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The best vacation homes in Oak Bluffs

Check out our selection of great vacation homes in Oak Bluffs

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Island Sanctuary, hotel in Oak Bluffs

Island Sanctuary offers accommodations in Oak Bluffs. Falmouth is 8 miles away. All units are air conditioned and feature a satellite TV. There is also a kitchen, equipped with a dishwasher and oven.

All went well & thank you. Enjoyed the property & surroundings.
Scored 8.5
8.5
Rated very good
Very Good
8 reviews
Yellow Brick Road House, hotel in Oak Bluffs

Yellow Brick Road House offers accommodations in Oak Bluffs, 7.5 miles from Edgartown Lighthouse. The air-conditioned accommodation is 1.4 miles from Oak Bluffs Town Beach.

Very close and convenient to everything. Quiet street, plenty of room, well stocked kitchen to cook and eat in
Scored 8.8
8.8
Rated excellent
Excellent
6 reviews
Winthrop Cottage, hotel in Oak Bluffs

Winthrop Cottage offers accommodations in Oak Bluffs, a 12-minute walk from Inkwell Beach and 0.7 miles from Oak Bluffs Town Beach.

I liked that the property was close to town. the property had the basics of what we needed. we didn’t stay at the house much, other than to sleep.
Scored 6.2
6.2
Rated pleasant
Pleasant
8 reviews
Oak Bluffs Cottage, hotel in Oak Bluffs

Oak Bluffs Cottage is located in Oak Bluffs, just a 13-minute walk from Oak Bluffs Town Beach and 0.8 miles from Inkwell Beach.

Great location
Scored 7.8
7.8
Rated good
Good
5 reviews
Island Time, hotel in Oak Bluffs

Just a 16-minute walk from Tisbury Town Beach and 1.2 miles from Eastville Beach, Island Time features accommodations in Vineyard Haven with a garden.

Great location and a very nice well equipped apartment
Scored 9.0
9.0
Rated wonderful
Wonderful
8 reviews
Vineyard Escape, hotel in Oak Bluffs

Providing a garden, Vineyard Escape provides accommodations in Vineyard Haven. Free Wifi is available throughout the property and Edgartown Lighthouse is 9.1 miles away.

We enjoyed the grill and screen porch, quiet location
Scored 9.2
9.2
Rated wonderful
Wonderful
6 reviews
The CAVU Mansion on Bellevue, hotel in Oak Bluffs

The CAVU Mansion on Bellevue offers accommodations in Oklahoma Heights. Falmouth is 8 miles away. All units include a TV. There is also a kitchen, fitted with a dishwasher.

We liked the size of the home and the beautiful grounds.
Scored 8.2
8.2
Rated very good
Very Good
9 reviews
Wooded Oasis, hotel in Oak Bluffs

Free Wifi is available throughout the property and Edgartown Lighthouse is 4.1 miles away.

Quiet and comfortable and convenient. We were close to everything on the island, and we could make dinner if we didn't feel like paying for another high-priced restaurant.
Scored 8.8
8.8
Rated excellent
Excellent
5 reviews
Dodgers Hole, hotel in Oak Bluffs

Guests staying at this vacation home have access to a patio. Free Wifi is available throughout the property and Edgartown Lighthouse is 4.7 miles away.

Location
Scored 7.3
7.3
Rated good
Good
6 reviews
Martha's Vineyard Vacation Home, hotel in Oak Bluffs

Featuring a garden, Martha's Vineyard Vacation Home features accommodations in Edgartown. Both Wifi and private parking are available at the vacation home free of charge.

Loved the location, hammock out back and clean and updated kitchen and baths.
Scored 7.0
7.0
Rated good
Good
5 reviews
All vacation homes in Oak Bluffs
Looking for a vacation home?
Great for families or large parties, vacation homes are privately owned accommodations, available for long or short-term rental. These homes are furnished and equipped with kitchen facilities, though breakfast might be offered as an add-on. These properties have their own independent front door, which makes them different than apartments.
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Most booked vacation homes in Oak Bluffs this month

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  • Yellow Brick Road House
    Scored 8.8
    8.8
    Rated excellent
    Excellent
     · 6 reviews

    Yellow Brick Road House offers accommodations in Oak Bluffs, 7.5 miles from Edgartown Lighthouse. The air-conditioned accommodation is 1.4 miles from Oak Bluffs Town Beach.

    comfortable furniture, great flow and walking distance to one of our events.

  • Island Sanctuary
    Scored 8.5
    8.5
    Rated very good
    Very Good
     · 8 reviews

    Island Sanctuary offers accommodations in Oak Bluffs. Falmouth is 8 miles away. All units are air conditioned and feature a satellite TV. There is also a kitchen, equipped with a dishwasher and oven.

    All went well & thank you. Enjoyed the property & surroundings.

  • Bird Street Breeze

    Bird Street Breeze is located in Oak Bluffs, just a 18-minute walk from Inkwell Beach and 1.3 miles from Eastville Beach.

  • Sankofa House
    Breakfast options

    Sankofa House offers accommodations in Oak Bluffs, a 16-minute walk from Inkwell Beach and 1.3 miles from Eastville Beach.

  • Oak Bluffs Darling
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 1 review

    Oak Bluffs Darling is located in Oak Bluffs, just 1.5 miles from Inkwell Beach and 1.6 miles from Oak Bluffs Town Beach. This vacation home is 7 miles from Edgartown Lighthouse.

  • Cozy Bluffs
    Breakfast options

    Cozy Bluffs offers accommodations in Oak Bluffs, 6.7 miles from Edgartown Lighthouse. This property offers access to a balcony and free private parking.

  • Blissful Island Haven

    Blissful Island Haven is located in Oak Bluffs, just a 8-minute walk from Inkwell Beach and 1.7 miles from Joseph Sylvia State Beach. The Edgartown Lighthouse is within 6 miles of the vacation home.

  • Walking to the Beach, Bars and Restaurant’s
    Scored 9.7
    9.7
    Rated exceptional
    Exceptional
     · 3 reviews

    Walking to the Beach, Bars and Restaurant’s offers accommodations in Oak Bluffs, 7 miles from Edgartown Lighthouse.

    The house is in a good walking location to town. It is out of the downtown area and we enjoyed the quiet.

Save money on vacation homes in Oak Bluffs – budget options available!

  • Birds of Paradise
    Budget options available

    Birds of Paradise offers accommodations in Oak Bluffs, 1.4 miles from Eastville Beach and 6.8 miles from Edgartown Lighthouse. The air-conditioned accommodation is a 15-minute walk from Inkwell Beach.

  • Gingerbread Dream
    Budget options available
    Scored 7.5
    7.5
    Rated good
    Good
     · 2 reviews

    Just a 17-minute walk from Inkwell Beach and 1.2 miles from Eastville Beach, Gingerbread Dream features accommodations in Oak Bluffs with a garden.

  • Set Sail
    Budget options available
    Scored 9.0
    9.0
    Rated wonderful
    Wonderful
     · 2 reviews

    Free Wifi is available throughout the property and Edgartown Lighthouse is 6.7 miles away.

  • Frazier Circle
    Budget options available

    Frazier Circle is located in Oak Bluffs, just 1.5 miles from Eastville Beach and 6.9 miles from Edgartown Lighthouse. The air-conditioned accommodation is a 17-minute walk from Inkwell Beach.

  • Tiffany's Treasure
    Budget options available

    This vacation home provides accommodations with a patio. Free Wifi is available throughout the property and Edgartown Lighthouse is 6.6 miles away.

  • Victorian by the Sea
    Budget options available

    Offering a garden, Victorian by the Sea features accommodations in Oak Bluffs.

  • Waterfront Newly Renovated w Amazing Views

    Featuring a garden, Waterfront Newly Renovated w Amazing Views offers accommodations in Oak Bluffs. The air-conditioned accommodation is 8 miles from Edgartown Lighthouse.

  • Fresh Pond Chateau Renovated Bright and Cozy Home
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 1 review

    Fresh Pond Chateau Renovated Bright and Cozy Home offers accommodations in Oak Bluffs, 5.1 miles from Edgartown Lighthouse.

Great access to the city center! Check these vacation homes in Oak Bluffs

  • Canary Cottage
    Central location
    Scored 9.7
    9.7
    Rated exceptional
    Exceptional
     · 3 reviews

    Canary Cottage offers accommodations in Oak Bluffs, 6.9 miles from Edgartown Lighthouse. This vacation home offers air-conditioned accommodations with a balcony and free Wifi.

  • Island Breeze
    Central location
    Scored 9.0
    9.0
    Rated wonderful
    Wonderful
     · 3 reviews

    Island Breeze is located in Oak Bluffs, just 1.9 miles from Oak Bluffs Town Beach and 7 miles from Edgartown Lighthouse. The air-conditioned accommodation is 1.8 miles from Inkwell Beach.

  • Bright Grove
    Central location
    Scored 8.8
    8.8
    Rated excellent
    Excellent
     · 4 reviews

    Featuring air conditioning, Bright Grove is located in Oak Bluffs, just 7 miles from Falmouth. Hyannis is 20 miles from the property. The accommodation is fitted with a satellite TV.

    The proper was clean, air conditioned and fully stocked for what we needed.

  • Wild Oak Oasis
    Central location
    Scored 8.5
    8.5
    Rated very good
    Very Good
     · 2 reviews

    Wild Oak Oasis is located in Oak Bluffs, just a few steps from Eastville Beach and 1.8 miles from Owen Park Beach. This beachfront property offers access to free Wifi.

  • Oak Bluffs Beauty
    Scored 8.3
    8.3
    Rated very good
    Very Good
     · 3 reviews

    Offering accommodations with air conditioning, Oak Bluffs Beauty is located in Oak Bluffs, just 7 miles from Falmouth. Hyannis is 20 miles away. All units include a satellite TV.

  • Vineyard Haven
    Central location
    Scored 8.0
    8.0
    Rated very good
    Very Good
     · 1 review

    Vineyard Haven offers accommodations in Oak Bluffs, 6.9 miles from Edgartown Lighthouse.

  • Oak Bluffs Cottage
    Scored 7.8
    7.8
    Rated good
    Good
     · 5 reviews

    Oak Bluffs Cottage is located in Oak Bluffs, just a 13-minute walk from Oak Bluffs Town Beach and 0.8 miles from Inkwell Beach.

  • Home in Oak Bluffs
    Scored 7.7
    7.7
    Rated good
    Good
     · 3 reviews

    Home in Oak Bluffs is located in Oak Bluffs, just 1.5 miles from Inkwell Beach and 1.6 miles from Oak Bluffs Town Beach. This property offers access to a balcony and free private parking.

  • The Pinkletink
    Central location
    Scored 7.0
    7.0
    Rated good
    Good
     · 1 review

    The Pinkletink is located in Oak Bluffs, just a 9-minute walk from Inkwell Beach and 1.7 miles from Joseph Sylvia State Beach.

  • Oak Leaf Cape Cottage
    Scored 6.3
    6.3
    Rated pleasant
    Pleasant
     · 3 reviews

    Oak Leaf Cape Cottage is located in Oak Bluffs, just 1.2 miles from Eastville Beach and 6.9 miles from Edgartown Lighthouse. The air-conditioned accommodation is a 18-minute walk from Inkwell Beach.

  • Brunswick Plain
    Scored 6.3
    6.3
    Rated pleasant
    Pleasant
     · 3 reviews

    Brunswick Plain is located in Oak Bluffs, just a 18-minute walk from Inkwell Beach and 1.2 miles from Eastville Beach. The vacation home is 6.9 miles from Edgartown Lighthouse.

  • Winthrop Cottage
    Scored 6.2
    6.2
    Rated pleasant
    Pleasant
     · 8 reviews

    Winthrop Cottage offers accommodations in Oak Bluffs, a 12-minute walk from Inkwell Beach and 0.7 miles from Oak Bluffs Town Beach.

  • The Samoset
    Central location
    Scored 5.5
    5.5
    Rated fair
    Average
     · 2 reviews

    The Samoset offers accommodations in Oak Bluffs. Falmouth is 7 miles away. The accommodation has a satellite TV. There is also a kitchen, fitted with a microwave and refrigerator.

  • Island Getaway
    Central location
    Scored 4.8
    4.8
    Rated disappointing
    Disappointing
     · 6 reviews

    Island Getaway offers accommodations in Oak Bluffs, 1.6 miles from Oak Bluffs Town Beach and 7.7 miles from Edgartown Lighthouse. The air-conditioned accommodation is 1.5 miles from Inkwell Beach.

  • Sea Glen Cottage
    Scored 4.8
    4.8
    Rated disappointing
    Disappointing
     · 4 reviews

    Free Wifi is available throughout the property and Edgartown Lighthouse is 6.4 miles away.

  • #OB Pool House
    Central location
    Scored 1.0
    1.0
    Rated very poor
    Very Poor
     · 1 review

    Guests can benefit from a patio and a children's playground. Free Wifi is available throughout the property and Edgartown Lighthouse is 5.2 miles away.

  • Traditional Marthas Vineyard Home with Porch and Yard

    Traditional Marthas Vineyard Home with Porch and Yard offers accommodations in Oak Bluffs, 1.3 miles from Eastville Beach and 7 miles from Edgartown Lighthouse.

  • Glenn Manor
    Central location

    Glenn Manor offers accommodations in Oak Bluffs, 1.4 miles from Oak Bluffs Town Beach and 7.7 miles from Edgartown Lighthouse. The air-conditioned accommodation is 1.4 miles from Inkwell Beach.

  • The Wayland Victorian

    The Wayland Victorian is located in Oak Bluffs, just 7 miles from Falmouth. Hyannis is 20 miles away. All units have a satellite TV. There is also a kitchen, fitted with a dishwasher and oven.

  • Sunset Meadows
    Central location

    Sunset Meadows offers accommodations in Oak Bluffs. Falmouth is 7 miles away. The accommodation is equipped with a TV. There is also a kitchen, equipped with a dishwasher, oven and microwave.

  • Brewster House
    Central location

    Brewster House is located in Oak Bluffs, just 1.3 miles from Inkwell Beach and 7 miles from Edgartown Lighthouse. The air-conditioned accommodation is a 17-minute walk from Oak Bluffs Town Beach.

  • Private Beach Waterfront Oak-Bluffs Family Cottage

    Private Beach Waterfront Oak-Bluffs Family Cottage offers accommodations in Oak Bluffs, 7.3 miles from Edgartown Lighthouse. This vacation home features air-conditioned accommodations with a patio.

  • The Burkeshire Manor - Charming Family Home

    The Burkeshire Manor - Charming Family Home offers accommodations in Oak Bluffs, 6 miles from Edgartown Lighthouse.

  • Bird's Paradise

    Free Wifi is available throughout the property and Edgartown Lighthouse is 5.6 miles away. Leading onto a patio with garden views, the spacious vacation home consists of 4 bedrooms.

  • Oak Bluff Bungalow

    Free Wifi is available throughout the property and Edgartown Lighthouse is 5.7 miles away. Opening onto a patio, the air-conditioned vacation home consists of 5 bedrooms.

  • Water Overlook
    Central location

    Free Wifi is available throughout the property and Edgartown Lighthouse is 5.5 miles away.

FAQ about vacation homes in Oak Bluffs

Vacation Homes That Guests Love in Oak Bluffs

  • Scored 9.7
    9.7
    Rated exceptional
    Exceptional
     · 3 reviews
    This was one of the nicest holiday houses I've ever stayed in. Not only was it in prime position to enjoy Oak Bluffs and Martha's Vineyard, but the house was beautifully appointed. Everything was clean, crisp, modern and extremely comfortable. Highly recommended!
    Sonja
    Young couple
  • Avg. price/night: $233.45
    Scored 8.6
    8.6
    Rated excellent
    Excellent
     · 523 reviews
    Great stay, great staff, very clean and a perfect location with perfect views
    Nirpal
    Family with young children
  • Avg. price/night: $233.45
    Scored 8.6
    8.6
    Rated excellent
    Excellent
     · 523 reviews
    The view was wonderful. Located near everything. Very clean and people very friendly.
    Audrey
    Group
  • Avg. price/night: $233.45
    Scored 8.6
    8.6
    Rated excellent
    Excellent
     · 523 reviews
    Hotel room was very clean, spacious and beautiful... small terrace outside, off of the room, was a bonus! Staff was extremely friendly and helpful! Front porch of the hotel was awesome in the evenings - lots of seating options and faces the water... was very nice!
    Michelle
    Family with young children
  • Scored 8.2
    8.2
    Rated very good
    Very Good
     · 363 reviews
    Very clean and fabulous amenities!!
    Kimberly
    Young couple
  • Scored 8.9
    8.9
    Rated excellent
    Excellent
     · 161 reviews
    Host was exceptional! Good breakfast each day! Location close to everything! Place was very clean!
    edmund
    Young couple
  • Scored 8.0
    8.0
    Rated very good
    Very Good
     · 1 review
    centrally located- equipped with washer and dryer- nice porch and yard -very clean- thankful for being pet friendly- Kitchen was set up well for cooking/meal prep, house perfect for mother/ daughter- small family get away.
    Anissa
    Solo traveler

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