Oak Bluffs Vacations

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Find the Best Oak Bluffs Vacation Packages

Oak Bluffs Beach Vacation

There's nothing like an Oak Bluffs vacation 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 center on your trip to Oak Bluffs, find a hotel around Inkwell Beach (0.64 kilometers away). If the plan is to hang around a while, consider securing one of our Oak Bluffs vacation 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 vacation 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 vacation in Oak Bluffs. Why not take a look at some private vacation 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 Harbor and Flying Horses Carousel are just some of the attractions that should be on your sightseeing list. With our Oak Bluffs vacation deals, you'll have more money in your back pocket to explore.

Oak Bluffs Hotel Deals

Summercamp

Summercamp

3.5 out of 5
70 Lake Avenue Oak Bluffs MA
9.2/10 Wonderful! (1,002 reviews)
Great location in Oak Bluffs - near a shuttle shop, lots of great shopping & restaurants. Room was nice size and room service was daily.

Reviewed on 2025/11/15

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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! (193 reviews)
Great little hotel. All communication is done via texting. There is no one on site at this hotel. However it’s a great little hotel near restaurants and bars.

Reviewed on 2025/11/3

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Morgan Hotel
The Island Inn on Martha's Vineyard

The Island Inn on Martha's Vineyard

2.5 out of 5
30 Island Inn Rd Oak Bluffs MA
8/10 Very Good! (31 reviews)
This was my second time staying at the island inn and no complaints here all good things. Very clean well kept, friendly staff and house keeping. I will definitely book again!

Reviewed on 2025/10/24

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The Island Inn on Martha's Vineyard
See all 3,007 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

Sandy beaches, farmlands, fishing docks, harbor towns and tall lighthouses, Its Martha's Vineyard! It is around an hour of boat ride from Cape Cod to the Oak Bluffs. MV accessible only by boat or air. This picture was of course taken in summer :) Bright sunny day with blue sky and lush green. In the background is the famous east chop lighthouse. The best of my memories of MV are from East Chop. We rented a bright Red scooter near the Oak Bluffs harbor after getting off from ferry, kicked off our slippers, rode to the sunset ;) I meant we drove to East Chop:) Must Do : Get that pretty but awfully slow red scooter, drive to the light house, live the dream :)

East Chop Light

You can find out about the history of East Chop with a visit to East Chop Light. Stroll along the area's seaside, or simply savor its wineries.

East Chop Light

Oak Bluffs Town Beach

4.5/5(10 reviews)

If a restful vacation is part of your travel plans, Oak Bluffs Town Beach might be the perfect place to seek out during your trip to Oak Bluffs. Stroll along the waterfront or visit the shops in this relaxing area.

Oak Bluffs Town Beach

Ocean Park

4.5/5(21 reviews)

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 seafood restaurants.

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