Title: Book the Best Wooster Square WINERY Hotels in 2025 | Expedia.ca [Vacation Rentals in New Haven](https://expedia.ca/New-Haven-Vacation-Rentals.d180036.Travel-Guide-VacationRentals)[Flights to New Haven](https://expedia.ca/Cheap-Flights-To-New-Haven.d180036.Travel-Guide-Flights)[Things to do in New Haven](https://expedia.ca/Things-To-Do-In-New-Haven.d180036.Travel-Guide-Activities)[Wooster Square Car Rentals](https://expedia.ca/Car-Rentals-In-Wooster-Square.d641785043103088640.Car-Rental-Guide)[Wooster Square Vacations](https://expedia.ca/Wooster-Square.d641785043103088640.Destination-Travel-Guides) ![Wooster Square New Haven Connecticut](https://images.trvl-media.com/place/641785043103088640/ead6c6c2-5864-4bd1-b9e2-52dab60c9c82.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Wooster Square, CT from CA $167 - ![](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 Wooster Square Winery Hotels Tonight [Nov 24 - Nov 25](https://www.expedia.ca/Hotel-Search?regionId=641785043103088640&startDate=2025-11-24&endDate=2025-11-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 25 - Nov 26](https://www.expedia.ca/Hotel-Search?regionId=641785043103088640&startDate=2025-11-25&endDate=2025-11-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=641785043103088640&startDate=2025-11-28&endDate=2025-11-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=641785043103088640&startDate=2025-12-05&endDate=2025-12-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Wooster Square Winery Hotels ![Lobby](https://images.trvl-media.com/lodging/1000000/210000/200400/200381/e6ef0843.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/210000/200400/200381/ad77ef5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/210000/200400/200381/4328324a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Down comforters, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/1000000/210000/200400/200381/cd756b94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn by Hilton Shelton Shelton 8.8/10 Excellent (1004) "Convenient to Yale New Haven hospital. Nice room layout. Red Barn restaurant nearby great food and cocktails. Great breakfast at hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carolyn CA $146 CA $167 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/New-Haven-Hotels-Hampton-Inn-By-Hilton-Shelton.h200381.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102010000/102009000/102008958/0888acaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/103000000/102010000/102009000/102008958/646c7316.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/103000000/102010000/102009000/102008958/bdac0629.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/103000000/102010000/102009000/102008958/2db3f072.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### All New 1BR with tons of Charm Wallingford Center 9.8/10 Exceptional (6) "I highly recommend this property!! We were in town for a wedding celebration, and it proved perfect. The property is completely updated, well-appointed and clean. The property is centrally located and close to restaurants, shops and grocery markets. Karl was a great host and communicated with us throughout our stay. I highly recommend!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Francis S. CA $162 CA $406 total includes taxes & fees Dec 8 - Dec 9 [](https://www.expedia.ca/Wallingford-Hotels-Seasons-Hospitality-Presents-All-New-1BR-With-Tons-Of-Charm.h102008958.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/19800/19783/7edf3766.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cooked-to-order breakfast for a fee](https://images.trvl-media.com/lodging/1000000/20000/19800/19783/1d0ef914.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/20000/19800/19783/2dfa38e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/19800/19783/aac3baa1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard New Haven Wallingford Wallingford 8.8/10 Excellent (780) "Clean room, friendly staff!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julie CA $190 CA $219 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/New-Haven-Hotels-Courtyard-New-Haven-Wallingford.h19783.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1280000/1273400/1273388/e8764690.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/2000000/1280000/1273400/1273388/b8beb7b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![37-inch flat-screen TV with cable channels, TV](https://images.trvl-media.com/lodging/2000000/1280000/1273400/1273388/6cc530a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1280000/1273400/1273388/7923d4f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Homewood Suites by Hilton Wallingford-Meriden Wallingford 9.0/10 Wonderful (887) "Friendly staff, clean, and quiet " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Katelyn CA $168 CA $193 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/New-Haven-Hotels-Homewood-Suites-By-Hilton-Wallingford-Meriden.h1273388.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102010000/102009000/102008956/9bb90df5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102010000/102009000/102008956/1391311d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/103000000/102010000/102009000/102008956/67a7f768.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/103000000/102010000/102009000/102008956/9a03fac1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### New Railside Residents Wallingford Center CA $162 CA $406 total includes taxes & fees Dec 11 - Dec 12 [](https://www.expedia.ca/Wallingford-Hotels-Seasons-Hospitality-Presents-New-Railside-Residents-1BR.h102008956.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) ![Terrace/patio](https://images.trvl-media.com/lodging/19000000/18770000/18760700/18760693/83198fbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/19000000/18770000/18760700/18760693/20bbb653.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) ### Historic New England home ,Reunions Beach pass Guilford 9.2/10 Wonderful (90) "The location of this place is best!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dr. Maureen C. CA $268 CA $613 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/Guilford-Hotels-Historic-New-England-Home.h18760693.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) ![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) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/65000000/64920000/64918800/64918771/5a3becbd.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) ### 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 $162 CA $406 total includes taxes & fees Nov 26 - Nov 27 [](https://www.expedia.ca/Wallingford-Hotels-All-New-Private-And-Cozy-In-Great-Location.h64918771.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105870000/105862500/105862474/ba77e4bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/106000000/105870000/105862500/105862474/w1280h848x0y2-72542981.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/106000000/105870000/105862500/105862474/w1280h851x0y0-915fd821.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/106000000/105870000/105862500/105862474/4bc18379.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Jewel of The Cove - Historic Coastal Retreat East Shore 10/10 Exceptional (5) "loved it so much, beautiful property 100 % would stay again " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Leilani R. CA $292 CA $723 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/East-Haven-Hotels-The-Jewel-Of-The-Cove-Historic-Coastal-Retreat.h105862474.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/94000000/93140000/93133100/93133074/190efae8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee/tea maker, electric kettle](https://images.trvl-media.com/lodging/94000000/93140000/93133100/93133074/79349d1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business Room | Bathroom](https://images.trvl-media.com/lodging/94000000/93140000/93133100/93133074/9dd943d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business Room | Living area](https://images.trvl-media.com/lodging/94000000/93140000/93133100/93133074/012f1989.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Jay's Ranch Hamden 7.6/10 Good (47) "Im so happy I found this place to stay. Meets all my needs and great service !!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Diana [](https://www.expedia.ca/Hamden-Hotels-Jays-Ranch.h93133074.Hotel-Information) ![Smart TV, books](https://images.trvl-media.com/lodging/101000000/100840000/100834300/100834240/w776h683x124y0-ae153ead.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/101000000/100840000/100834300/100834240/0845eb45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100840000/100834300/100834240/cd224da3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/101000000/100840000/100834300/100834240/93b50094.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Clear LI Sound waterview, Wedding pics, Yale&Beach East Shore 10/10 Exceptional (10) "Attended a wedding close by. This house was a comfortable clean place to rest in between events. Lovely water front. Calm and peaceful" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kacy R. CA $412 CA $882 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/East-Haven-Hotels-Clear-LI-Sound-Waterview.h100834240.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=2025-12-08&endDate=2025-12-09®ionId=641785043103088640&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Wooster Square Hotel Reviews ![Clarion Inn](https://images.trvl-media.com/lodging/1000000/10000/7600/7519/36377da0_y.jpg) ### Clarion Inn 10/10 Excellent "Clean room" [](https://expedia.ca/North-Haven-Hotels-Clarion-Inn.h7519.Hotel-Information) ![Motel 6 New Haven - Branford, CT](https://images.trvl-media.com/lodging/1000000/60000/50400/50320/c15293e5_y.jpg) ### Motel 6 New Haven - Branford, CT 10/10 Excellent "I enjoyed it " [](https://expedia.ca/New-Haven-Hotels-Motel-6-New-Haven-Branford.h50320.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [4 Star Hotels in Quinnipiac Meadows](https://www.expedia.ca/4Star-Quinnipiac-Meadows-New-Haven-Hotels.s40-n899951259073933312-0.Travel-Guide-Filter-Hotels) - [Hotels near Albertus Magnus College](https://www.expedia.ca/Albertus-Magnus-College-Hotels.0-l6176929-0.Travel-Guide-Filter-Hotels) - 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