Title: Wooster Square Vacation Packages & Trips 2025 from CA $684 | 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/180036/8c9473e7-26bb-47f5-b6f9-b77a4dbc6848.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Wooster Square Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings Photo by Anthony Salonga - ## 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. ![Economy Inn](https://images.trvl-media.com/lodging/1000000/20000/11600/11504/4b04ee95_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Economy Inn CA $684 per person Dec 9 - Dec 12 found 1 day ago Roundtrip non-stop flight included Winnipeg (YWG) to New Haven (HVN) 5.8/10 (546 reviews) I thought there would be breakfast, disappointed Reviewed on Oct 29, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-09/2025-12-12/?FromAirport=YWG&Destination=HVN&NumRoom=1&NumAdult=2&NumChild=0&hotelId=11504&paandie=true&dealMarker=12yv9CccbaW7db2uDmEm4tTZDmJTftMbr5bsblaS7yyzJwRxupvqFY5NPQjXB1m-) ![Hilton Garden Inn Hartford North/Bradley Int'l Airport](https://images.trvl-media.com/lodging/1000000/540000/531100/531022/fb287dbf_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Garden Inn Hartford North/Bradley Int'l Airport CA $784 per person Dec 9 - Dec 12 found 1 day ago Roundtrip non-stop flight included Winnipeg (YWG) to New Haven (HVN) 8.8/10 Excellent! (1,018 reviews) A really pleasant stay. Easy access to airport, but not so close you are in the flight path. Reviewed on Nov 2, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-09/2025-12-12/?FromAirport=YWG&Destination=HVN&NumRoom=1&NumAdult=2&NumChild=0&hotelId=531022&paandie=true&dealMarker=12yv9CccbaW7db2uDmEm4tTZDmJTftMbr5bsblaS7ywtowQBbECY7wqfTQIlK4gD) ![Residence Inn by Marriott Hartford/Windsor](https://images.trvl-media.com/lodging/1000000/20000/18200/18141/5604e365_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Residence Inn by Marriott Hartford/Windsor CA $733 per person Dec 9 - Dec 12 found 1 day ago Roundtrip non-stop flight included Winnipeg (YWG) to New Haven (HVN) 8.2/10 Very Good! (642 reviews) Clean, friendly, great location Reviewed on Nov 3, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-09/2025-12-12/?FromAirport=YWG&Destination=HVN&NumRoom=1&NumAdult=2&NumChild=0&hotelId=18141&paandie=true&dealMarker=12yv9CccbaW7db2uDmEm4tTZDmJTftMbr5bsblaS7yx5rU2WS-YgeOYYOeq27rYk) ## 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/dd69cbb4_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### New Haven Hotel 229 George Street, New Haven, CT Fully refundableReserve now, pay when you stay CA $139 CA $160 total Dec 1 - Dec 2 includes taxes & fees 9/10 Wonderful! (1,877 reviews) Room was clean, hotel staff were friendly, gym was excellent. Reviewed on Nov 1, 2025 [](https://expedia.ca/Hotel-Search?startDate=01%2F12%2F2025&endDate=02%2F12%2F2025&selected=36721&PinnedHotelID=36721&HadPinnedHotel=true®ionId=641785043103088640) ![Wyndham Southbury](https://images.trvl-media.com/lodging/16000000/15660000/15651900/15651820/412fe155_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Wyndham Southbury 1284 Strongtown Road, Southbury, CT Fully refundableReserve now, pay when you stay CA $130 CA $149 total Nov 19 - Nov 20 includes taxes & fees 8/10 Very Good! (1,005 reviews) Yes Reviewed on Oct 31, 2025 [](https://expedia.ca/Hotel-Search?startDate=19%2F11%2F2025&endDate=20%2F11%2F2025&selected=15651820&PinnedHotelID=15651820&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 $166 CA $190 total Nov 26 - Nov 27 includes taxes & fees 8.6/10 Excellent! (957 reviews) Clean room quiet and nice staff Reviewed on Nov 3, 2025 [](https://expedia.ca/Hotel-Search?startDate=26%2F11%2F2025&endDate=27%2F11%2F2025&selected=78614483&PinnedHotelID=78614483&HadPinnedHotel=true®ionId=641785043103088640) [See all 875 properties in Wooster Square](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=05%2F11%2F2025&endDate=06%2F11%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? > From as low as CA $684. Yes, you read that correctly. Our Wooster Square vacation packages are the quickest way to stretch your budget. Bundle your hotels, flights and rental car and get to know this top destination. ### How do I get a cheap travel package to Wooster Square? > Bundle your bookings with Expedia to save big on your next trip. With over 550 airlines and 1,000,000 properties across the world, your Wooster Square vacation package can be tailored exactly to suit your budget. With all that extra cash, why not throw in one or more awesome tours and experiences? It's an easy way to unlock even more savings. Your dream getaway to Wooster Square is much closer than you thought! ### Where should I stay in Wooster Square? > Make sightseeing easy by staying within walking distance of Wooster Square's main attractions. Yale University and Yale Bowl are two of the best in the area. ### What are the top hotels in Wooster Square? > [Historic Mansion Inn](https://www.expedia.ca/New-Haven-Hotels-Historic-Mansion-Inn.h912640.Hotel-Information) and [Stylish Luxury In New Haven, Ct](https://www.expedia.ca/New-Haven-Hotels-Stylish-Luxury-In-New-Haven.h67247853.Hotel-Information) are among the most popular hotels in Wooster Square. Why not have a look at the facilities and amenities at each and then make a decision? ### How far in advance should I book my Wooster Square vacation? > It's tricky picking the perfect time for airfares, but we generally suggest the earlier, the better. Many international flights on Expedia become available up to 12 months in advance. If you're booking last minute, don't despair. Bargain prices appear from time to time within a few weeks of departure dates. ### What does an Expedia Wooster Square travel package include? > With Expedia, you can select a combination of car rentals, hotels and flights to create your perfect Wooster Square travel package. Once you've made your booking, you can add on fun stuff like tours and activities. Don't forget — the more you bundle, the more you'll save! ### What should I know before booking a Wooster Square travel package? > A package can be more affordable than individually booking everything you need for your adventure. For example, combine your hotels, flights and rental cars and save a tidy sum. Whatever your vacation plans, there's sure to be a package within your budget. ### Can I choose my airline with a Wooster Square Expedia vacation package? > Most definitely. Expedia has over 550 airline partners to pick from around the globe. With all that choice, finding the ideal carrier to take you to Wooster Square won't be hard. ### If I'm not able to travel, can I cancel my Wooster Square vacation package? > Yes you can, and we're here to help. You may be able to change or cancel your Wooster Square vacation package at no cost within 24 hours of booking. But you may incur a fee from your airline, hotel or car rental company if your booking is older than that. If your circumstances unexpectedly change, visit our [Customer Service Portal](https://www.expedia.ca/service/?langid=4105) for further information. ### 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.