Wooster Square Vacation Packages for 2025

Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*

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Top Hotel Deals

New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street, New Haven, CT
1.21 km from Wooster Square
Stay at this 3.5-star business-friendly hotel in New Haven. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff and ...
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
6.38 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 ...
Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

2 out of 5
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. ...
Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

3 out of 5
190 Old Gate Lane, Milford, CT
12.67 km from Wooster Square
Stay at this 3-star business-friendly hotel in Milford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Wyndham Southbury

Wyndham Southbury

3 out of 5
1284 Strongtown Road, Southbury, CT
29.57 km from Wooster Square
Stay at this 3-star business-friendly hotel in Southbury. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
La Quinta Inn & Suites by Wyndham New Haven

La Quinta Inn & Suites by Wyndham New Haven

3 out of 5
400 Sargent Dr, New Haven, CT
1.28 km from Wooster Square
Stay at this 3-star business-friendly hotel in New Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Hilton Garden Inn Shelton

Hilton Garden Inn Shelton

3 out of 5
25 Old Stratford Rd, Shelton, CT
17.43 km from Wooster Square
Stay at this 3-star business-friendly hotel in Shelton. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
The Blake Hotel

The Blake Hotel

4 out of 5
9 High Street, New Haven, CT
1.39 km from Wooster Square
Stay at this 4-star business-friendly hotel in New Haven. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the bar and the helpful staff ...
Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
20 Dwight Street, New Haven, CT
2.04 km from Wooster Square
Stay at this 3-star business-friendly hotel in New Haven. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and ...
Clarion Inn

Clarion Inn

3 out of 5
201 Washington Avenue, North Haven, CT
11.9 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 ...
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
155 Temple St, New Haven, CT
1.05 km from Wooster Square
Stay at this 4-star business-friendly hotel in New Haven. Enjoy 2 restaurants, breakfast (surcharge), and room service. Our guests praise the helpful staff and ...
Courtyard by Marriott Waterbury Downtown

Courtyard by Marriott Waterbury Downtown

3 out of 5
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. ...
Hotel Marcel New Haven, Tapestry Collection By Hilton

Hotel Marcel New Haven, Tapestry Collection By Hilton

4 out of 5
500 Sargent Drive, New Haven, CT
1.04 km from Wooster Square
Stay at this 4-star business-friendly hotel in New Haven. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Quality Inn

Quality Inn

2 out of 5
7 Kimberly Ave, West Haven, CT
3.4 km from Wooster Square
Book a stay at this business-friendly hotel in West Haven. Enjoy free breakfast, free WiFi, and free parking. Popular attractions New Haven Harbor and Long Wharf ...
Home2 Suites by Hilton East Haven New Haven

Home2 Suites by Hilton East Haven New Haven

3 out of 5
30 Frontage Rd, East Haven, CT
3.85 km from Wooster Square
Stay at this 3-star business-friendly inn in East Haven. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Shoreline Trolley Museum and ...
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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.

Breeze Airways
Mon, Aug 25 - Thu, Sep 11
GSP
Greenville-Spartanburg Intl.
HVN
Tweed - New Haven Regional
$460 Roundtrip, found 2 days ago
$460
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Mon, Aug 25 from Greenville-Spartanburg Intl. to Tweed - New Haven Regional, returning Thu, Sep 11, priced at $460 found 2 days ago
Breeze Airways
Fri, Aug 29 - Thu, Sep 11
GSP
Greenville-Spartanburg Intl.
HVN
Tweed - New Haven Regional
$469 Roundtrip, found 2 days ago
$469
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Aug 29 from Greenville-Spartanburg Intl. to Tweed - New Haven Regional, returning Thu, Sep 11, priced at $469 found 2 days ago
Breeze Airways
Fri, Aug 22 - Thu, Sep 4
GSP
Greenville-Spartanburg Intl.
HVN
Tweed - New Haven Regional
$478 Roundtrip, found 2 days ago
$478
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Aug 22 from Greenville-Spartanburg Intl. to Tweed - New Haven Regional, returning Thu, Sep 4, priced at $478 found 2 days ago
Breeze Airways
Mon, Jul 28 - Sun, Aug 3
GSP
Greenville-Spartanburg Intl.
HVN
Tweed - New Haven Regional
$488 Roundtrip, found 2 days ago
$488
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Mon, Jul 28 from Greenville-Spartanburg Intl. to Tweed - New Haven Regional, returning Sun, Aug 3, priced at $488 found 2 days ago