Title: 5 Stars Hotels in Cheshire, Connecticut from CA $258 - Find Cheap Cheshire Hotels With 5 Stars | Expedia.ca [Cheshire Travel Guide](https://expedia.ca/Cheshire.dx183057)[Hotels in Cheshire](https://expedia.ca/Cheshire-Hotels.d183057.Travel-Guide-Hotels)[Vacation Rentals in Cheshire](https://expedia.ca/Cheshire-Vacation-Rentals.d183057.Travel-Guide-VacationRentals)[Flights to Cheshire](https://expedia.ca/Cheap-Flights-To-Cheshire.d183057.Travel-Guide-Flights)[Cheshire Car Rentals](https://expedia.ca/Car-Rentals-In-Cheshire.d183057.Car-Rental-Guide)[Cheshire Vacation Packages](https://expedia.ca/Cheshire.d183057.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/ab039a4411a79c16e7c533ffaba43069.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Tai Bui # 5 Stars Hotels in Cheshire, Connecticut from CA $258 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Cheshire 5 Star Hotels Tonight [Oct 7 - Oct 8](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2025-10-07&endDate=2025-10-08&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 8 - Oct 9](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2025-10-08&endDate=2025-10-09&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2025-10-10&endDate=2025-10-12&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2025-10-17&endDate=2025-10-19&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Cheshire 5 Star Hotels ![](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-Cheshire-Hotels.s50-0-d183057.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Cheshire-Hotels.s50-0-d183057.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 Cheshire. ![Omni New Haven Hotel at Yale](https://images.trvl-media.com/lodging/1000000/50000/50000/49957/7466af25_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Omni New Haven Hotel at Yale 155 Temple St, New Haven, CT CA $233 CA $268 total Oct 21 - Oct 22 includes taxes & fees 8.4/10 Very Good! (1,005 reviews) [](https://expedia.ca/New-Haven-Hotels-Omni-New-Haven-Hotel-At-Yale.h49957.Hotel-Information) ![The Blake Hotel](https://images.trvl-media.com/lodging/33000000/32130000/32129700/32129620/95723c61_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The Blake Hotel 9 High Street, New Haven, CT CA $319 CA $367 total Oct 28 - Oct 29 includes taxes & fees 9.4/10 Exceptional! (1,001 reviews) [](https://expedia.ca/New-Haven-Hotels-The-Blake-Hotel.h32129620.Hotel-Information) ![DoubleTree by Hilton Hartford Downtown](https://images.trvl-media.com/lodging/1000000/10000/1700/1637/1dfc2c6d_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### DoubleTree by Hilton Hartford Downtown 315 Trumbull St, Hartford, CT CA $224 CA $258 total Oct 30 - Oct 31 includes taxes & fees 7.4/10 Good! (1,001 reviews) [](https://expedia.ca/Hartford-Hotels-Hilton-Hartford.h1637.Hotel-Information) Still don't see what you're looking for? [See all properties in Cheshire.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=08%2F10%2F2025&endDate=09%2F10%2F2025®ionId=183057&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=08%2F10%2F2025&endDate=09%2F10%2F2025®ionId=183057&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=08%2F10%2F2025&endDate=09%2F10%2F2025®ionId=183057&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=08%2F10%2F2025&endDate=09%2F10%2F2025®ionId=183057&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=08%2F10%2F2025&endDate=09%2F10%2F2025®ionId=183057&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=08%2F10%2F2025&endDate=09%2F10%2F2025®ionId=183057&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 Cheshire Hikers and nature lovers flock to Cheshire's Farmington Canal Heritage Trail, where paved paths wind through scenic forests and historic landmarks. Families enjoy cooling off at Mixville Recreation Area's swimming pond in summer, while the annual Strawberry Festival offers local treats and community charm. [See all hotels in Cheshire](https://www.expedia.ca/Hotel-Search?startDate=2025-10-21&endDate=2025-10-22&adults=2®ionId=183057) ![](https://mediaim.expedia.com/destination/2/ab039a4411a79c16e7c533ffaba43069.jpg?impolicy=fcrop&w=900&h=640&p=1&q=high) Photo by Tai Bui ## Top Cheshire Hotel Reviews ## Find out more about Cheshire ## Five Star Hotels in Cheshire 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 Cheshire 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 Cheshire and get ready to be pampered like never before. #### Get a Great Deal on 5-Star Hotels in Cheshire 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 Cheshire The results are in, and Cheshire 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 Cheshire! Don't put off your dream vacation any longer. Choose one of the 5-star hotels in Cheshire 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 Cheshire? > How much you pay for a 5-star hotel in Cheshire can vary depending on when you prefer to travel and how long you plan to stay, among a range of factors. Use our price per night filter and other search tools to score the best rate on a luxurious getaway. > > > > - Search for the lowest price per night from CA $258 ### What makes a hotel 5 stars in Cheshire? > In Cheshire, a hotel is required to offer a certain number of high-end conveniences to be designated 5 stars. These may include on-site gyms, spas and saunas, gourmet restaurants, luxury toiletries, premium bedding and more. What also sets 5-star hotels apart is their guest-focused service. You can expect things like nightly turn-down services, in-room massages and concierge services. Some may also offer special touches like a welcome gift. ### Are there any 5-star all-inclusive resorts in Cheshire? > Our filter tool is the quickest way to search for exactly what you want. Select "5-star" and "All inclusive" to see the most upscale properties in Cheshire where your meals, room, entertainment and activities are included in the price. At these retreats, your trip is pure indulgence from the moment you pull up to the entrance. ## Explore a world of travel with Expedia - More ways to book - [Book 5 Star Hotels in Cheshire on Expedia.com](https://www.expedia.com/5Star-Cheshire-Hotels.s50-0-d183057.Travel-Guide-Filter-Hotels)