Wooster Square Holidays from £667

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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.

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Old Saybrook

Super 8 by Wyndham Old Saybrook

2 out of 5
per person
20 Sept - 26 Sept
found 1 day ago
Return direct flight included
Birmingham (BHX) to New Haven (HVN)
7/10 Good! (888 reviews)
The pool wasn’t open, the room needed to be updated, bathroom outlet didn’t work, tv was static, I wouldn’t stay again.

Reviewed on 27 Jul 2025

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 out of 5
Old Saybrook Center
per person
20 Sept - 26 Sept
found 1 day ago
Return direct flight included
Birmingham (BHX) to New Haven (HVN)
9.4/10 Exceptional! (1,003 reviews)
I love this property. But, very disappointed in the pool and lack of variety of food

Reviewed on 9 Aug 2025

Hilton Garden Inn Hartford North/Bradley Int'l Airport

Hilton Garden Inn Hartford North/Bradley Int'l Airport

3 out of 5
per person
14 Oct - 21 Oct
found 5 hours ago
Return direct flight included
London (LHR) to New Haven (HVN)
8.8/10 Excellent! (1,004 reviews)
Pillows are horrible.

Reviewed on 9 Aug 2025

James Pharmacy Bed & Breakfast

James Pharmacy Bed & Breakfast

4 out of 5
Old Saybrook Center
per person
20 Sept - 26 Sept
found 1 day ago
Return direct flight included
Birmingham (BHX) to New Haven (HVN)
9.4/10 Exceptional! (16 reviews)
We loved the convenient location and beautiful historic building, but we were very disappointed in the level of cleanliness (a layer of dust on shelves and fireplace, cobwebs under furniture). There were some other issues (loose shower head, broken coffee maker). There's no one on site to address in person. It's a lovely place, but needs some attention. For the price, it should be better! :(

Reviewed on 1 May 2025

Hampton Inn Hartford/Airport

Hampton Inn Hartford/Airport

2.5 out of 5
per person
14 Oct - 21 Oct
found 5 hours ago
Return direct flight included
London (LHR) to New Haven (HVN)
9/10 Wonderful! (1,004 reviews)
Always enjoy staying at this property as it close to the freeway and have in close proximity to restaurants.

Reviewed on 5 Aug 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 which includes 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
4.5/5(6 area reviews)

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

Find hotels in Downtown New Haven

Top hotels in Wooster Square

Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
20 Dwight Street, New Haven, CT
Fully refundableReserve now, pay when you stay
The price is £101 per night from 1 Sept to 2 Sept
£101
1 Sept - 2 Sept
includes taxes & fees
8.6/10 Excellent! (845 reviews)
"Parking was great, although we paid for late check out and was charged an additional fee because we didn’t check out at 11:30. Also, housekeeping did a great job with providing a clean room-but did not know we had late check out and attempted to come into our room at 10:00am. At check out, the front ..."

Reviewed on 10 Aug 2025

Cambria Hotel New Haven University Area
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 £89 per night from 24 Aug to 25 Aug
£89
24 Aug - 25 Aug
includes taxes & fees
7.8/10 Good! (1,265 reviews)
"Good place"

Reviewed on 9 Aug 2025

Best Western Executive Hotel Of New Haven - West 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 £129 per night from 26 Aug to 27 Aug
£129
26 Aug - 27 Aug
includes taxes & fees
8.2/10 Very Good! (1,010 reviews)
"Amazing stay, great view and comfortable accommodations. Only complaint is lower floors are subject to street noise which is out of the hotel’s control. Would 100% stay here again when returning to New Haven"

Reviewed on 12 Aug 2025

Omni New Haven Hotel at Yale
See all 883 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 £667. 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

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
New Haven City Hall

New Haven City Hall

New Haven City Hall is just one of the places to see in New Haven, so why not enjoy the other things to explore during your travels? Experience the area's art scene and museums.

New Haven City Hall
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

Things to do

Harkness Towner

Private Historic Yale Smart Phone Self Guided Walking Tour

£7
per adult
100% of travellers recommend
Private Historic Yale Smart Phone Self Guided Walking Tour
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. Flight-inclusive packages are ATOL protected.