Wooster Square Holidays

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Photo by Anthony Salonga

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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
New Haven featuring a river or creek and kayaking or canoeing as well as a couple

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 Beinecke Rare Book and Manuscript Library 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 NZ$211 per night from 30 Dec to 31 Dec
NZ$211
30 Dec - 31 Dec
includes taxes & fees
9/10 Wonderful! (1,956 reviews)
Lights in bathroom not bright enough.

Reviewed on 24 Dec 2025

New Haven Hotel
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 NZ$203 per night from 13 Jan to 14 Jan
NZ$203
13 Jan - 14 Jan 2026
includes taxes & fees
8.6/10 Excellent! (996 reviews)
it was great!

Reviewed on 15 Dec 2025

Cambria Hotel New Haven University Area
Hampton Inn by Hilton Shelton

Hampton Inn by Hilton Shelton

2.5 out of 5
695 Bridgeport Ave Shelton CT
Fully refundableReserve now, pay when you stay
The price is NZ$208 per night from 2 Jan to 3 Jan
NZ$208
2 Jan - 3 Jan 2026
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
Beautiful hotel in great location

Reviewed on 23 Dec 2025

Hampton Inn by Hilton Shelton
See all 901 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.

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

Yale University

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

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

Yale-New Haven Hospital

If Yale-New Haven Hospital is what brings you to town, hopefully you'll have a chance to explore more of New Haven.

Yale-New Haven Hospital

Activities

Harkness Towner

Private Historic Yale Smart Phone Self Guided Walking Tour

NZ$17
per adult
100% of travellers recommend
Private Historic Yale Smart Phone Self Guided Walking Tour
See all activities in New Haven
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.