Title: Book the Best HISTORIC Hotels in Chester in 2025 | 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 Historic Hotels in Chester, CT from CA $190 ![](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 Historic Hotels Tonight [Oct 20 - Oct 21](https://www.expedia.ca/Hotel-Search?regionId=183058&startDate=2025-10-20&endDate=2025-10-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 21 - Oct 22](https://www.expedia.ca/Hotel-Search?regionId=183058&startDate=2025-10-21&endDate=2025-10-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=183058&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=183058&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chester Historic Hotels ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/23400/23355/a796cf54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/23400/23355/7e451d41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, desk, iron/ironing board, rollaway beds](https://images.trvl-media.com/lodging/1000000/30000/23400/23355/78e7f910.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/23400/23355/b97a2e8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn New London - Mystic Area by IHG New London 8.4/10 Very good (1013) "Nice hotel. We would stay here again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Leann CA $165 CA $190 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/New-London-Hotels-Holiday-Inn-New-London-Mystic-Area.h23355.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/1000000/10000/400/330/4d5b6bcc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/10000/400/330/20de8a0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Serves lunch and dinner](https://images.trvl-media.com/lodging/1000000/10000/400/330/32169d09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/1000000/10000/400/330/a014fdb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Spa at Norwich Inn Norwich 8.8/10 Excellent (1006) "Great place!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jill CA $259 CA $316 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Norwich-Hotels-The-Spa-At-Norwich-Inn.h330.Hotel-Information) ![TV](https://images.trvl-media.com/lodging/65000000/64920000/64918800/64918771/ad8b03cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/65000000/64920000/64918800/64918771/81e8dff0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/65000000/64920000/64918800/64918771/5a3becbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/65000000/64920000/64918800/64918771/3f6d684e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### All New Private and Cozy in great location Wallingford 8.8/10 Excellent (6) "The pictures must have been old. Very deceiving. Expected it to be more spacious. Hard to get in and out because of the busy road" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ROBERT P. CA $161 CA $404 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Wallingford-Hotels-All-New-Private-And-Cozy-In-Great-Location.h64918771.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/35000000/34010000/34005600/34005592/18dbfa66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34010000/34005600/34005592/e7c56747.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34010000/34005600/34005592/b9d11ec0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34010000/34005600/34005592/94dacfe1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterfront Home with a View Groton 9.8/10 Exceptional (110) "Great place to stay, close to I95 for easy access to nearby attractions, attentive host. Beautiful property." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deb S. CA $221 CA $418 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Groton-Hotels-Waterfront-Home-With-A-View.h34005592.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/73000000/72610000/72604700/72604611/433807ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/73000000/72610000/72604700/72604611/e52f4129.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/73000000/72610000/72604700/72604611/71856d05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/73000000/72610000/72604700/72604611/825be1b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Driftwood Cottage @ Saybrook Point Marina, 2 King Beds Old Saybrook Center 9.6/10 Exceptional (38) "Great property, would stay here again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) charles b. CA $345 CA $718 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Old-Saybrook-Hotels-Luxury-Cottage-Walking-Distance-To-Saybrook-Point-Marina.h72604611.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111090000/111083400/111083345/0821ed97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/112000000/111090000/111083400/111083345/7dc8f777.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111090000/111083400/111083345/08508799.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/112000000/111090000/111083400/111083345/a477c629.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Coastal Cottage New London New London 9.4/10 Exceptional (9) "It was the perfect little place for a night away from the kids. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tonya B. CA $269 CA $619 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/New-London-Hotels-Cozy-Coastal-Cottage.h111083345.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/102000000/101130000/101120400/101120397/8b8f1c82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/102000000/101130000/101120400/101120397/e8085e2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/102000000/101130000/101120400/101120397/54ceb6fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/102000000/101130000/101120400/101120397/fa298b86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Upper 2 bedroom apartment >Free Wi-Fi and parking - 2nd floor-private space New London 6.6/10 (4) "Was a great time ." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Linda L. CA $215 CA $435 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/New-London-Hotels-Cozy-Upper-2-Bedroom-Apartment-Free-Wi-Fi-And-Parking-2nd-Floor-Private-Space.h101120397.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/19000000/18770000/18762100/18762073/f8cef332.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/19000000/18770000/18762100/18762073/w1283h960x0y0-cce9554c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/19000000/18770000/18762100/18762073/w1283h953x0y0-69414cc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/19000000/18770000/18762100/18762073/w1283h954x0y0-9b5015ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard Saybrook Manor 9.6/10 Exceptional (133) "Great older house with everything you need to have a great time. Family event with 6 adults and 2 dogs enjoyed the house, the yard, and the area. Strongly recommend." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ray S. CA $421 CA $815 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Old-Saybrook-Hotels-Capt-Nathaniel-Clarke-Historic-Homestead.h18762073.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/19000000/18770000/18760700/18760693/4aaa8de8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/19000000/18770000/18760700/18760693/20bbb653.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/19000000/18770000/18760700/18760693/419a745d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/19000000/18770000/18760700/18760693/e88adc9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic New England home ,Reunions Beach pass Guilford 9.2/10 Wonderful (90) "House was perfect for family get together. Enjoyed walking into town for afternoon shopping and dining." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer D. CA $231 CA $564 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Guilford-Hotels-Historic-New-England-Home.h18760693.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-11-03&endDate=2025-11-04®ionId=183058&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Chester Hotel Reviews ![Mohegan Sun](//images.trvl-media.com/lodging/1000000/900000/894300/894248/60dec0f3_y.jpg) ### Mohegan Sun 10/10 Excellent "Some staff was amazing. But unfortunately most just hunted at you or turned the other way" [](https://expedia.ca/Montville-Hotels-Mohegan-Sun.h894248.Hotel-Information) ![Red Roof Inn Meriden](//images.trvl-media.com/lodging/1000000/10000/2900/2831/05873179_y.jpg) ### Red Roof Inn Meriden 10/10 Excellent "Clean with a nice staff. Great value too." [](https://expedia.ca/Hartford-Hotels-Red-Roof-Inn-Meriden.h2831.Hotel-Information) ![Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area](//images.trvl-media.com/lodging/1000000/810000/800500/800485/75539c58_y.jpg) ### Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area 10/10 Excellent "Clean and relatively modern hotel. Breakfast was great with good options. My sink was slow to drain and iron was leaking water, but minor issues in an otherwise solid hotel. Would definitely stay again." [](https://expedia.ca/Montville-Hotels-Fairfield-By-Marriott-Inn-Suites-Uncasville-Groton-Area.h800485.Hotel-Information) ![Holiday Inn Norwich by IHG](//images.trvl-media.com/lodging/1000000/10000/1500/1450/d9b5e4b8_y.jpg) ### Holiday Inn Norwich by IHG 10/10 Excellent "Nice and clean " [](https://expedia.ca/Norwich-Hotels-Holiday-Inn-Norwich.h1450.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 "Great hotel. Very clean and very nice staff. I’ve stayed here many times for shows at Mohegan sun. " [](https://expedia.ca/Montville-Hotels-Microtel-Inn-Suites-By-Wyndham-Uncasville.h801773.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 "Staff was very helpful and room was nice and clean." [](https://expedia.ca/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.Hotel-Information) ![Comfort Inn & Suites Meriden East](//images.trvl-media.com/lodging/6000000/5770000/5767400/5767371/1515d698_y.jpg) ### Comfort Inn & Suites Meriden East 10/10 Excellent "The smell of the cleaning supplies" [](https://expedia.ca/Hartford-Hotels-Comfort-Inn-Suites.h5767371.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 "Loved the pool" [](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 "Easy parking. Great shuttle service to the Casino. Great views from the hotel. Loved our stay here and wish we could have stayed longer" [](https://expedia.ca/Montville-Hotels-Hyatt-Place-Mohegan-Sun.h2593874.Hotel-Information) ## Frequently asked questions ### What should a history buff expect from a stay in Chester? > Significant historical sites in Chester are probably at the top of your travel itinerary. You can also discover all there is to see and do such as the waterfront and parks ### How many historical hotels will I find in Chester? > In Chester, you'll find 7 hotels and other lodging options bookable on Expedia but not many designated as historic hotels. ### What are the must-see historical places and other sights in Chester? > Chester is notable for landmarks like Connecticut Valley Railroad State Park Trail. A couple of additional sights to add to your agenda are Connecticut River and Norma Terris Theater. ### What is a historic hotel like in Chester? > By choosing a historic hotel, you can enjoy a vacation in a place that has an official historic designation. A castle, a palace or even a pub or an old police station can be transformed into a historic hotel provided that it's a place of special interest. Traditional architecture and period features can be admired in the communal spaces and guestrooms of such hotels in Chester, giving a historical feel. ### What is the difference between a historic hotel and a heritage hotel? > "Heritage hotel" is more common in Asia and Europe, while "historic hotel" is more common in the U.S. though overall the terms are quite similar. The physical building and architecture of a historic hotel is generally the most significant aspect. For a heritage hotel, often it's the cultural value as well as how it shaped the community. ### Do historic hotels in Chester have modern facilities? > Hotels have the safety features and modern conveniences you might expect, though efforts have been made to preserve the historic aspects and traditions. WiFi, heating and air conditioning, updated bathroom facilities, and the usual amenities found at a contemporary hotel will also be available in a historic hotel. Rest assured that when you choose a historic hotel in Chester, you won't be staying at a place that's uncomfortable for guests or simply rundown. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [4 Star Hotels in Chester Center](https://www.expedia.ca/4Star-Chester-Center-Chester-Hotels.s40-n553248635976479536-0.Travel-Guide-Filter-Hotels) - [Hotels near Chamard Vineyards](https://www.expedia.ca/Chamard-Vineyards-Hotels.0-l6309929-0.Travel-Guide-Filter-Hotels) - [Historic Hotels in Chester Center](https://www.expedia.ca/Chester-Center-Chester-Hotels-Historic-Hotel.0-n553248635976479536-0-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Hotels with an Indoor Pool in Chester Center](https://www.expedia.ca/Chester-Center-Chester-Hotels-Hotels-With-Indoor-Pool.0-n553248635976479536-0-tHotelswithIndoorPool.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Chester Center](https://www.expedia.ca/Chester-Center-Chester-Hotels-Luxury-Hotel.0-n553248635976479536-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - 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