Wooster Square Holidays

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Photo by Anthony Salonga

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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
Five Mile Point Lighthouse, also known as Old New Haven Harbor Lighthouse

Downtown New Haven

5 out of top 10 points of interest in this area
4/5(1 area review)

If you're spending some time in Downtown New Haven, Woolsey Hall and Sterling Memorial Library at Yale University are top sights worth seeing.

Find hotels in Downtown New Haven

Our pick of the best Wooster Square Hotel Deals

New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street New Haven CT
Fully refundableReserve now, pay when you stay
The price is AU$166 per night from 27 Jan to 28 Jan
AU$166
27 Jan - 28 Jan
includes taxes & fees
9/10 Wonderful! (2,001 reviews)
They didn't have breakfast available

Reviewed on 16 Jan 2026

New Haven Hotel
Motel 6 Milford, CT

Motel 6 Milford, CT

2 out of 5
111 Schoolhouse Road Milford CT
Fully refundableReserve now, pay when you stay
The price is AU$94 per night from 3 Feb to 4 Feb
AU$94
3 Feb - 4 Feb
includes taxes & fees
6/10 (1,005 reviews)
The elevator i still not working

Reviewed on 31 Dec 2025

Motel 6 Milford, CT
Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
20 Dwight Street New Haven CT
Fully refundable
The price is AU$177 per night from 15 Feb to 16 Feb
AU$177
15 Feb - 16 Feb
includes taxes & fees
8.6/10 Excellent! (1,003 reviews)
Friendly & helpful staff & bartenders

Reviewed on 16 Jan 2026

Cambria Hotel New Haven University Area
See all 917 properties in Wooster Square
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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

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.

Discover the most popular places to visit in Wooster Square

Yale university buildings in spring blue sky in New Haven, CT USA

Yale University

5/5(2 reviews)

Walk around the campus of Yale University, a top university in New Haven. Stroll along the beaches or experience the area's art scene.

Yale University

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.

Sterling Memorial Library at Yale University

Woolsey Hall

Get tickets for a show at Woolsey Hall, a theatre with a story to tell in New Haven. Experience the area's art scene and museums.

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