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.
Econo Lodge Inn & Suites Old Saybrook Westbrook

Econo Lodge Inn & Suites Old Saybrook Westbrook

2 out of 5
Price was CA $352, price is now CA $349 per person
CA $349
per person
Jun 21 - Jun 24
just found
Roundtrip flight included
Detroit (DTW) to New Haven (HVN)
7.2/10 Good! (469 reviews)
The room was clean and comfortable. The Ac unit worked well. I was able to get a good nights sleep. Although I didn't need to use them, there were plenty of shops nearby.

Reviewed on Apr 16, 2026

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
Saybrook Manor
Price was CA $1,074, price is now CA $753 per person
CA $753
per person
May 27 - Jun 1
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
8/10 Very Good! (1,001 reviews)
Great place to stay on the shoreline. Privately owned so you.are supporting local businesses!

Reviewed on Apr 10, 2026

Westbrook Inn B&B

Westbrook Inn B&B

3 out of 5
Westbrook Center
Price was CA $838, price is now CA $795 per person
CA $795
per person
Jun 21 - Jun 24
just found
Roundtrip flight included
Detroit (DTW) to New Haven (HVN)
9.8/10 Exceptional! (183 reviews)
Breakfast was amazing! Staff was so kind, and place was very clean.

Reviewed on Apr 9, 2026

Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

3 out of 5
Price was CA $2,336, price is now CA $2,283 per person
CA $2,283
per person
Jun 8 - Jun 11
found 21 hours ago
Roundtrip non-stop flight included
Québec (YQB) to New Haven (HVN)
8.6/10 Excellent! (1,294 reviews)
Nothing much around hotel within walking distance

Reviewed on Apr 19, 2026

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 CA $2,229, price is now CA $2,182 per person
CA $2,182
per person
Jun 8 - Jun 11
found 19 hours ago
Roundtrip non-stop flight included
Québec (YQB) to New Haven (HVN)
8/10 Very Good! (1,582 reviews)
The room was clean but old and the first room , the flush box wasn't working so we changed the room .. overall the rooms are old ... anything else was good.

Reviewed on Apr 18, 2026

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
Downtown New Haven

Downtown New Haven

5 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 $163 per night from May 3 to May 4
CA $163
CA $188 total
May 3 - May 4
includes taxes & fees
9.2/10 Wonderful! (2,089 reviews)
Nice stay, well located and near campus.

Reviewed on Apr 19, 2026

New Haven Hotel
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
The price is CA $245 per night from Apr 26 to Apr 27
CA $245
CA $282 total
Apr 26 - Apr 27
includes taxes & fees
8.6/10 Excellent! (1,007 reviews)
Helpful staff, great restaurants nearby, the cafe on-site was great for a quick grab (especially early in the morning)

Reviewed on Apr 20, 2026

Omni New Haven Hotel at Yale
Hilton Garden Inn Shelton

Hilton Garden Inn Shelton

3 out of 5
25 Old Stratford Rd Shelton CT
Fully refundableReserve now, pay when you stay
The price is CA $169 per night from Apr 26 to Apr 27
CA $169
CA $194 total
Apr 26 - Apr 27
includes taxes & fees
8/10 Very Good! (1,102 reviews)
Other than the 6 squad cars to arrest a disgruntled person it was a great restful night

Reviewed on Apr 19, 2026

Hilton Garden Inn Shelton
See all 975 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
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Frequently asked questions

How much does a Wooster Square vacation package cost?
From as low as CA $349. 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 buildings in spring blue sky in New Haven, CT USA

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

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