Wooster Square Holidays
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Your Wooster Square Holiday
Immerse yourself in the best that Wooster Square offers with a Wooster Square holiday package. From its festivals to every other thing that makes it unique, this neighbourhood will charm you from start to finish. Some leading nearby attractions to see during your trip to Wooster Square include Yale University, Yale Bowl and East Rock Park. No matter what your ideal Wooster Square holiday looks like, you can make it a reality with Expedia.
Our guide on 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
Downtown New Haven
4 out of top 10 points of interest in this area
If you're spending some time in Downtown New Haven, New Haven City Hall and Shubert Theater are top sights worth seeing.
The Hill
1 out of top 10 points of interest in this area
When in The Hill, you can plan a visit to Shubert Theater and Knights of Columbus Museum, some noteworthy sights in the nearby area.
Long Wharf
Long Wharf is popular for its ample dining options, and you might make a stop by Long Wharf Theatre, a top place to visit in the area.
East Rock
Travellers like the monuments in East Rock, and East Rock Park is a top attraction you might want to visit.
West New Haven
1 out of top 10 points of interest in this area
While visiting West New Haven, you might make a stop by sights like Yale Bowl and Yale Golf Course.
Our pick of the best Wooster Square Hotel Deals
Trumbull Marriott Shelton
180 Hawley Ln Trumbull CT
Fully refundableReserve now, pay when you stay
AU$239
7 Sept - 8 Sept
includes taxes & fees
7.8/10 Good! (1,008 reviews)
"Website said there was a hot tub but there wasn’t one. Otherwise it was a good experience."
Reviewed on 30 Aug 2026
New Haven Hotel
229 George Street New Haven CT
Fully refundableReserve now, pay when you stay
AU$215
27 Sept - 28 Sept
includes taxes & fees
9.2/10 Wonderful! (2,296 reviews)
"I always stay at the New Haven hotel when I visit my daughter. Sadly the standards have declined"
Reviewed on 31 Aug 2026
Best Western Executive Hotel Of New Haven - West Haven
490 Saw Mill Rd West Haven CT
Fully refundableReserve now, pay when you stay
AU$182
29 Sept - 30 Sept
includes taxes & fees
8.2/10 Very good! (1,828 reviews)
"The room was clean but the carpet was stained in places, and the bed was very comfortable. I did not utilize the pool or the breakfast so I can’t comment on them. There is not a lot of parking in the front of the building and didn’t feel safe parking in back at night. I feel it was a good value for ..."
Reviewed on 31 Aug 2026
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.
Frequently asked questions
How much does a Wooster Square holiday package cost?
From as low as . Yes, you read that correctly. Our Wooster Square holiday 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 holiday 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 holiday?
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 holiday plans, there's sure to be a package within your budget.
Can I choose my airline with a Wooster Square Expedia holiday 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 holiday package?
Yes you can, and we're here to help. You may be able to change or cancel your Wooster Square holiday 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.
Stay near popular Wooster Square attractions
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.
Activities
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.