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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: 51

Chilmark

Beautiful Sunsets On Menemsha Pond
8BR
5 ½ baths
Sleeps 16

Please call 508-560-9901 for winter rental options

Contact: Casandra, Realtor, Property ID: 34454

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

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

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 $2600 per month which includes utilities (electr...

Contact: Joshua Finn, Property ID: 21009

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

Available off-season weekends, weeks or long-term winter rental. available from October to end April. Please inquire.

Contact: Barbara, Property ID: 2395

Classy, Katama Contemporary-
3BR
2 baths
Sleeps 8

The house will be available for Fall and holiday weeks and weekends October 4- May 31.Long term monthly or winter rental is also available. No smoki...

Contact: Kathleen Collins, Property ID: 3863

Charming Edgartown Village Cottage - Walk to everything!
3BR
2 ½ baths
Sleeps 8

October- May $2,500 utilities not included.

Contact: Eunice, Property ID: 3985

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

Private Katama House Close to Town and Beaches/Pets Welcome
3BR
2 baths
Sleeps 7

Mid September to mid June

Contact: Julie , Property ID: 36538

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

Available from November thru April for school teachers or other professionals looking for long term rental. $2000 per month. Includes Electric, Heat,...

Contact: David Brady, Property ID: 11620

Felix Domus It's Location! Edgartown Home Top of Main Street
3BR
1 bath
Sleeps 6

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

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: linda drew, Property ID: 9612

Edgartown pied-à-terre
1BR
1 bath
Sleeps 2

Inquire about a winter rental.

Contact: Lee, Property ID: 33357

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

Air Conditioned Oak Bluffs Waterview Victorian. In Town
6BR
2 baths
Sleeps 13

*Inquire about winter rental* Mini Split (A/C-Heating) units throughout

Contact: Cummings Manor, Property ID: 35046

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

32 day rental priced at $8,500 per week, $400 housecleaning fee, one free mid-month cleaning, $1,000 security fee. Until now our only long term renta...

Contact: Marion, Property ID: 31261

Boyd’s Bungalow
5BR
2 ½ baths
Sleeps 12

Potential winter rental 3500/mo

Contact: Joe, Property ID: 36517

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 is Ready!
5BR
3 baths
Sleeps 10

$20K per month off-season. May accept less than 7 day rentals off-season.

Contact: Wendy , Property ID: 35217

Akwaaba Manor Elegant Oak Bluffs Victorian ALL SEASONS Vaca
5BR
3 baths
Sleeps 10

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

Contact: Deirdre, Property ID: 33204

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

Walk To Everything Oak Bluffs! 4bedrms, 2bath A/C, Pets
4BR
2 baths
Sleeps 8

Cozy Oak Bluffs Home available in the off-season 2023. Perfect for the contractor looking for a place while working on a winter project, or perhaps a ...

Contact: Christine Rose, Property ID: 28871

Spring & Summer 2023 Weeks Still Available!
4BR
4 ½ baths
Sleeps 8

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

Contact: Carol, Property ID: 29775

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

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

Quiet Oak Bluffs Neighborhood walk to Harbor, Beach,Village
3BR
2 baths
Sleeps 6

possible

Contact: Susan Austin, Broker, Property ID: 33701

Jupiter House: Recently Renovated, Open-concept 3 BR Home
3BR
2 baths
Sleeps 6

Our home is not available for long-term, off season rentals.

Contact: Barbara, Property ID: 34548

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

Charming Cottage Located in Heart of Oak Bluffs
2BR
2 ½ baths
Sleeps 4

Contact: Jolanta, Property ID: 35127

OAK BLUFFS GETAWAY
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

''The Nest'' Guest House: Steps to Beach, Water Views!
1BR
1 bath
Sleeps 2

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

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

West Tisbury

Lovely, Spacious Home in Quiet Area of West Tisbury
4BR
3 baths
Sleeps 10

not available

Contact: Kathleen Noble, Property ID: 19012

''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

Pet Friendly Quaint MV Getaway on Private 1 acre
3BR
2 ½ baths
Sleeps 8

We will consider any long term rentals, off and on season

Contact: Alan, Property ID: 35848

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

7.500. Oct to may.

Contact: Nancy Polucci, Property ID: 26305