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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: 51

Aquinnah

Aquinnah Rental
Kingtide Escape with Ocean Views
3BR
2 ½ baths
Sleeps 8

November 2024 - February 2025 is available for monthly rentals. $3500/month

Contact: Jessica Ward, ID: 36194

Chilmark

Chilmark Rental
Nocket Downs, located in Blacksmith Valley
5BR
2 ½ baths
Sleeps 9

Yes, but usually no more than 32 days. The rates vary throughout the year.

Contact: Wendy, ID: 8790

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

This property is available for Fall/Winter rental from mid September until June. It is available this season from April through Mid June. Long term re...

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

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, ID: 2395

Edgartown Rental
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, ID: 39513

Edgartown Rental
Secluded Retreat on South Shore Edgartown w/ Private Beach
4BR
4 baths
Sleeps 8

For 2025, long term rental is available from August 31 to November 16. $7,000 per week thru October 12, $5,000 per week through November 16.

Contact: Chris, ID: 39870

Edgartown Rental
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, ID: 3863

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

Will consider. $3500-4500 per month.

Contact: Alicia Casucci, ID: 27034

Edgartown Rental
Perfect Edgartown Retreat
3BR
2 ½ baths
Sleeps 8

Please email to inquire.

Contact: Alex Kogan, ID: 17438

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
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
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, ID: 39790

Edgartown Rental
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, ID: 38130

Edgartown Rental
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, 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

Harthaven Rental
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, ID: 31261

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
Spacious Oak Bluffs Farmhouse w/ Ferry Tickets
4BR
2 ½ baths
Sleeps 8

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

Contact: Studio Realty, ID: 38312

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
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
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
Ellen’s Quintessential Cape w/ Tennis/Bike Path
3BR
4 ½ baths
Sleeps 8

30-60 day Rental option Months: November 1- March 1. $ 6000 per month (non state of emergency/pandemic) No cleaning service

Contact: Les and Andrea, ID: 31356

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

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, 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

Oak Bluffs Rental
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, ID: 20575

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

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

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

Contact: Kim , ID: 34492

Oak Bluffs Rental
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, ID: 21977

Vineyard Haven

Near Town Rental
In Town
3BR
2 ½ baths
Sleeps 8

We have June and July available until July 20th and all of August and into September - Monthly $20,000

Contact: Emma & Casandra, Landmarks at TODAY Real Estate, ID: 40022

Vineyard Haven Rental
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, ID: 29492

Vineyard Haven Rental
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, ID: 19399

Vineyard Haven Rental
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, ID: 34386

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-...

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

West Chop Rental
Walk to Beach; Close to Town & Dining; Newly Renovated
2BR
2 baths
Sleeps 4

This home can be rented long-term for June, July and September. Ranging from $14,000 to $20,000 (these rates have already been discounted for a month...

Contact: Susan , ID: 39912

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
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. No pets. Utilities not included. Please inquire fo...

Contact: Nancy Polucci, ID: 26305

West Tisbury Rental
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, ID: 38093

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