Wooster Square Vacation Packages

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Top Holiday Package Deals in Wooster Square

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Hartford North/Bradley Int'l Airport

Hilton Garden Inn Hartford North/Bradley Int'l Airport

3 out of 5
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
8.8/10 Excellent! (1,002 reviews)
Great relaxing overnight stay & safe for a woman traveling alone

Reviewed on Jul. 13, 2025

Hyatt Place Uncasville - Casino Area

Hyatt Place Uncasville - Casino Area

3 out of 5
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
9.2/10 Wonderful! (2,445 reviews)
Clean rooms, good breakfast

Reviewed on Jul. 16, 2025

Microtel Inn & Suites by Wyndham Uncasville Casino Area

Microtel Inn & Suites by Wyndham Uncasville Casino Area

2.5 out of 5
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
8.8/10 Excellent! (1,703 reviews)
No microwave or fridge. Had a funny smell, no daily house keeping had to go ask for clean towels

Reviewed on Jul. 15, 2025

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 out of 5
Old Saybrook Center
per person
Sep 2 - Sep 6
found 9 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to New Haven (HVN)
9.4/10 Exceptional! (1,003 reviews)
Lack of restaurant options - small pool - restaurant stopped serving too early

Reviewed on Jul. 16, 2025

Spark by Hilton Guilford

Spark by Hilton Guilford

2.5 out of 5
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
8.8/10 Excellent! (6 reviews)
Going with family to visit the annual firework in Guilford. This is closest hotel and actually not much better option around. Price super high over $300 per night in weekend. But 2.5 star…..and really simple breakfast…..

Reviewed on Jul. 14, 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 showing kayaking or canoeing and a river or creek as well as a couple

Downtown New Haven

6 out of top 10 points of interest in this area
5/5(4 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

New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street, New Haven, CT
Fully refundableReserve now, pay when you stay
The price is CA $177 per night from Jul 28 to Jul 29
CA $177
CA $204 total
Jul 28 - Jul 29
includes taxes & fees
8.8/10 Excellent! (1,651 reviews)
"My family has stayed here a few times and we have always found it clean and comfortable. It was a little noisy this visit, but the bed was comfortable so we still all slept great."

Reviewed on Jul. 13, 2025

New Haven Hotel
Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

2.5 out of 5
490 Saw Mill Rd, West Haven, CT
Fully refundableReserve now, pay when you stay
The price is CA $132 per night from Jul 20 to Jul 21
CA $132
CA $151 total
Jul 20 - Jul 21
includes taxes & fees
7.6/10 Good! (1,197 reviews)
"Good"

Reviewed on Jul. 15, 2025

Best Western Executive Hotel Of New Haven - West Haven
Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

2 out of 5
320 E Main St, Branford, CT
Fully refundable
The price is CA $98 per night from Jul 22 to Jul 23
CA $98
CA $114 total
Jul 22 - Jul 23
includes taxes & fees
6.8/10 (1,013 reviews)
"Enjoyed my stay and will do it again."

Reviewed on Jul. 12, 2025

Motel 6 New Haven - Branford, CT
See all 893 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

Family Vacations

Family Vacations

Frequently asked questions

How much does a Wooster Square vacation package cost?
From as low as CA $640. Yes, you read that correctly. Our Wooster Square vacation packages are the quickest way to stretch your budget. Bundle your hotels, flights and rental car and get to know this top destination.
How do I get a cheap travel package to Wooster Square?
Bundle your bookings with Expedia to save big on your next trip. With over 550 airlines and 1,000,000 properties across the world, your Wooster Square vacation package can be tailored exactly to suit your budget. With all that extra cash, why not throw in one or more awesome tours and experiences? It's an easy way to unlock even more savings. Your dream getaway to Wooster Square is much closer than you thought!
Where should I stay in Wooster Square?
Make sightseeing easy by staying within walking distance of Wooster Square's main attractions. Yale University and Yale Bowl are two of the best in the area.
What are the top hotels in Wooster Square?
Historic Mansion Inn and Stylish Luxury In New Haven, Ct are among the most popular hotels in Wooster Square. Why not have a look at the facilities and amenities at each and then make a decision?
How far in advance should I book my Wooster Square vacation?
It's tricky picking the perfect time for airfares, but we generally suggest the earlier, the better. Many international flights on Expedia become available up to 12 months in advance. If you're booking last minute, don't despair. Bargain prices appear from time to time within a few weeks of departure dates.
What does an Expedia Wooster Square travel package include?
With Expedia, you can select a combination of car rentals, hotels and flights to create your perfect Wooster Square travel package. Once you've made your booking, you can add on fun stuff like tours and activities. Don't forget --- the more you bundle, the more you'll save!
What should I know before booking a Wooster Square travel package?
A package can be more affordable than individually booking everything you need for your adventure. For example, combine your hotels, flights and rental cars and save a tidy sum. Whatever your vacation plans, there's sure to be a package within your budget.
Can I choose my airline with a Wooster Square Expedia vacation package?
Most definitely. Expedia has over 550 airline partners to pick from around the globe. With all that choice, finding the ideal carrier to take you to Wooster Square won't be hard.
If I'm not able to travel, can I cancel my Wooster Square vacation package?
Yes you can, and we're here to help. You may be able to change or cancel your Wooster Square vacation package at no cost within 24 hours of booking. But you may incur a fee from your airline, hotel or car rental company if your booking is older than that. If your circumstances unexpectedly change, visit our Customer Service Portal for further information.

Discover the most popular places to visit in Wooster Square

Yale University

Yale University

4.5/5(21 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
Sterling Memorial Library at Yale University

Sterling Memorial Library at Yale University

After visiting Sterling Memorial Library at Yale University, make a plan to see the other sights and activities in New Haven. Experience the area's art scene and museums.

Sterling Memorial Library at Yale University

Yale University Art Gallery

4/5(1 review)

You can spend an afternoon exploring the galleries in Yale University Art Gallery during your trip to New Haven. Stroll along the beaches or experience the area's art scene.

Yale University Art Gallery
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.