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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: 46

Edgartown

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, Property ID: 35180

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 $3000 per month which includes all utilities (el...

Contact: Joshua Finn, Property ID: 21009

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

2024-2025: Winder rental: Available for up to 4 persons, October 15, 2024-May 15, 2025 $3000-$5500 per month. ( 4 month minimum ) Utilities are add...

Contact: Barbara, Property ID: 2395

Designer Retreat With Saltwater Heated Pool & Hot Tub
4BR
3 ½ baths
Sleeps 8

Long term rentals are welcomed - July and August is $100K per month. Other months are negotiable.

Contact: Jarrett Hurwitz, Property ID: 39513

Classy, Katama Contemporary-
3BR
2 baths
Sleeps 8

The house will be available for Fall and holiday weeks and weekends. One month Fall rentals are $5500 per month. No smoking and no pets Price is ne...

Contact: Kathleen Collins, Property ID: 3863

Carefree, Quiet, Centrally Located Vineyard Retreat w/AC
3BR
3 baths
Sleeps 8

Will consider. $3500-4500 per month.

Contact: Alicia Casucci, Property ID: 27034

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, Property ID: 11620

Hamletts' Haven - The Perfect Vacation Escape
3BR
2 baths
Sleeps 6

Winter Rental Available October 1 - May 1 (months flexible) $2,200 monthly + utilities First, Last & Security Deposit References required No pet...

Contact: Katherine, Property ID: 38130

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

October- May $2,500 utilities not included.

Contact: Eunice, Property ID: 3985

Cozy Couples Hideaway - Contemporary
1BR
1 bath
Sleeps 4

Will rent during the off season to no more than two persons for $1600. per month plus utilities.

Contact: Kathleen Collins, Property ID: 2937

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

Monthly rentals considered. $2500-4000

Contact: Margaret, Property ID: 35154

Oak Bluffs

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, Property ID: 39526

The Beach House: Historic Harthaven Gem on a Private Beach
5BR
3 ½ baths
Sleeps 12

32 day rental priced at $9,000 per week, $450 housecleaning fee, one free mid-month cleaning, $500 security fee. August-September. Late Fall not off...

Contact: Marion, Property ID: 31261

Glorious Sunsets On and Over the Water. Beautiful Home
4BR
3 ½ baths
Sleeps 12

Month-long rental available beginning in September into at least October. Rate is $6000-7500 weekly. No pets, smoking of subletting. Great Derby locat...

Contact: Richard, Property ID: 27817

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, Property ID: 34601

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

$20K per month off-season.

Contact: Wendy , Property ID: 35217

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, Property ID: 39489

Spacious Oak Bluffs Farmhouse
4BR
2 ½ baths
Sleeps 8

Available as a long-term rental from approximately September-May (depending on bookings) for $3500/month.

Contact: Compass | MV Team, Property ID: 38312

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, Property ID: 31304

Fun, Family, Vineyard Getaway
4BR
2 baths
Sleeps 8

If you are interested in long term rental please reach out to me. $5000 - $15000 monthly depending on month, I give a percentage off the market rate.

Contact: Steve, Property ID: 31476

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

Available October thru May (2800-3200/month)

Contact: Greg Ehrman, Property ID: 19178

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, Property ID: 31215

NOBLE HOUSE: Charming Oasis Near Town & Beach
3BR
2 baths
Sleeps 8

Long-term rentals available from October - May. Please inquire for details and availability.

Contact: DiDi Noble, Property ID: 39654

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: $5000-8000 Thanksgiving we...

Contact: Nancy, Property ID: 28831

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, Property ID: 32946

Heated saltwater pool, stunning sunsets, 2 kayaks!
3BR
2 ½ baths
Sleeps 6

Available in September/October. $16,000 for 32 days.

Contact: Kim , Property ID: 34492

History and Heritage Awaits/Walk to Beach
3BR
1 ½ bath
Sleeps 6

Long term rental is available from Oct. 1 through May 1. Monthly rate during this period is $2,500. Tenant is responsible for heat, utilities, landsca...

Contact: Abby, Property ID: 38381

Bright Modern House w/ AC-Sleeps 7 Walk to Beach & Shops
3BR
3 baths
Sleeps 6

Fall winter prices for 3-4 month stays range between $4000-$4,500 per month. We are only interested in inquiries for 8 week stays or more between Octo...

Contact: Jeanine, Property ID: 20575

Wooded Haven, Martha's Vineyard Oasis
1BR
1 bath
Sleeps 3

Winter rental available $1800 per month for a 9-month lease, October to June. Near the hospital.

Contact: Julia, Property ID: 21977

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

The Bellevue - Stunning 4/2.5 Water View, Hot Tub
4BR
2 ½ baths
Sleeps 8

Please inquire about longer term rentals.

Contact: James, Property ID: 39682

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

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

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

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

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

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 @ 6,000 plus utilities

Contact: Bill, Property ID: 18138

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, Property ID: 38099

West Tisbury Country Home
3BR
2 baths
Sleeps 6

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

Contact: Rich, Property ID: 21460

Lambert's Cove Home poss flex w/arrival dates!
3BR
3 baths
Sleeps 6

This outstanding, private setting is available for $4500 per month through May for a winter rental. Two people maximum. No pets. Utilities not include...

Contact: Nancy Polucci, Property ID: 26305

NEW for 2024! Charming West Tisbury House in town center
3BR
2 ½ baths
Sleeps 6

Home available January 2025 to June 2025, $3500/mo

Contact: Jude, Property ID: 38093

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, Property ID: 38906