Title: Wooster Square Vacation Packages | Holiday Packages & Trips 2026/2026 from CA $536 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://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?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. ![Courtyard by Marriott New Haven Orange-Milford](https://images.trvl-media.com/lodging/1000000/80000/79500/79426/bdad3f31_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Courtyard by Marriott New Haven Orange-Milford CA $536 per person Feb 21 - Feb 23 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to New Haven (HVN) 8.4/10 Very Good! (1,000 reviews) We didn't eat breakfast. The Staff were friendly and the property well kept Reviewed on Dec 6, 2025 ![Homewood Suites by Hilton Orange New Haven](https://images.trvl-media.com/lodging/39000000/38980000/38980000/38979983/cf46bed4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Homewood Suites by Hilton Orange New Haven CA $625 per person Feb 21 - Feb 23 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to New Haven (HVN) 9.2/10 Wonderful! (1,000 reviews) Room was really big, no issues whatsoever. Reviewed on Dec 14, 2025 ![Quality Suites Stratford](https://images.trvl-media.com/lodging/2000000/1770000/1764400/1764336/1f6d98e1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Quality Suites Stratford CA $851 per person Jan 17 - Jan 22 found 1 day ago Roundtrip non-stop flight included Vancouver (YVR) to New Haven (HVN) 8/10 Very Good! (1,005 reviews) Excellent place! Super clean, nice staff, great breakfast, comfortable! Reviewed on Nov 26, 2025 ## 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) ![New Haven showing kayaking or canoeing and a river or creek as well as a couple](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/26000/26192-New-Haven.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Downtown New Haven 5 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) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.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) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.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) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.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) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.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 refundableReserve now, pay when you stay 9/10 Wonderful! (1,928 reviews) Room very clean, staff very helpful kind and professional (Stephanie a gem). I gave it 4 star just because my room was facing a dumpster and a bit noisy with trucks and the proximity to the elevator. If you park in the garage the hotel charges $ 24 nightly. The garage itself charges $ 22 daily. The ... Reviewed on Dec 15, 2025 [Get rates](https://expedia.ca/Hotel-Search?startDate=30%2F12%2F2025&endDate=31%2F12%2F2025&selected=36721&PinnedHotelID=36721&HadPinnedHotel=true®ionId=641785043103088640) [](https://expedia.ca/Hotel-Search?startDate=30%2F12%2F2025&endDate=31%2F12%2F2025&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 $142 CA $163 total Jan 6 - Jan 7, 2026 includes taxes & fees 8.6/10 Excellent! (990 reviews) It was a nice stay. I enjoyed the breakfast that we paid for. I did not enjoy paying for parking. The room was what I would expect for the price... Very nice and clean Reviewed on Dec 13, 2025 [](https://expedia.ca/Hotel-Search?startDate=06%2F01%2F2026&endDate=07%2F01%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 $233 CA $268 total Dec 21 - Dec 22 includes taxes & fees 8.4/10 Very Good! (1,005 reviews) Great traditional New Haven Hotel. From check in to check out staff was very professional and welcoming. Great job for all of your staff. Reviewed on Dec 14, 2025 [](https://expedia.ca/Hotel-Search?startDate=21%2F12%2F2025&endDate=22%2F12%2F2025&selected=49957&PinnedHotelID=49957&HadPinnedHotel=true®ionId=641785043103088640) [See all 905 properties in Wooster Square](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=17%2F12%2F2025&endDate=18%2F12%2F2025®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](https://mediaim.expedia.com/destination/1/adca140aaae3dfe2d27069d109d05ce7.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](https://mediaim.expedia.com/destination/2/8b93b69ddb16d798d901e620d0a338ff.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### 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.