Wooster Square Vacation Packages for 2026
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Top Hotel Deals
New Haven Hotel
229 George Street New Haven CT
1.21 km from Wooster Square
Book a stay at this business-friendly hotel in New Haven. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and ...
Omni New Haven Hotel at Yale
155 Temple St New Haven CT
1.05 km from Wooster Square
Book a stay at this business-friendly hotel in New Haven. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the helpful ...
Hilton Garden Inn Shelton
25 Old Stratford Rd Shelton CT
17.43 km from Wooster Square
Book a stay at this business-friendly hotel in Shelton. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Hyatt Place Milford / New Haven
190 Old Gate Lane Milford CT
12.67 km from Wooster Square
Book a stay at this business-friendly hotel in Milford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Courtyard by Marriott Waterbury Downtown
63 Grand St Waterbury CT
29.49 km from Wooster Square
Stay at this hotel in Waterbury. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Best Western Executive Hotel Of New Haven - West Haven
490 Saw Mill Rd West Haven CT
6.43 km from Wooster Square
Book a stay at this business-friendly hotel in West Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
La Quinta Inn & Suites by Wyndham New Haven
400 Sargent Dr New Haven CT
1.28 km from Wooster Square
Book a stay at this business-friendly hotel in New Haven. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the helpful ...
Courtyard by Marriott New Haven Orange-Milford
136 Marsh Hill Rd Orange CT
8.99 km from Wooster Square
Book a stay at this business-friendly hotel in Orange. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
Hotel Marcel New Haven, Tapestry Collection By Hilton
500 Sargent Drive New Haven CT
1.03 km from Wooster Square
Book a stay at this business-friendly hotel in New Haven. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Motel 6 Milford, CT
111 Schoolhouse Road Milford CT
17.67 km from Wooster Square
Book a stay at this business-friendly motel in Milford. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Silver Sands State Park ...
Trumbull Marriott Shelton
180 Hawley Ln Trumbull CT
21.11 km from Wooster Square
Stay at this hotel in Trumbull. Enjoy an outdoor pool, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
Wyndham Southbury
1284 Strongtown Road Southbury CT
29.57 km from Wooster Square
Book a stay at this business-friendly hotel in Southbury. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Clarion Inn North Haven - New Haven North
201 Washington Avenue North Haven CT
11.89 km from Wooster Square
Book a stay at this business-friendly hotel in North Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Mon, Jun 15 - Thu, Jun 18
ORD
O'Hare Intl.
HVN
Tweed - New Haven Regional
$254 Roundtrip, found 1 day ago
$254
Roundtrip
found 1 day ago