Wooster Square Vacations from $251

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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.
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
Price was $310, price is now $251 per person
$251
per person
Dec 6 - Dec 8
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to New Haven (HVN)
8.8/10 Excellent! (1,092 reviews)
Staff was great. Room was clean.

Reviewed on Oct 13, 2025

Madison Beach Hotel

Madison Beach Hotel

4 out of 5
Madison Center
Save 100% on your flight
Price was $1,976, price is now $1,462 per person
$1,462
per person
Dec 24 - Dec 29
just found
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
9.4/10 Exceptional! (316 reviews)
Beautiful sunrise from balcony and sunset from other parts of the property. Staff was very very helpful and attentive. Restaurant offers many wonderful food options

Reviewed on Oct 9, 2025

Hilton Garden Inn Hartford North/Bradley Int'l Airport

Hilton Garden Inn Hartford North/Bradley Int'l Airport

3 out of 5
Price was $785, price is now $611 per person
$611
per person
Dec 7 - Dec 13
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
8.8/10 Excellent! (1,005 reviews)
Allicia was amazing staff

Reviewed on Oct 10, 2025

Cambria Hotel Manchester South Windsor

Cambria Hotel Manchester South Windsor

3 out of 5
Price was $889, price is now $735 per person
$735
per person
Dec 7 - Dec 13
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
9.2/10 Wonderful! (784 reviews)
Very very noisy on the 3rd floor from aprox 11:00 until 12:30 or so. Running down the hallway and carrying on loudly.

Reviewed on Oct 13, 2025

Courtyard by Marriott New Haven Orange-Milford

Courtyard by Marriott New Haven Orange-Milford

3 out of 5
Price was $382, price is now $342 per person
$342
per person
Dec 5 - Dec 8
found 7 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to New Haven (HVN)
8.4/10 Very Good! (1,006 reviews)
Could use more bar counter options.

Reviewed on Oct 10, 2025

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

5 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 hotels in Downtown New Haven

Wooster Square Hotel Deals

Trumbull Marriott Shelton

Trumbull Marriott Shelton

3.5 out of 5
180 Hawley Ln, Trumbull, CT
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $160 total per night from Oct 26 to Oct 27
$160 total
Oct 26 - Oct 27
Total with taxes and fees
8/10 Very Good! (1,007 reviews)
"Clean room, Staff was great - parking was simple"

Reviewed on Oct 9, 2025

Trumbull Marriott Shelton
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
155 Temple St, New Haven, CT
Fully refundableReserve now, pay when you stay
$167 nightly
The price is $192 total per night from Oct 27 to Oct 28
$192 total
Oct 27 - Oct 28
Total with taxes and fees
8.4/10 Very Good! (1,011 reviews)
"Friendly staff, very clean and the bed was great. We had the king deluxe room. I’ve never stayed in a big fancy hotel like that before so it was a little overwhelming but I got through it. Would stay there again if I ever came back to the area."

Reviewed on Oct 11, 2025

Omni New Haven Hotel at Yale
New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street, New Haven, CT
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $137 total per night from Oct 26 to Oct 27
$137 total
Oct 26 - Oct 27
Total with taxes and fees
9/10 Wonderful! (1,834 reviews)
"The hotel was very nice. The room was clean and the staff was very friendly."

Reviewed on Oct 13, 2025

New Haven Hotel
See all 876 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Wooster Square

Stairs detail in an apartment complex

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
Yale University

Yale University

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
Over Yale University

New Haven City Hall

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

Things to do

Harkness Towner

Private Historic Yale Smart Phone Self Guided Walking Tour

$10
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.