Title: Wooster Square Vacation Packages | Holiday Packages & Trips 2026/2027 from Expedia.ca [Hotels in Wooster Square](https://expedia.ca/Wooster-Square-New-Haven-Hotels.0-n641785043103088640-0.Travel-Guide-Filter-Hotels)[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) ![](https://images.trvl-media.com/place/641785043103088640/ead6c6c2-5864-4bd1-b9e2-52dab60c9c82.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Wooster Square Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ## Where to stay in Wooster Square Find the best Wooster Square areas and neighborhoods for the activities you enjoy most. [Learn more about Wooster Square](https://expedia.ca/New-Haven-Wooster-Square.dx641785043103088640) ![Five Mile Point Lighthouse, also known as Old New Haven Harbor Lighthouse](https://images.trvl-media.com/place/180036/ce434c6e-2419-4e3f-8cac-7319da523623.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Downtown New Haven 4 out of top 10 points of interest in this area 5/5(4 area reviews) In the heart of New Haven, this residential downtown area boasts a variety of restaurants, cafes, theaters, and stores. Explore the arts at Chapel Street Historic District, Broadway area, and Ninth Square district, or visit the Shops at Yale. [Find hotel + flight trips in Downtown New Haven](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Downtown%20New%20Haven&DestID=553248635976008334&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Yale university buildings in spring blue sky in New Haven, CT USA](https://images.trvl-media.com/place/502016/c8263c5b-7395-40ba-832e-d611eebd12f8.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### The Hill 1 out of top 10 points of interest in this area Southwesternmost New Haven, this area boasts historic structures, Union Station, and Yale-New Haven Hospital. Explore Trowbridge Square and City Point, or visit the Lupi-Legna Bakery. [Find hotel + flight trips in The Hill](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=The%20Hill&DestID=553248635976470810&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![New England Winter Landscape over the Mill River, East Rock Park in New Haven, Connecticut, USA](https://images.trvl-media.com/place/553248635976472385/ccbd7156-0609-4a6a-a023-12e74745296c.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Mill River 1 out of top 10 points of interest in this area If you're spending some time in Mill River, Wooster Square and Thread City Crossing are top sights worth seeing. [Find hotel + flight trips in Mill River](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Mill%20River&DestID=553248635976472385&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Green Waterfront along New Haven Harbor at Long Wharf Park in New Haven Connecticut](https://images.trvl-media.com/place/6349506/c940a85c-5fa7-45c2-801b-0ecbf9aa66a3.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Long Wharf 3.5/5(7 area reviews) Waterfront district with a mix of commercial, industrial, and recreational facilities, Long Wharf offers attractions like Long Wharf Theatre and Vietnam Veterans Memorial Park. Easily accessible via Interstates 95 and 91, and Church Street Bridge. [Find hotel + flight trips in Long Wharf](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Long%20Wharf&DestID=6349506&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![New Haven Connecticut Skyline, downtown buildings and houses viewed from East Rock Park Summit](https://images.trvl-media.com/place/6349501/b952ef8e-45aa-492c-b179-33c29029adb3.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### East Rock Prominent trap rock ridge East Rock lends its name to this neighborhood, popular among Yale affiliates and cyclists. Explore East Rock Park or visit the lively Upper State Street commercial district. [Find hotel + flight trips in East Rock](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=East%20Rock&DestID=6349501&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ## Wooster Square Hotel Deals ![New Haven Hotel](https://images.trvl-media.com/lodging/1000000/40000/36800/36721/d665dc9c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### New Haven Hotel 229 George Street New Haven CT Fully refundable CA $182 CA $209 total Feb 15 - Feb 16 includes taxes & fees 9/10 Wonderful! (2,016 reviews) Excellent desk staff. Clean and quite room. Good location. Reviewed on Feb 4, 2026 [](https://expedia.ca/Hotel-Search?startDate=15%2F02%2F2026&endDate=16%2F02%2F2026&selected=36721&PinnedHotelID=36721&HadPinnedHotel=true®ionId=641785043103088640) ![Cambria Hotel New Haven University Area](https://images.trvl-media.com/lodging/79000000/78620000/78614500/78614483/a6a28eee_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Cambria Hotel New Haven University Area 20 Dwight Street New Haven CT Fully refundable CA $145 CA $167 total Mar 8 - Mar 9 includes taxes & fees 8.6/10 Excellent! (1,010 reviews) Lovely Reviewed on Feb 3, 2026 [](https://expedia.ca/Hotel-Search?startDate=08%2F03%2F2026&endDate=09%2F03%2F2026&selected=78614483&PinnedHotelID=78614483&HadPinnedHotel=true®ionId=641785043103088640) ![Omni New Haven Hotel at Yale](https://images.trvl-media.com/lodging/1000000/50000/50000/49957/7466af25_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Omni New Haven Hotel at Yale 155 Temple St New Haven CT Fully refundableReserve now, pay when you stay CA $206 CA $237 total Feb 15 - Feb 16 includes taxes & fees 8.4/10 Very Good! (1,004 reviews) Love the staff very nice and attentive. Very clean nice bar!!! Close to everything, I’ll definitely will stay there again!! Reviewed on Feb 6, 2026 [](https://expedia.ca/Hotel-Search?startDate=15%2F02%2F2026&endDate=16%2F02%2F2026&selected=49957&PinnedHotelID=49957&HadPinnedHotel=true®ionId=641785043103088640) [See all 931 properties in Wooster Square](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=12%2F02%2F2026&endDate=13%2F02%2F2026®ionId=641785043103088640) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ## Frequently asked questions ### How much does a Wooster Square vacation package cost? ### How do I get a cheap travel package to Wooster Square? ### Where should I stay in Wooster Square? ### What are the top hotels in Wooster Square? ### How far in advance should I book my Wooster Square vacation? ### What does an Expedia Wooster Square travel package include? ### What should I know before booking a Wooster Square travel package? ### Can I choose my airline with a Wooster Square Expedia vacation package? ### If I'm not able to travel, can I cancel my Wooster Square vacation package? ### Discover the most popular places to visit in Wooster Square ![Yale university buildings in spring blue sky in New Haven, CT USA](https://images.trvl-media.com/place/502016/c8263c5b-7395-40ba-832e-d611eebd12f8.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Yale University 4.5/5(21 reviews) Enjoy the collegiate vibe around Yale University, a top college in New Haven. Stroll along the beaches or experience the area's art scene. [](https://expedia.ca/Yale-University-Downtown-New-Haven.d502016.Vacation-Attraction) #### Sterling Memorial Library at Yale University After visiting Sterling Memorial Library at Yale University, make a plan to see the other sights and activities in New Haven. Experience the area's art scene and museums. [](https://expedia.ca/Sterling-Memorial-Library-At-Yale-University-Downtown-New-Haven.d6071481.Vacation-Attraction) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.