Wooster Square Holidays

Book a Hotel + Flight or Car together to unlock savings

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

Downtown New Haven

5 out of top 10 points of interest in this area
4.5/5(6 area reviews)

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

Top hotels in Wooster Square

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 3.337.201 ₫ per night from 20 May to 21 May
3.337.201 ₫
3.837.781 ₫ total
20 May - 21 May
includes taxes & fees
9.2/10 Wonderful! (2,100 reviews)
The room has an unusual smell when we check in. I tried opening the window for hours, but the smell persists. I suspect it’s the old air conditioning system that’s causing the issue.

Reviewed on 21 Apr 2026

New Haven Hotel
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
155 Temple St New Haven CT
Fully refundableReserve now, pay when you stay
The price is 4.005.945 ₫ per night from 26 Apr to 27 Apr
4.005.945 ₫
4.606.836 ₫ total
26 Apr - 27 Apr
includes taxes & fees
8.6/10 Excellent! (1,009 reviews)
Front desk personnel was awesome

Reviewed on 21 Apr 2026

Omni New Haven Hotel at Yale
Hilton Garden Inn Shelton

Hilton Garden Inn Shelton

3 out of 5
25 Old Stratford Rd Shelton CT
Fully refundableReserve now, pay when you stay
The price is 3.527.952 ₫ per night from 26 Apr to 27 Apr
3.527.952 ₫
4.057.145 ₫ total
26 Apr - 27 Apr
includes taxes & fees
8/10 Very Good! (1,104 reviews)
Very noisy on lower floor

Reviewed on 20 Apr 2026

Hilton Garden Inn Shelton
See all 977 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 1null000null000 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.

Popular places to visit

Wooster Square

Wooster Square

Find out about the history of New Haven when you take a trip to Wooster Square. Experience the area's art scene and museums.

Wooster Square
View of the New Haven Green and downtown, in New Haven, Connecticut

New Haven Green

3/5(1 review)

After visiting New Haven Green, make a plan to see the other sights and activities in New Haven. Stroll along the beaches or experience the area's art scene.

New Haven Green
Peabody Museum of Natural History

Peabody Museum of Natural History

You can browse the exhibits at Peabody Museum of Natural History, a museum with a story of its own, during your travels to New Haven. Experience the area's art scene and museums.

Peabody Museum of Natural History