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) ![Enjoying a #weekend out in #Connecticut #Marina #River #Autumn](https://images.trvl-media.com/place/6004513/c0f041d5-f895-44ec-b954-f8bc1e935e1c.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Erick # Find luxury hotels in Chester, CT - ![](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 Chester Luxury Hotels Tonight [Nov 11 - Nov 12](https://www.expedia.ca/Hotel-Search?regionId=183058&startDate=2025-11-11&endDate=2025-11-12&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Tomorrow [Nov 12 - Nov 13](https://www.expedia.ca/Hotel-Search?regionId=183058&startDate=2025-11-12&endDate=2025-11-13&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) This weekend [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=183058&startDate=2025-11-14&endDate=2025-11-16&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Next weekend [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=183058&startDate=2025-11-21&endDate=2025-11-23&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) ## 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 ![Days Inn by Wyndham Berlin Meriden](//images.trvl-media.com/lodging/1000000/60000/50100/50056/2ce804b3_y.jpg) ### Days Inn by Wyndham Berlin Meriden 10/10 Excellent "Everyone and everything was just great " [](https://expedia.ca/Hartford-Hotels-Days-Inn-By-Wyndham-Berlin-Meriden.h50056.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 "🙂" [](https://expedia.ca/Montville-Hotels-Hyatt-Place-Mohegan-Sun.h2593874.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 "Yes" [](https://expedia.ca/Montville-Hotels-Microtel-Inn-Suites-By-Wyndham-Uncasville.h801773.Hotel-Information) ![Mohegan Sun](//images.trvl-media.com/lodging/1000000/900000/894300/894248/60dec0f3_y.jpg) ### Mohegan Sun 10/10 Excellent "Room service was very slow " [](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 "Hospitality at its finest! Bed here was beyond comfortable❤️" [](https://expedia.ca/Old-Saybrook-Hotels-Saybrook-Point-Resort-Marina.h38715.Hotel-Information) ![The Spa at Norwich Inn](//images.trvl-media.com/lodging/1000000/10000/400/330/4d5b6bcc_y.jpg) ### The Spa at Norwich Inn 10/10 Excellent "The spa was wonderful! My friend and I had facials massages and foot massages and they were perfect! The people working at the Norwich Inn are so friendly and helpful. The best part is that you can hang out in your robe and enjoy the spa facilities all day! We absolutely loved it and didn’t want to leave … we already booked a return trip for June!" [](https://expedia.ca/Norwich-Hotels-The-Spa-At-Norwich-Inn.h330.Hotel-Information) ![Regency Inn & Suites New London, Mystic](//images.trvl-media.com/lodging/1000000/10000/6400/6341/fbddb1be_y.jpg) ### Regency Inn & Suites New London, Mystic 10/10 Excellent "My room was exceptionally clean and staff was kind and friendly." [](https://expedia.ca/New-London-Hotels-Regency-Inn-And-Suites-New-London.h6341.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 "Everything was good, had a quiet happy stay." [](https://expedia.ca/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.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 "Always a great stay at Pier Blue. Comfy bed and plenty of room." [](https://expedia.ca/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.Hotel-Information) ## Frequently asked questions ### Which area of Chester is best to stay in for luxury hotels? > The best areas to stay in Chester for luxury hotels are the town centre and the immediate surrounding countryside. > > > > Chester's town centre is compact and picturesque, with a main street, North Main Street, featuring a collection of independent shops, art galleries, and restaurants. It's a very walkable area with historic buildings and access to the Connecticut River. > > > > Couples looking for a refined getaway will appreciate the town centre. It's ideal for enjoying leisurely strolls, browsing local crafts, and dining at quality restaurants, all within easy reach of your accommodation. The proximity to the river also offers opportunities for scenic views and boat trips. > > > > For those seeking privacy and expansive grounds, the luxury options just outside the town centre offer a tranquil setting. These properties often feature larger estates, offering amenities like extensive gardens, fine dining, and wellness facilities, including high-end fitness equipment. ### How much does a luxury hotel in Chester cost? > Luxury hotel prices in Chester vary, but you can find a great deal on Expedia. To find the best prices on luxury stays, be flexible with your dates—typically, off-peak and mid-week stays are cheaper. Sort your search results by "Price: low to high" to see our lowest rates. ### What luxury activities and experiences are there in Chester? > The best area to stay for luxury activities and experiences in Chester is the town centre, particularly around Main Street and North Main Street. > > > > This area is the heart of Chester, a charming village located along the Connecticut River. It's known for its well-preserved historic buildings, independent boutiques, and art galleries. You'll find a relaxed pace of life here, with a focus on quality local offerings. > > > > Couples looking for a refined getaway will find the town centre perfect. They can enjoy a performance at the local playhouse, explore the art scene, or take a leisurely stroll down to the riverfront. Dining experiences here often feature locally sourced ingredients in sophisticated settings, providing a delightful evening out. > > > > For those seeking bespoke experiences, the town centre offers access to unique workshops and bespoke shopping. You can find handcrafted items in local shops or participate in a cooking class, allowing for a personalised and memorable trip. ### How can I save on a luxury hotel in Chester with Expedia? > There are plenty of ways to save on a luxury hotel in Chester. Unlock our lowest prices by joining [One Key™](https://www.expedia.ca/welcome-one-key), Expedia's travel rewards program. It's free and easy to sign up, and you can access member perks too. Typically, booking in advance will help you save on your luxury hotel booking. If you're feeling spontaneous, be sure to check for last-minute deals. ### Is it cheaper to book a luxury Chester hotel and flights as a package? > Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates, and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect travel package. ### Can I cancel my luxury hotel reservation on Expedia? > Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline. This is often within 24-48 hours of your scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. 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