Wooster Square Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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Price found within the past 48 hours. Click for updated prices.
  • Individually decorated, individually furnished, desk, laptop workspace
    Jul 12 - Jul 15

    Econo Lodge Inn & Suites Old Saybrook Westbrook + Flight

    Old Saybrook
    3 nights
    2.0 star property
    7.2/10 - Good (477 reviews)
    "The bedding smelled and the mattress was old. The rugs in the hallways were old and smelled . There was an odor throughout the motel. The staff was friendly and the price was reasonable but I will never book an Econo Lodge again. Extremely disappointed"
    Reviewed May 23, 2026
    Roundtrip • Toronto (YYZ) - New York (LGA)
    YYZ - LGA • Nonstop LGA - YYZ • Nonstop
    CA $578
    CA $564
    per traveller
    found 1 day ago
    Econo Lodge Inn & Suites Old Saybrook Westbrook
  • Front of property
    Jul 30 - Aug 3

    Beechmont - Perfect for Family Retreat! + Flight

    North End
    4 nights
    5.0 star property
    Roundtrip • Toronto (YYZ) - New York (LGA)
    YYZ - LGA • Nonstop LGA - YYZ • Nonstop
    CA $3,739
    CA $2,729
    per traveller
    found 1 day ago
    Beechmont - Perfect for Family Retreat!
  • Property grounds
    Jul 31 - Aug 3

    Pier Blue Inn Old Saybrook - Essex + Flight

    Saybrook Manor
    3 nights
    2.0 star property
    8.0/10 - Very good (1,002 reviews)
    "The mold was seen visible in the bathroom and the floors were not clean. Old furniture and asked for a rebate to no avail. Was told the property was updated. Beds are old and furniture is not new. TV has very few stations. Was not satisfied at all."
    Reviewed May 25, 2026
    Roundtrip • Toronto (YYZ) - New York (LGA)
    YYZ - LGA • Nonstop LGA - YYZ • Nonstop
    CA $1,005
    CA $737
    per traveller
    found 1 day ago
    Pier Blue Inn Old Saybrook - Essex
  • Exterior
    Jul 31 - Aug 3

    Saybrook Point Resort & Marina + Flight

    Old Saybrook Center
    3 nights
    3.5 star property
    9.6/10 - Exceptional (1,001 reviews)
    "Beautiful view, comfortable nice and clean rooms and two restaurants. I have not felt so relaxed in a long time. "
    Reviewed May 21, 2026
    Roundtrip • Toronto (YYZ) - New York (LGA)
    YYZ - LGA • Nonstop LGA - YYZ • Nonstop
    CA $1,762
    CA $1,674
    per traveller
    found 1 day ago
    Saybrook Point Resort & Marina

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

4 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 $190 per night from Jun 7 to Jun 8
CA $190
CA $218 total
Jun 7 - Jun 8
includes taxes & fees
9.2/10 Wonderful! (2,142 reviews)
"Front desk staff made my check in quick and easy, answered my questions re: parking w/o issue. Since we arrived after 8pm, I really appreciated the security of the parking garage across the street (gated w/ key card access) and the ease of getting to the hotel from the sky bridge. The room was clean ..."

Reviewed on May 27, 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 $175 per night from May 31 to Jun 1
CA $175
CA $202 total
May 31 - Jun 1
includes taxes & fees
8.6/10 Excellent! (1,010 reviews)
"The bathroom was too small. The coffee maker didn’t work well."

Reviewed on May 27, 2026

Omni New Haven Hotel at Yale
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 $179 per night from May 31 to Jun 1
CA $179
CA $205 total
May 31 - Jun 1
includes taxes & fees
8/10 Very Good! (1,624 reviews)
"The staff was wonderful, but the parking area could use more lighting at night"

Reviewed on May 27, 2026

Best Western Executive Hotel Of New Haven - West Haven
See all 967 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 . 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

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

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.