Wooster Square Holidays

Book a Hotel + Flight or Car together to unlock savings

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    Save up to NZ$616 when you book a flight and hotel together*
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    Find the right fit
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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 which includes kayaking or canoeing and a river or creek as well as a couple

Downtown New Haven

6 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, Sterling Memorial Library at Yale University and New Haven City Hall 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$272 per night from 16 July to 17 July
NZ$272
16 July - 17 July
includes taxes & fees
8.8/10 Excellent! (1,623 reviews)
"The air conditioning could not keep up. The hotel clerk was very friendly"

Reviewed on 1 Jul. 2025

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 NZ$158 per night from 20 July to 21 July
NZ$158
20 July - 21 July
includes taxes & fees
6/10 (1,001 reviews)
If you like weed this hotel is for you!
"It was good because it was pet friendly and we had to travel with our 2 dogs. The repairs in our room that have been done over time, unfortunately look like they were not done by professionals. I'm more disappointed about the fact that people loiter in the parking lot smoking marijuana and the hotel ..."

Reviewed on 2 Jul. 2025

Motel 6 Milford, CT
Red Roof Inn Milford - New Haven
Red Roof Inn Milford - New Haven
2 out of 5
10 Rowe Ave, Milford, CT
Fully refundableReserve now, pay when you stay
The price is NZ$176 per night from 7 July to 8 July
NZ$176
7 July - 8 July
includes taxes & fees
7/10 Good! (1,006 reviews)
"This is an old not updated hotel. There are alot of new amenities that could be added, but for 100$ a night its hard to complain. There was not a refrigerator or coffee maker in the room. The AC was medicore and a large gap between the door and wall. They do not have USB ports in the room, however ..."

Reviewed on 21 Jun. 2025

Red Roof Inn Milford - New Haven
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

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

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$16
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.