Wooster Square Holidays

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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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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 kayaking or canoeing and a river or creek as well as a couple

Downtown New Haven

5 out of top 10 points of interest in this area
4.5/5(6 area reviews)

If you're spending some time in Downtown New Haven, Woolsey Hall and Sterling Memorial Library at Yale University are top sights worth seeing.

Find hotels in Downtown New Haven

Top hotels in Wooster Square

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 S$199 per night from 22 Dec to 23 Dec
S$199
includes taxes & fees
22 Dec - 23 Dec
8.8/10 Excellent! (1,327 reviews)
"The staff friendly and helpful . Room was comfortable,quiet and clean ."

Reviewed on 17 Nov,2024

New Haven Hotel
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 S$109 per night from 1 Dec to 2 Dec
S$109
includes taxes & fees
1 Dec - 2 Dec
6.6/10 (1,003 reviews)
"Excellent service"

Reviewed on 19 Nov,2024

Motel 6 New Haven - Branford, CT
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 S$148 per night from 22 Dec to 23 Dec
S$148
includes taxes & fees
22 Dec - 23 Dec
7.4/10 Good! (1,004 reviews)
"They should update when the pool isn't workung we looked forward to that part to relax without the kids but upon arriving it was said at that time."

Reviewed on 19 Nov,2024

Best Western Executive Hotel Of New Haven - West Haven
See all 854 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.

Frequently asked questions

How much does a Wooster Square holiday package cost?
From as low as . Yes, you read that correctly. Our Wooster Square holiday 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 holiday 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 holiday?
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 holiday plans, there’s sure to be a package within your budget.
Can I choose my airline with a Wooster Square Expedia holiday 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 holiday package?
Yes you can, and we’re here to help. You may be able to change or cancel your Wooster Square holiday 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.

Things to do

Anniversaries or special occasions

Private sailing trips around Fishers island from New London, CT

S$933
Per adult
Private sailing trips around Fishers island from New London, CT
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.