Title: Book the Best ROMANTIC Hotels in Cheshire, CT from CA $141 - Cheshire Romantic Getaways | 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) ![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) # Find Romantic Hotels in Cheshire, CT from CA $141 - ![](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 Romantic Hotels Tonight [Dec 18 - Dec 19](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2025-12-18&endDate=2025-12-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Tomorrow [Dec 19 - Dec 20](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2025-12-19&endDate=2025-12-20&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) This weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Next weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) ## Our top choices for Cheshire romantic hotels ![Lobby](https://images.trvl-media.com/lodging/1000000/40000/34300/34227/5fee96a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/40000/34300/34227/f62eb852.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/40000/34300/34227/45ba9e4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/40000/34300/34227/c0e669e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Waterbury Downtown [](https://www.expedia.ca/New-Haven-Hotels-Courtyard-By-Marriott-Waterbury-Downtown.h34227.Hotel-Information) Waterbury 8.4/10 Very good (1067) "The staff were amazing,The rooms were very clean,when ever i'm in town this is were I always stay. thank you to the staff for all you do to always make my stay comfortable." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Diana CA $122 CA $141 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/New-Haven-Hotels-Courtyard-By-Marriott-Waterbury-Downtown.h34227.Hotel-Information) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/40000/36800/36721/d665dc9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/1000000/40000/36800/36721/ce9d1772.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/40000/36800/36721/cefd8f92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/40000/36800/36721/a42cca00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### New Haven Hotel [](https://www.expedia.ca/New-Haven-Hotels-New-Haven-Hotel.h36721.Hotel-Information) Downtown New Haven 9.0/10 Wonderful (1935) "Location, friendly staff, clean a comfortable room. Will stay again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kim [](https://www.expedia.ca/New-Haven-Hotels-New-Haven-Hotel.h36721.Hotel-Information) ![](https://images.trvl-media.com/lodging/2000000/1810000/1802800/1802750/9672e16a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1810000/1802800/1802750/fce9c835.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds](https://images.trvl-media.com/lodging/2000000/1810000/1802800/1802750/e12904c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/2000000/1810000/1802800/1802750/9cda9029.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Cheshire - Southington by IHG [](https://www.expedia.ca/New-Haven-Hotels-Holiday-Inn-Cheshire-Southington.h1802750.Hotel-Information) Southington 8.2/10 Very good (1000) "Highly recommend staying here. The rooms are clean and the staff go above and beyond to make sure that guests have a comfortable stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Veronica CA $125 CA $144 total includes taxes & fees Dec 25 - Dec 26 [](https://www.expedia.ca/New-Haven-Hotels-Holiday-Inn-Cheshire-Southington.h1802750.Hotel-Information) ![Breakfast, lunch, dinner served; American cuisine ](https://images.trvl-media.com/lodging/7000000/6750000/6747900/6747876/f9a612a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/7000000/6750000/6747900/6747876/eb9b6c2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/7000000/6750000/6747900/6747876/4e71c540.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/7000000/6750000/6747900/6747876/eff2fea9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn at Middletown [](https://www.expedia.ca/Hartford-Hotels-Inn-At-Middletown.h6747876.Hotel-Information) Washington Street Historic District 9.0/10 Wonderful (541) "The Inn was very nice!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Traci CA $225 CA $286 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Hartford-Hotels-Inn-At-Middletown.h6747876.Hotel-Information) ![Double Room, 2 Double Beds](https://images.trvl-media.com/lodging/1000000/20000/15200/15113/a0632219.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/15200/15113/d178bb52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio Suite, 1 Queen Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/20000/15200/15113/e210c0b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast area](https://images.trvl-media.com/lodging/1000000/20000/15200/15113/a5ca44fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Baymont by Wyndham Branford/New Haven [](https://www.expedia.ca/New-Haven-Hotels-Baymont-By-Wyndham-BranfordNew-Haven.h15113.Hotel-Information) Branford 6.6/10 (1000) "Good Breakfast, nice atmosphere " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jessie CA $136 CA $157 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/New-Haven-Hotels-Baymont-By-Wyndham-BranfordNew-Haven.h15113.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/12000000/11450000/11440200/11440147/15d5ef38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Snack bar](https://images.trvl-media.com/lodging/12000000/11450000/11440200/11440147/adaca4d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/12000000/11450000/11440200/11440147/1b9db1ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/12000000/11450000/11440200/11440147/ad096b9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Wallingford/Meriden [](https://www.expedia.ca/New-Haven-Hotels-Hilton-Garden-Inn-WallingfordMeriden.h11440147.Hotel-Information) Wallingford 8.8/10 Excellent (999) "Clean room and staff wonderful " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Liliana CA $158 CA $181 total includes taxes & fees Jan 8 - Jan 9, 2026 [](https://www.expedia.ca/New-Haven-Hotels-Hilton-Garden-Inn-WallingfordMeriden.h11440147.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/1000000/10000/2700/2635/d997675e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Banquet hall](https://images.trvl-media.com/lodging/1000000/10000/2700/2635/d9f37f65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/10000/2700/2635/20124035.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fountain](https://images.trvl-media.com/lodging/1000000/10000/2700/2635/22690654.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Avon Old Farms Hotel [](https://www.expedia.ca/Hartford-Hotels-Avon-Old-Farms-Hotel.h2635.Hotel-Information) Avon 8.4/10 Very good (1001) "Very nice place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alvero CA $136 CA $187 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Hartford-Hotels-Avon-Old-Farms-Hotel.h2635.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/8300/8221/b8fd3dea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Building design](https://images.trvl-media.com/lodging/1000000/10000/8300/8221/fe5d083b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/1000000/10000/8300/8221/f54b808b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast and dinner served, American cuisine](https://images.trvl-media.com/lodging/1000000/10000/8300/8221/826c1c12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sheraton Hartford South Hotel [](https://www.expedia.ca/Hartford-Hotels-Sheraton-Hartford-South-Hotel.h8221.Hotel-Information) Rocky Hill 8.4/10 Very good (1003) "Very clean room, inviting lobby, and very nice employees at check in and checkout " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Caroline CA $144 CA $166 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Hartford-Hotels-Sheraton-Hartford-South-Hotel.h8221.Hotel-Information) ![Breakfast and brunch served](https://images.trvl-media.com/lodging/1000000/50000/50000/49957/b7b5473a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/50000/50000/49957/776a13da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/50000/50000/49957/d634e2d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](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 [](https://www.expedia.ca/New-Haven-Hotels-Omni-New-Haven-Hotel-At-Yale.h49957.Hotel-Information) Downtown New Haven 8.6/10 Excellent (1007) "Great traditional New Haven Hotel. From check in to check out staff was very professional and welcoming. Great job for all of your staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christopher CA $233 CA $268 total includes taxes & fees Dec 19 - Dec 20 [](https://www.expedia.ca/New-Haven-Hotels-Omni-New-Haven-Hotel-At-Yale.h49957.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/210000/203500/203496/46de1f34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/210000/203500/203496/a4febc34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/210000/203500/203496/07b77cc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/210000/203500/203496/463bda09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Homewood Suites by Hilton Hartford-Farmington [](https://www.expedia.ca/Hartford-Hotels-Homewood-Suites-By-Hilton-Hartford-Farmington.h203496.Hotel-Information) Farmington 8.4/10 Very good (1000) "The young woman who greeted my daughter and I was very sweet and kind. The room was clean and the beds very comfortable. Would definitely stay here again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa CA $157 CA $180 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Hartford-Hotels-Homewood-Suites-By-Hilton-Hartford-Farmington.h203496.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=2026-01-01&endDate=2026-01-02®ionId=183057&adults=2&travelerType=romantic&sort=RECOMMENDED&openPlayBack=true) ## Top Cheshire Hotel Reviews ![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 "Great traditional New Haven Hotel. From check in to check out staff was very professional and welcoming. Great job for all of your staff." [](https://expedia.ca/New-Haven-Hotels-Omni-New-Haven-Hotel-At-Yale.h49957.Hotel-Information) ![Hampton Inn by Hilton Shelton](https://images.trvl-media.com/lodging/1000000/210000/200400/200381/e6ef0843_y.jpg) ### Hampton Inn by Hilton Shelton 10/10 Excellent "Perfect staff room exceptional service" [](https://expedia.ca/New-Haven-Hotels-Hampton-Inn-By-Hilton-Shelton.h200381.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 "The room was very clean and the staff was incredibly nice. We did not arrive until 2am due to traffic and weather issues during our travel and the front desk was more that helpful checking us in and making us feel welcomed, even at such a late hour." [](https://expedia.ca/New-Haven-Hotels-Hyatt-Place-Milford-New-Haven.h1562702.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 "Everything was great 👍 " [](https://expedia.ca/New-Haven-Hotels-Courtyard-By-Marriott-Waterbury-Downtown.h34227.Hotel-Information) ![The Goodwin Hotel](https://images.trvl-media.com/lodging/1000000/20000/10300/10232/64a5e77a_y.jpg) ### The Goodwin Hotel 10/10 Excellent "Beautiful hotel" [](https://expedia.ca/Hartford-Hotels-The-Goodwin-Hotel.h10232.Hotel-Information) ## Frequently asked questions ### Searching for romantic hotels in Cheshire? ### When is the best time of year for a romantic getaway to Cheshire? ### What is there to do in Cheshire? ### What's the best way to get to Cheshire and around town during my romantic getaway? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - 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