Wooster Square Holidays

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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
A lighthouse on a rocky shoreline with people near the water.

Downtown New Haven

5 out of top 10 points of interest in this area

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.

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A large brick building with arched windows and domed towers, surrounded by a well-maintained lawn and a stone pathway.

The Hill

1 out of top 10 points of interest in this area

When in The Hill, you can plan a visit to Shubert Theater and Knights of Columbus Museum, some noteworthy sights in the nearby area.

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A riverside walkway with a gazebo, a dock, and a boat.

Long Wharf

Long Wharf is popular for its ample dining options, and you might make a stop by Long Wharf Theatre, a top place to visit in the area.

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A cityscape at sunset with a mix of residential and commercial buildings, a prominent clock tower, and a river in the background.

East Rock

Travellers like the monuments in East Rock, and East Rock Park is a top attraction you might want to visit.

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A green field, a hill with trees, and a blue sky with clouds.

West New Haven

1 out of top 10 points of interest in this area

While visiting West New Haven, you might make a stop by sights like Yale Bowl and Yale Golf Course.

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Top hotels in Wooster Square

New Haven Hotel

New Haven Hotel

229 George Street New Haven CT
Fully refundableReserve now, pay when you stay
S$179
27 Oct - 28 Oct
includes taxes & fees
9.2/10 Wonderful! (2,374 reviews)
"The room was clean enough, I have been in better. The staff was fine, nothing special to note. The amenities - well I didn't see many perks to staying there, just overpriced beverages and snacks for purchase."

Reviewed on 10 Oct, 2026

New Haven Hotel
Trumbull Marriott Shelton

Trumbull Marriott Shelton

180 Hawley Ln Trumbull CT
Fully refundableReserve now, pay when you stay
S$224
18 Oct - 19 Oct
includes taxes & fees
Trumbull Marriott Shelton
Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

320 E Main St Branford CT
Fully refundable
S$98
1 Nov - 2 Nov
includes taxes & fees
Motel 6 New Haven - Branford, CT
See all 972 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.

Stay near popular Wooster Square attractions

Wooster Square

8.8/10 (201 reviews)
Find out about the history of New Haven when you take a trip to Wooster Square. Experience the area's art scene and museums.
See properties

Things to do

New Haven - It Zip It Adventure Indoor Ropes Course

New Haven - It Zip It Adventure Indoor Ropes Course

S$36
per adult
100% of travellers recommend
New Haven - It Zip It Adventure Indoor Ropes Course
Yale University Self‐Guided Walking Tour

Yale University Self‐Guided Walking Tour

S$13
per adult
Yale University Self‐Guided Walking Tour
New Haven's Ghost Walk

New Haven's Ghost Walk

S$33
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.