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 $244 - ![](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 Cheshire Historic Hotels Tonight [Nov 2 - Nov 3](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2025-11-02&endDate=2025-11-03&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 3 - Nov 4](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2025-11-03&endDate=2025-11-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2025-11-14&endDate=2025-11-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Cheshire Historic Hotels ![Exterior](https://images.trvl-media.com/lodging/108000000/107560000/107557500/107557460/282f9b3e.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) ![Interior](https://images.trvl-media.com/lodging/108000000/107560000/107557500/107557460/a0e0c5f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107560000/107557500/107557460/d4937d76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Studio| Near Yale| Downtown New Haven Downtown New Haven 9.0/10 Wonderful (9) "Nice location in downtown New Haven. The room itself is nice and convenient. The window near the bed does not close because there is a large tube going through the window with tape around it. On a chilly day/night this is not comfortable and there is nothing one can do since the window does not close. You can also hear everything going on outside because the window does not close. Bedsheets were not clean either. Contacted the host about the window and bedsheets and the host gave me the... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Noel CA $135 CA $282 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/New-Haven-Hotels-Charming-Studio-Near-Yale-Downtown-New-Haven.h107557460.Hotel-Information) ![2 restaurants, breakfast, dinner, brunch served; American cuisine](https://images.trvl-media.com/lodging/1000000/50000/50000/49957/7466af25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/50000/50000/49957/499b41f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/50000/50000/49957/79e76132.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/50000/50000/49957/d9b0e3ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Omni New Haven Hotel at Yale Downtown New Haven 8.4/10 Very good (1011) "Very nice hotel, clean and add to walk around downtown " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ZVEZDELINA CA $212 CA $244 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/New-Haven-Hotels-Omni-New-Haven-Hotel-At-Yale.h49957.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) ![Interior](https://images.trvl-media.com/lodging/65000000/64920000/64918800/64918771/3f6d684e.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) ![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) ### 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 Nov 3 - Nov 4 [](https://www.expedia.ca/Wallingford-Hotels-All-New-Private-And-Cozy-In-Great-Location.h64918771.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/116000000/115210000/115203100/115203011/fe6daafb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/116000000/115210000/115203100/115203011/6c34181a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/116000000/115210000/115203100/115203011/9dabed89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/115210000/115203100/115203011/4d630799.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 (2) "This property was great! Good location and loved the design of the place. I wish I could’ve stayed longer." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lucas C. CA $185 CA $509 total includes taxes & fees Nov 3 - Nov 4 [](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.h115203011.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/97000000/96780000/96774900/96774831/w1020h1352x2y0-4c9f9702.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/97000000/96780000/96774900/96774831/5536d3f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/97000000/96780000/96774900/96774831/7f41124c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/97000000/96780000/96774900/96774831/w1023h768x0y0-61973062.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Loft apartment in the heart of downtown New Haven and blocks from the Omni Hotel Downtown New Haven CA $145 CA $259 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/New-Haven-Hotels-Loft-Apartment-In-The-Heart-Of-Downtown-New-Haven-And-Blocks-From-The-Omni-Hotel.h96774831.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) ![In-room safe, free WiFi](https://images.trvl-media.com/lodging/105000000/104370000/104369400/104369320/bbee8887.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Abner Hotel Litchfield Historic District 9.4/10 Exceptional (41) "Beautifully restored building- excellent service " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) JOHN CA $419 CA $482 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Litchfield-Hotels-Hotel-Abner.h104369320.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) ![Dining](https://images.trvl-media.com/lodging/52000000/51690000/51685500/51685419/4f70f9c0.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. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amanda W. CA $364 CA $637 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Canton-Hotels-Gorgeous-River-Views-On-Rails-To-Trails-And-Just-Steps-To-Quaint-Collinsville.h51685419.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) ![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) ![Terrace/patio](https://images.trvl-media.com/lodging/19000000/18770000/18760700/18760693/83198fbf.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 $252 CA $595 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Guilford-Hotels-Historic-New-England-Home.h18760693.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) ![Smart TV](https://images.trvl-media.com/lodging/116000000/115180000/115179200/115179179/a420dc0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/116000000/115180000/115179200/115179179/2f2baac2.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!! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daniel L. CA $242 CA $584 total includes taxes & fees Nov 24 - Nov 25 [](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) 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=2025-11-16&endDate=2025-11-17®ionId=183057&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Cheshire Hotel Reviews ![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 "My 3, well (2½) day stay was overall not bad untill........ On My 2 day of booking the room i was asked by the the woman with a clip board who im assuming was the head of in house keeping if i was staying for another day which i had told her yes and she asked would i be needing house keeping to go in my room which i replied no alls i need is fresh towels......" [](https://expedia.ca/New-Haven-Hotels-Best-Western-Executive-Hotel-Of-New-Haven-West-Haven.h23217.Hotel-Information) ![Avon Old Farms Hotel](//images.trvl-media.com/lodging/1000000/10000/2700/2635/d997675e_y.jpg) ### Avon Old Farms Hotel 10/10 Excellent "We did not have breakfast. The staff was friendly. However, they should stock more complimentary items such as hot tea and not just say "oh, we are out". " [](https://expedia.ca/Hartford-Hotels-Avon-Old-Farms-Hotel.h2635.Hotel-Information) ![Hilton Garden Inn Shelton](//images.trvl-media.com/lodging/1000000/290000/287700/287687/18ff21f4_y.jpg) ### Hilton Garden Inn Shelton 10/10 Excellent "the room was very clean and fragrant" [](https://expedia.ca/New-Haven-Hotels-Hilton-Garden-Inn-Shelton.h287687.Hotel-Information) ![Best Western Hartford Hotel & Suites](//images.trvl-media.com/lodging/1000000/20000/12200/12156/cfbe36c4_y.jpg) ### Best Western Hartford Hotel & Suites 10/10 Excellent "Great Place, recommend to others." [](https://expedia.ca/Hartford-Hotels-Best-Western-Hartford-Hotel-Suites.h12156.Hotel-Information) ![New Haven Hotel](//images.trvl-media.com/lodging/1000000/40000/36800/36721/dd69cbb4_y.jpg) ### New Haven Hotel 10/10 Excellent "Great that there was an iron and fridge in the room, as well as bathrobes. Very comfortable mattress. Gold star to front desk staff for being genuinely friendly!" [](https://expedia.ca/New-Haven-Hotels-New-Haven-Hotel.h36721.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 "Very nice hotel, clean and add to walk around downtown " [](https://expedia.ca/New-Haven-Hotels-Omni-New-Haven-Hotel-At-Yale.h49957.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 "." [](https://expedia.ca/Hartford-Hotels-Motel-6-Wethersfield.h986068.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 "Thank Staff was Great! Very very nice and attentive. Room very clean, Quiet we rested well! The Great was awesome and exit was wonderful. Parking was smoothe. We’ll return to enjoy another quiet night get away. " [](https://expedia.ca/Hartford-Hotels-Extended-Stay-America-Suites-Hartford-Farmington.h151013.Hotel-Information) ![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 " Very helpful with a 2nd party reservation " [](https://expedia.ca/New-Haven-Hotels-Hyatt-Place-Milford-New-Haven.h1562702.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 5 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, Cheshire Hollow Farm, and Maplecroft Plaza Shopping Center. A couple of additional sights to add to your agenda are Drazen Orchards and Bartlem Park. ### 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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