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Our top choices for Wooster Square hotels

Courtyard by Marriott Waterbury Downtown

Courtyard by Marriott Waterbury Downtown
3.0 star property
29.5 km from Wooster Square
8.4 out of 10, Very Good, (1083)
"The room vas spacious and clean. Staff were very helpful and cordial."
United States
Ivan
The price is NT$2,798
NT$3,217 total
includes taxes & fees
Jan 4 - 2026/1/5
Courtyard by Marriott Waterbury Downtown

Spark by Hilton Guilford

Spark by Hilton Guilford
2.5 star property
21.6 km from Wooster Square
8.8 out of 10, Excellent, (72)
"Comfortable beds, friendly staff "
United States
Taylor
The price is NT$3,454
NT$3,972 total
includes taxes & fees
Jan 4 - 2026/1/5
Spark by Hilton Guilford

Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven
3.0 star property
12.7 km from Wooster Square
8.6 out of 10, Excellent, (1206)
"Hotel for Pleasant Stay"
United States
Rajesh
The price is NT$3,244
NT$3,731 total
includes taxes & fees
Dec 30 - Dec 31
Hyatt Place Milford / New Haven

Hilton Garden Inn Milford

Hilton Garden Inn Milford
3.0 star property
12.3 km from Wooster Square
8.4 out of 10, Very Good, (1006)
"Very nice hotel clean friendly convenient location "
United States
Karen
The price is NT$3,067
NT$3,527 total
includes taxes & fees
Jan 9 - 2026/1/10
Hilton Garden Inn Milford

The Surfside Hotel

The Surfside Hotel
2.0 star property
25.1 km from Wooster Square
9.4 out of 10, Exceptional, (172)
"Great place to stay"
United States
Craig
The price is NT$4,244
NT$4,880 total
includes taxes & fees
Jan 4 - 2026/1/5
The Surfside Hotel

New Haven Hotel

New Haven Hotel
3.5 star property
Downtown New Haven, 1.2 km from Wooster Square
9.0 out of 10, Wonderful, (1963)
"Great value and close to everything!"
United States
kevin
The price is NT$3,932
NT$4,522 total
includes taxes & fees
Dec 30 - Dec 31
New Haven Hotel

Holiday Inn Cheshire - Southington by IHG

Holiday Inn Cheshire - Southington by IHG
3.0 star property
28.5 km from Wooster Square
8.2 out of 10, Very Good, (1009)
"Pool was nice, breakfast was very good. "
United States
Matthew
The price is NT$2,892
NT$3,326 total
includes taxes & fees
Jan 4 - 2026/1/5
Holiday Inn Cheshire - Southington by IHG

Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area
3.0 star property
West River, 2 km from Wooster Square
8.8 out of 10, Excellent, (1004)
"Great stay overall. Wish it was easier to walk to good restaurants. Had to drive to good food."
United States
James
The price is NT$3,269
NT$3,760 total
includes taxes & fees
Jan 25 - 2026/1/26
Cambria Hotel New Haven University Area

Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT
2.0 star property
10.7 km from Wooster Square
7.2 out of 10, Good, (1004)
"This motel is very clean staff is friendly."
United States
Stacey-Ann
The price is NT$2,295
NT$2,670 total
includes taxes & fees
Jan 3 - 2026/1/4
Motel 6 New Haven - Branford, CT

Hampton Inn by Hilton Shelton

Hampton Inn by Hilton Shelton
2.5 star property
17.7 km from Wooster Square
8.6 out of 10, Excellent, (1004)
"Beautiful hotel in great location "
United States
Tara
The price is NT$3,325
NT$3,824 total
includes taxes & fees
Jan 9 - 2026/1/10
Hampton Inn by Hilton Shelton

Hyatt House Shelton

Hyatt House Shelton
3.0 star property
18.3 km from Wooster Square
8.4 out of 10, Very Good, (1002)
"Place was great quiet and relaxing I enjoyed my time there thank you. "
United States
Jeanette
The price is NT$3,649
NT$4,197 total
includes taxes & fees
Jan 2 - 2026/1/3
Hyatt House Shelton

Courtyard New Haven at Yale

Courtyard New Haven at Yale
3.0 star property
Dixwell, 1.8 km from Wooster Square
8.6 out of 10, Excellent, (1005)
"Clean room, great location and friendly staff! "
United States
Gina
The price is NT$2,993
NT$3,441 total
includes taxes & fees
Jan 11 - 2026/1/12
Courtyard New Haven at Yale

Holiday Inn Express Branford-New Haven by IHG

Holiday Inn Express Branford-New Haven by IHG
3.0 star property
10.6 km from Wooster Square
8.8 out of 10, Excellent, (1002)
"Great place to stay"
United States
Craig
The price is NT$3,395
NT$3,904 total
includes taxes & fees
Jan 11 - 2026/1/12
Holiday Inn Express Branford-New Haven by IHG

Homewood Suites by Hilton Orange New Haven

Homewood Suites by Hilton Orange New Haven
3.0 star property
9.1 km from Wooster Square
9.2 out of 10, Wonderful, (1003)
"Clean room, close to mamy amenities restaurants, bars, etc "
United States
Kerry- Ann
The price is NT$3,042
NT$3,498 total
includes taxes & fees
Jan 25 - 2026/1/26
Homewood Suites by Hilton Orange New Haven

Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven
2.5 star property
6.4 km from Wooster Square
8.0 out of 10, Very Good, (1500)
"Room is big and clean. Breakfast is very good."
United States
Youai
The price is NT$3,015
NT$3,467 total
includes taxes & fees
Jan 1 - 2026/1/2
Best Western Executive Hotel Of New Haven - West Haven

Wyndham Southbury

Wyndham Southbury
3.0 star property
29.6 km from Wooster Square
8.2 out of 10, Very Good, (1090)
"Clean room, staff was pleasant and welcoming. Restaurant was great! "
United States
Kenneth
The price is NT$2,912
NT$3,349 total
includes taxes & fees
Jan 6 - 2026/1/7
Wyndham Southbury

Hilton Garden Inn Shelton

Hilton Garden Inn Shelton
3.0 star property
17.4 km from Wooster Square
7.8 out of 10, Good, (1057)
"What stood out for me is how nice the staff was and how clean and quiet the hotel is ,I would go back and I will definitely tell my friends and family to book, my stay was wonderful."
United States
Simone
The price is NT$3,122
NT$3,591 total
includes taxes & fees
Jan 8 - 2026/1/9
Hilton Garden Inn Shelton

Comfort Inn & Suites Meriden East

Comfort Inn & Suites Meriden East
2.5 star property
27.4 km from Wooster Square
7.2 out of 10, Good, (1001)
"Very nice property "
United States
DAVIDA
The price is NT$2,771
NT$3,187 total
includes taxes & fees
Jan 26 - 2026/1/27
Comfort Inn & Suites Meriden East

Motel 6 Milford, CT

Motel 6 Milford, CT
2.0 star property
17.7 km from Wooster Square
6.2 out of 10, (1007)
"everything was very good."
United States
Marian
The price is NT$2,357
NT$2,711 total
includes taxes & fees
Dec 30 - Dec 31
Motel 6 Milford, CT

Hampton Inn & Suites New Haven - South - West Haven

Hampton Inn & Suites New Haven - South - West Haven
2.5 star property
6.5 km from Wooster Square
8.4 out of 10, Very Good, (1006)
"Overall great stay!"
United States
Michael
The price is NT$3,041
NT$3,497 total
includes taxes & fees
Jan 5 - 2026/1/6
Hampton Inn & Suites New Haven - South - West Haven
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.

Where to stay in Wooster Square

Find the best Wooster Square areas and neighborhoods for the activities you enjoy most.

Downtown New Haven

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.

Mill River

If you're spending some time in Mill River, Wooster Square and Thread City Crossing are top sights worth seeing.

The Hill

Southwesternmost New Haven, this area boasts historic structures, Union Station, and Yale-New Haven Hospital. Explore Trowbridge Square and City Point, or visit the Lupi-Legna Bakery.

Long Wharf

Waterfront district with a mix of commercial, industrial, and recreational facilities, Long Wharf offers attractions like Long Wharf Theatre and Vietnam Veterans Memorial Park. Easily accessible via Interstates 95 and 91, and Church Street Bridge.

East Rock

Prominent trap rock ridge East Rock lends its name to this neighborhood, popular among Yale affiliates and cyclists. Explore East Rock Park or visit the lively Upper State Street commercial district.

Top Wooster Square Hotel Reviews

Find out more about Wooster Square

Top reasons to visit Wooster Square

  • Historic Charm: Explore the elegant homes and storied neighborhoods that showcase Wooster Square's rich history.
  • Cultural Experiences: Enjoy educational attractions and vibrant local community events that highlight the area's culture.
  • Wooster Square Park: Relax and engage in outdoor activities in this beautiful urban park, perfect for families.
  • Local Cuisine: Indulge in delicious food offerings, experiencing the flavors unique to the region.
  • Accommodations: Find a range of comfortable rental options, catering to diverse traveler needs.

Find great hotels near Wooster Square

Discover a variety of accommodation options in Wooster Square, New Haven, catering to both leisure and business travelers. With pet-friendly amenities and a welcoming atmosphere for the LGBTQIA community, you’ll find the perfect spot for your stay. Explore modern apartments and rentals that offer all the comforts of home, making your visit to this charming neighborhood both enjoyable and convenient.

  • Red Roof Inn Milford - New Haven: Situated 17.7km from Wooster Square, Red Roof Inn Milford - New Haven offers a welcoming atmosphere for all travelers, especially those seeking an LGBTQIA-friendly, family, and pet-friendly experience. This hotel prides itself on inclusivity and is affiliated with LGBTQI travel guides. Families will appreciate the complimentary crib service for infants. The property is also pet-friendly, allowing pets with certain restrictions, making it a convenient choice for guests traveling with furry companions.
  • Motel 6 Milford, CT: Also located 17.7km away from Wooster Square, Motel 6 Milford, CT provides a budget-friendly option for travelers focused on business or pet-friendly accommodations. This motel allows pets for free, making it an economical choice for those traveling with animals. The straightforward, no-frills atmosphere is complemented by essential amenities, ensuring a comfortable stay without breaking the bank. Service animals are welcome at no additional charge, catering to the needs of all guests.
  • Hyatt Place Milford / New Haven: Just 12.9km from Wooster Square, Hyatt Place Milford / New Haven is a 3-star hotel ideal for business travelers and pet owners alike. The hotel features spacious rooms equipped with modern amenities, making it a comfortable base for both work and relaxation. Pets are allowed with some restrictions, and service animals are welcomed without fees. Guests can enjoy an array of facilities, including a fitness center and complimentary breakfast, ensuring a pleasant stay for both business and leisure travelers.

Where to stay near Wooster Square

Discover the charm of Wooster Square, New Haven, where elegant homes and storied neighborhoods create a picturesque backdrop for your vacation. This family-friendly area is perfect for cultural exploration, with close proximity to New York. Stroll through beautiful parks, indulge in local cuisine, and soak in the vibrant atmosphere. With friendly locals and budget-friendly excursions, Wooster Square offers a delightful blend of relaxation and adventure for every traveler.

  • New Haven: As the city where Wooster Square is located, New Haven is a vibrant hub of culture and education. With a steady stream of visitors year-round, it comes alive, especially from June to August. Known for its rich artistic scene, you can explore historic college campuses, enjoy shopping in local boutiques, and attend captivating music concerts. Key attractions include the iconic Yale University and the picturesque Wooster Square itself, famous for its cherry blossoms in spring, making it a delightful spot for both families and solo travelers.
  • West Haven: Just 4.8km from Wooster Square, West Haven offers a blend of cultural and outdoor experiences. Peak tourist season runs from June to August, with visitors drawn to its beautiful beaches and recreational areas. This city is perfect for families looking to soak up the sun or enjoy outdoor activities. Highlights include the historic college university and family-friendly beaches, making it an excellent destination for relaxation and adventure alike.
  • Branford: Located 9.7km from Wooster Square, Branford is an idyllic city known for its stunning scenery and outdoor activities, attracting visitors throughout the year. The summer months see the highest number of tourists, drawn by its beautiful beaches and the peaceful allure of local lakes. Branford offers a romantic setting, perfect for couples, with opportunities for music concerts and recreational pursuits. Don't miss the chance to explore the picturesque waterfront and enjoy the charm of this coastal town.

Things to do near Wooster Square

Wooster Square in New Haven is perfect for culture-themed family vacations. Visitors can enjoy educational attractions, explore local shopping centers, and relax in recreational areas. The neighborhood is rich in history and offers various rental options for a comfortable stay. With its vibrant atmosphere, Wooster Square provides a delightful mix of activities for everyone, making it an ideal destination for a memorable getaway.

Shopping

Visit Louis' Lunch, a renowned eatery just 1.1km from Wooster Square, known for its iconic burgers. For a larger shopping experience, head to Westfield Connecticut Post Mall, 12.9km away, featuring a variety of stores and entertainment options. Don't miss Polished, a charming store 9.7km from Wooster Square.

Recreation

Connecticut Sportsplex, located 8.0km away, offers a vibrant atmosphere for sports enthusiasts. Woolsey Hall, just 966m away, provides an entertaining musical experience. For relaxation, East Rock Park, 3.2km from Wooster Square, is perfect for unwinding amidst nature's beauty.

Adventure

Experience thrilling adventures at Powder Ridge Mountain Park and Resort, located 25.7km from Wooster Square, where you can ski and embrace the winter sports vibes. Enjoy outdoor water sports at Waterski Connecticut, situated 17.7km away, or challenge yourself at Foote Memorial Park Tennis Center, just 9.7km away.

Nightlife

In Wooster Square, the Shubert Theater and Long Wharf Theatre provide captivating performances in a romantic atmosphere, just 0.7 and 1.3km away, respectively. For a family-friendly option, the Lighthouse Point Carousel, located 6.4km away, offers delightful outdoor fun, perfect for a lively evening.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Wooster Square

To save money on your trip to Wooster Square, consider visiting between December and February, when prices are lower compared to the peak months of May and July to August. Book your stay on a Tuesday for the best rates, while Saturdays tend to be the most expensive. Use Expedia to filter accommodations by price and combine hotel reservations with flights for potential savings. Additionally, explore free activities in the area and leverage public transport options to keep costs down. Always check for additional fees and compare prices across rental sites for the best deals.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay around Wooster Square are December to February, where the prices are slightly lower. This is in comparison to May and July to August, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay around Wooster Square is Tuesday. The most expensive day to stay around Wooster Square is Saturday.
  • Find cheap hotels on Expedia: Utilize Expedia’s search tool to customize your options based on your budget, desired location, and preferred hotel style. To find the best deals and lowest prices, simply arrange the price filter from low to high.
  • Consider bundling your trip: You can save money by combining your Wooster Square hotel reservation with your flights and activities through an Expedia package deal.

Find the best attractions near Wooster Square

Wooster Square in New Haven, Connecticut, is an ideal destination for culture enthusiasts, families, and beach lovers. Visitors can explore historic sites, enjoy the urban park, and experience the vibrant local community. Popular attractions include Wooster Square Park, offering a perfect blend of outdoor activities and cultural experiences, making it a great spot for travelers seeking both relaxation and adventure.

  • Yale University: A prestigious institution with stunning Gothic architecture, Yale University offers visitors a glimpse into its rich history and vibrant campus culture. Explore its museums, libraries, and beautiful courtyards, all while soaking in the scholarly atmosphere.
  • Wooster Square: This charming neighborhood is known for its picturesque park and historic Italian heritage. Stroll through the square, enjoy local eateries, and take in the seasonal beauty of cherry blossoms in spring.
  • New Haven Green: A central urban park that serves as a gathering place for families and events. It's perfect for picnics, outdoor concerts, and leisurely walks among historic monuments and lush greenery.

The nearest major airports for your trip to Wooster Square

When planning your visit to Wooster Square in New Haven, Connecticut, you have several airport options. New Haven's Tweed Airport (HVN) is the closest, located only 4.8km away. Nearby hotels include the Omni New Haven Hotel at Yale, The Blake Hotel, and Graduate by Hilton New Haven, all within 4.8km of the airport. Hartford's Bradley International Airport (BDL) is 72.4km away, with hotels like DoubleTree by Hilton Hartford - Bradley Airport, Simsbury 1820 House, and Marriott Hartford Downtown offering comfortable stays. Additionally, White Plains Airport (HPN) is 70.8km away with options like The Opus Westchester and Sonesta White Plains Downtown, providing convenient access to transport services.

Frequently asked questions

What is Wooster Square like?
You'll be sure to have fun visiting New Haven's Wooster Square neighborhood. Consider a visit to Wooster Square as part of your Wooster Square travel plans.
How many hotels will I be able to find in Wooster Square?
If you're searching for places to stay in New Haven, Expedia has something to meet your needs with 21 Wooster Square hotels and other accommodations to choose from.
If I need to cancel my hotel reservation in Wooster Square, will I receive a refund?
Yes! The majority of hotel bookings are refundable if you cancel prior to the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of your check-in date. If you booked a non-refundable reservation, it may still be possible to cancel it and receive a refund within 24 hours of booking. Put your dates in and click on "Search", then you can filter by "fully refundable" to view the best deals available in Wooster Square.
Where can I learn more about changing or cancelling my trip to Wooster Square?
For additional details about updating your trip to Wooster Square or cancelling it, click here.
What is there to do around this New Haven neighborhood?
Wooster Square is an attraction you might want to check out while you're in Wooster Square. When you're sightseeing in New Haven, Thread City Crossing and Connecticut Children's Museum are also worth a stop.

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