Title: Book the Best BOUTIQUE 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)[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 Boutique Hotels in Cheshire, CT from CA $126 - ![](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 Boutique Hotels Tonight [Dec 8 - Dec 9](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2025-12-08&endDate=2025-12-09&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 9 - Dec 10](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2025-12-09&endDate=2025-12-10&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2025-12-12&endDate=2025-12-14&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2025-12-19&endDate=2025-12-21&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Cheshire Boutique Hotels No exact matches found, but these alternatives could be just right ## Recommended hotels in Cheshire ![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) ![Interior](https://images.trvl-media.com/lodging/112000000/111830000/111824500/111824460/624102e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/112000000/111830000/111824500/111824460/6969660b.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) ### Quiet 2bd Townhome apt in the heart of Cheshire. Backyard. Cheshire 9.4/10 Exceptional (13) "Needed a place to sleep for a couple of nights and this worked for us." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James (Jim) L. [](https://www.expedia.ca/Cheshire-Hotels-Quiet-2-Bedroom-Apartment-In-Wonderful-Cheshire-With-WiFi-And-Beautiful-Views.h111824460.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1900000/1896600/1896545/c0034c2e.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) ![Lobby](https://images.trvl-media.com/lodging/2000000/1900000/1896600/1896545/00c69c09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Double Beds](https://images.trvl-media.com/lodging/2000000/1900000/1896600/1896545/47147cef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cheshire Welcome Inn Cheshire 8.4/10 Very good (761) "This is our 5 th stay, allways clean, friendly staff Very economical, will definitely be a return customer..Quiet and centrally located…no complaints…" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John CA $111 CA $127 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/New-Haven-Hotels-Cheshire-Welcome-Inn.h1896545.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/1000000/990000/983200/983128/08241fb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Combined shower/tub, hair dryer, towels, soap](https://images.trvl-media.com/lodging/1000000/990000/983200/983128/afd83ae8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds](https://images.trvl-media.com/lodging/1000000/990000/983200/983128/bc78fd2a.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) ### Spark by Hilton Guilford Guilford 8.8/10 Excellent (64) "Good clean property with great staff " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David CA $139 CA $160 total includes taxes & fees Jan 3 - Jan 4, 2026 [](https://www.expedia.ca/Guilford-Hotels-Spark-By-Hilton-Guilford.h983128.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/4000/3929/120068a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free buffet breakfast](https://images.trvl-media.com/lodging/1000000/10000/4000/3929/cb3d49ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/10000/4000/3929/ec5a48cd.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 Southington 8.6/10 Excellent (1163) "Clean rooms, Good breakfast, Solid Coffee" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anthony CA $109 CA $126 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Hartford-Hotels-Holiday-Inn-Express-Southington.h3929.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) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/40000/36800/36721/92e73287.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) ![Reception](https://images.trvl-media.com/lodging/1000000/40000/36800/36721/cefd8f92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### New Haven Hotel Downtown New Haven 9.0/10 Wonderful (1919) "Very nice hotel. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) REINA [](https://www.expedia.ca/New-Haven-Hotels-New-Haven-Hotel.h36721.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/95000000/94950000/94946700/94946614/74bd7e00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room](https://images.trvl-media.com/lodging/95000000/94950000/94946700/94946614/31e09d21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ### Home2 Suites by Hilton Bristol Bristol 9.6/10 Exceptional (163) "I would stay here again! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jael CA $165 CA $189 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Bristol-Hotels-Home2-Suites-By-Hilton-Bristol.h94946614.Hotel-Information) ![Deluxe Room, 1 Queen Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/30000/23300/23217/b63e42e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/23300/23217/c4603508.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/23300/23217/7d962b8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/30000/23300/23217/a63d7cf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Executive Hotel Of New Haven - West Haven West Haven 8.0/10 Very good (1482) "Carpet in room needs changing Breakfast very good Staff is great" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) carolyn CA $133 CA $152 total includes taxes & fees Dec 12 - Dec 13 [](https://www.expedia.ca/New-Haven-Hotels-Best-Western-Executive-Hotel-Of-New-Haven-West-Haven.h23217.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/40000/34300/34227/c0e669e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/40000/34300/34227/db5c54a9.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/e1028a1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, coffee/tea maker](https://images.trvl-media.com/lodging/1000000/40000/34300/34227/8d58fa7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Waterbury Downtown Waterbury 8.4/10 Very good (1062) "This is my second time, and I think I will be coming more often." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Linda CA $123 CA $141 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/New-Haven-Hotels-Courtyard-By-Marriott-Waterbury-Downtown.h34227.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/3000000/2950000/2943100/2943093/5cf369a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Snack bar](https://images.trvl-media.com/lodging/3000000/2950000/2943100/2943093/w3824h2560x0y0-44110bed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Two Queen and One Sofa Bed | Living area](https://images.trvl-media.com/lodging/3000000/2950000/2943100/2943093/215f7d40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, coffee/tea maker](https://images.trvl-media.com/lodging/3000000/2950000/2943100/2943093/fb23f66f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Hartford/East Hartford East Hartford 9.0/10 Wonderful (1069) "Wonderful place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Margarita CA $132 CA $151 total includes taxes & fees Dec 20 - Dec 21 [](https://www.expedia.ca/Hartford-Hotels-Hampton-Inn-Suites-HartfordEast-Hartford.h2943093.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/4000000/3490000/3482200/3482162/0d731ede.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/4000000/3490000/3482200/3482162/a12e56fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/4000000/3490000/3482200/3482162/ff093bb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds](https://images.trvl-media.com/lodging/4000000/3490000/3482200/3482162/3cac8d02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt House Shelton Shelton 8.4/10 Very good (1005) "The staff was friendly, efficient and place was very family oriented " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael CA $152 CA $174 total includes taxes & fees Dec 12 - Dec 13 [](https://www.expedia.ca/New-Haven-Hotels-HYATT-House-Shelton.h3482162.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=2025-12-23&endDate=2025-12-24®ionId=183057&adults=2&specialized_stays_group_explore=boutique_property&sort=RECOMMENDED&openPlayBack=true) ## Top Cheshire Hotel Reviews ![The Farmington Inn & Suites](https://images.trvl-media.com/lodging/1000000/20000/10200/10185/1c89931a_y.jpg) ### The Farmington Inn & Suites 10/10 Excellent "Great time" [](https://expedia.ca/Hartford-Hotels-The-Farmington-Inn-Suites.h10185.Hotel-Information) ![New Haven Hotel](https://images.trvl-media.com/lodging/1000000/40000/36800/36721/d665dc9c_y.jpg) ### New Haven Hotel 10/10 Excellent "No issues. Just did not know about the paid parking. " [](https://expedia.ca/New-Haven-Hotels-New-Haven-Hotel.h36721.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 ### What's there to see and do in Cheshire? ### What kind of weather should I plan for when I travel to Cheshire? ### What's the best way to get to my boutique hotel in Cheshire? ## 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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