Title: 4 Stars Hotels in Chester, Connecticut from CA $386 - Find Cheap Chester Hotels With 4 Stars | Expedia.ca [Chester Travel Guide](https://expedia.ca/Chester.dx183058)[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) ![Connecticut River Autumn Landscape with the view of landmark architectures on the woodland hill, a tranquil New England scenery](https://images.trvl-media.com/place/183058/c14a28ee-62e4-4e76-85a4-650e5a230000.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/183058/c14a28ee-62e4-4e76-85a4-650e5a230000.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 Chester 4 Star Hotels Tonight [Apr 2 - Apr 3](https://www.expedia.ca/Hotel-Search?regionId=183058&startDate=2026-04-02&endDate=2026-04-03&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Apr 3 - Apr 4](https://www.expedia.ca/Hotel-Search?regionId=183058&startDate=2026-04-03&endDate=2026-04-04&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=183058&startDate=2026-04-03&endDate=2026-04-05&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=183058&startDate=2026-04-10&endDate=2026-04-12&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chester 4-star hotels ![2 indoor pools, open 6 AM to 10 PM, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/1000000/900000/894300/894248/37130fc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/900000/894300/894248/3c373018.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![19 restaurants, lunch, dinner served; Italian cuisine](https://images.trvl-media.com/lodging/1000000/900000/894300/894248/d3354fa8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/900000/894300/894248/w3836h2560x4y0-b563ecb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mohegan Sun [](https://www.expedia.ca/Montville-Hotels-Mohegan-Sun.h894248.Hotel-Information) Montville 9.2/10 Wonderful (2,046 reviews) "Phenomenal stay can’t wait to go back." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert S [](https://www.expedia.ca/Montville-Hotels-Mohegan-Sun.h894248.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/1ec18076.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed, Accessible (Roll In Shower)](https://images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/w5759h3835x0y5-4148a2a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Bedrooms | View from room](https://images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/d4dd4a63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach, sun loungers, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/c4093211.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Madison Beach Hotel [](https://www.expedia.ca/Madison-Hotels-Madison-Beach-Hotel.h1209378.Hotel-Information) Madison Center 9.4/10 Exceptional (350 reviews) "We toured the Spa but did not have an opportunity to take advantage of the services during our overnight stay. The staff was very helpful and the spa calm and inviting." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Per CA $374 CA $430 total includes taxes & fees Apr 16 - Apr 17 [](https://www.expedia.ca/Madison-Hotels-Madison-Beach-Hotel.h1209378.Hotel-Information) ![Breakfast and dinner served](https://images.trvl-media.com/lodging/2000000/1490000/1484300/1484254/fb2335a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1490000/1484300/1484254/a99c206a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Room, 1 Bedroom, Non Smoking (Room 322)](https://images.trvl-media.com/lodging/2000000/1490000/1484300/1484254/e11ede87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Room, 1 Bedroom, Non Smoking (Room 314)](https://images.trvl-media.com/lodging/2000000/1490000/1484300/1484254/61b576aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Copper Beech Inn [](https://www.expedia.ca/Old-Saybrook-Hotels-Copper-Beech-Inn.h1484254.Hotel-Information) Ivoryton 8.6/10 Excellent (509 reviews) "Very nice property. Very clean. Staff was very nice - very good breakfast. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marilyn CA $387 CA $445 total includes taxes & fees Apr 5 - Apr 6 [](https://www.expedia.ca/Old-Saybrook-Hotels-Copper-Beech-Inn.h1484254.Hotel-Information) ![Miss Anna James Room](https://images.trvl-media.com/lodging/79000000/78200000/78191100/78191036/w848h631x48y3-ad11e9c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/79000000/78200000/78191100/78191036/1891e70e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Katharine Hepburn Room](https://images.trvl-media.com/lodging/79000000/78200000/78191100/78191036/20c673f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miss Anna James Room](https://images.trvl-media.com/lodging/79000000/78200000/78191100/78191036/dc6ad011.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### James Pharmacy Bed & Breakfast [](https://www.expedia.ca/Old-Saybrook-Hotels-James-Pharmacy-Bed-Breakfast.h78191036.Hotel-Information) Old Saybrook Center 9.0/10 Wonderful (23 reviews) "Cute B&B, very nice room, check-in worked well" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Isolde CA $348 CA $386 total includes taxes & fees Apr 28 - Apr 29 [](https://www.expedia.ca/Old-Saybrook-Hotels-James-Pharmacy-Bed-Breakfast.h78191036.Hotel-Information) ![Apartment (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94370000/94367800/94367757/e8585bd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94370000/94367800/94367757/02f02fcc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94370000/94367800/94367757/d82f1928.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94370000/94367800/94367757/1fea83c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### New London Hideaway Near Beaches & Local Spots! [](https://www.expedia.ca/New-London-Hotels-New-London-Hideaway-Near-Beaches-Local-Spots.h94367757.Hotel-Information) New London 10/10 Exceptional (1 review) "Amazing stay place was super cozy and clean. Jim and Nancy were awesome and super kind! 10/10" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christine [](https://www.expedia.ca/New-London-Hotels-New-London-Hideaway-Near-Beaches-Local-Spots.h94367757.Hotel-Information) ![Apartment (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94540000/94530800/94530784/2003edba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94540000/94530800/94530784/eca7fb24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94540000/94530800/94530784/d8ac57fd_edited_602e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94540000/94530800/94530784/3b1699bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern Middletown Retreat, Minutes to Downtown! [](https://www.expedia.ca/Middletown-Hotels-Modern-Middletown-Retreat.h94530784.Hotel-Information) Middletown 10/10 Exceptional (2 reviews) "Perfect location and layout for our group." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David [](https://www.expedia.ca/Middletown-Hotels-Modern-Middletown-Retreat.h94530784.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%2F4Star-Chester-Hotels.s40-0-d183058.Travel-Guide-Filter-Hotels)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F4Star-Chester-Hotels.s40-0-d183058.Travel-Guide-Filter-Hotels) ## Learn more about Chester Charming galleries and local shops line Main Street, where you'll find handcrafted jewellery and Connecticut River Valley artwork. Catch a performance at the Goodspeed Opera House in East Haddam or kayak Chester Creek when summer temperatures rise. [See all hotels in Chester](https://www.expedia.ca/Hotel-Search?startDate=2026-04-16&endDate=2026-04-17&adults=2®ionId=183058) ![Connecticut River Autumn Landscape with the view of landmark architectures on the woodland hill, a tranquil New England scenery](https://images.trvl-media.com/place/183058/c14a28ee-62e4-4e76-85a4-650e5a230000.jpg?impolicy=fcrop&w=900&h=600&p=1&q=high) ## Top Chester Hotel Reviews ## Find out more about Chester If you’re looking for a spot with great rates, just-for-you amenities, and a world of luxurious little perks, the best 4 Stars hotels in Chester are calling your name. Known for providing first-rate service in amazing locations, each of the Chester 4 Stars hotels lets discerning travelers bask in an unforgettable experience. Kick back in your spacious room. Relax in the lobby’s sumptuous surroundings. Start the day with delicious room service, and then use the complimentary body care items to freshen up before you head out for the day. It’s all waiting for you at the top four star hotels in Chester. Plus, when you book with Expedia.ca, you might find a cheap deal on a 4 Stars hotel in Chester, Connecticut, neighbourhoods near the most popular attractions, so you can see the sights and bask in the discounts all in one trip. Whether you’re planning a romantic retreat or simply want to experience everything the area has to offer, the top Chester hotels with 4 Stars provide everything you need to unwind in style. ## Frequently asked questions ### What are the best 4-star hotels in Chester? ### How much does it cost to stay in a 4-star hotel in Chester? > - Search for the lowest price from CA $386 ### What's the difference between 5-star and 4-star hotels in Chester? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [3 Star Hotels in Northford ](https://www.expedia.ca/3Star-Northford-Hotels.s30-0-d6004524.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Windsor ](https://www.expedia.ca/3Star-Windsor-Hotels.s30-0-d7880.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Beacon Falls ](https://www.expedia.ca/4Star-Beacon-Falls-Hotels.s40-0-d6348182.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Chester Center ](https://www.expedia.ca/4Star-Chester-Center-Chester-Hotels.s40-n553248635976479536-0.Travel-Guide-Filter-Hotels) - 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