Wooster Square Trips (flight + hotel)

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

Downtown New Haven

6 out of top 10 points of interest in this area

While visiting Downtown New Haven, you might make a stop by sights like Sterling Memorial Library at Yale University and New Haven City Hall.

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 P8,345 per night from Jul 13 to Jul 14
P8,345
P9,597 total
Jul 13 - Jul 14
includes taxes & fees
8.8/10 Excellent! (1,621 reviews)
"Nice staff and great room."

Reviewed on Jul 2, 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 P4,702 per night from Jul 16 to Jul 17
P4,702
P5,408 total
Jul 16 - Jul 17
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 Jul 2, 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 P5,146 per night from Jul 9 to Jul 10
P5,146
P5,918 total
Jul 9 - Jul 10
includes taxes & fees
7/10 Good! (1,004 reviews)
"Nice place clean will book again"

Reviewed on Jul 4, 2025

Red Roof Inn Milford - New Haven
See all 902 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.

Popular places to visit

Yale Bowl

You can take time to visit Yale Bowl during your travels to New Haven. You can attend a sporting event while in the area.

Yale Bowl

Things to do

Harkness Towner

Private Historic Yale Smart Phone Self Guided Walking Tour

P548
per adult
100% of travellers recommend
Private Historic Yale Smart Phone Self Guided Walking Tour
New Haven's Ghost Walk

New Haven's Ghost Walk

P1,460
per adult
New Haven's Ghost Walk
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.