Title: Wooster Square Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $522 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 ## Top Holiday Package Deals in Wooster Square Price found within the past 48 hours. Click for updated prices. ![Super 8 by Wyndham Old Saybrook](https://images.trvl-media.com/lodging/1000000/860000/855300/855251/820065e6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Super 8 by Wyndham Old Saybrook CA $522 per person Mar 18 - Mar 22 found 1 day ago Roundtrip flight included Toronto (YTO) to New Haven (HVN) 7/10 Good! (905 reviews) Just motel , clean. No breakfast there, no coffee either. At 10 AM nobody showed up into front office for check out. Reviewed on Jan 1, 2026 ![Graduate by Hilton New Haven](https://images.trvl-media.com/lodging/38000000/37210000/37200100/37200005/f203cc93_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Graduate by Hilton New Haven Downtown New Haven CA $779 per person Mar 18 - Mar 22 found 1 day ago Roundtrip flight included Toronto (YTO) to New Haven (HVN) 9.2/10 Wonderful! (908 reviews) Loved everything about the hotel - great location, quaint and cozy rooms, clean, friendly staff and lots of character! Reviewed on Feb 12, 2026 ### Landing Modern 2bd, Gym West New Haven CA $781 per person Mar 18 - Mar 22 found 1 day ago Roundtrip flight included Toronto (YTO) to New Haven (HVN) No reviews ![Comfort Inn Naugatuck-Shelton, CT](https://images.trvl-media.com/lodging/2000000/1940000/1932400/1932357/fcd29dce_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Comfort Inn Naugatuck-Shelton, CT CA $628 per person Mar 18 - Mar 22 found 1 day ago Roundtrip flight included Toronto (YTO) to New Haven (HVN) 7.8/10 Good! (729 reviews) Everything was great and the price matched. I am a nurse and had to stay through the storm. Reviewed on Jan 28, 2026 ![New Haven Hotel](https://images.trvl-media.com/lodging/1000000/40000/36800/36721/d665dc9c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### New Haven Hotel Downtown New Haven CA $714 per person Mar 18 - Mar 22 found 1 day ago Roundtrip flight included Toronto (YTO) to New Haven (HVN) 9/10 Wonderful! (1,874 reviews) Great staff, no hot water in floor 2 had to move. Reviewed on Feb 12, 2026 ## 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) ![The New Haven Lighthouse, at Lighthouse Point Park in New Haven, Connecticut.](https://images.trvl-media.com/place/6349499/d6fd2d55-410c-4597-b530-609331ba8ba8.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### City Point If you're looking for some top things to see and do in City Point and surrounding area, you can visit Long Wharf Theatre and Shubert Theater. [Find hotel + flight trips in City Point](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=City%20Point&DestID=6349499&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) ![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) ## 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 $195 CA $224 total Feb 19 - Feb 20 includes taxes & fees 9/10 Wonderful! (2,012 reviews) A+ and great location. Reviewed on Feb 11, 2026 [](https://expedia.ca/Hotel-Search?startDate=19%2F02%2F2026&endDate=20%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 $160 CA $184 total Mar 8 - Mar 9 includes taxes & fees 8.6/10 Excellent! (1,011 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 $207 CA $238 total Feb 22 - Feb 23 includes taxes & fees 8.4/10 Very Good! (1,000 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=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=49957&PinnedHotelID=49957&HadPinnedHotel=true®ionId=641785043103088640) [See all 935 properties in Wooster Square](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=16%2F02%2F2026&endDate=17%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 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.