Skip to main content

Cottages in Oak Bluffs

Find the cottages that appeal to you the most

The best cottages in Oak Bluffs

Check out our pick of great cottages in Oak Bluffs

Show all

Looking for a cottage?

Cottages are perfect for travellers who enjoy feeling cosy and independent in the countryside. Usually small, traditionally built houses, cottages spread across one or two floors, making them great for families, or holidays with a little more privacy.

Most booked cottages in Oak Bluffs and surroundings in the past month

See all

Popular with guests booking cottages in Oak Bluffs

Popular with guests booking cottages in Oak Bluffs

Scored out of 10, guest rating 7.8
Good - What previous guests thought, 7 reviews

Popular with guests booking cottages in Oak Bluffs

Scored out of 10, guest rating 6.0
Pleasant - What previous guests thought, 4 reviews

Popular with guests booking cottages in Oak Bluffs

Scored out of 10, guest rating 8.0
Very good - What previous guests thought, 1 review

Popular with guests booking cottages in Oak Bluffs

Popular with guests booking cottages in Oak Bluffs

Scored out of 10, guest rating 8.0
Very good - What previous guests thought, 2 reviews

Popular with guests booking cottages in Oak Bluffs

Popular with guests booking cottages in Oak Bluffs

Scored out of 10, guest rating 7.0
Good - What previous guests thought, 1 review

Popular with guests booking cottages in Oak Bluffs

Scored out of 10, guest rating 8.0
Very good - What previous guests thought, 5 reviews

Popular with guests booking cottages in Oak Bluffs

Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 180 reviews

Enjoy breakfast in Oak Bluffs and nearby

Situated in Oak Bluffs in the Massachusetts region, Bird Street Breeze features a patio. Guests can benefit from a balcony and an outdoor fireplace.

Vineyard Haven

Oak Bluffs
Breakfast options
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 1 review

Situated 1.6 km from Oak Bluffs Town Beach and 11 km from Edgartown Lighthouse, Vineyard Haven features accommodation located in Oak Bluffs. Guests can benefit from a patio and a picnic area.

Scored out of 10, guest rating 7.6
Good - What previous guests thought, 8 reviews

Boasting air-conditioned accommodation with a terrace, Oak Bluffs Cottage is situated in Oak Bluffs. This holiday home features accommodation with a balcony.

Located in Oak Bluffs, Birds of Paradise features accommodation 11 km from Edgartown Lighthouse. The property is non-smoking and is situated 1.1 km from Oak Bluffs Town Beach.

Scored out of 10, guest rating 6.0
Pleasant - What previous guests thought, 4 reviews

Set in Oak Bluffs, Oak Leaf Cape Cottage features accommodation within 11 km of Edgartown Lighthouse. Guests can benefit from a patio and a children's playground.

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 2 reviews

11 km from Edgartown Lighthouse in Vineyard Haven, Marthas Vineyard Home Walk to Oak Bluffs Beach! provides accommodation with access to a spa centre.

The Rootskeller

Oak Bluffs
Breakfast options

Boasting air-conditioned accommodation with a patio, The Rootskeller is situated in Oak Bluffs. The holiday home is 1.5 km from Eastville Beach.

Scored out of 10, guest rating 8.0
Very good - What previous guests thought, 3 reviews

Set in Oak Bluffs in the Massachusetts region, Gingerbread Dream features a balcony. Guests can benefit from a terrace and a children's playground.

Travelling by car? These cottages in Oak Bluffs and nearby offer free parking

Scored out of 10, guest rating 7.7
Good - What previous guests thought, 3 reviews

Boasting garden views, Home in Oak Bluffs features accommodation with a garden and a patio, around 3 km from Eastville Beach.

Set in Edgartown, 600 metres from Lighthouse Beach and 800 metres from Edgartown Lighthouse, Downtown Edgartown Home offers a garden and air conditioning.

Set in Edgartown, 1.7 km from Lighthouse Beach and 1.5 km from Edgartown Lighthouse, Modern Saltbox in Edgartown Village offers free bikes and air conditioning.

Featuring a balcony with sea views, a garden and a tennis court, Captain Morse House - Luxury, Waterfront, Town, & Beaches - 5 stars can be found in Edgartown, close to Lighthouse Beach and 600 metres...

These cottages in Oak Bluffs and nearby have options with free cancellation

Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 1 review

Set in Oak Bluffs in the Massachusetts region, Charming MV Cottage Walk to Dtwn Oak Bluffs! features a balcony. It is located 1.2 km from Oak Bluffs Town Beach and offers a 24-hour front desk.

Canary Cottage

Oak Bluffs
Free cancellation options available
Scored out of 10, guest rating 7.8
Good - What previous guests thought, 7 reviews

Set in Oak Bluffs in the Massachusetts region, Canary Cottage has a terrace. Guests staying at this holiday home have access to a balcony. The holiday home also offers facilities for disabled guests.

Sunny Side Up

Oak Bluffs
Free cancellation options available

Located in Oak Bluffs, 2 km from Eastville Beach and 12 km from Edgartown Lighthouse, Sunny Side Up provides a restaurant. Guests staying at this holiday home have access to a patio.

Oak Bluffs Beauty

Oak Bluffs
Free cancellation options available
Scored out of 10, guest rating 8.0
Very good - What previous guests thought, 2 reviews

Boasting air-conditioned accommodation with a patio, Oak Bluffs Beauty is set in Oak Bluffs. This holiday home is 1.2 km from Eastville Beach and 12 km from Edgartown Lighthouse.

Island Getaway

Oak Bluffs
Free cancellation options available
Scored out of 10, guest rating 3.4
Poor - What previous guests thought, 7 reviews

Offering garden views, Island Getaway is an accommodation set in Oak Bluffs, 1.2 km from Eastville Beach and 12 km from Edgartown Lighthouse. The property has a restaurant with an outdoor dining area.

Sunset Meadows

Oak Bluffs
Free cancellation options available

Offering lake views, Sunset Meadows is an accommodation situated in Oak Bluffs, 1.1 km from Eastville Beach and 12 km from Edgartown Lighthouse.

Brewster House

Oak Bluffs
Free cancellation options available
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 1 review

Brewster House enjoys a location in Oak Bluffs, just 1.4 km from Eastville Beach and 11 km from Edgartown Lighthouse. Guests can benefit from a patio and a children's playground.

Sankofa Martha's Vineyard

Oak Bluffs
Free cancellation options available

Located in Oak Bluffs, less than 1 km from Oak Bluffs Town Beach and 11 km from Edgartown Lighthouse, Sankofa Martha's Vineyard offers air conditioning.

FAQ about cottages in Oak Bluffs

Cottages that guests love in Oak Bluffs

See all

Inkwell Beach Cottage

Cottage in Oak Bluffs
Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 180 reviews
The cottage is directly across from the ocean and is very conveniently located to many restaurants, shops and other attractions. The staff at the Inkwell was very friendly and helpful, particularly Colleen, who went above and beyond to make sure our stay was very pleasant and was delightful to chat with! She also cooked a delicious breakfast each morning!
Guest review by
Joshua
Group

Inkwell Beach Cottage

Cottage in Oak Bluffs
Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 180 reviews
We loved the location. We were across the street from the beach, Inkwell Beach, to be exact. We were within walking distance from Oak Bluffs' city center and loved the access to shops and restaurants. Our room was clean and comfortable. The Inkwell Beach Cottage staff was pleasant and helpful.
Guest review by
Victoria
Young couple

Inkwell Beach Cottage

Cottage in Oak Bluffs
Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 180 reviews
The Inkwell Beach Cottage was hands down the best stay we’ve had in years. The staff went absolutely above and beyond to make sure my girlfriend’s birthday was as special as possible.
Guest review by
LJ
Young couple

Charming MV Cottage Walk to Dtwn Oak Bluffs!

Cottage in Oak Bluffs
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 1 review
The location is close enough to walk to all of the excitement but far enough away from the excitement to enjoy peace. This home will easily remind you of a Grandparent's old country cottage stocked with board games and room for the grandkids to come play! Very cozy yet accommodating.
Guest review by
Victor
Solo traveller

Research, refine and make plans for your whole trip

Cottages in New York

Take a look at cottages in New York and explore more of the United States.

Cottages in Las Vegas

Discover another destination in the United States.

Cottages in Massachusetts

Extend your search and explore the surrounding area.

Cottages in Martha's Vineyard

Extend your search and explore the surrounding area.

Car hire in Oak Bluffs

Hire a car and hit the road.

Hotels in Oak Bluffs

More great accommodation options for your trip.

When to visit the United States

Events, prices, the weather – everything you need to know about the best time to visit the United States.

Cheap holidays in Oak Bluffs

Book the best flights, stays and more – all in one place

Cottages in the United States

Pack a bigger bag and see more of the country.