Wooster Square Vacation Packages for 2026
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Wooster Square Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Quality Suites Stratford
Price was $555, price is now $529 per person
$529
per person
Sep 2 - Sep 5
found 2 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) to New Haven (HVN)
Book a stay at this golf hotel in Stratford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Hartford HealthCare Amphitheater and Perry House are located nearby.
Pool was closed. Pool should always be operational
Reviewed on Jul 22, 2026
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Motel 6 New Haven - Branford, CT
320 E Main St Branford CT
10.71 km from Wooster Square
Stay at this motel in Branford. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
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 ...
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 ...
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 ...
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 Hartford HealthCare Amphitheater ...
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 ...
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 ...
Cambria Hotel New Haven University Area
20 Dwight Street New Haven CT
2.04 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 ...
Hilton Garden Inn Milford
291 Old Gate Lane Milford CT
12.33 km from Wooster Square
Stay at this hotel in Milford. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ...
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. ...
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 ...
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 ...
Hamden Hotel and Suites – Hamden New Haven
2260 Whitney Ave Hamden CT
8.35 km from Wooster Square
Book a stay at this business-friendly hotel in Hamden. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast in our reviews. Popular ...
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.
Fri, Sep 18 - Mon, Sep 21
MYR
Myrtle Beach Intl.
HVN
Tweed - New Haven Regional
$120 Roundtrip, found 3 days ago
$120
Roundtrip
found 3 days ago
Thu, Sep 17 - Sun, Sep 20
MYR
Myrtle Beach Intl.
HVN
Tweed - New Haven Regional
$130 Roundtrip, found 3 days ago
$130
Roundtrip
found 3 days ago
Thu, Sep 10 - Thu, Sep 24
GSP
Greenville-Spartanburg Intl.
HVN
Tweed - New Haven Regional
$135 Roundtrip, found 3 days ago
$135
Roundtrip
found 3 days ago
Thu, Sep 17 - Sat, Sep 19
MYR
Myrtle Beach Intl.
HVN
Tweed - New Haven Regional
$140 Roundtrip, found 1 day ago
$140
Roundtrip
found 1 day ago