Wooster Square Holidays from £1,817
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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
4 out of top 10 points of interest in this area
If you're spending some time in Downtown New Haven, New Haven City Hall and Shubert Theater are top sights worth seeing.
The Hill
1 out of top 10 points of interest in this area
When in The Hill, you can plan a visit to Shubert Theater and Knights of Columbus Museum, some noteworthy sights in the nearby area.
Long Wharf
Long Wharf is popular for its ample dining options, and you might make a stop by Long Wharf Theatre, a top place to visit in the area.
West New Haven
1 out of top 10 points of interest in this area
While visiting West New Haven, you might make a stop by sights like Yale Bowl and West Rock Ridge State Park.
Mill River
1 out of top 10 points of interest in this area
If you're spending some time in Mill River, Wooster Square and Thread City Crossing are top sights worth seeing.
Top hotels in Wooster Square
Motel 6 New Haven - Branford, CT
320 E Main St Branford CT
Fully refundable
£55
3 Sept - 4 Sept
includes taxes & fees
7.2/10 Good! (1,015 reviews)
"I need my money"
Reviewed on 7 Aug 2026
Trumbull Marriott Shelton
180 Hawley Ln Trumbull CT
Fully refundableReserve now, pay when you stay
£130
16 Aug - 17 Aug
includes taxes & fees
7.8/10 Good! (1,002 reviews)
"This was a dump It truly should be condemned and never put humans in this property From no pillows as requested no towels and understaffed!!!! The Elevators were out and toilet overflowing all in less than 15 hours it was truly awful …"
Reviewed on 6 Aug 2026
Best Western Executive Hotel Of New Haven - West Haven
490 Saw Mill Rd West Haven CT
Fully refundableReserve now, pay when you stay
£94
12 Aug - 13 Aug
includes taxes & fees
8/10 Very good! (1,775 reviews)
"Friendly staff , convenient location ."
Reviewed on 6 Aug 2026
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 travel package cost?
Explore the best of Wooster Square from as little as £1,817. 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.
Stay near popular Wooster Square attractions
Wooster Square
8.8/10 (201 reviews)
Find out about the history of New Haven when you take a trip to Wooster Square. Experience the area's art scene and museums.
Things to do
Private Historic Yale Smart Phone Self Guided Walking Tour
£7
per adult
100% of travellers recommend
* 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.