Oak Bluffs, MA

Travel Guide

A row of colorful, historic houses with a central path.
A row of colorful Victorian-style houses with front porches and a well-maintained lawn.
A row of colorful Victorian-style houses with blue and yellow trim, a tree with white blossoms, and a paved street.
A rocky shoreline at sunset with a calm sea reflecting the colors of the sky.
A white lighthouse with a black top, surrounded by trees and a bench, overlooking a body of water.
Summercamp

Summercamp

3.5 out of 5
70 Lake Avenue Oak Bluffs MA
Book a stay at this beach hotel in Oak Bluffs. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Our guests praise the helpful staff and the clean ...
9.4/10 Exceptional! (1,002 reviews)
"The staff was so friendly and hospitable! We loved our wonderful stay! Thank you❣️😃❤️😍"

Reviewed on 30 October 2026

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Summercamp
MV Surfside Hotel

MV Surfside Hotel

2.5 out of 5
7 Oak Bluffs Avenue Oak Bluffs MA
Stay at this hotel in Oak Bluffs. Enjoy parking (surcharge), daily housekeeping, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions ...
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MV Surfside Hotel
Pequot Hotel

Pequot Hotel

3 out of 5
19 Pequot Avenue Oak Bluffs MA
Stay at this hotel in Oak Bluffs. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
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Pequot Hotel
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Quaint, ranch style home in Oak Bluffs with central air

Quaint, ranch style home in Oak Bluffs with central air

Oak Bluffs MA
Stay at this vacation home in Oak Bluffs. Enjoy a garden, balconies, and an in-room coffeemaker. Popular attractions Inkwell Beach and Oak Bluffs Public Library ...
8.4/10 Very Good! (5 reviews)
"Would book again"

Reviewed on 27 July 2026

Quaint, ranch style home in Oak Bluffs with central air
Luxury Loft Historic Center Oak Bluffs

Luxury Loft Historic Center Oak Bluffs

Oak Bluffs MA
Stay at this vacation home in Oak Bluffs. Enjoy a garden, laundry facilities, and tennis courts. Popular attractions Inkwell Beach and Trinity Park Tabernacle ...
9.6/10 Exceptional! (51 reviews)
"The loft was not suited for adult occupancy."

Reviewed on 7 August 2026

Luxury Loft Historic Center Oak Bluffs
Charming, cozy spacious home within 1 mile walking distance to Oak Bluffs

Charming, cozy spacious home within 1 mile walking distance to Oak Bluffs

Oak Bluffs MA
Stay at this vacation home in Oak Bluffs. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Inkwell Beach and Oak Bluffs Harbor are located ...
9.8/10 Exceptional! (52 reviews)
"The house was amazing, the communication with the host superb, and the proximity of the space to Oak Bluffs, Vineyard Haven/Oak Bluff ferry terminals, shops and locations was unbeatable. It’s a must see and stay if you are planning a family trip."

Reviewed on 18 October 2026

Charming, cozy spacious home within 1 mile walking distance to Oak Bluffs
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Stay near popular Oak Bluffs attractions

A beach with a lifeguard tower, a rocky breakwater, and the ocean.

Inkwell Beach

9.0/10 (154 reviews)
If a restful vacation is part of your travel plans, Inkwell Beach might be the perfect place to seek out during your trip to Oak Bluffs. Stroll along this relaxing area's waterfront, or simply enjoy its wineries.
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