Search Deals onCheshire Vacation Packages
Photo by Tai Bui
Cheshire Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

Holiday Inn Express Southington by IHG
per person
Oct 3 - Oct 6
found 1 day 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.

Hilton Garden Inn Hartford North/Bradley Int'l Airport
Save 100% on your flight
per person
Oct 3 - Oct 6
found 1 day 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 Windsor Arts Center and Oliver Ellsworth Homestead are located nearby.

Residence Inn by Marriott New Haven Hamden
Save 100% on your flight
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Stay at this 3-star business-friendly hotel in Hamden. Enjoy free breakfast, free parking, and a 24-hour front desk. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Laurel View Country Club and Acme Mall Shopping Center are located nearby.

Residence Inn by Marriott Southington
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Stay at this 3-star business-friendly hotel in Southington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Lake Compounce and Barnes Museum are located nearby.

Residence Inn by Marriott Hartford/Windsor
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Stay at this 3-star business-friendly hotel in Windsor. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Xfinity Theatre and Windsor Arts Center are located nearby.

HYATT house Hartford North/Windsor
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Stay at this 3-star business-friendly hotel in Windsor. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Windsor Arts Center and Oliver Ellsworth Homestead are located nearby.

Economy Inn
per person
Oct 23 - Oct 29
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to New Haven (HVN)
Book a stay at this family-friendly hotel in East Hartford. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Xfinity Theatre and East Hartford Shopping Center are located nearby.

Comfort Inn & Suites East Hartford - Hartford
per person
Oct 23 - Oct 29
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to New Haven (HVN)
Book a stay at this business-friendly hotel in East Hartford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Xfinity Theatre and Rentschler Field are located nearby.
Cheshire Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.



Cheshire Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.



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

Thu, Aug 28 - Sun, Aug 31
MCO
Orlando Intl.
BDL
Bradley Intl.
$92 Roundtrip, found 1 day ago
$92
Roundtrip
found 1 day ago

Fri, Sep 5 - Fri, Sep 12
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$98 Roundtrip, found 16 hours ago
$98
Roundtrip
found 16 hours ago

Thu, Sep 18 - Thu, Sep 25
ATL
Hartsfield-Jackson Atlanta Intl.
BDL
Bradley Intl.
$109 Roundtrip, found 3 days ago
$109
Roundtrip
found 3 days ago

Tue, Sep 30 - Tue, Sep 30
ORD
O'Hare Intl.
BDL
Bradley Intl.
$132 Roundtrip, found 5 hours ago
$132
Roundtrip
found 5 hours ago
Discover Other Travel Deals
- Cheshire Hollow Farm Vacations
- Barker Character Vacations
- Cheshire Golf Course Vacations
- Roaring Brook Park Vacations
- Bartlem Park Vacations
- Maplecroft Plaza Shopping Center Vacations
- Quinnipiac Recreation Area Vacations
- Drazen Orchards Vacations
- Yale University Vacations
- Connecticut Convention Center Vacations
- Yale-New Haven Hospital Vacations
- Quinnipiac University Vacations
- Las Vegas Vacations
- Cancun Vacations
- Miami Vacations
- Corona Vacations
- Cabo San Lucas Vacations
- Disneyland Park Vacations
- New York Vacations
- Honolulu Vacations
- Los Angeles Vacations
- Maui Vacations
- Orlando Vacations
- New Orleans Vacations
- Canada Vacations
- Tulum Vacations
- Bali Vacations
- Maldives Vacations
- Clearwater Beach Vacations
- Denver Vacations
- South Beach Vacations
- Key West Vacations
Car Rentals in Cheshire
- Car rentals in New Haven
- Car rentals in Hartford
- Car rentals in Milford
- Car rentals in Madison
- Car rentals in Shelton
- Car rentals in Waterbury
- Car rentals in Branford
- Car rentals in Meriden
- Car rentals in Stratford
- Car rentals in West Haven
- Car rentals in Coastal Connecticut
- Car rentals in East Hartford