Wooster Square Vacations

Book a Hotel + Flight or Car together to unlock savings

Photo by Anthony Salonga

Your Wooster Square Vacation

Book your vacation package to Wooster Square and prepare to explore its festivals and plenty more. Whether you're craving adventure or relaxation, you'll find it in this inviting neighborhood. When it's time to get out and explore, you'll find lots of awesome attractions nearby including Yale University, Yale Bowl and East Rock Park. Visit one or all during your trip to Wooster Square. Stop daydreaming and start doing. When it's time to lock in your next vacation to Wooster Square, Expedia will help get you there.

The Latest Wooster Square Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express Southington, an IHG Hotel

Holiday Inn Express Southington, an IHG Hotel

2.5 out of 5
per person
Aug 30 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) to New Haven (HVN)
8.4/10 Very Good! (1,001 reviews)
The property was well kept and clean

Reviewed on May 26, 2024

Graduate New Haven

Graduate New Haven

4 out of 5
Downtown New Haven
per person
Jul 19 - Jul 22
found 7 hours ago
Roundtrip flight included
Philadelphia (PHL) to New Haven (HVN)
9.2/10 Wonderful! (664 reviews)
This hotel is BEAUTIFUL

Reviewed on Jun 5, 2024

New Haven Hotel

New Haven Hotel

3.5 out of 5
Downtown New Haven
per person
Jul 19 - Jul 22
found 7 hours ago
Roundtrip flight included
Philadelphia (PHL) to New Haven (HVN)
8.8/10 Excellent! (1,240 reviews)
Very close to Yale University and clean

Reviewed on May 26, 2024

Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
Downtown New Haven
per person
Jul 19 - Jul 22
found 7 hours ago
Roundtrip flight included
Philadelphia (PHL) to New Haven (HVN)
8.2/10 Very Good! (1,000 reviews)
Great property, great value!

Reviewed on Jun 4, 2024

Hilton Garden Inn Hartford North/Bradley Int'l Airport

Hilton Garden Inn Hartford North/Bradley Int'l Airport

3 out of 5
per person
Aug 30 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) to New Haven (HVN)
8.8/10 Excellent! (1,003 reviews)
This property is great if you need a quiet, near the airport hotel.. Thanks

Reviewed on Jun 3, 2024

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
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 hotel + flight trips 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 $149 per night from Jun 30 to Jul 1
$149
$171 total
includes taxes & fees
Jun 30 - Jul 1
8.8/10 Excellent! (1,249 reviews)
Amazing stay!!!
"Clean, friendly staff, great location, easy parking. Would absolutely stay again. Beautiful hotel."

Reviewed on Jun 4, 2024

New Haven Hotel
Hilton Garden Inn Shelton
Hilton Garden Inn Shelton
3 out of 5
25 Old Stratford Rd, Shelton, CT
Fully refundableReserve now, pay when you stay
The price is $110 per night from Jul 1 to Jul 2
$110
$126 total
includes taxes & fees
Jul 1 - Jul 2
7.4/10 Good! (1,019 reviews)
"Always a pleasure to stay at this property when in the area. Staff is very helpful and friendly."

Reviewed on Jun 4, 2024

Hilton Garden Inn Shelton
Courtyard by Marriott Waterbury Downtown
Courtyard by Marriott Waterbury Downtown
3 out of 5
63 Grand St, Waterbury, CT
Fully refundableReserve now, pay when you stay
The price is $93 per night from Jun 16 to Jun 17
$93
$107 total
includes taxes & fees
Jun 16 - Jun 17
8.2/10 Very Good! (1,016 reviews)
"The only thing bad about my stay was that fire alarm at 6am"

Reviewed on Jun 6, 2024

Courtyard by Marriott Waterbury Downtown
See all 864 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Wooster Square vacation package cost?
From as low as $331. 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

Image for Wooster Square

Wooster Square

Find out about the history of New Haven when you take a trip to Wooster Square. Experience the area's art scene and museums.

Wooster Square
Image for Yale University

Yale University

4.5/5(528 reviews)

Enjoy the collegiate vibe around Yale University, a top college in New Haven. Stroll along the beaches or experience the area's art scene.

Yale University
Image for New Haven City Hall

New Haven City Hall

3/5(1 review)

New Haven City Hall is just one of the places to see in New Haven, so why not enjoy the other things to explore during your travels? Experience the area's art scene and museums.

New Haven City Hall

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