Title: Book the Best HISTORIC Hotels in Cheshire in 2026 | 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)[Things to do in Cheshire](https://expedia.ca/Things-To-Do-In-Cheshire.d183057.Travel-Guide-Activities)[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) ![Castle Craig at Hubbard Park, Meriden, CT. easily replaceable sky. with a clean, classic view of the tower. Very recognizable image of this historic structure.](https://images.trvl-media.com/place/183057/92c74fd9-1a45-4931-a43e-251e181e803f.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/183057/92c74fd9-1a45-4931-a43e-251e181e803f.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 Cheshire Historic Hotels Tonight [Feb 25 - Feb 26](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2026-02-25&endDate=2026-02-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Feb 26 - Feb 27](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2026-02-26&endDate=2026-02-27&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2026-02-27&endDate=2026-03-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2026-03-06&endDate=2026-03-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) No exact matches found, but these alternatives could be just right ## Recommended hotels in Cheshire ![Exterior](https://images.trvl-media.com/lodging/2000000/1900000/1896600/1896545/6132396a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Double Beds](https://images.trvl-media.com/lodging/2000000/1900000/1896600/1896545/7c4d427d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1900000/1896600/1896545/d936e083.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1900000/1896600/1896545/c0034c2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cheshire Welcome Inn [](https://www.expedia.ca/New-Haven-Hotels-Cheshire-Welcome-Inn.h1896545.Hotel-Information) Cheshire 8.4/10 Very good (785 reviews) "Great location, comfortable and clean" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) MARK CA $110 CA $126 total includes taxes & fees Feb 26 - Feb 27 [](https://www.expedia.ca/New-Haven-Hotels-Cheshire-Welcome-Inn.h1896545.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/112000000/111830000/111824500/111824460/62b2e5a8_edited_33e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/112000000/111830000/111824500/111824460/a5ee2415.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111830000/111824500/111824460/624102e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111830000/111824500/111824460/efeecab7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quiet 2bd Townhome apt in the heart of Cheshire. Backyard. [](https://www.expedia.ca/Cheshire-Hotels-Quiet-2-Bedroom-Apartment-In-Wonderful-Cheshire-With-WiFi-And-Beautiful-Views.h111824460.Hotel-Information) Cheshire 9.4/10 Exceptional (16 reviews) "Great Location - all the amenities you need for a nice restful stay. Did not have to reach-out to the host at all during our stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert S. CA $122 CA $231 total includes taxes & fees Mar 1 - Mar 2 [](https://www.expedia.ca/Cheshire-Hotels-Quiet-2-Bedroom-Apartment-In-Wonderful-Cheshire-With-WiFi-And-Beautiful-Views.h111824460.Hotel-Information) ![Desk, WiFi](https://images.trvl-media.com/lodging/125000000/124240000/124230500/124230490/w1416h960x24y0-3b37d4e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/125000000/124240000/124230500/124230490/3844fcda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/125000000/124240000/124230500/124230490/w1440h957x0y3-3eba8e53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/125000000/124240000/124230500/124230490/w1437h960x0y0-d206619d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### #43- Modern Luxury Log Cabin Retreat | Fire Pit [](https://www.expedia.ca/Cheshire-Hotels-43-Modern-Luxury-Log-Cabin-Retreat-Fire-Pit.h124230490.Hotel-Information) Prospect CA $410 CA $793 total includes taxes & fees Feb 28 - Mar 1 [](https://www.expedia.ca/Cheshire-Hotels-43-Modern-Luxury-Log-Cabin-Retreat-Fire-Pit.h124230490.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/93000000/92710000/92700300/92700288/d59c3f6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/93000000/92710000/92700300/92700288/6ecb42f6.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/93000000/92710000/92700300/92700288/240f0a22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/93000000/92710000/92700300/92700288/e720f79f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quiet and cozy studio apartment on premier Cheshire street close to New Haven [](https://www.expedia.ca/Cheshire-Hotels-Quiet-And-Cozy-Studio-Apartment-On-Premier-Cheshire-Street-Close-To-New-Haven.h92700288.Hotel-Information) Cheshire CA $169 CA $245 total includes taxes & fees Mar 1 - Mar 2 [](https://www.expedia.ca/Cheshire-Hotels-Quiet-And-Cozy-Studio-Apartment-On-Premier-Cheshire-Street-Close-To-New-Haven.h92700288.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/95000000/94950000/94946700/94946614/ebe022ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sports facility](https://images.trvl-media.com/lodging/95000000/94950000/94946700/94946614/d26781d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/95000000/94950000/94946700/94946614/10e91fff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/95000000/94950000/94946700/94946614/7588ab8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Home2 Suites by Hilton Bristol [](https://www.expedia.ca/Bristol-Hotels-Home2-Suites-By-Hilton-Bristol.h94946614.Hotel-Information) Bristol 9.6/10 Exceptional (193 reviews) "Clean room, great staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tamiya CA $178 CA $205 total includes taxes & fees Mar 5 - Mar 6 [](https://www.expedia.ca/Bristol-Hotels-Home2-Suites-By-Hilton-Bristol.h94946614.Hotel-Information) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/990000/983200/983128/dc9b088b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/990000/983200/983128/735ceae9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/990000/983200/983128/174f7a84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/990000/983200/983128/08241fb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spark by Hilton Guilford [](https://www.expedia.ca/Guilford-Hotels-Spark-By-Hilton-Guilford.h983128.Hotel-Information) Guilford 8.8/10 Excellent (98 reviews) "The front desk staff were excellent, clean and comfortable stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) JUstine CA $138 CA $159 total includes taxes & fees Mar 9 - Mar 10 [](https://www.expedia.ca/Guilford-Hotels-Spark-By-Hilton-Guilford.h983128.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/1000000/40000/35400/35389/a84dbb59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/40000/35400/35389/beb7cb97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, in-room safe, blackout drapes](https://images.trvl-media.com/lodging/1000000/40000/35400/35389/7ba7bc43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Combined shower/tub, designer toiletries, hair dryer, towels](https://images.trvl-media.com/lodging/1000000/40000/35400/35389/w3294h2193x7y7-9a763751.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Heritage Hotel, Golf & Conference Center [](https://www.expedia.ca/Southbury-Hotels-Heritage-Hotel.h35389.Hotel-Information) Southbury 8.4/10 Very good (1,014 reviews) "Most amazing place " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maria CA $152 CA $198 total includes taxes & fees Mar 10 - Mar 11 [](https://www.expedia.ca/Southbury-Hotels-Heritage-Hotel.h35389.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1400000/1400000/1399998/7368827e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV](https://images.trvl-media.com/lodging/2000000/1400000/1400000/1399998/98bad297.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, coffee/tea maker](https://images.trvl-media.com/lodging/2000000/1400000/1400000/1399998/42c9a535.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/2000000/1400000/1400000/1399998/7fef8cbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tower Inn And Suites Of Guilford - Madison [](https://www.expedia.ca/New-Haven-Hotels-Tower-Inn-And-Suites-Of-Guilford-Madison.h1399998.Hotel-Information) Guilford 7.4/10 Good (238 reviews) "I really enjoy staying here. The family who runs this motel are so nice. I used to live in Guilford and moved out of state. I return to Conn frequently and always stay here. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susan B CA $123 CA $141 total includes taxes & fees Mar 1 - Mar 2 [](https://www.expedia.ca/New-Haven-Hotels-Tower-Inn-And-Suites-Of-Guilford-Madison.h1399998.Hotel-Information) ![Free buffet breakfast](https://images.trvl-media.com/lodging/1000000/10000/4000/3929/06fc08bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/1000000/10000/4000/3929/da165588.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, pillowtop beds, individually furnished](https://images.trvl-media.com/lodging/1000000/10000/4000/3929/3627bf8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/4000/3929/d045ec83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Southington by IHG [](https://www.expedia.ca/Hartford-Hotels-Holiday-Inn-Express-Southington.h3929.Hotel-Information) Southington 8.6/10 Excellent (1,222 reviews) "Clean comfortable room, friendly staff, great breakfast" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Megan CA $104 CA $119 total includes taxes & fees Mar 6 - Mar 7 [](https://www.expedia.ca/Hartford-Hotels-Holiday-Inn-Express-Southington.h3929.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/50000/50000/49987/fd0bf8f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/50000/50000/49987/a68c10b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/50000/50000/49987/814e9800.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/50000/50000/49987/5802b8df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Days Inn by Wyndham Southington [](https://www.expedia.ca/Hartford-Hotels-Days-Inn-By-Wyndham-Southington.h49987.Hotel-Information) Southington 7.4/10 Good (1,007 reviews) "Clean room, very nice staff, great breakfast! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Barbara CA $110 CA $126 total includes taxes & fees Feb 26 - Feb 27 [](https://www.expedia.ca/Hartford-Hotels-Days-Inn-By-Wyndham-Southington.h49987.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=2026-03-11&endDate=2026-03-12®ionId=183057&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=AFFINITY_SPRING_PROMO_183057) ## Top Cheshire Hotel Reviews ![Inn at Middletown](https://images.trvl-media.com/lodging/7000000/6750000/6747900/6747876/4e71c540_y.jpg) ### Inn at Middletown 10/10 Excellent "Clean room" [](https://expedia.ca/Hartford-Hotels-Inn-At-Middletown.h6747876.Hotel-Information) ![Home2 Suites by Hilton East Haven New Haven](https://images.trvl-media.com/lodging/1000000/10000/1500/1461/b5c018f9_y.jpg) ### Home2 Suites by Hilton East Haven New Haven 10/10 Excellent "perfect room and ammenities. great place to stay. " [](https://expedia.ca/East-Haven-Hotels-Home2-Suites-By-Hilton-East-Haven-New-Haven.h1461.Hotel-Information) ![New Haven Hotel](https://images.trvl-media.com/lodging/1000000/40000/36800/36721/d665dc9c_y.jpg) ### New Haven Hotel 10/10 Excellent "The room was great, I love that it had a separate sink outside of the bathroom. Beds were comfortable and linens cozy." [](https://expedia.ca/New-Haven-Hotels-New-Haven-Hotel.h36721.Hotel-Information) ![Omni New Haven Hotel at Yale](https://images.trvl-media.com/lodging/1000000/50000/50000/49957/7466af25_y.jpg) ### Omni New Haven Hotel at Yale 10/10 Excellent "Comfortable, clean, quiet. Perfect atay" [](https://expedia.ca/New-Haven-Hotels-Omni-New-Haven-Hotel-At-Yale.h49957.Hotel-Information) ![Hyatt House Shelton](https://images.trvl-media.com/lodging/4000000/3490000/3482200/3482162/0d731ede_y.jpg) ### Hyatt House Shelton 10/10 Excellent "The room was very tidy and the front desk greeted us warmly. We enjoyed using the pool as well as the breakfast in the morning." [](https://expedia.ca/New-Haven-Hotels-HYATT-House-Shelton.h3482162.Hotel-Information) ![Holiday Inn Cheshire - Southington by IHG](https://images.trvl-media.com/lodging/2000000/1810000/1802800/1802750/a3c0d287_y.jpg) ### Holiday Inn Cheshire - Southington by IHG 10/10 Excellent "The room was spotless. The bed was super comfortable only issue I had was this morning. The water pressure in the shower was low but other than that very beautiful hotel very clean will definitely be back again." [](https://expedia.ca/New-Haven-Hotels-Holiday-Inn-Cheshire-Southington.h1802750.Hotel-Information) ![Hyatt Place Milford / New Haven](https://images.trvl-media.com/lodging/2000000/1570000/1562800/1562702/0336d577_y.jpg) ### Hyatt Place Milford / New Haven 10/10 Excellent "Excellent place, welcomed by desk staff, smooth and fast check in. Room clean and spacious." [](https://expedia.ca/New-Haven-Hotels-Hyatt-Place-Milford-New-Haven.h1562702.Hotel-Information) ![Heritage Hotel, Golf, Spa & Conference Center, BW Premier Collection](https://images.trvl-media.com/lodging/1000000/40000/35400/35389/d1cdaed7_y.jpg) ### Heritage Hotel, Golf, Spa & Conference Center, BW Premier Collection 10/10 Excellent "Great pool. Staff was friendly and room.waa clean" [](https://expedia.ca/Southbury-Hotels-Heritage-Hotel.h35389.Hotel-Information) ![Hampton Inn & Suites Hartford/East Hartford](https://images.trvl-media.com/lodging/3000000/2950000/2943100/2943093/5cf369a5_y.jpg) ### Hampton Inn & Suites Hartford/East Hartford 10/10 Excellent "The staff were very friendly, the hotel and rooms were very clean, and the breakfast was very good. Excellent hotel." [](https://expedia.ca/Hartford-Hotels-Hampton-Inn-Suites-HartfordEast-Hartford.h2943093.Hotel-Information) ## Frequently asked questions ### What should a history enthusiast expect from a trip to Cheshire? ### How many historical hotels are there in Cheshire? ### What are the most important historical places and other sights in Cheshire? ### What is a historic hotel like in Cheshire? ### What is the difference between a historic hotel and a heritage hotel? ### Do historic hotels in Cheshire have modern facilities? ## 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) - 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