Title: Book the Best Oak Bluffs LUXURY Hotels - Upscale Hotels in Oak Bluffs, MA | Expedia.ca [Hotels in Oak Bluffs](https://expedia.ca/Oak-Bluffs-Hotels.d140231.Travel-Guide-Hotels)[Vacation Rentals in Oak Bluffs](https://expedia.ca/Oak-Bluffs-Vacation-Rentals.d140231.Travel-Guide-VacationRentals)[Flights to Oak Bluffs](https://expedia.ca/Cheap-Flights-To-Oak-Bluffs.d140231.Travel-Guide-Flights)[Oak Bluffs Car Rentals](https://expedia.ca/Car-Rentals-In-Oak-Bluffs.d140231.Car-Rental-Guide)[Oak Bluffs Vacation Packages](https://expedia.ca/Oak-Bluffs.d140231.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/1/8bd66a7ae7636691016dd57f41ee8c80.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find luxury hotels in Oak Bluffs, MA ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Oak Bluffs Luxury Hotels Tonight [Oct 15 - Oct 16](https://www.expedia.ca/Hotel-Search?regionId=140231&startDate=2025-10-15&endDate=2025-10-16&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 16 - Oct 17](https://www.expedia.ca/Hotel-Search?regionId=140231&startDate=2025-10-16&endDate=2025-10-17&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=140231&startDate=2025-10-17&endDate=2025-10-19&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=140231&startDate=2025-10-24&endDate=2025-10-26&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Oak Bluffs Luxury Hotels ## Top Oak Bluffs Hotel Reviews ![Inn on the Square](//images.trvl-media.com/lodging/1000000/10000/10000/9953/27ed2889_y.jpg) ### Inn on the Square 10/10 Excellent "Nicest hotel I’ve found in Falmouth yet for when you can’t make the ferry home." [](https://expedia.ca/Falmouth-Hotels-Inn-On-The-Square.h9953.Hotel-Information) ![Harbor View Hotel](//images.trvl-media.com/lodging/1000000/10000/8600/8504/7b9d68f4_y.jpg) ### Harbor View Hotel 10/10 Excellent "This is an absolutely gorgeous hotel with beautiful grounds. Every member of the staff was helpful, polite and professional. We decided to indulge ourselves for a special anniversary, and it was so worth it." [](https://expedia.ca/Edgartown-Hotels-Harbor-View-Hotel.h8504.Hotel-Information) ![Faraway Martha's Vineyard](//images.trvl-media.com/lodging/1000000/70000/65700/65623/10e4fb42_y.jpg) ### Faraway Martha's Vineyard 10/10 Excellent "Quick overnight, nice facility room better than adequate." [](https://expedia.ca/Edgartown-Hotels-Faraway-Marthas-Vineyard.h65623.Hotel-Information) ![Sea Crest Beach Resort](//images.trvl-media.com/lodging/1000000/30000/25600/25567/19fd0067_y.jpg) ### Sea Crest Beach Resort 10/10 Excellent "Loved the beach view from ocean front rooms. Clean , beds comfortable, loved new shower. They now only offer 2 small bottles of water for whole stay Use to be be 2, daily." [](https://expedia.ca/North-Falmouth-Hotels-Sea-Crest-Beach-Hotel.h25567.Hotel-Information) ## Frequently asked questions ### Are you searching for the perfect hotel for your luxury trip to Oak Bluffs? > Use Expedia and let us help you arrange a flight to Vineyard Haven, MA (MVY-Martha's Vineyard) airport or Hyannis, MA (HYA-Barnstable Municipal) airport, and then select from different places to stay that will deliver the luxury you want. Amenities are an important consideration when you plan a vacation, so we make it easy to get what you'd like to make your stay special. If you want a posh hotel that has fine dining, a spa, or several swimming pools, Expedia can assist you in finding the best luxury hotel experience that Oak Bluffs offers. During your visit, you might want to enjoy the port which Oak Bluffs is known for. ### When can I expect good weather in Oak Bluffs? > Planning for the weather is a good way to make your trip to Oak Bluffs relaxing and enjoyable, especially when you're splurging. The hottest months are usually August and July with an average temp of 68°F, while the coldest months are February and January with an average of 38°F. Average annual precipitation for Oak Bluffs is 47 inches. ### What's there to see and do in Oak Bluffs? > Experience Oak Bluffs and visit Circuit Avenue, Flying Horses Carousel, and Oak Bluffs Harbor. 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