Title: Book the Best Chester LUXURY Hotels - Upscale Hotels in Chester, CT | Expedia.ca [Hotels in Chester](https://expedia.ca/Chester-Hotels.d183058.Travel-Guide-Hotels)[Vacation Rentals in Chester](https://expedia.ca/Chester-Vacation-Rentals.d183058.Travel-Guide-VacationRentals)[Flights to Chester](https://expedia.ca/Cheap-Flights-To-Chester.d183058.Travel-Guide-Flights)[Chester Car Rentals](https://expedia.ca/Car-Rentals-In-Chester.d183058.Car-Rental-Guide)[Chester Vacation Packages](https://expedia.ca/Chester.d183058.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/c5d2a9a368de96fc49a7ea71252ca638.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Annette Babek # Find luxury hotels in Chester, CT ![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 Chester Luxury Hotels Tonight [Sep 17 - Sep 18](https://www.expedia.ca/Hotel-Search?regionId=183058&startDate=2025-09-17&endDate=2025-09-18&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Sep 18 - Sep 19](https://www.expedia.ca/Hotel-Search?regionId=183058&startDate=2025-09-18&endDate=2025-09-19&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Sep 19 - Sep 21](https://www.expedia.ca/Hotel-Search?regionId=183058&startDate=2025-09-19&endDate=2025-09-21&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Sep 26 - Sep 28](https://www.expedia.ca/Hotel-Search?regionId=183058&startDate=2025-09-26&endDate=2025-09-28&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chester Luxury Hotels ## Find out more about Chester ### Chesterand its attractions for luxury travelers Chester, Connecticut, offers a delightful array of experiences for luxury travellers seeking both relaxation and adventure. Begin your exploration at the stunning Chester Historical Society, where you can immerse yourself in the town's rich heritage while enjoying exclusive guided tours of the picturesque buildings. For those who appreciate nature, the nearby Cockaponset State Forest invites you to indulge in scenic hikes, with lush trails that lead to breathtaking views, perfect for a family outing or a peaceful retreat. Art enthusiasts will be captivated by the local galleries, such as the Chester Gallery, showcasing exquisite works from both established and emerging artists, often hosting exclusive events for discerning visitors. For a culinary adventure, dine at the renowned River Tavern, where the chef crafts seasonal dishes that reflect the region's bounty, ensuring a memorable dining experience. After a day of exploration, unwind at one of Chester's luxury hotels, such as the charming Inn at Chester, which boasts elegant rooms and personalised service, allowing you to feel truly pampered. Nestled in the heart of the town, this area not only offers easy access to local attractions but also provides a serene backdrop for relaxation, making it a perfect base for your luxurious getaway. ## Top Chester Hotel Reviews ![Mohegan Sun](//images.trvl-media.com/lodging/1000000/900000/894300/894248/60dec0f3_y.jpg) ### Mohegan Sun 10/10 Excellent "Your Hotel is beyond wonderful! I love everything about it!" [](https://expedia.ca/Montville-Hotels-Mohegan-Sun.h894248.Hotel-Information) ![Saybrook Point Resort & Marina](//images.trvl-media.com/lodging/1000000/40000/38800/38715/5e605108_y.jpg) ### Saybrook Point Resort & Marina 10/10 Excellent "Very pleasant property with friendly staff in all areas we experienced. We had a very good stay and can recommend the property. " [](https://expedia.ca/Old-Saybrook-Hotels-Saybrook-Point-Resort-Marina.h38715.Hotel-Information) ![Microtel Inn & Suites by Wyndham Uncasville Casino Area](//images.trvl-media.com/lodging/1000000/810000/801800/801773/ed4520c7_y.jpg) ### Microtel Inn & Suites by Wyndham Uncasville Casino Area 10/10 Excellent "None" [](https://expedia.ca/Montville-Hotels-Microtel-Inn-Suites-By-Wyndham-Uncasville.h801773.Hotel-Information) ![Best Western Plus New England Inn & Suites](//images.trvl-media.com/lodging/1000000/930000/922200/922173/ff6d89d5_y.jpg) ### Best Western Plus New England Inn & Suites 10/10 Excellent "Excellent property I would stay at this location again" [](https://expedia.ca/Hartford-Hotels-Best-Western-Plus-New-England-Inn-Suites.h922173.Hotel-Information) ![Hyatt Place Uncasville - Casino Area](//images.trvl-media.com/lodging/3000000/2600000/2593900/2593874/46d6d7fc_y.jpg) ### Hyatt Place Uncasville - Casino Area 10/10 Excellent "Staff " [](https://expedia.ca/Montville-Hotels-Hyatt-Place-Mohegan-Sun.h2593874.Hotel-Information) ![Pier Blue Inn Old Saybrook - Essex](//images.trvl-media.com/lodging/1000000/20000/12200/12143/a912ee6f_y.jpg) ### Pier Blue Inn Old Saybrook - Essex 10/10 Excellent "We were in town for a party. Very convenient location and friendly staff. " [](https://expedia.ca/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.Hotel-Information) ![Sleep Inn & Suites Niantic](//images.trvl-media.com/lodging/1000000/860000/851700/851700/cf19af3a_y.jpg) ### Sleep Inn & Suites Niantic 10/10 Excellent "Rooms look clean and nice" [](https://expedia.ca/Niantic-Hotels-Sleep-Inn-Suites-Niantic.h851700.Hotel-Information) ![Quality Inn Old Saybrook - Westbrook](//images.trvl-media.com/lodging/1000000/10000/4000/3988/228c4607_y.jpg) ### Quality Inn Old Saybrook - Westbrook 10/10 Excellent "Great staff, easy check in, nice room and has a pool. Generally pleasant atmosphere. " [](https://expedia.ca/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.Hotel-Information) ## Frequently asked questions ### Are you searching for the perfect hotel for your luxury getaway to Chester? > Expedia can help you arrange a flight to New Haven, CT (HVN-Tweed - New Haven Regional) airport or New London, CT (GON-Groton - New London) airport, and then you can select from various places to stay that will deliver the luxury you'd like to find. Amenities are an important consideration when you plan a vacation, so we make it easy to find what you need to make your stay special. If you want a posh hotel that has a spa, an indoor pool, or luxury bedding, Expedia can assist you in finding the best luxury hotel experience that Chester offers. Chester has some interesting things to see and do including Connecticut River and Norma Terris Theater, so you might want to take in the local sights during your visit. ### When can I expect good weather in Chester? > Planning for the weather is a good way to make your trip to Chester relaxing and enjoyable, especially when you're splurging. The hottest months are usually July and August with an average temp of 70°F, while the coldest months are January and February with an average of 35°F. Average annual precipitation for Chester is 54 inches. ### What's there to see and do in Chester? > When you're in Chester, enjoy exploring the sights and attractions here including Connecticut River, Norma Terris Theater, and Connecticut Valley Railroad State Park Trail. 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