Wooster Square Vacations from $384
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Your Wooster Square Vacation
Immerse yourself in the best that Wooster Square offers with a Wooster Square vacation package. From its festivals to every other thing that makes it unique, this neighborhood will charm you from start to finish. Some leading nearby attractions to see during your trip to Wooster Square include Yale University, Yale Bowl and East Rock Park. No matter what your ideal Wooster Square vacation looks like, you can make it a reality with Expedia.
The Latest Wooster Square Vacation Packages
Price found within the past 48 hours. Click for updated prices.
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.
Wooster Square Hotel Deals
New Haven Hotel
229 George Street New Haven CT
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $155 total per night from Nov 25 to Nov 26
$155 total
Nov 25 - Nov 26
Total with taxes and fees
Motel 6 Milford, CT
111 Schoolhouse Road Milford CT
Fully refundableReserve now, pay when you stay
$70 nightly
The price is $80 total per night from Nov 24 to Nov 25
$80 total
Nov 24 - Nov 25
Total with taxes and fees
6.6/10 (1,062 reviews)
"Idk"
Reviewed on Oct 30, 2026
Best Western Executive Hotel Of New Haven - West Haven
490 Saw Mill Rd West Haven CT
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $126 total per night from Nov 3 to Nov 4
$126 total
Nov 3 - Nov 4
Total with taxes and 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.
Stay near popular Wooster Square attractions
Things to do
New Haven - It Zip It Adventure Indoor Ropes Course
$28
per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.