Wooster Square Vacations

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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(138 area reviews)

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.

Find hotels in Downtown New Haven

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 ₩154,164 per night from Feb 8 to Feb 9
₩154,164
₩177,288 total
Feb 8 - Feb 9
includes taxes & fees
9/10 Wonderful! (2,014 reviews)
Room was a safe haven during a bad winter storm. The front desk attendant - I believe his name was Suvar was incredibly kind and accommodating - let us know the only place that was open and where we could get a hot meal after a 12 hour shift in the hospital.

Reviewed on Jan 29, 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 ₩79,106 per night from Feb 23 to Feb 24
₩79,106
₩90,978 total
Feb 23 - Feb 24
includes taxes & fees
6.2/10 (1,003 reviews)
Apathetic and slow moving staff. Sink clogged. Heater wouldn't adjust lower so i had to open the windows to keep from roasting. elevator has been down for over two months now. Parking lot was not cleared of snow.

Reviewed on Jan 30, 2026

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 ₩153,516 per night from Mar 1 to Mar 2
₩153,516
₩176,544 total
Mar 1 - Mar 2
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
Nice fromt desk staff. Clean & comfortable room.

Reviewed on Jan 26, 2026

Cambria Hotel New Haven University Area
See all 925 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 vacation package cost?
From as low as . 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.

Discover the most popular places to visit in Wooster Square

Yale Bowl

Catch an event at Yale Bowl during your trip to New Haven. You can attend a sporting event while in the area.

Yale Bowl

Hospital of Saint Raphael

Though Hospital of Saint Raphael might be what brings you to town, perhaps you'll have a chance to explore more of New Haven while you are here.

Hospital of Saint Raphael

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