. Please inquire. Monthy charge $5,000.00 plus utilities. Trash pick up will be the responsibiity of ...

Contact: Joan or Monica, ID: 34601

Oak Bluffs Rental
The “Summer Wind” House - Walk to the Beach!
5BR
3 baths
Sleeps 10

$20K per month off-season.

Contact: Wendy , ID: 35217

Oak Bluffs Rental
The Purple Door in Heart of OB/Close to Beaches & Town
3BR
2 ½ baths
Sleeps 10

Available Fall | Winter | Spring September through June monthly range $4,000.00 - $10,000.00

Contact: Maxey, ID: 39489

Oak Bluffs Rental
Classic waterfront Vict. cottage, walk to town; huge porch
4BR
2 baths
Sleeps 8

$6200 per month; discount for multiple months. Jan, Feb., March, April, available for a month or more. Great place to read, write, contemplate the cha...

Contact: Jamie, ID: 31304

Oak Bluffs Rental
Beachfront Oasis within Minutes from Downtown
4BR
1 ½ bath
Sleeps 8

April-October Summer 2025: Monthly price: $45,000- $60,000 Off Season 2025: Monthly price: $20,000- $30,000

Contact: Eric, ID: 39711

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

Available October thru May (2800-3200/month)

Contact: Greg Ehrman, ID: 19178

Oak Bluffs Rental
Happy house 0.5mi Nancy’s & Jetty Beach: 1 2025 wk left!
3BR
2 baths
Sleeps 8

Long-term rental during winter months for $2,500/month

Contact: Emily, ID: 31215

Historic Copeland District/ In Rental
Perfect! 7 houses from the Beach-Walk to Ferry & Town!
3BR
2 ½ baths
Sleeps 7

Monthly Off-season rentals: $5000-8000

Contact: Nancy, ID: 28831

Vineyard Hills Rental
Oak Bluffs Escape - Close to Town and Beaches!
3BR
2 ½ baths
Sleeps 7

Available November - April $3,500/mo plus utilities

Contact: Robin and Rodney, ID: 39962

East Chop Rental
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. $3300 + utilities. Perfect for travelling nurses as we are close to the hospit...

Contact: Debra Moran, ID: 32946

Vineyard Haven

Vineyard Haven Rental
Pine Tree Cottage; Steps from the Beach, Close to Town
3BR
1 bath
Sleeps 6

Longer-term rentals are available from 32-60 days. Monthly rates range from $9,750 to $11,250. November through April are not available.

Contact: Nancy, ID: 40537

Vineyard Haven Rental
Warm & Cozy Three Bedroom Bungalow
3BR
1 ½ bath
Sleeps 5

Our home is open for long-term rentals from November 1- May 1 $3400-$3900. Our cozy home is easily accessible and is located in the heart of Vineyard...

Contact: Ingrid, ID: 40456

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

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

Contact: Darlene Webb, ID: 19399

Vineyard Haven Rental
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-se...

Contact: Maggie, ID: 38039

Tisbury Rental
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, ID: 38371

Vineyard Haven Rental
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, ID: 7436

Vineyard Haven Rental
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, ID: 7718

West Tisbury

West Tisbury Lambert's Cove Rental
''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, ID: 23921

Deep Bottom Pond Rental
Vineyard Meadow and Pond Views
4BR
3 baths
Sleeps 8

Monthly rental November - May @ 6,000 plus utilities

Contact: Bill, ID: 18138

West Tisbury Rental
Centrally Located Great Pond/Walking Trails - Kayak & Tennis
3BR
2 ½ baths
Sleeps 8

Currently entire home may be available November through April for $5000 per month plus all utilities.

Contact: Paul and Jennifer Naumoff, ID: 38099

West Tisbury Rental
West Tisbury Country Home
3BR
2 baths
Sleeps 6

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

Contact: Rich, ID: 21460

West Tisbury Rental
West Tisbury Winter Apartment/Bike Path/Close to School
2BR
1 bath
Sleeps 4

Available from September to the end of April. $4000 per month, utilities included.

Contact: Maria, ID: 38906