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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: 21

Oak Bluffs

Oceanfront Family Compound, Walk to Everything!
5BR
3 ½ baths
Sleeps 14

Yes, longer term (shoulder season especially).

Contact: Laurie, Property ID: 31591

AKWAABA (''Welcome'') House Walk to Circuit Ave & Beach
5BR
3 baths
Sleeps 10

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

Contact: Deirdre, Property ID: 33204

Beautiful 4 BR/2 Bath w/AC. Walk to Park, Beach, & Downtown!
4BR
2 baths
Sleeps 10

N/A

Contact: David, Property ID: 33937

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

Now booking for Summer 2021! Classic, 4-bed,4-bath MV home
4BR
4 baths
Sleeps 9

Ask about monthly rental rates.

Contact: Carrington, Property ID: 33074

In-Town Victorian near Niantic Park
4BR
1 ½ bath
Sleeps 9

Long Term Rentals considered. $5500 monthly.

Contact: Leslie, Property ID: 34089

Ocean View East Chop Victorian Cottage - 6 Bedrooms Sleeps 8
6BR
1 ½ bath
Sleeps 8

Ask about long term spring and fall rentals, and August Monthly rentals. The house is not rented in the winter.

Contact: Ted Meleney, Property ID: 5746

Renovated Victorian Home - 2 Blocks to Beach, Town & Parks
4BR
2 baths
Sleeps 8

Available October thru May $1,200-$1,800/month (depending on number of people)

Contact: Greg Ehrman, Property ID: 19178

Cozy home...walk to Oak Bluffs Marina & Gingerbread Houses
4BR
2 baths
Sleeps 8

n/a

Contact: Susan , Property ID: 29717

Enjoy Spring on the Vineyard and flexible check-in dates!
3BR
4 ½ baths
Sleeps 8

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

Contact: Carol, Property ID: 29775

3 Bedroom, 2 Bath Home for Rent Now in Oak Bluffs
3BR
2 baths
Sleeps 8

Monthly rentals and prices are posted. Prices vary by month, from 1700 to 3500.

Contact: Donna Drottar, Property ID: 19425

Cozy, REMODELED Vineyard home. 10-min walk to Downtown OB.
3BR
2 ½ baths
Sleeps 7

Ask about monthly rental rates.

Contact: Carrington, Property ID: 33063

Charming, Cute 3 Bedroom Summer Cottage
3BR
2 baths
Sleeps 7

Long-term winter rental available from 9/1/2021 to 6/01/2022. Price ranges from $2800 to $2900/month which includes electricity, heat, tv, cable and l...

Contact: Patricia , Property ID: 8278

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 to $8000 Thanksgivin...

Contact: Nancy, Property ID: 28831

Walk To Everything Oak Bluffs! 3+bedrms, 2bath A/C, Pets
3BR
2 baths
Sleeps 6

Cozy three bedroom Oak Bluffs Home available in the off-season 2021. Perfect for the contractor looking for a place while working on a winter project,...

Contact: Christine Rose, Property ID: 28871

Waterfront Cottage on Oak Bluffs Harbor w/ Small Beach!
3BR
2 baths
Sleeps 6

N/A

Contact: Laurie Welch, Property ID: 9098

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. $2500 + utilities. Perfect for travelling nurses as we are close to the hospit...

Contact: Debra Moran, Property ID: 32946

Rear half of duplex
2BR
1 bath
Sleeps 5

Winter rental available October through May.Price range 1500-2500. Contact owner by e-mail for more details.

Contact: Mary, Property ID: 29465

2 SUMMER WEEKS LEFT: JULY 3-10 and AUG 21-28.
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

Guest House, Steps to Beach, Water Views!
1BR
1 bath
Sleeps 3

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

East Chop Perfect Hide-Away
1BR
1 bath
Sleeps 3

September - $2800; October - $2200: add gas and electric

Contact: Jim, Property ID: 17396