Wooster Square Holidays

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Your Wooster Square Holiday

Book your holiday package to Wooster Square and prepare to explore its festivals and plenty more. Whether you're craving adventure or relaxation, you'll find it in this inviting neighbourhood. When it's time to get out and explore, you'll find lots of awesome attractions nearby including Yale University, Yale Bowl and East Rock Park. Visit one or all during your trip to Wooster Square. Stop daydreaming and start doing. When it's time to lock in your next holiday to Wooster Square, Expedia will help get you there.

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
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
The price is £92 per night from 12 Apr to 13 Apr
£92
12 Apr - 13 Apr
includes taxes & fees
9/10 Wonderful! (2,058 reviews)
Was booked for three nights at this hotel. Got there and they had given my room away. Said that they had run my card before I even got there and that it declined, which it actually didn’t, my credit card company froze my card because I thought it was fraudulent, so they canceled my reservation. No ...

Reviewed on 30 Mar 2026

New Haven Hotel
Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

3 out of 5
190 Old Gate Lane Milford CT
Fully refundableReserve now, pay when you stay
The price is £111 per night from 14 Apr to 15 Apr
£111
14 Apr - 15 Apr
includes taxes & fees
8.6/10 Excellent! (1,287 reviews)
I was surprised how outdated the building was. Very loud and noisy. You can hear everything in your room from the hallway to slamming doors, people walking around on the upper level, the ice maker all hours of the day. Lighting in the bathroom was very dim. It was fine for the 3 nights we were there, ...

Reviewed on 30 Mar 2026

Hyatt Place Milford / New Haven
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 £133 per night from 4 Apr to 5 Apr
£133
4 Apr - 5 Apr
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
The hotel looked great, the staff was very friendly, the breakfast was great but the heat didn`t work. The maintenance man brought up a portable heater. Therefore the overnight stay was terrible & we woke up in the morning sweating because the heat was working again.

Reviewed on 30 Mar 2026

Omni New Haven Hotel at Yale
See all 944 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 Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Wooster Square travel package cost?
Explore the best of Wooster Square from as little as . Choose from a great selection of rental cars, hotels and flights to suit every budget. Land even more discounts when you add some sightseeing activities to your travel package.
If I'm not able to travel, can I cancel my Wooster Square travel package?
We totally understand — the universe can throw the odd curveball. If you've booked a Wooster Square travel package and have to cancel or change it, we can help. We recommend taking a look at our Customer Service Portal first for information. But in general, if you've booked your package in the last 24 hours, you may be able to cancel or amend your itinerary at no cost. If it's been more than 24 hours, your hotel, airline or car rental company may impose a charge.
How do I get a cheap travel package to Wooster Square?
Bundling your flight and hotel with Expedia won't just save precious time — it'll save you dollars too. A Wooster Square travel package makes it simple to organise the ideal trip. With more than 550 airlines worldwide to pick from, finding flights that suit your schedule won't be difficult. On top of that, we have over 1,000,000 hotel options globally to select from. Now that's what you call choice. Whatever your budget, Expedia brings the world within your reach.
Does Expedia offer Book Now, Pay Later Wooster Square holidays?
Your bank balance shouldn't stop you from going on holiday, so Expedia has come up with a solution to help. Now that we've teamed up with online lender Klarna, it's easier than ever to book your dream getaway without exhausting your savings. Klarna offers flexible payment options during the checkout process that take the worry out of budgeting for your break. Check out these flexible payment options:

  • Pay monthly holidays: If paying small amounts each month is something that would work for you, Klarna can help. Paying in convenient monthly instalments will make your holiday dreams possible.
  • Pay in instalments holidays: Like the idea of paying for your holiday in multiple transactions? Consider this Book Now, Pay Later option with Klarna.
  • Low deposit holidays: When you want to grab an incredible deal but don't have the full amount yet, Klarna's low deposit holiday plan will help you get what you want.

Where should I stay in Wooster Square?
Urban adventurers come from all corners of the globe to see Yale University and Yale Bowl in Wooster Square. Book a room near these top attractions and visit them at your leisure.
What are the top hotels in Wooster Square?
If this will be your first time in Wooster Square, lock in a room at La Quinta Inn & Suites by Wyndham New Haven or New Haven Hotel. Both offer friendly service and are top options with lots of travellers.
How far in advance should I book my Wooster Square holiday?
Reserving your flights early with Expedia means one less thing to have to worry about. Most carriers advertise tickets up to 12 months prior to departure dates. This is usually the cheapest time to book. If circumstances have left you booking late, incredible deals to Wooster Square will sometimes occur in the weeks leading up to departure.
What does an Expedia Wooster Square travel package include?
Flights, rental cars and hotels — we have them covered. With Expedia, you can shape your Wooster Square package however you want. All you have to do is determine just what you need. Once you've made your booking, you can add on extras like activities and tours. The more you bundle, the bigger your savings!
What should I know before booking a Wooster Square travel package?
You can save a tidy sum by bundling your flights, hotels and rental cars. Once you've made your booking, add on fun stuff like tours and activities. Your next awesome adventure is only a couple of clicks away.
Can I choose my airline with a Wooster Square Expedia travel package?
Expedia offers access to more than 550 partner airlines globally, so you certainly can. Simply pick the carrier you want and put together the perfect Wooster Square trip.

Popular places to visit

Yale university buildings in spring blue sky in New Haven, CT USA

Yale University

Walk around the campus of Yale University, a top university in New Haven. Stroll along the beaches or experience the area's art scene.

Yale University
Peabody Museum of Natural History

Peabody Museum of Natural History

You can browse the exhibits at Peabody Museum of Natural History, a museum with a story of its own, during your travels to New Haven. Experience the area's art scene and museums.

Peabody Museum of Natural History

Yale-New Haven Hospital

If Yale-New Haven Hospital is what brings you to town, hopefully you'll have a chance to explore more of New Haven.

Yale-New Haven Hospital

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.