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Vacation Rentals in Oak Bluffs

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August 2026

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The best vacation rentals in Oak Bluffs

Check out our selection of great vacation rentals in Oak Bluffs

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Capricorn House

Oak Bluffs

Housed in a historic building, Capricorn House features accommodations with a terrace and free Wifi in Oak Bluffs, a 1-minute walk from Oak Bluffs Town Beach.

G
Graeme
From
United Kingdom
Everything ! The perfect property.
Scored out of 10, guest rating 8.9
Excellent - What previous guests thought, 166 reviews
Price from
$245
1 night, 2 adults

Island Inn

Hotel in Oak Bluffs

Located in scenic Oak Bluffs on Martha’s Vineyard, the Island Inn offers a relaxed coastal retreat with modern amenities.

A
Antroyne
From
United States
My family and I loved the 2 bedroom suite. It was very clean and comfortable. The heat was on for us when we arrived so that was great!
Scored out of 10, guest rating 8.2
Very Good - What previous guests thought, 207 reviews
Price from
$385.50
1 night, 2 adults

Edgartown Commons

Edgartown (Near Oak Bluffs)

Just a 14-minute walk from Lighthouse Beach and 0.6 miles from Edgartown Lighthouse, Edgartown Commons features accommodations in Edgartown, with a garden and barbecue facilities.

K
Kathy
From
United States
The location and grounds were beautiful. Beds were comfy and the rooms were clean.
Scored out of 10, guest rating 9.1
Wonderful - What previous guests thought, 109 reviews
Price from
$462.83
1 night, 2 adults

The Christopher, The Edgartown Collection

Edgartown (Near Oak Bluffs)

Featuring free WiFi, The Christopher, The Edgartown Collection offers accommodations in Edgartown. The rooms include a flat-screen TV. Certain units have a seating area where you can relax.

J
James
From
United States
Breakfast was top notch! Proximity to great restaurants/bars was outstanding. If you are into watching the sun rise, just walk down to the corner and take a quick right. Sheer beauty!
Scored out of 10, guest rating 9.1
Wonderful - What previous guests thought, 81 reviews
Price from
$404
1 night, 2 adults

Narragansett House

Oak Bluffs

Relax at this Martha’s Vineyard bed and breakfast, located only 5 minutes’ walk from the beach. Each charming guestroom features free Wi-Fi access and an private bathroom.

E
Elisabeth
From
Germany
The spirit of the house: friendly, cool and relaxed. In a nice, quiet street, but short walking distance to the port, the town beach and restaurants and shops. Enjoyed sitting on the beautiful veranda. Omar and Chavel took perfect care of all my needs!
Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 147 reviews

Inkwell Beach Cottage

Oak Bluffs

This oceanfront bed and breakfast in Martha’s Vineyard is just a 5 minute walk from the ferry and features free Wi-Fi and full daily breakfast. The Niantic Park Tennis Courts are a 10 minute walk...

Scored out of 10, guest rating 8.5
Very Good - What previous guests thought, 193 reviews

The Attleboro House

Oak Bluffs

The air-conditioned accommodation is 6.4 miles from Edgartown Lighthouse. Free Wifi is available throughout the property and Oak Bluffs Town Beach is a 4-minute walk away.

J
Jelena
From
Croatia
This is such a lovely place. It is within walking distance to the ferry terminal. The room is very tastefully decorated. Comfortable beds and clean bathrooms. Great view. The front desk lady is so kind and friendly and knowledgeable. Excellent WiFi. I enjoyed my stay and would love to stay here again.
Scored out of 10, guest rating 8.6
Excellent - What previous guests thought, 7 reviews

Canary Cottage

Oak Bluffs

Canary Cottage offers accommodations in Oak Bluffs, a 13-minute walk from Oak Bluffs Town Beach and 6.8 miles from Edgartown Lighthouse.

m
marian
From
United States
The property was clean and mainly comfortable. It is not in the bustling part of Oak Bluffs, but an easy walk into the town. It is exceptionally quiet, ensuring a good night’s rest.
Scored out of 10, guest rating 7.8
Good - What previous guests thought, 5 reviews

Yellow Brick Road House

Oak Bluffs

Yellow Brick Road House offers accommodations in Oak Bluffs, a 10-minute walk from Eastville Beach and 7.5 miles from Edgartown Lighthouse. Outdoor seating is also available at the vacation home.

L
Larry
From
United States
3 bedroom ranch style home. Accessible for me and my wife as we are both in our 70’s.
Scored out of 10, guest rating 6.6
Pleasant - What previous guests thought, 12 reviews

Oak Bluffs Cottage

Oak Bluffs

Oak Bluffs Cottage is located in Oak Bluffs, just a 12-minute walk from Oak Bluffs Town Beach and 6.8 miles from Edgartown Lighthouse.

Scored out of 10, guest rating 7.6
Good - What previous guests thought, 6 reviews
All vacation rentals in Oak Bluffs

Most booked vacation rentals in Oak Bluffs and surrounding area in the past month

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Popular with guests booking vacation rentals in Oak Bluffs

Scored out of 10, guest rating 8.9
Excellent - What previous guests thought, 166 reviews

Popular with guests booking vacation rentals in Oak Bluffs

Scored out of 10, guest rating 8.2
Very Good - What previous guests thought, 207 reviews

Popular with guests booking vacation rentals in Oak Bluffs

Scored out of 10, guest rating 8.5
Very Good - What previous guests thought, 194 reviews

Popular with guests booking vacation rentals in Oak Bluffs

Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 147 reviews

Popular with guests booking vacation rentals in Oak Bluffs

Scored out of 10, guest rating 8.7
Excellent - What previous guests thought, 4 reviews

Popular with guests booking vacation rentals in Oak Bluffs

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

Popular with guests booking vacation rentals in Oak Bluffs

Scored out of 10, guest rating 6.8
Pleasant - What previous guests thought, 6 reviews

Popular with guests booking vacation rentals in Oak Bluffs

Popular with guests booking vacation rentals in Oak Bluffs

Scored out of 10, guest rating 7.6
Good - What previous guests thought, 6 reviews

Popular with guests booking vacation rentals in Oak Bluffs

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

Enjoy breakfast in Oak Bluffs and nearby

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Scored out of 10, guest rating 9.1
Wonderful - What previous guests thought, 81 reviews

Featuring free WiFi, The Christopher, The Edgartown Collection offers accommodations in Edgartown. The rooms include a flat-screen TV. Certain units have a seating area where you can relax.

Scored out of 10, guest rating 7.6
Good - What previous guests thought, 6 reviews

Oak Bluffs Cottage is located in Oak Bluffs, just a 12-minute walk from Oak Bluffs Town Beach and 6.8 miles from Edgartown Lighthouse.

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

Winthrop Cottage is located in Oak Bluffs, just a 13-minute walk from Oak Bluffs Town Beach and 6.4 miles from Edgartown Lighthouse.

Sunny Side Up

Oak Bluffs
Breakfast options

Sunny Side Up offers accommodations in Oak Bluffs, 1.2 miles from Eastville Beach and 7.2 miles from Edgartown Lighthouse. This vacation home provides air-conditioned accommodations with a balcony.

Island Getaway

Oak Bluffs
Breakfast options
Scored out of 10, guest rating 3.4
Poor - What previous guests thought, 5 reviews

Island Getaway is located in Oak Bluffs, just a 14-minute walk from Eastville Beach and 7.7 miles from Edgartown Lighthouse. Outdoor seating is also available at the vacation home.

Scored out of 10, guest rating 4.5
Disappointing - What previous guests thought, 2 reviews

Oak Bluffs Beauty is located in Oak Bluffs, just a 14-minute walk from Eastville Beach and 7.2 miles from Edgartown Lighthouse. Guests staying at this vacation home have access to a patio.

Brewster House

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

Brewster House is located in Oak Bluffs, just a 16-minute walk from Eastville Beach and 7 miles from Edgartown Lighthouse. Guests staying at this vacation home have access to a patio.

Sunset Meadows

Oak Bluffs
Breakfast options

Sunset Meadows offers accommodations in Oak Bluffs, 7.5 miles from Edgartown Lighthouse. The air-conditioned accommodation is a 11-minute walk from Eastville Beach.

Vacation Rentals with swimming pools in Oak Bluffs and nearby

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Scored out of 10, guest rating 9.1
Wonderful - What previous guests thought, 109 reviews

Just a 14-minute walk from Lighthouse Beach and 0.6 miles from Edgartown Lighthouse, Edgartown Commons features accommodations in Edgartown, with a garden and barbecue facilities.

These vacation rentals in Oak Bluffs and nearby have options with free cancellation

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

Breezy Oak Bluffs Condo - Steps to Inkwell Beach! is located in Oak Bluffs, just a few steps from Oak Bluffs Town Beach and 5.9 miles from Edgartown Lighthouse.

Scored out of 10, guest rating 8.7
Excellent - What previous guests thought, 4 reviews

Martha's Vineyard Apt ~ 1 Mile to Inkwell Beach! is located in Oak Bluffs, just a 17-minute walk from Eastville Beach and 7.3 miles from Edgartown Lighthouse.

Island Sanctuary

Oak Bluffs
Free cancellation options available
Scored out of 10, guest rating 7.6
Good - What previous guests thought, 9 reviews

Island Sanctuary is located in Oak Bluffs, just 6.8 miles from Edgartown Lighthouse and 3.1 miles from Martha'S Vineyard Hist'L Island Trs.

Main Street Upper

Vineyard Haven
Free cancellation options available
Scored out of 10, guest rating 8.7
Excellent - What previous guests thought, 16 reviews

Main Street Upper offers accommodations in Vineyard Haven, a 4-minute walk from Owen Park Beach and 8.6 miles from Edgartown Lighthouse. Outdoor seating is also available at the apartment.

Island Home

Vineyard Haven
Free cancellation options available
Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 2 reviews

8.9 miles from Edgartown Lighthouse in Vineyard Haven, Island Home features accommodations with access to a spa center. The air-conditioned accommodation is a 2-minute walk from Owen Park Beach.

Everyday is Saturday

Vineyard Haven
Free cancellation options available
Scored out of 10, guest rating 7.4
Good - What previous guests thought, 5 reviews

A 3-minute walk from Owen Park Beach in Vineyard Haven, Everyday is Saturday provides accommodations with access to a spa center. This apartment offers accommodations with a patio.

Just a 19-minute walk from Louisa Gould Gallery and one mile from Kennedy Studios, Cozy Vineyard Haven Cottage < 1 Mi to Beach!

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

Easy Access to Beaches: Vineyard Haven House is located in Vineyard Haven, just a 6-minute walk from Tisbury Town Beach and 9.3 miles from Edgartown Lighthouse. This vacation home features a garden.

Highly rated vacation rentals in Oak Bluffs and nearby

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Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 7 reviews

Family-Friendly Tisbury Escape - Walk to Town is located in Vineyard Haven, just 1.3 miles from Owen Park Beach and 1.1 miles from Louisa Gould Gallery.

Scored out of 10, guest rating 8.2
Very Good - What previous guests thought, 5 reviews

Little Cozy Corner is located in Edgartown, just 1.1 miles from Lighthouse Beach and a 19-minute walk from Edgartown Lighthouse. Guests staying at this apartment have access to a patio.

FAQ about vacation rentals in Oak Bluffs