Wooster Square Vacations from $461

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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.
Hampton Inn Milford

Hampton Inn Milford

2.5 out of 5
Save 100% on your flight
Price was $596, price is now $461 per person
$461
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
8/10 Very Good! (1,002 reviews)
I stayed here a year ago and the property and common areas were in much better condition. I was a bit disappointed this time around. Will likely look elsewhere when I'm in town next

Reviewed on Aug 31, 2025

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
Save 100% on your flight
Price was $2,637, price is now $1,607 per person
$1,607
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
No reviews
Luxury Apartments by Hyatus at Pierpont

Luxury Apartments by Hyatus at Pierpont

4 out of 5
The Hill
Save 100% on your flight
Price was $1,405, price is now $1,035 per person
$1,035
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.4/10 Exceptional! (19 reviews)
Excellent location downtown and close to yale. A lot of complimentary amenities and activities. Very nice size rooms. A nice residential feel for a weeks stay.

Reviewed on Jun 27, 2025

Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Save 100% on your flight
Price was $1,177, price is now $873 per person
$873
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.2/10 Wonderful! (865 reviews)
Really close to Yale. No on site parking so we had to search for parking and walk back to the hotel late at night after we arrived…and there were some iffy characters around the area. More iffy characters greeted us near our parked car at 8:30am the next morning. The best part was Kristina at the front desk! She was really friendly and helpful.

Reviewed on Aug 31, 2025

Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
Downtown New Haven
Save 100% on your flight
Price was $1,380, price is now $1,043 per person
$1,043
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
8.4/10 Very Good! (1,010 reviews)
Staff was very friendly

Reviewed on Aug 31, 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

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 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
$156 nightly
The price is $179 total per night from Sep 14 to Sep 15
$179 total
Sep 14 - Sep 15
Total with taxes and fees
Trumbull Marriott Shelton
Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

2 out of 5
320 E Main St, Branford, CT
Fully refundable
$66 nightly
The price is $76 total per night from Oct 1 to Oct 2
$76 total
Oct 1 - Oct 2
Total with taxes and fees
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
$143 nightly
The price is $165 total per night from Sep 21 to Sep 22
$165 total
Sep 21 - Sep 22
Total with taxes and fees
Omni New Haven Hotel at Yale
See all 887 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.