Oak Bluffs Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to NZ$616 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Oak Bluffs Holiday

Oak Bluffs Beach Holiday

There's nothing like an Oak Bluffs holiday to put a bounce in your step. The soothing melody of rolling surf and the smell of fresh ocean air will help refresh your mind and body. To be close to the town centre on your trip to Oak Bluffs, find a hotel around Inkwell Beach (0.64 kilometres away). If the plan is to hang around a while, consider securing one of our Oak Bluffs holiday packages. Not only will you save some money, you'll also have other stunning beaches around you to explore, like Joseph Sylvia State Beach and Eastville Point Beach. We call that a win-win!

Things You Should Know About Oak Bluffs

  • Spend your holiday by the water and let the hassles of daily life drift away with the ocean breeze. Book one of our Oak Bluffs beach hotels and enjoy a little beachside bliss.
  • No matter your budget or style, you'll find an ideal place to stay for your holiday in Oak Bluffs. Why not take a look at some private holiday homes, like The Attleboro House and Marthas Vineyard Resort? They're popular with visitors of all sorts.
  • Some 3 800 people live in Oak Bluffs. If you'd like advice about what to see and do in this area, why not start a conversation with one or two of the locals? Our Oak Bluffs things to do page is also a handy source of information.
  • Inkwell Beach, Oak Bluffs Harbour and Flying Horses Carousel are just some of the attractions that should be on your sightseeing list. With our Oak Bluffs holiday deals, you'll have more money in your back pocket to explore.

Our pick of the best Oak Bluffs Hotel Deals

Summercamp

Summercamp

3.5 out of 5
70 Lake Avenue Oak Bluffs MA
9.2/10 Wonderful! (1,001 reviews)
Lovely stay and the staff was friendly and helpful. Excellent location.

Reviewed on 17 Dec 2025

Summercamp
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
5.4/10 (21 reviews)
The place was exactly as listed. It is an older house but very clean conditions. I just think they need to supply it better you definitely need a car. There was no coffee or anything in the house. You have to bring everything.

Reviewed on 16 Sept 2025

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

Morgan Hotel

2.5 out of 5
9 Healy Way Oak Bluffs MA
8.4/10 Very Good! (202 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 Dec 2025

Morgan Hotel
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

What to do in Oak Bluffs

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.