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Long-Term Vacation Rentals in Oak Bluffs

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: 17

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

Boyd’s Bungalow
5BR
2 ½ baths
Sleeps 12

Potential winter rental 3500/mo

Contact: Joe, Property ID: 36517

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

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

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

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

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