Wooster Square Vacations from $263

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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.
Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

2.5 out of 5
Price was $310, price is now $263 per person
$263
per person
Dec 11 - Dec 14
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
8/10 Very Good! (1,409 reviews)
Nice room on 6th floor, facing highway. Very good temperature control. Clean hotel for that level of accommodation. Breakfast was typical hotel, and nicely done.

Reviewed on Oct 29, 2025

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
Price was $1,626, price is now $1,057 per person
$1,057
per person
Dec 11 - Dec 14
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
No reviews
The Surfside Hotel

The Surfside Hotel

2 out of 5
Lordship
Price was $394, price is now $323 per person
$323
per person
Dec 11 - Dec 14
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
9.4/10 Exceptional! (163 reviews)
Everyone was friendly and the facility was nice and clean. We would stay again.

Reviewed on Oct 20, 2025

Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

3 out of 5
Price was $320, price is now $279 per person
$279
per person
Dec 11 - Dec 14
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
8.6/10 Excellent! (1,164 reviews)
The best breakfast of our whole trip. The dinning area is almost in the front desk but the food was delicious and many options to choose from. Was only one night but we like it. Very friendly staff.

Reviewed on Oct 25, 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 $396, price is now $349 per person
$349
per person
Dec 30 - Jan 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
8.8/10 Excellent! (1,018 reviews)
非常喜欢这里，安静，相对于对面的Hyatt房间里面味道更清新，家具和用品更加新一点。穿梭巴士司机都非常好。

Reviewed on Oct 26, 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

Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

2 out of 5
320 E Main St, Branford, CT
Fully refundable
$74 nightly
The price is $85 total per night from Nov 4 to Nov 5
$85 total
Nov 4 - Nov 5
Total with taxes and fees
7/10 Good! (1,009 reviews)
Room clean and comfortable. No fridge but ice available and microwave available for guest use. Staff friendly. Nice pizza restaurant attached to hotel.

Reviewed on Oct 28, 2025

Motel 6 New Haven - Branford, CT
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
$151 nightly
The price is $174 total per night from Nov 23 to Nov 24
$174 total
Nov 23 - Nov 24
Total with taxes and fees
8.4/10 Very Good! (1,005 reviews)
Very nice hotel, clean and add to walk around downtown

Reviewed on Oct 26, 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
$112 nightly
The price is $129 total per night from Nov 30 to Dec 1
$129 total
Nov 30 - Dec 1
Total with taxes and fees
9/10 Wonderful! (1,861 reviews)
Great that there was an iron and fridge in the room, as well as bathrobes. Very comfortable mattress. Gold star to front desk staff for being genuinely friendly!

Reviewed on Oct 27, 2025

New Haven Hotel
See all 875 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

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
Over Yale University

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

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.