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Cheshire Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Clarion Hotel & Suites Hamden - New Haven

Clarion Hotel & Suites Hamden - New Haven

2.5 out of 5
per person
Jun 17 - Jun 21
found 1 day 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 Acme Mall Shopping Center and Putnam Cottage Museum are located nearby.
Hilton Garden Inn Hartford North/Bradley Int'l Airport

Hilton Garden Inn Hartford North/Bradley Int'l Airport

3 out of 5
Save 100% on your flight
per person
Jul 10 - Jul 16
found 13 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Stay at this 3-star business-friendly hotel in Windsor. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Vintage Radio and Communications Museum of Connecticut and Windsor Historical Society are located nearby.
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
Save 100% on your flight
per person
Jul 10 - Jul 16
found 13 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Book a stay at this business-friendly hotel in Southington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Crystal Bees and Hawks Landing Country Club are located nearby.
Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Save 100% on your flight
per person
Jun 17 - Jun 21
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Stay at this 4-star 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 Yale University Art Gallery and Yale Repertory Theater are located nearby.
New Haven Hotel

New Haven Hotel

3.5 out of 5
Save 100% on your flight
per person
Jun 17 - Jun 21
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
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 the convenient parking in our reviews. Popular attractions Shubert Theater and Schubert Performing Arts Center are located nearby.
Hilton Garden Inn Milford

Hilton Garden Inn Milford

3 out of 5
Save 100% on your flight
per person
Jun 17 - Jun 21
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Stay at this 3-star hotel in Milford. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Westfield Connecticut Post Mall and Milford Plaza Shopping Center are located nearby.
Luxury Apartments by Hyatus at Pierpont

Luxury Apartments by Hyatus at Pierpont

4 out of 5
Save 100% on your flight
per person
Jun 17 - Jun 21
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Stay at this 4-star aparthotel in New Haven. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Knights of Columbus Museum and Shubert Theater are located nearby.
Quality Inn

Quality Inn

2 out of 5
per person
Jun 17 - Jun 21
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 free parking. Popular attractions New Haven Harbor and Long Wharf Theatre are located nearby.

Cheshire Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
New Haven Hotel

New Haven Hotel

3.5 out of 5
Downtown New Haven
Save 100% on your flight
per person
Jun 17 - Jun 21
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Hilton Garden Inn Hartford North/Bradley Int'l Airport

Hilton Garden Inn Hartford North/Bradley Int'l Airport

3 out of 5
Save 100% on your flight
per person
Jun 19 - Jun 23
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
Save 100% on your flight
per person
Jun 17 - Jun 21
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Hilton Garden Inn Milford

Hilton Garden Inn Milford

3 out of 5
Save 100% on your flight
per person
Jun 17 - Jun 21
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)

Cheshire Vacation Packages 5-7 Night Stays

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
Save 100% on your flight
per person
Jul 10 - Jul 16
found 13 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Hilton Garden Inn Hartford North/Bradley Int'l Airport

Hilton Garden Inn Hartford North/Bradley Int'l Airport

3 out of 5
Save 100% on your flight
per person
Jul 10 - Jul 16
found 13 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Residence Inn by Marriott Southington

Residence Inn by Marriott Southington

3 out of 5
per person
Jun 4 - Jun 11
found 3 hours ago
Roundtrip non-stop flight included
San Antonio (SAT) to New Haven (HVN)
Residence Inn by Marriott Hartford/Windsor

Residence Inn by Marriott Hartford/Windsor

3 out of 5
per person
Jun 4 - Jun 11
found 3 hours ago
Roundtrip non-stop flight included
San Antonio (SAT) to New Haven (HVN)

Top Flight Deals

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

Spirit Airlines
Sun, May 11 - Sun, May 11
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$96 Roundtrip, found 1 day ago
$96
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sun, May 11 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Sun, May 11, priced at $96 found 1 day ago
Avelo Airlines
Fri, May 9 - Sun, May 11
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$108 Roundtrip, found 2 days ago
$108
Roundtrip
found 2 days ago
Select Avelo Airlines flight, departing Fri, May 9 from Fort Lauderdale - Hollywood Intl. to Tweed - New Haven Regional, returning Sun, May 11, priced at $108 found 2 days ago
Frontier Airlines
Thu, Jun 12 - Sat, Jun 21
MCO
Orlando Intl.
BDL
Bradley Intl.
$109 Roundtrip, found 6 days ago
$109
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Thu, Jun 12 from Orlando Intl. to Bradley Intl., returning Sat, Jun 21, priced at $109 found 6 days ago
American Airlines
Tue, Aug 5 - Tue, Aug 12
CLT
Charlotte-Douglas Intl.
BDL
Bradley Intl.
$145 Roundtrip, found 1 day ago
$145
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Aug 5 from Charlotte-Douglas Intl. to Bradley Intl., returning Tue, Aug 12, priced at $145 found 1 day ago