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Long-Term Vacation Rentals in Oak Bluffs

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: 13

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

Oak Bluffs Rental
Ideal Coastal Home Close to Circuit Ave
4BR
3 ½ baths
Sleeps 12

Available November - March 31 $7,500 - $10,000 negotiable

Contact: Keisha, ID: 38638

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
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
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 East Chop Rental
East Chop Charmer
4BR
2 ½ baths
Sleeps 8

Please inquire regarding longer term rentals

Contact: Emma & Casandra, Landmarks at TODAY Real Estate, ID: 40590

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
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

Monthly Off-season rentals: $5000-8000

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

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
CozyBluffs - Walk to Beach/Circuit Ave/OB ferries!
1BR
1 ½ bath
Sleeps 2

Monthly rental available Nov-April 30, 2026 - 1 month minimum. No pets. Email for further information.

Contact: Fran M., ID: 34909