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The best holiday homes in Oak Bluffs

Check out our pick of great holiday homes in Oak Bluffs

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Island Sanctuary, hotel in Oak Bluffs

Island Sanctuary offers accommodation in Oak Bluffs. Falmouth is 12 km away. All units are air conditioned and feature a satellite TV. There is also a kitchen, equipped with a dishwasher and oven.

Scored 8.5
8.5
Rated very good
Very good
8 reviews
Yellow Brick Road House, hotel in Oak Bluffs

Located in Oak Bluffs, 2.3 km from Oak Bluffs Town Beach and 12 km from Edgartown Lighthouse, Yellow Brick Road House offers air conditioning.

comfortable furniture, great flow and walking distance to one of our events.
Scored 8.8
8.8
Rated fabulous
Fabulous
6 reviews
Winthrop Cottage, hotel in Oak Bluffs

Located in Oak Bluffs, 1 km from Inkwell Beach and 1.2 km from Oak Bluffs Town Beach, Winthrop Cottage provides air-conditioned accommodation with a patio and free WiFi.

Scored 6.2
6.2
Rated pleasant
Pleasant
8 reviews
Oak Bluffs Cottage, hotel in Oak Bluffs

Situated in Oak Bluffs, 1.1 km from Oak Bluffs Town Beach and 1.2 km from Inkwell Beach, Oak Bluffs Cottage features air-conditioned accommodation with a balcony and free WiFi.

Lovely looking 3 bedroom house in a great location - 10 minutes walk into Oak Bluffs.
Scored 7.8
7.8
Rated good
Good
5 reviews
Island Time, hotel in Oak Bluffs

Island Time, a property with a garden, is situated in Vineyard Haven, 1.3 km from Tisbury Town Beach, 1.9 km from Eastville Beach, as well as 13 km from Edgartown Lighthouse.

Code was provided well in advance, communication with host was good. Also ability to use beach equipment (chairs etc.) was a plus Dedicated parking space was a big plus
Scored 9.0
9.0
Rated superb
Superb
8 reviews
Vineyard Escape, hotel in Oak Bluffs

Vineyard Escape is located in Vineyard Haven. Free WiFi is available throughout the property and Edgartown Lighthouse is 15 km away.

All Good.
Scored 9.2
9.2
Rated superb
Superb
6 reviews
The CAVU Mansion on Bellevue, hotel in Oak Bluffs

The CAVU Mansion on Bellevue offers accommodation in Oklahoma Heights. Falmouth is 12 km away. All units include a TV. There is also a kitchen, fitted with a dishwasher.

Big comfortable house, historical atmosphere. Great for big family.
Scored 8.2
8.2
Rated very good
Very good
9 reviews
Wooded Oasis, hotel in Oak Bluffs

Wooded Oasis is situated in Edgartown. Free WiFi is available throughout the property and Edgartown Lighthouse is 6.6 km away.

Scored 8.8
8.8
Rated fabulous
Fabulous
5 reviews
Dodgers Hole, hotel in Oak Bluffs

Situated in Edgartown in the Massachusetts region, Dodgers Hole features a patio. Free WiFi is available throughout the property and Edgartown Lighthouse is 7.5 km away.

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

Martha's Vineyard Vacation Home is situated in Edgartown and offers a garden and barbecue facilities. This property offers access to a terrace, free private parking and free WiFi.

Scored 7.0
7.0
Rated good
Good
5 reviews
All holiday homes in Oak Bluffs
Looking for a holiday home?
Great for families or large parties, holiday homes are privately owned accommodation, available for long or short-term rental. These homes are furnished and equipped with kitchen facilities for self-catering, although breakfast may be offered as an add-on. These properties have their own independent front door, which makes them different to apartments.
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Most booked holiday homes in Oak Bluffs this month

Enjoy breakfast in Oak Bluffs!

  • Yellow Brick Road House
    Scored 8.8
    8.8
    Rated fabulous
    Fabulous
     · 6 reviews

    Located in Oak Bluffs, 2.3 km from Oak Bluffs Town Beach and 12 km from Edgartown Lighthouse, Yellow Brick Road House offers air conditioning.

    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 accommodation in Oak Bluffs. Falmouth is 12 km 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

    Situated in Oak Bluffs, 1.5 km from Oak Bluffs Town Beach and 1.5 km from Inkwell Beach, Bird Street Breeze features air-conditioned accommodation with a patio and free WiFi.

  • Sankofa House
    Breakfast options

    Set in Oak Bluffs, less than 1 km from Oak Bluffs Town Beach and a 16-minute walk from Inkwell Beach, Sankofa House offers air-conditioned accommodation with a patio and free WiFi.

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

    Situated 2.4 km from Inkwell Beach, 2.5 km from Oak Bluffs Town Beach and 11 km from Edgartown Lighthouse, Oak Bluffs Darling features accommodation set in Oak Bluffs.

  • Cozy Bluffs
    Breakfast options

    Boasting air-conditioned accommodation with a patio, Cozy Bluffs is situated in Oak Bluffs. This property offers access to a balcony, free private parking and free WiFi.

  • Blissful Island Haven

    Located in Oak Bluffs, 700 metres from Oak Bluffs Town Beach and 700 metres from Inkwell Beach, Blissful Island Haven provides air-conditioned accommodation with a patio and free WiFi.

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

    Set in Oak Bluffs in the Massachusetts region, Walking to the Beach, Bars and Restaurant’s has a garden.

    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 holiday homes in Oak Bluffs – budget options available!

  • Birds of Paradise
    Budget options available

    Situated in Oak Bluffs, 1.3 km from Inkwell Beach and 2.2 km from Eastville Beach, Birds of Paradise offers air conditioning.

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

    Gingerbread Dream is set in Oak Bluffs, 1.5 km from Inkwell Beach, 1.9 km from Eastville Beach, as well as 11 km from Edgartown Lighthouse.

  • Set Sail
    Budget options available
    Scored 9.0
    9.0
    Rated superb
    Superb
     · 2 reviews

    Set Sail is situated in Oak Bluffs. The property features garden views. Free WiFi is available throughout the property and Edgartown Lighthouse is 11 km away.

  • Frazier Circle
    Budget options available

    Located in Oak Bluffs, 1.2 km from Oak Bluffs Town Beach and 1.4 km from Inkwell Beach, Frazier Circle provides air-conditioned accommodation with a balcony and free WiFi.

  • Tiffany's Treasure
    Budget options available

    Situated in Oak Bluffs, 11 km from Edgartown Lighthouse, Tiffany's Treasure features air-conditioned accommodation with a balcony and free WiFi.

  • Victorian by the Sea
    Budget options available

    Situated in Oak Bluffs, 400 metres from Oak Bluffs Town Beach and 400 metres from Inkwell Beach, Victorian by the Sea features air-conditioned accommodation with a balcony and free WiFi.

  • Waterfront Newly Renovated w Amazing Views

    Set in Oak Bluffs, within 13 km of Edgartown Lighthouse, Waterfront Newly Renovated w Amazing Views offers accommodation with air conditioning. This holiday home has a garden.

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

    Set in Oak Bluffs, 8.2 km from Edgartown Lighthouse, Fresh Pond Chateau Renovated Bright and Cozy Home offers air-conditioned accommodation with a balcony and free WiFi.

Great access to the city centre! Check these holiday homes in Oak Bluffs

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

    Set in Oak Bluffs, 1.1 km from Oak Bluffs Town Beach and 1.5 km from Inkwell Beach, Canary Cottage offers air-conditioned accommodation with a balcony and free WiFi.

  • Island Breeze
    Central location
    Scored 9.0
    9.0
    Rated superb
    Superb
     · 3 reviews

    Situated in Oak Bluffs, 2.6 km from Eastville Beach and 2.8 km from Inkwell Beach, Island Breeze features air-conditioned accommodation with a patio and free WiFi.

  • Bright Grove
    Central location
    Scored 8.8
    8.8
    Rated fabulous
    Fabulous
     · 4 reviews

    Featuring air conditioning, Bright Grove offers accommodation in Oak Bluffs. Falmouth is 11 km from the property. All units include a TV and DVD player.

    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

    Situated in Oak Bluffs, just 100 metres from Eastville Beach, Wild Oak Oasis features beachfront accommodation with free WiFi.

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

    Oak Bluffs Beauty is located in Oak Bluffs, 11 km from Falmouth. Hyannis is 32 km away. The accommodation is air conditioned and is equipped with a TV with satellite channels.

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

    Vineyard Haven is located in Oak Bluffs, 1.5 km from Oak Bluffs Town Beach, 2.1 km from Eastville Beach, as well as 11 km from Edgartown Lighthouse.

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

    Situated in Oak Bluffs, 1.1 km from Oak Bluffs Town Beach and 1.2 km from Inkwell Beach, Oak Bluffs Cottage features air-conditioned accommodation with a balcony and free WiFi.

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

    Boasting garden views, Home in Oak Bluffs features accommodation with a garden and a patio, around 2.4 km from Inkwell Beach.

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

    Offering a garden and garden view, The Pinkletink is located in Oak Bluffs, 800 metres from Inkwell Beach and 2.8 km from Joseph Sylvia State Beach.

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

    Situated in Oak Bluffs, 1.4 km from Oak Bluffs Town Beach and 1.5 km from Inkwell Beach, Oak Leaf Cape Cottage features air-conditioned accommodation with a patio and free WiFi.

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

    Brunswick Plain, a property with a garden, is set in Oak Bluffs, 1.5 km from Inkwell Beach, 1.9 km from Eastville Beach, as well as 11 km from Edgartown Lighthouse.

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

    Located in Oak Bluffs, 1 km from Inkwell Beach and 1.2 km from Oak Bluffs Town Beach, Winthrop Cottage provides air-conditioned accommodation with a patio and free WiFi.

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

    The Samoset offers accommodation in Oak Bluffs. Falmouth is 12 km away. The accommodation has a satellite TV. There is also a kitchen, fitted with a microwave and fridge.

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

    Set in Oak Bluffs, 2.5 km from Inkwell Beach and 2.6 km from Oak Bluffs Town Beach, Island Getaway offers air conditioning. The holiday home is 12 km from Edgartown Lighthouse.

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

    Sea Glen Cottage is set in Oak Bluffs. Guests can benefit from a patio and a children's playground. Free WiFi is available throughout the property and Edgartown Lighthouse is 10 km away.

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

    Featuring air-conditioned accommodation with a private pool, garden view and a balcony, #OB Pool House is located in Oak Bluffs. Guests can benefit from a patio and a children's playground.

  • Traditional Marthas Vineyard Home with Porch and Yard

    Located in Oak Bluffs, 1.5 km from Inkwell Beach and 2 km from Eastville Beach, Traditional Marthas Vineyard Home with Porch and Yard offers air conditioning.

  • Glenn Manor
    Central location

    Situated in Oak Bluffs, 2.2 km from Inkwell Beach and 2.3 km from Oak Bluffs Town Beach, Glenn Manor offers a garden and air conditioning.

  • The Wayland Victorian

    The Wayland Victorian is situated in Oak Bluffs, 11 km from Falmouth. Hyannis is 32 km away. The accommodation features a TV. There is also a kitchen, fitted with a dishwasher and oven.

  • Sunset Meadows
    Central location

    Sunset Meadows offers accommodation in Oak Bluffs. Falmouth is 11 km away. The accommodation is equipped with a TV. There is also a kitchen, equipped with a dishwasher, oven and microwave.

  • Brewster House
    Central location

    Set in Oak Bluffs, 1.4 km from Eastville Beach and 1.5 km from Oak Bluffs Town Beach, Brewster House offers air-conditioned accommodation with a patio and free WiFi.

  • Private Beach Waterfront Oak-Bluffs Family Cottage

    Boasting air-conditioned accommodation with a patio, Private Beach Waterfront Oak-Bluffs Family Cottage is set in Oak Bluffs.

  • The Burkeshire Manor - Charming Family Home

    Situated in Oak Bluffs, 10 km from Edgartown Lighthouse, The Burkeshire Manor - Charming Family Home features air-conditioned accommodation with a balcony and free WiFi.

  • Bird's Paradise

    Bird's Paradise is located in Oak Bluffs. Free WiFi is available throughout the property and Edgartown Lighthouse is 9 km away.

  • Oak Bluff Bungalow

    Located in Oak Bluffs, 9.2 km from Edgartown Lighthouse, Oak Bluff Bungalow provides air-conditioned accommodation with a balcony and free WiFi. This holiday home features accommodation with a patio.

  • Water Overlook
    Central location

    Situated in Oak Bluffs, 8.8 km from Edgartown Lighthouse, Water Overlook features air-conditioned accommodation with a patio and free WiFi. This holiday home provides a garden.

FAQ about holiday homes in Oak Bluffs

Holiday 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: £177.48
    Scored 8.6
    8.6
    Rated fabulous
    Fabulous
     · 523 reviews
    Great stay, great staff, very clean and a perfect location with perfect views
    Nirpal
    Family with young children
  • Avg. price/night: £177.48
    Scored 8.6
    8.6
    Rated fabulous
    Fabulous
     · 523 reviews
    The view was wonderful. Located near everything. Very clean and people very friendly.
    Audrey
    Group
  • Avg. price/night: £177.48
    Scored 8.6
    8.6
    Rated fabulous
    Fabulous
     · 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 fabulous
    Fabulous
     · 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 traveller

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