Wooster Square Vacations from $387

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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.
Residence Inn by Marriott Southington

Residence Inn by Marriott Southington

3 out of 5
Price was $480, price is now $387 per person
$387
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to New Haven (HVN)
8.6/10 Excellent! (575 reviews)
Great place and great view

Reviewed on Oct 26, 2025

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
Price was $1,770, price is now $1,159 per person
$1,159
per person
Nov 28 - Dec 1
found 20 hours ago
Roundtrip flight included
Dallas (DFW) to New Haven (HVN)
No reviews
Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Price was $660, price is now $495 per person
$495
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to New Haven (HVN)
9.2/10 Wonderful! (889 reviews)
Beautiful hotel, well-decorated

Reviewed on Oct 27, 2025

Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
West River
Price was $610, price is now $475 per person
$475
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to New Haven (HVN)
8.8/10 Excellent! (934 reviews)
Clean and comfortable. Helpful staff and convenient location to local businesses.

Reviewed on Oct 28, 2025

New Haven Hotel

New Haven Hotel

3.5 out of 5
Downtown New Haven
Price was $617, price is now $495 per person
$495
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to New Haven (HVN)
9/10 Wonderful! (1,842 reviews)
Great hotel ! Well maintained, very professional staff, walkable location.

Reviewed on Oct 29, 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
$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
$117 nightly
The price is $135 total per night from Nov 25 to Nov 26
$135 total
Nov 25 - Nov 26
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 878 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.