Explore top 2026 5 Star Hotels in Oak Bluffs

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Top Oak Bluffs 5 Star hotels

Harbor View Hotel

131 N Water Street Marthas Vineyard Edgartown MA

This smoke-free hotel's 2 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the free WiFi in ...

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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.

Oak Bluffs Resorts & 5 Star Hotels

Looking for your own little slice of heaven during your next trip? Check out all the best 5-star hotels in Oak Bluffs to make sure your trip is as extravagantly comfortable as you expect.

Whether you plan on staying in your room the whole time or getting out and enjoying the city, you’ll be living the life while staying at your luxury accommodation. With so many amenities at your beck and call, you might try to turn your stay into a staycation!

Many of the 5-star hotels have award-winning restaurants you can dine at, as well as plush bedding and a concierge service to take care of your every need. Most also offer pools and modern fitness centers, not to mention high-speed Wi-Fi.

For your next trip, book a hotel that can be your own little hideaway, whether you’re in town for business or leisure. Oak Bluffs 5-star hotels provide you with all the comforts and amenities you expect from a sophisticated hotel, with a staff that’s happy to ensure you have everything you need to feel at home.

Whether you’re a first-time guest, or you’ve stayed in 5-star hotels in Oak Bluffs before, you’ll have no shortage of options to choose from on your next trip when you book with Travelocity. Browse our vast selection and find great deals on luxury lodging.

Recent Oak Bluffs hotel reviews by fellow wanderers

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

5 out of 5

Posted 16 hours ago

Travelocity Verified Review

"great place to stay!"

A verified traveler stayed at Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

Bright old-world cottage with two porches & large yard - walk to town & beaches

4 out of 5

Posted 3 weeks ago

Travelocity Verified Review

"The cottage met our expectations and provides a good value for the money. My wife and I were a little unsure about the double beds but the mattresses were comfortable we slept just fine. The mini splits worked great to quickly cool the spaces and provides nice ambient noise for sleeping. The house was clean and the furniture in good condition. The house is in a quiet location with a 10 minute walk to core Oak Bluffs area restaurants/marina and 15 minutes to the beach area. We enjoyed the front porch the kitchen provided the basics and utensils to cook meals including lobster one night. The only minor complaint is the water quality is not to my taste so we bought jugs of water for drinking. Not the host fault but perhaps could install a water filter. And the freezer did not produce ice cubes though there was a few old school ice cube trays but perhaps this is related to the taste issue so making your own ice or buying is the best option. It was my first trip to Marthas Vineyard so I was most focused on exploring the island and this property provided my family with a good home base to rest."

A verified traveler stayed at Bright old-world cottage with two porches & large yard - walk to town & beaches