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Wooster Square Vacation Packages

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Wooster Square Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Cheshire - Southington by IHG

Holiday Inn Cheshire - Southington by IHG

3 out of 5
Price was $503, price is now $394 per person
$394
per person
Dec 30 - Jan 4
found 2 days ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Book a stay at this business-friendly hotel in Southington. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Panthorn Park and Cheshire Hollow Farm are located nearby.
The Blake Hotel

The Blake Hotel

4 out of 5
Downtown New Haven
Price was $927, price is now $686 per person
$686
per person
Dec 30 - Jan 4
found 2 days ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Book a stay at this business-friendly hotel in New Haven. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Shubert Theater and White Space Gallery are located nearby.
New Haven Hotel

New Haven Hotel

3.5 out of 5
Downtown New Haven
Price was $625, price is now $476 per person
$476
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
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 the convenient parking in our reviews. Popular attractions Shubert Theater and White Space Gallery are located nearby.
Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Price was $675, price is now $515 per person
$515
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Stay at this hotel in New Haven. Enjoy free WiFi, breakfast (surcharge), and free bicycles on site. Our guests praise the helpful staff and the comfy rooms in our reviews. Popular attractions Art Plus Studio and White Space Gallery are located nearby.
Hampton Inn & Suites New Haven - South - West Haven

Hampton Inn & Suites New Haven - South - West Haven

2.5 out of 5
Price was $606, price is now $475 per person
$475
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Book a stay at this business-friendly hotel in West Haven. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Seabluff Beach and Bradley Point Beach are located nearby.
Hamden Hotel and Suites – Hamden New Haven

Hamden Hotel and Suites – Hamden New Haven

2.5 out of 5
Price was $519, price is now $411 per person
$411
per person
Dec 30 - Jan 4
found 2 days ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
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 attractions Laurel View Country Club and Putnam Place Shopping Center are located nearby.
Clarion Inn

Clarion Inn

3 out of 5
Price was $529, price is now $419 per person
$419
per person
Dec 30 - Jan 4
found 2 days ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
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 staff in our reviews. Popular attractions Quinnipiac River State Park and Wharton Brook State Park are located nearby.
La Quinta Inn & Suites by Wyndham New Haven

La Quinta Inn & Suites by Wyndham New Haven

3 out of 5
Long Wharf
Price was $572, price is now $454 per person
$454
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
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 staff in our reviews. Popular attractions Long Wharf Theatre and Knights of Columbus Museum are located nearby.

3-4 Night Vacations in Wooster Square

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
Price was $530, price is now $441 per person
$441
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
Residence Inn by Marriott Southington

Residence Inn by Marriott Southington

3 out of 5
Price was $700, price is now $541 per person
$541
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
Hyatt Place Uncasville - Casino Area

Hyatt Place Uncasville - Casino Area

3 out of 5
Price was $872, price is now $701 per person
$701
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
Microtel Inn & Suites by Wyndham Uncasville Casino Area

Microtel Inn & Suites by Wyndham Uncasville Casino Area

2.5 out of 5
Price was $824, price is now $677 per person
$677
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)

5-7 Night Vacations in Wooster Square

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Cheshire - Southington by IHG

Holiday Inn Cheshire - Southington by IHG

3 out of 5
Price was $503, price is now $394 per person
$394
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
The Blake Hotel

The Blake Hotel

4 out of 5
Downtown New Haven
Price was $928, price is now $687 per person
$687
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
New Haven Hotel

New Haven Hotel

3.5 out of 5
Downtown New Haven
Price was $625, price is now $476 per person
$476
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Price was $675, price is now $515 per person
$515
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)

Cheap Hotel Deals in Wooster Square

New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street New Haven CT
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 ...
Opens in a new windowNew Haven Hotel
Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
20 Dwight Street New Haven CT
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 ...
Opens in a new windowCambria Hotel New Haven University Area
Wyndham Southbury

Wyndham Southbury

3 out of 5
1284 Strongtown Road Southbury CT
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 ...
Opens in a new windowWyndham Southbury
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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
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 ...
Opens in a new windowHotel Marcel New Haven, Tapestry Collection By Hilton
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
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 ...
Opens in a new windowBest Western Executive Hotel Of New Haven - West Haven
Trumbull Marriott Shelton

Trumbull Marriott Shelton

3.5 out of 5
180 Hawley Ln Trumbull CT
Stay at this hotel in Trumbull. Enjoy free parking, an outdoor pool, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Opens in a new windowTrumbull Marriott Shelton
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
155 Temple St New Haven CT
Book a stay at this business-friendly hotel in New Haven. Enjoy 2 restaurants, breakfast (surcharge), and room service. Our guests praise the helpful staff and ...
Opens in a new windowOmni New Haven Hotel at Yale
Hilton Garden Inn Shelton

Hilton Garden Inn Shelton

3 out of 5
25 Old Stratford Rd Shelton CT
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 ...
Opens in a new windowHilton Garden Inn Shelton
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

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Breeze Airways
Wed, Nov 26 - Sun, Dec 7
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$819 Roundtrip, found 4 days ago
$819
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Wed, Nov 26 from Fort Lauderdale - Hollywood Intl. to Tweed - New Haven Regional, returning Sun, Dec 7, priced at $819 found 4 days ago
Breeze Airways
Wed, Nov 26 - Thu, Dec 4
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$860 Roundtrip, found 4 days ago
$860
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Wed, Nov 26 from Fort Lauderdale - Hollywood Intl. to Tweed - New Haven Regional, returning Thu, Dec 4, priced at $860 found 4 days ago
Breeze Airways
Wed, Nov 26 - Fri, Dec 5
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$861 Roundtrip, found 4 days ago
$861
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Wed, Nov 26 from Fort Lauderdale - Hollywood Intl. to Tweed - New Haven Regional, returning Fri, Dec 5, priced at $861 found 4 days ago
Breeze Airways
Mon, Nov 24 - Sun, Dec 7
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$1,004 Roundtrip, found 4 days ago
$1,004
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Mon, Nov 24 from Fort Lauderdale - Hollywood Intl. to Tweed - New Haven Regional, returning Sun, Dec 7, priced at $1,004 found 4 days ago