Oak Bluffs Vacations

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Find the Best Oak Bluffs Vacation Packages

Oak Bluffs Hotel Deals

Summercamp

Summercamp

3.5 out of 5
70 Lake Avenue Oak Bluffs MA
9.2/10 Wonderful! (1,000 reviews)
Lovely stay and the staff was friendly and helpful. Excellent location.

Reviewed on 17 December 2025

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Summercamp
Morgan Hotel

Morgan Hotel

2.5 out of 5
9 Healy Way Oak Bluffs MA
8.4/10 Very Good! (204 reviews)
The room was clean. The only problem I had was not getting my key prior to 3. Called the day before because the text I received said you can try the app and it will should your reservation but it did not it states that there may be a problem because you booked on a third party site. Called and they ...

Reviewed on 13 December 2025

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Morgan Hotel
MV Surfside Hotel

MV Surfside Hotel

2.5 out of 5
7 Oak Bluffs Avenue Oak Bluffs MA
8.8/10 Excellent! (830 reviews)
The location was convenient and the property was exactly what we needed - clean, basic, accommodations. Two minor issues - the room reeked of bleach when we arrived and we had to open the windows to air it out. Second, the frint desk hours aren’t posted and it was hard to reach someone to check in ...

Reviewed on 12 October 2025

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MV Surfside Hotel
See all 2,991 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.

Discover the most popular places to visit in Oak Bluffs

Oak Bluffs Harbor

Oak Bluffs Harbor

Explore the waterfront in Oak Bluffs with a trip to Oak Bluffs Harbor. Wander the area's beautiful beaches or simply enjoy one of its seafood restaurants.

Oak Bluffs Harbor
Oak Bluffs skyline, well-preserved landmark houses, and dramatic winter sunset cloudscape over the Ocean Park on the island of Martha's Vineyard in Dukes County, Massachusetts, United States

Ocean Park

Ocean Park is just one of the places to see in Oak Bluffs, so why not enjoy the other things to explore during your travels? Wander the area's waterfront or simply enjoy one of its wineries.

Ocean Park
Carousel in Boston Massachusetts

Flying Horses Carousel

Enjoy an outing to Flying Horses Carousel during your stay in Oak Bluffs. Wander the beautiful beaches and waterfront in the area.

Flying Horses Carousel

Frequently asked questions

How do I find cheap flights to Oak Bluffs that have flexible change policies?
When it comes to flying these days, flexibility is essential. That's why we've added a "No change fee" search function to help you find flexible, cheap airfares to Oak Bluffs. It's on the left of your screen directly underneath the "Flexible change policies" subheading.
Which airlines fly to Oak Bluffs?
Let Cape Air take you there. This well-known carrier lists 234 services a month to Martha's Vineyard Airport (MVY), an Oak Bluffs gateway.
How can I find cheap tickets to Oak Bluffs?
An excellent strategy for getting your hands on cheap fares is to be flexible with your travel dates. Begin with searching for your flight to Oak Bluffs, then click on the "flexible dates" box for a list of prices for nearby days. Want another good tip? Book well in advance. For an idea of costs, was the best price for a flight to Oak Bluffs in the last seven days.
How much is a flight to Oak Bluffs?
The cost of a round-trip ticket to Oak Bluffs in the last seven days ranged between and . If you were journeying one way from (), you could have nabbed a great deal from only .
What are the most popular airports to fly into in Oak Bluffs?
Oak Bluffs's main entryway is Martha's Vineyard Airport (MVY). Get your next awesome adventure underway by reserving an airfare on one of the 234 flights every month to this destination.
When is the cheapest time to fly to Oak Bluffs?
Consider traveling early in the week to book the best airfare to Oak Bluffs. Tuesday is generally the cheapest day to depart, with Monday a close second. Saturday typically has the costliest fares. This is because lots of people choose to kick off their vacation on a weekend.
How much is a plane ticket to Oak Bluffs?
In the last seven days, plane tickets to Oak Bluffs ranged between and . Prices depend on a number of things, particularly the time of departure, airline, seating class and when the fare is booked.
What months are the cheapest to book a flight to Oak Bluffs?
The ideal month to find a top deal to Oak Bluffs is February, while the priciest month is December. Avoid this time if you're on a budget.
How long is a flight to Oak Bluffs?
Flight durations can vary for various reasons, including where you're coming from. Here's a list of average flight times for a few of the top domestic routes to Oak Bluffs:

  • Boston, MA (BOS-Logan Intl.) to Martha's Vineyard Airport (MVY) - 40 minutes
  • Nantucket, MA (ACK-Nantucket Memorial) to Martha's Vineyard Airport (MVY) - 20 minutes
  • New York, NY (JFK-John F. Kennedy Intl.) to Martha's Vineyard Airport (MVY) - 1 hour and 13 minutes