Search Deals on
Windsor Vacation Packages

Build your package with 2 more options

Windsor Flight + Hotel Packages

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
per person
Jun 25 - Jun 29
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.
Residence Inn by Marriott Southington

Residence Inn by Marriott Southington

3 out of 5
per person
Jun 25 - Jun 29
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 Barnes Museum and Southington Public Library are located nearby.
Courtyard by Marriott Southington

Courtyard by Marriott Southington

3 out of 5
per person
Jun 5 - Jun 9
found 1 day ago
Roundtrip non-stop flight included
Las Vegas (LAS) to New Haven (HVN)
Stay at this 3-star business-friendly hotel in Southington. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Crystal Bees and Barnes Museum are located nearby.
Homewood Suites by Hilton Southington, CT

Homewood Suites by Hilton Southington, CT

3 out of 5
per person
Jun 25 - Jun 29
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Stay at this 3-star hotel in Southington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Crystal Bees and Barnes 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
per person
Jun 25 - Jun 29
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 Vintage Radio and Communications Museum of Connecticut and Windsor Historical Society are located nearby.
HYATT house Hartford North/Windsor

HYATT house Hartford North/Windsor

3 out of 5
per person
Jun 25 - Jun 29
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 Vintage Radio and Communications Museum of Connecticut and Windsor Historical Society are located nearby.
Residence Inn by Marriott Hartford/Windsor

Residence Inn by Marriott Hartford/Windsor

3 out of 5
per person
Jun 25 - Jun 29
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 XL Center and Windsor Arts Center are located nearby.
Luxury Apartments by Hyatus at Pierpont

Luxury Apartments by Hyatus at Pierpont

4 out of 5
per person
Jun 6 - Jun 9
found 1 day ago
Roundtrip non-stop flight included
Las Vegas (LAS) 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.

Windsor Vacation Packages 3-4 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
per person
Jun 25 - Jun 29
found 1 day 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 25 - Jun 29
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Homewood Suites by Hilton Southington, CT

Homewood Suites by Hilton Southington, CT

3 out of 5
per person
Jun 25 - Jun 29
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
per person
Jun 25 - Jun 29
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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
Wed, Apr 30 - Sat, May 3
MCO
Orlando Intl.
BDL
Bradley Intl.
$78 Roundtrip, found 6 days ago
$78
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Wed, Apr 30 from Orlando Intl. to Bradley Intl., returning Sat, May 3, priced at $78 found 6 days ago
Spirit Airlines
Fri, May 9 - Sun, May 11
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$84 Roundtrip, found 5 days ago
$84
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Fri, May 9 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Sun, May 11, priced at $84 found 5 days ago
American Airlines
Sat, May 17 - Wed, May 28
CLT
Charlotte-Douglas Intl.
BDL
Bradley Intl.
$145 Roundtrip, found 2 days ago
$145
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, May 17 from Charlotte-Douglas Intl. to Bradley Intl., returning Wed, May 28, priced at $145 found 2 days ago
Frontier Airlines
Thu, May 1 - Sun, May 4
ATL
Hartsfield-Jackson Atlanta Intl.
BDL
Bradley Intl.
$146 Roundtrip, found 3 days ago
$146
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Thu, May 1 from Hartsfield-Jackson Atlanta Intl. to Bradley Intl., returning Sun, May 4, priced at $146 found 3 days ago