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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).

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

# of Rentals: 42

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 $3,000/week, utilities not included.

Contact: Eunice, Property ID: 3985

Beautiful Outdoor Living w/ Hot Tub, Lush Gardens/Near Town
3BR
3 baths
Sleeps 6

Available for monthly rental in August for $32,000

Contact: Linda, Property ID: 39790

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

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

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, Property ID: 39711

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

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

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

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

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

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

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 Country Home
3BR
2 baths
Sleeps 6

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

Contact: Rich, Property ID: 21460

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