Title: Cheshire Historic District Vacation Home Rentals from CA $206: Search Top Private Vacation Homes for Rent | Expedia.ca [Hotels in Cheshire Historic District](https://expedia.ca/Cheshire-Historic-District-Hotels.d6346724.Travel-Guide-Hotels)[Vacation Rentals in Cheshire Historic District](https://expedia.ca/Cheshire-Historic-District-Vacation-Rentals.d6346724.Travel-Guide-VacationRentals)[Cheshire Historic District Car Rentals](https://expedia.ca/Car-Rentals-In-Cheshire-Historic-District.d6346724.Car-Rental-Guide)[Cheshire Historic District Vacation Packages](https://expedia.ca/Cheshire-Historic-District.d6346724.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Cheshire Historic District Vacation Rentals - ![](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 prices for these dates Next weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=6346724&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=6346724&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=6346724&startDate=2026-01-16&endDate=2026-01-18&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=6346724&startDate=2026-02-13&endDate=2026-02-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Find vacation rentals that suit your style Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Cheshire+Historic+District%2C+Connecticut%2C+United+States+of+America®ionId=6346724&latLong=41.498489%2C-72.901885&adults=2&startDate=2026-03-21&d1=2026-03-21&endDate=2026-03-24&d2=2026-03-24&lodging=APART_HOTEL) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Cheshire+Historic+District%2C+Connecticut%2C+United+States+of+America®ionId=6346724&latLong=41.498489%2C-72.901885&adults=2&startDate=2026-03-21&d1=2026-03-21&endDate=2026-03-24&d2=2026-03-24&lodging=APARTMENT) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Cheshire+Historic+District%2C+Connecticut%2C+United+States+of+America®ionId=6346724&latLong=41.498489%2C-72.901885&adults=2&startDate=2026-03-21&d1=2026-03-21&endDate=2026-03-24&d2=2026-03-24&lodging=VACATION_HOME) Condos [](https://www.expedia.ca/Hotel-Search?destination=Cheshire+Historic+District%2C+Connecticut%2C+United+States+of+America®ionId=6346724&latLong=41.498489%2C-72.901885&adults=2&startDate=2026-03-21&d1=2026-03-21&endDate=2026-03-24&d2=2026-03-24&lodging=CONDO) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Cheshire+Historic+District%2C+Connecticut%2C+United+States+of+America®ionId=6346724&latLong=41.498489%2C-72.901885&adults=2&startDate=2026-03-21&d1=2026-03-21&endDate=2026-03-24&d2=2026-03-24&lodging=COTTAGE) Cabins [](https://www.expedia.ca/Hotel-Search?destination=Cheshire+Historic+District%2C+Connecticut%2C+United+States+of+America®ionId=6346724&latLong=41.498489%2C-72.901885&adults=2&startDate=2026-03-21&d1=2026-03-21&endDate=2026-03-24&d2=2026-03-24&lodging=CABIN) ![](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%2FCheshire-Historic-District-Private-Vacation-Homes.d6346724-aaPrivateVacationHomes.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FCheshire-Historic-District-Private-Vacation-Homes.d6346724-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Cheshire Historic District Hotel Reviews ![New Haven Hotel](https://images.trvl-media.com/lodging/1000000/40000/36800/36721/d665dc9c_y.jpg) ### New Haven Hotel 10/10 Excellent "Clean room. Convenient location." [](https://expedia.ca/New-Haven-Hotels-New-Haven-Hotel.h36721.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 "Helpful.Easy check in!" [](https://expedia.ca/East-Haven-Hotels-Home2-Suites-By-Hilton-East-Haven-New-Haven.h1461.Hotel-Information) ![Wyndham Southbury](https://images.trvl-media.com/lodging/16000000/15660000/15651900/15651820/412fe155_y.jpg) ### Wyndham Southbury 10/10 Excellent "Fast checkin, friendly staff, room was nice and clean" [](https://expedia.ca/Danbury-Hotels-Wyndham-Southbury.h15651820.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 "Clean, comfortable room" [](https://expedia.ca/New-Haven-Hotels-Omni-New-Haven-Hotel-At-Yale.h49957.Hotel-Information) ![Hamden Hotel and Suites – Hamden New Haven](https://images.trvl-media.com/lodging/1000000/20000/18000/17931/c3c836db_y.jpg) ### Hamden Hotel and Suites – Hamden New Haven 10/10 Excellent "Clean room -comfortable bed. no complaints " [](https://expedia.ca/New-Haven-Hotels-Clarion-Hotel-Suites-Hamden-New-Haven.h17931.Hotel-Information) ![Hotel Marcel New Haven, Tapestry Collection By Hilton](https://images.trvl-media.com/lodging/72000000/71430000/71427300/71427300/1699c03c_y.jpg) ### Hotel Marcel New Haven, Tapestry Collection By Hilton 10/10 Excellent "Loved that EV charging is on site with no need to pay for parking." [](https://expedia.ca/New-Haven-Hotels-Hotel-Marcel-New-Haven.h71427300.Hotel-Information) ![Cambria Hotel New Haven University Area](https://images.trvl-media.com/lodging/79000000/78620000/78614500/78614483/a6a28eee_y.jpg) ### Cambria Hotel New Haven University Area 10/10 Excellent "it was great!" [](https://expedia.ca/New-Haven-Hotels-Cambria-Hotel-New-Haven-University-Area.h78614483.Hotel-Information) ![Holiday Inn Express Southington by IHG](https://images.trvl-media.com/lodging/1000000/10000/4000/3929/120068a2_y.jpg) ### Holiday Inn Express Southington by IHG 10/10 Excellent "Clean room. Great location. Very nice staff." [](https://expedia.ca/Hartford-Hotels-Holiday-Inn-Express-Southington.h3929.Hotel-Information) ![Courtyard by Marriott Waterbury Downtown](https://images.trvl-media.com/lodging/1000000/40000/34300/34227/c0e669e8_y.jpg) ### Courtyard by Marriott Waterbury Downtown 10/10 Excellent "We are always happy at Courtyard, and this location was extra special because the staff were super friendly and helpful! " [](https://expedia.ca/New-Haven-Hotels-Courtyard-By-Marriott-Waterbury-Downtown.h34227.Hotel-Information) ## Find out more about Cheshire Historic District ## Cheshire Historic District Vacation Homes information | Number of reviews | 137 | | ----------------- | ------------------ | | Accommodation | 213 Vacation Homes | | Lowest Price | CA $206 | | Highest Price | CA $708 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [5 Star Hotels in Coastal Connecticut ](https://www.expedia.ca/5Star-Coastal-Connecticut-Hotels.s50-0-d6233741.Travel-Guide-Filter-Hotels) - [Hotels near Brookside Park ](https://www.expedia.ca/Brookside-Park-Hotels.0-l553248621557919974-0.Travel-Guide-Filter-Hotels) - [Aparthotels in Cheshire ](https://www.expedia.ca/Cheshire-Apart-Hotels.d183057-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Cheshire ](https://www.expedia.ca/Cheshire-Bed-And-Breakfast.d183057-aaBedAndBreakfast.Travel-Guide-Accommodation) - 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