Title: Book the Best HISTORIC Hotels in Cheshire in 2025 | Expedia.ca [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 # Find Historic Hotels in Cheshire, CT from CA $279 ![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 Historic Hotels Tonight [Oct 8 - Oct 9](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2025-10-08&endDate=2025-10-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 9 - Oct 10](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2025-10-09&endDate=2025-10-10&adults=2&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&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&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Cheshire Historic Hotels ![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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/65000000/64920000/64918800/64918771/f17b3396.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) ### 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" CA $160 CA $402 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Wallingford-Hotels-All-New-Private-And-Cozy-In-Great-Location.h64918771.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/108000000/107560000/107557500/107557460/282f9b3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107560000/107557500/107557460/a0e0c5f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, coffee/tea maker, cookware/dishes/utensils](https://images.trvl-media.com/lodging/108000000/107560000/107557500/107557460/a10e81b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107560000/107557500/107557460/d820b069.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Studio| Near Yale| Downtown New Haven Downtown New Haven 8.6/10 Excellent (7) "A great place to stay during reunions! Prime campus-adjacent location, an easy walk to all things on campus!" CA $137 CA $279 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/New-Haven-Hotels-Charming-Studio-Near-Yale-Downtown-New-Haven.h107557460.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/105000000/104370000/104369400/104369320/f403f26b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/105000000/104370000/104369400/104369320/efe74a4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/105000000/104370000/104369400/104369320/5288546f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite (Chamber)](https://images.trvl-media.com/lodging/105000000/104370000/104369400/104369320/786946b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Abner Hotel Litchfield 9.4/10 Exceptional (40) "Beautiful property and great service." CA $429 CA $493 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Litchfield-Hotels-Hotel-Abner.h104369320.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/116000000/115180000/115179200/115179179/ee04346f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/116000000/115180000/115179200/115179179/7918b066.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/115180000/115179200/115179179/78d159fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/116000000/115180000/115179200/115179179/a420dc0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DTWN I Near Yale I King Beds I Free Parking I Gym I Free Coffee I Pets Welcome! Downtown New Haven 10/10 Exceptional (1) "We stayed here on our last night of a month long vacation. After a month of travel, you want convenience and comfort. This place offered us a fantastic last night away from home. It’s right across the street from the train station, easy walking to shops and dining, and just an overall beautiful apartment. It was clean and cozy with immaculate decorating. The entry and exit were easy. Accommodations were superior. Don’t forget to grab pizza!! " CA $201 CA $530 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/New-Haven-Hotels-DTWN-I-Near-Yale-I-King-Beds-I-Free-Parking-I-Gym-I-Free-Coffee-I-Pets-Welcome.h115179179.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/52000000/51690000/51685500/51685419/1bc1a012.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/52000000/51690000/51685500/51685419/w1026h680x0y3-1207c37a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/52000000/51690000/51685500/51685419/cd7d0c00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/52000000/51690000/51685500/51685419/010bda9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville Collinsville 10/10 Exceptional (61) "There is a lot of fun things to do close by. The house was spotless and it was nice to relax on the sofa or outside patio and look at the river. " CA $403 CA $684 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Canton-Hotels-Gorgeous-River-Views-On-Rails-To-Trails-And-Just-Steps-To-Quaint-Collinsville.h51685419.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=2025-10-22&endDate=2025-10-23®ionId=183057&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Cheshire Hotel Reviews ![Hyatt Place Milford / New Haven](//images.trvl-media.com/lodging/2000000/1570000/1562800/1562702/0336d577_y.jpg) ### Hyatt Place Milford / New Haven 10/10 Excellent "Overall good" [](https://expedia.ca/New-Haven-Hotels-Hyatt-Place-Milford-New-Haven.h1562702.Hotel-Information) ![New Haven Hotel](//images.trvl-media.com/lodging/1000000/40000/36800/36721/dd69cbb4_y.jpg) ### New Haven Hotel 10/10 Excellent "There is no breakfast possibility offered😟" [](https://expedia.ca/New-Haven-Hotels-New-Haven-Hotel.h36721.Hotel-Information) ![Best Western Executive Hotel Of New Haven - West Haven](//images.trvl-media.com/lodging/1000000/30000/23300/23217/b63e42e2_y.jpg) ### Best Western Executive Hotel Of New Haven - West Haven 10/10 Excellent "Very neat and tidy, in and around the property. All basic necessities available. Good value for money. " [](https://expedia.ca/New-Haven-Hotels-Best-Western-Executive-Hotel-Of-New-Haven-West-Haven.h23217.Hotel-Information) ![Hampton Inn & Suites Hartford/East Hartford](//images.trvl-media.com/lodging/3000000/2950000/2943100/2943093/5cf369a5_y.jpg) ### Hampton Inn & Suites Hartford/East Hartford 10/10 Excellent "The room was nice and the staff was nice. " [](https://expedia.ca/Hartford-Hotels-Hampton-Inn-Suites-HartfordEast-Hartford.h2943093.Hotel-Information) ![Extended Stay America Suites Hartford Farmington](//images.trvl-media.com/lodging/1000000/160000/151100/151013/02939ae3_y.jpg) ### Extended Stay America Suites Hartford Farmington 10/10 Excellent "I loved my spacious room, kitchen facilities, comfy bed, easy parking. The staff was friendly and helpful, but what I liked best was the feeling of being in my own space, not a hotel. " [](https://expedia.ca/Hartford-Hotels-Extended-Stay-America-Suites-Hartford-Farmington.h151013.Hotel-Information) ![Omni New Haven Hotel at Yale](//images.trvl-media.com/lodging/1000000/50000/50000/49957/7466af25_y.jpg) ### Omni New Haven Hotel at Yale 10/10 Excellent "We have a lovely stay at the Omni New Haven. The room was clean and quiet with a super comfy bed and pillows. The staff were friendly and helpful. If you are visiting Yale, it's right on the campus. Very walkable!" [](https://expedia.ca/New-Haven-Hotels-Omni-New-Haven-Hotel-At-Yale.h49957.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 "The staff was nice and the facilities were clean" [](https://expedia.ca/Hartford-Hotels-Red-Roof-Inn-Meriden.h2831.Hotel-Information) ![Motel 6 Wethersfield, CT - Hartford](//images.trvl-media.com/lodging/1000000/990000/986100/986068/692a6601_y.jpg) ### Motel 6 Wethersfield, CT - Hartford 10/10 Excellent "Clean room friendly staff respectable of my animals" [](https://expedia.ca/Hartford-Hotels-Motel-6-Wethersfield.h986068.Hotel-Information) ![Hamden Hotel and Suites – Hamden New Haven](//images.trvl-media.com/lodging/1000000/20000/18000/17931/c3c836db_y.jpg) ### Hamden Hotel and Suites – Hamden New Haven 10/10 Excellent "The room was very clean. The staff was very nice and very good customer services. The breakfast in morning was wonderful. Everything was great." [](https://expedia.ca/New-Haven-Hotels-Clarion-Hotel-Suites-Hamden-New-Haven.h17931.Hotel-Information) ## Frequently asked questions ### What should a history enthusiast expect from a trip to Cheshire? > You'll probably want to seek out the sights of historical relevance during your trip to Cheshire. Why not absorb the local color with a visit to the restaurants? ### How many historical hotels are there in Cheshire? > Cheshire is home to 4 hotels and other accommodations bookable on Expedia though not many historic hotels to choose from. ### What are the most important historical places and other sights in Cheshire? > Favorite places to visit include Barker Character, Comic and Cartoon Museum, Roaring Brook Park, and Cheshire Hollow Farm. A couple of additional sights to add to your agenda are Maplecroft Plaza Shopping Center and Drazen Orchards. ### What is a historic hotel like in Cheshire? > By choosing a historic hotel, you can spend a night or two someplace that has an officially recognized national historic designation. A castle, stately home, palace or even a pub, lodge, old police station, or skyscraper can be turned into a historic hotel provided that it has special significance. Traditional architecture and period features are often preserved within the guestrooms or public spaces of these historic hotels in Cheshire, giving a historical feel. ### What is the difference between a historic hotel and a heritage hotel? > "Heritage hotel" is a term often used in Asia and Europe, wheareas the term "historic hotel" is more commonly used in the U.S. though overall the terms are quite similar. The architecture and actual building of historic hotels are generally what's most significant. For a heritage hotel, mainly, it's cultural value as well as how it inspired the community. ### Do historic hotels in Cheshire have modern facilities? > Hotels include modern conveniences and safety features you expect to find, though efforts have been made to preserve historic facades and treasured traditions. Smart TVs, WiFi, updated bathroom facilities, and the popular amenities found in most hotels should be available at a historic hotel. Rest assured that when you select a historic hotel in Cheshire, you won't find yourself staying at a place that's uncomfortable for guests or simply rundown. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [Hotels near Brookside Park](https://www.expedia.ca/Brookside-Park-Hotels.0-l553248621557919974-0.Travel-Guide-Filter-Hotels) - [B&B in Cheshire Historic District](https://www.expedia.ca/Cheshire-Historic-District-Bed-And-Breakfast.d6346724-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Country Houses in Cheshire Historic District](https://www.expedia.ca/Cheshire-Historic-District-Country-House.d6346724-aaCountryHouse.Travel-Guide-Accommodation) - [Guest Houses in Cheshire Historic District](https://www.expedia.ca/Cheshire-Historic-District-Guest-Houses.d6346724-aaGuestHouses.Travel-Guide-Accommodation) - [Villas in Cheshire Historic District](https://www.expedia.ca/Cheshire-Historic-District-Villas.d6346724-aaVillas.Travel-Guide-Accommodation) - 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