Title: Book the Best HISTORIC Hotels in Wooster Square 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) ![](https://mediaim.expedia.com/destination/2/415484820687fbf8e195b93597fcdbd2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Anthony Salonga # Find Historic Hotels in Wooster Square, CT ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 Historic Hotels Tonight [Oct 3 - Oct 4](https://www.expedia.ca/Hotel-Search?regionId=641785043103088640&startDate=2025-10-03&endDate=2025-10-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 4 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=641785043103088640&startDate=2025-10-04&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=641785043103088640&startDate=2025-10-03&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=641785043103088640&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Wooster Square Historic Hotels ## Top Wooster Square Hotel Reviews ![New Haven Hotel](//images.trvl-media.com/lodging/1000000/40000/36800/36721/dd69cbb4_y.jpg) ### New Haven Hotel 10/10 Excellent "Great hotel Lobby!" [](https://expedia.ca/New-Haven-Hotels-New-Haven-Hotel.h36721.Hotel-Information) ![Best Western Executive Hotel Of New Haven - West Haven](//images.trvl-media.com/lodging/1000000/30000/23300/23217/b63e42e2_y.jpg) ### Best Western Executive Hotel Of New Haven - West Haven 10/10 Excellent "Room service was great made sure we had everything we needed daily. Front desk very helpful. Was quiet until last night party on 2nd floor people running up and down hallway child kicked our door very hard around 2am. I believe mother worked for hotel and had family party out of control my husband got up and went out they quieted down after that.Overall the place was great though." [](https://expedia.ca/New-Haven-Hotels-Best-Western-Executive-Hotel-Of-New-Haven-West-Haven.h23217.Hotel-Information) ![Motel 6 Milford, CT](//images.trvl-media.com/lodging/1000000/10000/300/291/03aae393_y.jpg) ### Motel 6 Milford, CT 10/10 Excellent "Both great " [](https://expedia.ca/New-Haven-Hotels-Motel-6-Milford.h291.Hotel-Information) ![Hyatt Place Milford / New Haven](//images.trvl-media.com/lodging/2000000/1570000/1562800/1562702/0336d577_y.jpg) ### Hyatt Place Milford / New Haven 10/10 Excellent "Clean room" [](https://expedia.ca/New-Haven-Hotels-Hyatt-Place-Milford-New-Haven.h1562702.Hotel-Information) ![Hilton Garden Inn Shelton](//images.trvl-media.com/lodging/1000000/290000/287700/287687/18ff21f4_y.jpg) ### Hilton Garden Inn Shelton 10/10 Excellent "The property was well maintained and the staff was friendly. I had plenty of options for meals around which was convenient. " [](https://expedia.ca/New-Haven-Hotels-Hilton-Garden-Inn-Shelton.h287687.Hotel-Information) ![La Quinta Inn & Suites by Wyndham New Haven](//images.trvl-media.com/lodging/1000000/10000/1300/1241/92ca5e77_y.jpg) ### La Quinta Inn & Suites by Wyndham New Haven 8/10 Good "Under construction." [](https://expedia.ca/New-Haven-Hotels-La-Quinta-Inn-Suites-By-Wyndham-New-Haven.h1241.Hotel-Information) ![Trumbull Marriott Shelton](//images.trvl-media.com/lodging/1000000/10000/1200/1166/b3c487eb_y.jpg) ### Trumbull Marriott Shelton 10/10 Excellent "awesome" [](https://expedia.ca/New-Haven-Hotels-Trumbull-Marriott-Shelton.h1166.Hotel-Information) ![Red Roof Inn Meriden](//images.trvl-media.com/lodging/1000000/10000/2900/2831/05873179_y.jpg) ### Red Roof Inn Meriden 10/10 Excellent "Ok for the money " [](https://expedia.ca/Hartford-Hotels-Red-Roof-Inn-Meriden.h2831.Hotel-Information) ![Red Roof Inn Milford - New Haven](//images.trvl-media.com/lodging/1000000/10000/7200/7188/a7d6f81c_y.jpg) ### Red Roof Inn Milford - New Haven 10/10 Excellent "Yes" [](https://expedia.ca/New-Haven-Hotels-Red-Roof-Inn-Milford-New-Haven.h7188.Hotel-Information) ## Frequently asked questions ### What should a history enthusiast expect from a trip to Wooster Square? > The historical sites in Wooster Square are probably a big part of your travel plans. And while you're visiting the area, why not also take some time enjoying all of the sights in the area? ### How many historically relevant hotels are located in Wooster Square? > Wooster Square is home to 22 hotels and other accommodations bookable on Expedia though not many historic hotels to choose from. ### What are the most important historical places and other sights to visit in Wooster Square? > A favorite place to visit is Wooster Square. You'll also find New Haven City Hall and Shubert Theater in the area. ### What is a historic hotel like in Wooster Square? > Guests who choose historic hotels have an opportunity to stay in a place officially recognized with a historic designation. Historic hotels throughout the world come in all forms like stately homes, palaces or even lodges, old police stations or skyscrapers. These types of hotels in Wooster Square often preserve authentic characteristics like traditional architecture and period features within the guestrooms or public spaces. ### What is the difference between a historic hotel and a heritage hotel? > These are quite similar. The term "historic hotel" is more common in the U.S., while you'll often hear "heritage hotel" in Asia and Europe. Historic hotels tend to focus on the architecture and actual building. Mainly heritage hotels draw meaning from the cultural value that the place has and how it inspired the community. ### Do historic hotels in Wooster Square have modern facilities? > Hotels include modern conveniences and safety features you've come to expect, while every effort is made to preserve historic facades and treasured traditions. Smart TVs, WiFi, updated bathroom facilities, and the amenities found at a contemporary hotel should be available at a historic hotel. 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