Wooster Square Vacation Packages
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Top Holiday Package Deals in Wooster Square
Price found within the past 48 hours. Click for updated prices.
Hamden Hotel and Suites – Hamden New Haven
CA $815
per person
Oct 3 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Abilene (ABI) to New Haven (HVN)
6.8/10 (1,012 reviews)
The place was fine. I enjoyed it., unfortunately, we couldn’t use the tub in the pool cause it was closed down for maintenance. The only issue that I have was in the room the way the AC is set up. It was kinda hard to get cool, air coming through the room, it was kinda hot for most part, but then somehow it got cool in the middle of the night, but I don’t know but other than that, the stay was pretty well breakfast was great
Reviewed on Aug 31, 2026
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
Downtown New Haven
4 out of top 10 points of interest in this area
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.
The Hill
1 out of top 10 points of interest in this area
Southwesternmost New Haven, this area boasts historic structures, Union Station, and Yale-New Haven Hospital. Explore Trowbridge Square and City Point, or visit the Lupi-Legna Bakery.
Long Wharf
Waterfront district with a mix of commercial, industrial, and recreational facilities, Long Wharf offers attractions like Long Wharf Theatre and Vietnam Veterans Memorial Park. Easily accessible via Interstates 95 and 91, and Church Street Bridge.
East Rock
Prominent trap rock ridge East Rock lends its name to this neighborhood, popular among Yale affiliates and cyclists. Explore East Rock Park or visit the lively Upper State Street commercial district.
West New Haven
1 out of top 10 points of interest in this area
If you're spending some time in West New Haven, Yale Bowl and Yale Golf Course are top sights worth seeing.
Wooster Square Hotel Deals
Trumbull Marriott Shelton
180 Hawley Ln Trumbull CT
Fully refundableReserve now, pay when you stay
CA $206
CA $237 total
Sep 3 - Sep 4
includes taxes & fees
New Haven Hotel
229 George Street New Haven CT
Fully refundableReserve now, pay when you stay
CA $165
CA $190 total
Sep 7 - Sep 8
includes taxes & fees
9.2/10 Wonderful! (2,299 reviews)
"I truly enjoy staying here. Front desk staff is outstanding. My concern is housekeeping. Marble rims on the bathroom sink were very dirty. I cleaned them myself after a sneezing session. Bathroom lighting is dreadful for applying makeup. Beds are comfortable."
Reviewed on Sep 2, 2026
Best Western Executive Hotel Of New Haven - West Haven
490 Saw Mill Rd West Haven CT
Fully refundableReserve now, pay when you stay
CA $157
CA $181 total
Sep 29 - Sep 30
includes taxes & fees
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 CA $813. 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.
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.
Things to do
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.