Title: 5 Stars Hotels in Oak Bluffs, Massachusetts from CA $292 - Find Cheap Oak Bluffs Hotels With 5 Stars | Expedia.ca [Oak Bluffs Travel Guide](https://expedia.ca/Oak-Bluffs.dx140231)[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)[Things to do in Oak Bluffs](https://expedia.ca/Things-To-Do-In-Oak-Bluffs.d140231.Travel-Guide-Activities)[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) # 5 Stars Hotels in Oak Bluffs, Massachusetts from CA $292 ![](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 5 Star Hotels Tonight [Oct 30 - Oct 31](https://www.expedia.ca/Hotel-Search?regionId=140231&startDate=2025-10-30&endDate=2025-10-31&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 31 - Nov 1](https://www.expedia.ca/Hotel-Search?regionId=140231&startDate=2025-10-31&endDate=2025-11-01&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=140231&startDate=2025-10-31&endDate=2025-11-02&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=140231&startDate=2025-11-07&endDate=2025-11-09&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Oak Bluffs 5 Star Hotels ![View from room](https://images.trvl-media.com/lodging/1000000/10000/8600/8504/7b9d68f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, pool umbrellas](https://images.trvl-media.com/lodging/1000000/10000/8600/8504/b242e02b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony view](https://images.trvl-media.com/lodging/1000000/10000/8600/8504/7c321ede.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/8600/8504/8ca88d65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Harbor View Hotel Edgartown 8.8/10 Excellent (1004) "The area was safe and the dining experience was great. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Albert [](https://www.expedia.ca/Edgartown-Hotels-Harbor-View-Hotel.h8504.Hotel-Information) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Oak-Bluffs-Hotels.s50-0-d140231.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Oak-Bluffs-Hotels.s50-0-d140231.Travel-Guide-Filter-Hotels) ## Explore similar 4-star hotels Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Oak Bluffs. ![AutoCamp Cape Cod](https://images.trvl-media.com/lodging/50000000/49180000/49175900/49175859/3458b4d1_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### AutoCamp Cape Cod 836 Palmer Avenue, Falmouth, MA CA $206 CA $292 total Nov 25 - Nov 26 includes taxes & fees 9.2/10 Wonderful! (296 reviews) [](https://expedia.ca/Falmouth-Hotels-AutoCamp-Cape-Cod.h49175859.Hotel-Information) ![Vineyard Square Hotel & Suites](https://images.trvl-media.com/lodging/1000000/700000/694900/694842/2026bafa_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Vineyard Square Hotel & Suites 38 North Water Street, Edgartown, MA [Get rates](https://expedia.ca/Hotel-Search?startDate=13%2F11%2F2025&endDate=14%2F11%2F2025&selected=694842&PinnedHotelID=694842&HadPinnedHotel=true®ionId=140231) 9.2/10 Wonderful! (307 reviews) [](https://expedia.ca/Edgartown-Hotels-Vineyard-Square-Hotel-Suites.h694842.Hotel-Information) ![Sea Street Inn](https://images.trvl-media.com/lodging/27000000/26470000/26468700/26468676/c0638e2f_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Sea Street Inn 328 Sea St, Hyannis, MA CA $345 CA $395 total Nov 3 - Nov 4 includes taxes & fees 9.8/10 Exceptional! (45 reviews) [](https://expedia.ca/Hyannis-Hotels-Sea-Street-Inn.h26468676.Hotel-Information) Still don't see what you're looking for? [See all properties in Oak Bluffs.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=31%2F10%2F2025&endDate=01%2F11%2F2025®ionId=140231&star=50) You can also use these popular filters to refine your search. [Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=31%2F10%2F2025&endDate=01%2F11%2F2025®ionId=140231&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=31%2F10%2F2025&endDate=01%2F11%2F2025®ionId=140231&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=31%2F10%2F2025&endDate=01%2F11%2F2025®ionId=140231&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=31%2F10%2F2025&endDate=01%2F11%2F2025®ionId=140231&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=31%2F10%2F2025&endDate=01%2F11%2F2025®ionId=140231&star=50&star=50&amenities=WATER_PARK) 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. ## Learn more about Oak Bluffs The colourful gingerbread cottages of the Martha's Vineyard Campground will charm you with their whimsical Victorian details. Take the Flying Horses carousel for a spin, then stroll along Ocean Park's waterfront where locals gather for sunset picnics. [See all hotels in Oak Bluffs](https://www.expedia.ca/Hotel-Search?startDate=2025-11-13&endDate=2025-11-14&adults=2®ionId=140231) ![Sunrise striking the houses at Oak Bluffs on Martha's Vineyard, MA.](https://images.trvl-media.com/place/140231/627e7d6f-2e16-4413-8110-e90b28f97709.jpg?impolicy=fcrop&w=900&h=598&p=1&q=high) ## Top Oak Bluffs Hotel Reviews ![Harbor View Hotel](//images.trvl-media.com/lodging/1000000/10000/8600/8504/7b9d68f4_y.jpg) ### Harbor View Hotel 10/10 Excellent "The area was safe and the dining experience was great. " [](https://expedia.ca/Edgartown-Hotels-Harbor-View-Hotel.h8504.Hotel-Information) ## Find out more about Oak Bluffs ## Five Star Hotels in Oak Bluffs There's nothing wrong with enjoying the finer things in life. Indulge yourself on your next leisure time. After all, this is one of the Top 10 locations in Expedia's portfolio. You'll join the multitudes of vacationers who have made Oak Bluffs so fashionable in the last year. We should also mention, the hotels in this area receive outstanding marks for guest services, so you know you'll be looked after during your getaway. You deserve the great vacation you're dreaming about. Book one of Expedia's luxurious 5-star hotels in Oak Bluffs and get ready to be pampered like never before. #### Get a Great Deal on 5-Star Hotels in Oak Bluffs Don't be afraid to live the high life while you're on vacation, along with pristine rooms. Excellent customer care, spacious rooms, and fabulous spa offerings are all on offer. We have a huge number of hotels in the region, and all of them offer outstanding amenities. Besides that, you'll find that these hotels are kept in fantastic condition and provide a fine place to kick back after your daily adventures. What kind of amenities will make your stay a wonderful one? A concierge to help you plan every detail of your day? A Swedish massage to help your cares fall away? Fluffy down pillows, piping hot coffees, and even space for your family pet in some cases...these hotels have it all. Want to see for yourself? Then explore the 31,943 reviews various guests have left on Expedia and get to know these places. Can't wait to get outside? We've got you covered. You'll find lots of attractions to see in a sprawling city like this one, like visiting art galleries and taking in live performances. Say hi to the locals—they're sure to have advice on what kind of excitement you can find in town. #### Make Your Escape to Oak Bluffs The results are in, and Oak Bluffs 5-star hotels are the place to be when you book your next vacation. Many visitors recommend a trip to this location, so don't wait any longer. This is a great time to find 5-star hotel deals in Oak Bluffs! Don't put off your dream vacation any longer. Choose one of the 5-star hotels in Oak Bluffs today and settle down in the lap of luxury tomorrow. ## Frequently asked questions ### What are the best 5-star hotels in Oak Bluffs? > Boasting exceptional amenities and services, Expedia travellers rate [Harbour View Hotel](https://www.expedia.ca/Edgartown-Hotels-Harbor-View-Hotel.h8504.Hotel-Information) as one of the leading 5-star hotels in Oak Bluffs. You'll be in the lap of luxury from the minute you step foot into the lobby. ### How much does it cost to stay in a 5-star hotel in Oak Bluffs? > How much you pay for a 5-star hotel in Oak Bluffs depends on things like when you plan to travel and the length of your vacation. An insider tip for landing the best deal? Use our pricing filters to check out all of the available hotels for your chosen dates. > > > > - Search for the lowest price per night from CA $292 ### What makes a hotel 5 stars in Oak Bluffs? > In Oak Bluffs, a hotel must offer a certain level of high-end amenities to be designated 5 stars. These may include on-site gyms, gourmet restaurants, saunas and spas, premium bedding, luxury toiletries and more. What also sets 5-star hotels apart is their extraordinary service. You can expect things like concierge services, nightly turn-down services and in-room massage. 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[Things to do in Vineyard Haven](https://www.expedia.ca/Things-To-Do-In-Vineyard-Haven.d6213.Travel-Guide-Activities) - [Book 5 Star Hotels in Oak Bluffs on Expedia.com](https://www.expedia.com/5Star-Oak-Bluffs-Hotels.s50-0-d140231.Travel-Guide-Filter-Hotels)