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
$187 nightly
The price is $209 total per night from Oct 13 to Oct 14
$209 total
Oct 13 - Oct 14
Total with taxes and fees
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 ...
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 ...
8.8/10 Excellent! (921 reviews)
"Traveler beware. Do not stay at this property. 1. Many basic security lapses occurred during my stay. 2. Front desk staff was lacksadaisical and unprofessional. 3. Severe street noise past 1 AM. Went to discuss with front desk staff but lobby was locked and lights were out. I was told by staff that ..."

Reviewed on Sep 20, 2026

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MV Surfside Hotel
Morgan Hotel

Morgan Hotel

2.5 out of 5
9 Healy Way Oak Bluffs MA
$197 nightly
The price is $220 total per night from Oct 22 to Oct 23
$220 total
Oct 22 - Oct 23
Total with taxes and fees
Stay at this hotel in Oak Bluffs. Enjoy free WiFi, concierge services, and cable TV channels. Popular attractions Inkwell Beach and Circuit Avenue are located ...
Morgan Hotel
See all 3,123 properties in Oak Bluffs
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.
Coastal Retreat | Walk to Inkwell Beach, Dining & Flying Horses Carousel

Coastal Retreat | Walk to Inkwell Beach, Dining & Flying Horses Carousel

Oak Bluffs MA
Stay at this vacation home in Oak Bluffs. Enjoy a garden, balconies, and cable/satellite TV service. Popular attractions Inkwell Beach and Oak Bluffs Public ...
Coastal Retreat | Walk to Inkwell Beach, Dining & Flying Horses Carousel
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

Oak Bluffs MA
Stay at this apartment in Oak Bluffs. Enjoy free WiFi, laundry facilities, and cable/satellite TV service. Popular attractions Inkwell Beach and Oak Bluffs Ferry ...
9.4/10 Exceptional! (96 reviews)
"Great place in OB"

Reviewed on Sep 3, 2026

Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

Oak Bluffs MA
Stay at this vacation home in Oak Bluffs. Enjoy a water park, a garden, and cable/satellite TV service. Popular attractions Inkwell Beach and Oak Bluffs Public ...
6.6/10 (7 reviews)
"Nice, quiet and private streetReasonable distance to Downtown OBClean"

Reviewed on Sep 13, 2026

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs
See all properties in Oak Bluffs
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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Things to do

Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours

Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours

$50
per adult
Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours
Massachusetts Self-Guided Driving and Walking Tours Bundle

Massachusetts: Smartphone-Based Audio Tour Bundle

$50
per traveler
Massachusetts: Smartphone-Based Audio Tour Bundle
Cape Cod: Explorer Kayak Tour

Cape Cod: Explorer Kayak Tour

$77
per adult
Cape Cod: Explorer Kayak Tour
See all activities in Oak Bluffs

Cities near Oak Bluffs

An aerial view of a coastal area with a sandy beach, a small island with buildings, and numerous boats in the water.

Vineyard Haven

An aerial view of a coastal area with a lighthouse, a sandy beach, and a marina.

Edgartown

A marina with numerous sailboats docked at the pier.

West Tisbury

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