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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: 14

Oak Bluffs
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. August-September. Late Fall not o...

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
Steps to Beach! Newly Updated Cottage! Walk to Town/Ferry,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
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
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
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
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 Sleeps 8 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 pool, stunning sunsets, 2 kayaks!
3BR
2 ½ baths
Sleeps 6

Available in September/October. $17,000 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 $3,500. Tenant is responsible for heat, utilities, landsca...

Contact: Abby, Property ID: 38381
Newly-Renovated 3BR/3.5Bath House
3BR
3 ½ baths
Sleeps 6

Available long-term Nov-Apr from $5k/mo plus utilities. Rate varies based on month and number of months. Email owner to inquire. Lease to be negotiate...

Contact: K Minor, Property ID: 38229