Wooster Square Holidays

Photo by Anthony Salonga

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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 showing kayaking or canoeing and a river or creek as well as a couple

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 Beinecke Rare Book and Manuscript Library 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 €125 per night from 19 Jan to 20 Jan
€125
19 Jan - 20 Jan
includes taxes & fees
9/10 Wonderful! (1,988 reviews)
Customer service is top-notch, they are always very accommodating and friendly. We found the hotel to be very clean, the location is extremely convenient to dining shopping and the areas of New Haven. You would want to explore. Parking is extremely convenient and attached to the hotel. There are ...

Reviewed on 4 Jan 2026

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 €102 per night from 8 Feb to 9 Feb
€102
8 Feb - 9 Feb
includes taxes & fees
8.6/10 Excellent! (1,014 reviews)
clean room, helpful staff

Reviewed on 4 Jan 2026

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 €104 per night from 23 Jan to 24 Jan
€104
23 Jan - 24 Jan
includes taxes & fees
8.6/10 Excellent! (1,007 reviews)
great bib room comfortable nice large shower good breakfast

Reviewed on 5 Jan 2026

Hampton Inn by Hilton Shelton
See all 920 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.

Popular places to visit

Woolsey Hall

Woolsey Hall

Get tickets for a show at Woolsey Hall, a theatre with a story to tell in New Haven. Experience the area's art scene and museums.

Woolsey Hall

Things to do

Harkness Towner

Private Historic Yale Smart Phone Self Guided Walking Tour

€8
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.