A park with cherry blossom trees, a paved walkway, and people walking.

Wooster Square Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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The Latest Wooster Square Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A hotel room with two beds, a red chair, a nightstand with a lamp, and framed artwork on the wall.
    Dec 23 - Dec 27

    Quality Suites Stratford + Flight

    Stratford
    4 nights
    2.5 star property
    8.2/10 - Very good (1,002 reviews)
    "It was convenient to town and shopping. Our air conditioner leaked all over the rug and it was soaking wet. Pillows were awful. We would not stay there again."
    Reviewed November 6, 2026
    Roundtrip • Toronto (YYZ) - New Haven (HVN)
    YYZ - EWR • Nonstop EWR - YYZ • Nonstop
    CA $890
    CA $888
    per traveller
    found 17 hours ago
    Quality Suites Stratford
  • A two-story house with a blue exterior, a front porch, and a driveway leading to the entrance.
    Dec 14 - Dec 17

    Beechmont - Perfect for Family Retreat! + Flight

    North End
    3 nights
    5.0 star property
    Roundtrip • Toronto (YYZ) - New Haven (HVN)
    YYZ - LGA • Nonstop LGA - YYZ • Nonstop
    CA $2,120
    CA $1,858
    per traveller
    found 17 hours ago
    Beechmont - Perfect for Family Retreat!
  • A room with a view of the ocean at sunset, a dining table with plates and glasses, and a wicker chair.
    Dec 24 - Dec 30

    The Surfside Hotel + Flight

    Lordship
    6 nights
    2.0 star property
    9.2/10 - Wonderful (229 reviews)
    Roundtrip • Toronto (YYZ) - New Haven (HVN)
    YYZ - EWR • Nonstop LGA - YYZ • Nonstop
    CA $1,263
    CA $1,118
    per traveller
    found 8 hours ago
    The Surfside Hotel
  • A hotel lobby with a reception desk, a television mounted on the wall, a trash can, and a seating area with orange chairs and a table.
    Dec 27 - Jan 2

    Motel 6 Milford, CT + Flight

    Milford
    6 nights
    2.0 star property
    6.6/10 - (1,066 reviews)
    Roundtrip • Saskatoon (YXE) - New Haven (HVN)
    YXE - EWR • 1 stop EWR - YXE • 2 stops
    CA $1,809
    CA $1,766
    per traveller
    found 2 hours ago
    Motel 6 Milford, CT

Where to stay in Wooster Square

Find the best Wooster Square areas and neighborhoods for the activities you enjoy most.
A historic building with a prominent white tower and a golden weather vane.

Downtown New Haven

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.
A large brick building with arched windows and domed towers, surrounded by a well-maintained lawn and a stone pathway.

The Hill

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.
A riverside walkway with a gazebo, a dock, and a boat.

Long Wharf

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.
A green field, a hill with trees, and a blue sky with clouds.

West New Haven

If you're spending some time in West New Haven, Yale Bowl and Yale Golf Course are top sights worth seeing.
A cityscape at sunset with a mix of residential and commercial buildings, a prominent clock tower, and a river in the background.

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.

Discover the most popular places to visit in Wooster Square

Wooster Square

8.8/10 (201 reviews)
Find out about the history of New Haven when you take a trip to Wooster Square. Experience the area's art scene and museums.
See properties

Wooster Square Hotel Deals

A spacious lobby with a central seating area, a chandelier, and wooden paneling.

Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale
4.0 star property
Downtown New Haven, 1 km from Wooster Square
8.8 out of 10, Excellent, (1,122 reviews)
"Everything was great- from staff to food to rooms"
The price is CA $227
CA $261 total
includes taxes & fees
Nov 22 - Nov 23
Omni New Haven Hotel at Yale
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.
See all properties in Wooster Square

Frequently Asked Questions

How much does a Wooster Square vacation package cost?

From as low as CA $888. 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 and Stylish Luxury In New Haven, Ct 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 for further information.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.