Title: 5 Stars Hotels in Osterville, Massachusetts from CA $209 - Find Cheap Osterville Hotels With 5 Stars | Expedia.ca [Osterville Travel Guide](https://expedia.ca/Osterville.dx183338)[Hotels in Osterville](https://expedia.ca/Osterville-Hotels.d183338.Travel-Guide-Hotels)[Vacation Rentals in Osterville](https://expedia.ca/Osterville-Vacation-Rentals.d183338.Travel-Guide-VacationRentals)[Flights to Osterville](https://expedia.ca/Cheap-Flights-To-Osterville.d183338.Travel-Guide-Flights)[Osterville Car Rentals](https://expedia.ca/Car-Rentals-In-Osterville.d183338.Car-Rental-Guide)[Osterville Vacation Packages](https://expedia.ca/Osterville.d183338.Destination-Travel-Guides) ![Osterville showing a bay or harbor](https://images.trvl-media.com/place/183338/9e86bb9d-85b4-4f43-92cb-366f884ac7ba.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/183338/9e86bb9d-85b4-4f43-92cb-366f884ac7ba.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 Osterville 5 Star Hotels Tonight [Feb 6 - Feb 7](https://www.expedia.ca/Hotel-Search?regionId=183338&startDate=2026-02-06&endDate=2026-02-07&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Feb 7 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=183338&startDate=2026-02-07&endDate=2026-02-08&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=183338&startDate=2026-02-06&endDate=2026-02-08&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=183338&startDate=2026-02-13&endDate=2026-02-15&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Osterville 5-star hotels ![36-inch flat-screen TV with cable channels, TV](https://images.trvl-media.com/lodging/1000000/10000/8600/8504/d518b4f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/1000000/10000/8600/8504/3f1a493f.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) ![Garden view](https://images.trvl-media.com/lodging/1000000/10000/8600/8504/b0e1e614.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Harbor View Hotel [](https://www.expedia.ca/Edgartown-Hotels-Harbor-View-Hotel.h8504.Hotel-Information) Edgartown 8.8/10 Excellent (1,000 reviews) "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-Osterville-Hotels.s50-0-d183338.Travel-Guide-Filter-Hotels)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Osterville-Hotels.s50-0-d183338.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 Osterville. ![Margaritaville Resort Cape Cod](https://images.trvl-media.com/lodging/1000000/20000/12900/12897/b57e0b1f_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Margaritaville Resort Cape Cod 1225 Iyannough Rd Hyannis MA CA $211 CA $320 total Feb 10 - Feb 11 includes taxes & fees 8.6/10 Excellent! (438 reviews) [](https://expedia.ca/Hyannis-Hotels-Cape-Codder-Resort-And-Spa.h12897.Hotel-Information) ![Doubletree by Hilton Cape Cod - Hyannis](https://images.trvl-media.com/lodging/1000000/50000/40500/40461/9f940314_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Doubletree by Hilton Cape Cod - Hyannis 287 Iyannough Rd Hyannis MA CA $183 CA $209 total Feb 22 - Feb 23 includes taxes & fees 8.2/10 Very Good! (887 reviews) [](https://expedia.ca/Hyannis-Hotels-Doubletree-By-Hilton-Cape-Cod-Hyannis.h40461.Hotel-Information) ![The Mansion at Ocean Edge](https://images.trvl-media.com/lodging/1000000/10000/8000/7948/5d8fbc52_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The Mansion at Ocean Edge 2907 Main Street Brewster MA CA $218 CA $327 total Feb 11 - Feb 12 includes taxes & fees 8.2/10 Very Good! (1,001 reviews) [](https://expedia.ca/Brewster-Hotels-The-Mansion-At-Ocean-Edge.h7948.Hotel-Information) Still don't see what you're looking for? [See all properties in Osterville.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=07%2F02%2F2026&endDate=08%2F02%2F2026®ionId=183338&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=07%2F02%2F2026&endDate=08%2F02%2F2026®ionId=183338&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=07%2F02%2F2026&endDate=08%2F02%2F2026®ionId=183338&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=07%2F02%2F2026&endDate=08%2F02%2F2026®ionId=183338&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=07%2F02%2F2026&endDate=08%2F02%2F2026®ionId=183338&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=07%2F02%2F2026&endDate=08%2F02%2F2026®ionId=183338&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 Osterville Elegant boutiques and seafood restaurants line Main Street in this charming Cape Cod village with New England coastal appeal. Spend sunny afternoons at Joshua's Pond or Dowses Beach, where calm waters welcome swimmers and kayakers. [See all hotels in Osterville](https://www.expedia.ca/Hotel-Search?startDate=2026-02-20&endDate=2026-02-21&adults=2®ionId=183338) ![Osterville showing a bay or harbor](https://images.trvl-media.com/place/183338/9e86bb9d-85b4-4f43-92cb-366f884ac7ba.jpg?impolicy=fcrop&w=900&h=506&p=1&q=high) ## Top Osterville Hotel Reviews ![Harbor View Hotel](https://images.trvl-media.com/lodging/1000000/10000/8600/8504/7b9d68f4_y.jpg) ### Harbor View Hotel 10/10 Excellent "Cannot wait to return 😊" [](https://expedia.ca/Edgartown-Hotels-Harbor-View-Hotel.h8504.Hotel-Information) ## Find out more about Osterville ## Five Star Hotels in Osterville 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 Osterville 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 Osterville and get ready to be pampered like never before. #### Get a Great Deal on 5-Star Hotels in Osterville 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 Osterville The results are in, and Osterville 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 Osterville! Don't put off your dream vacation any longer. Choose one of the 5-star hotels in Osterville today and settle down in the lap of luxury tomorrow. ## Frequently asked questions ### How much does it cost to stay in a 5-star hotel in Osterville? > - Search for the lowest price per night from CA $209 ### What makes a hotel 5 stars in Osterville? ### Are there any 5-star all-inclusive resorts in Osterville? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [1 Star Hotels in Chappaquiddick Island ](https://www.expedia.ca/1Star-Chappaquiddick-Island-Hotels.s10-0-d6287412.Travel-Guide-Filter-Hotels) - [1 Star Hotels in Orleans ](https://www.expedia.ca/1Star-Orleans-Hotels.s10-0-d142149.Travel-Guide-Filter-Hotels) - [1 Star Hotels in Quaise ](https://www.expedia.ca/1Star-Quaise-Hotels.s10-0-d553248635975748377.Travel-Guide-Filter-Hotels) - [2 Star Hotels in Cape Cod ](https://www.expedia.ca/2Star-Cape-Cod-Hotels.s20-0-d180061.Travel-Guide-Filter-Hotels) - [2 Star Hotels in Martha's Vineyard ](https://www.expedia.ca/2Star-Marthas-Vineyard-Hotels.s20-0-d6047691.Travel-Guide-Filter-Hotels) - 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