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Cheshire Vacation Packages

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Cheshire 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
Price was $618, price is now $475 per person
$475
per person
Dec 7 - Dec 14
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

Hilton Garden Inn Hartford North/Bradley Int'l Airport

3 out of 5
Save 100% on your flight
Price was $810, price is now $600 per person
$600
per person
Dec 7 - Dec 14
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 Northwest Park are located nearby.
Hampton Inn Hartford/Airport

Hampton Inn Hartford/Airport

2.5 out of 5
Price was $756, price is now $613 per person
$613
per person
Dec 7 - Dec 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Book a stay at this business-friendly hotel in Windsor. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Northwest Park and Connecticut Fallen Firefighters Memorial are located nearby.
Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
Price was $3,741, price is now $3,057 per person
$3,057
per person
Dec 7 - Dec 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Stay at this 5-star luxury vacation home in Bridgeport. Enjoy free WiFi, free parking, and a garden. Popular attractions Svihra Park and Glenwood Park are located nearby.
Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Price was $962, price is now $796 per person
$796
per person
Dec 7 - Dec 14
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 Harkness Tower and White Space Gallery are located nearby.
Homewood Suites by Hilton Wallingford-Meriden

Homewood Suites by Hilton Wallingford-Meriden

3 out of 5
Price was $973, price is now $832 per person
$832
per person
Dec 7 - Dec 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Stay at this 3-star business-friendly hotel in Wallingford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions United House Wrecking, Inc. and YMCA Mountain Mist Day Outdoor Center are located nearby.
Hilton Garden Inn Wallingford/Meriden

Hilton Garden Inn Wallingford/Meriden

3 out of 5
Price was $959, price is now $822 per person
$822
per person
Dec 7 - Dec 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Stay at this 3-star business-friendly hotel in Wallingford. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions United House Wrecking, Inc. and YMCA Mountain Mist Day Outdoor Center are located nearby.
La Quinta Inn & Suites by Wyndham New Haven

La Quinta Inn & Suites by Wyndham New Haven

3 out of 5
Price was $787, price is now $675 per person
$675
per person
Dec 7 - Dec 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Stay at this 3-star 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 Wooster Square are located nearby.

Cheshire Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Wallingford/Meriden

Hilton Garden Inn Wallingford/Meriden

3 out of 5
Price was $416, price is now $357 per person
$357
per person
Dec 11 - Dec 14
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
Price was $510, price is now $412 per person
$412
per person
Jan 30 - Feb 2
found 1 day ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Price was $437, price is now $359 per person
$359
per person
Dec 11 - Dec 14
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
Price was $508, price is now $429 per person
$429
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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
Price was $618, price is now $475 per person
$475
per person
Dec 7 - Dec 14
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
Price was $810, price is now $600 per person
$600
per person
Dec 7 - Dec 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Hampton Inn Hartford/Airport

Hampton Inn Hartford/Airport

2.5 out of 5
Price was $756, price is now $613 per person
$613
per person
Dec 7 - Dec 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
Price was $3,741, price is now $3,057 per person
$3,057
per person
Dec 7 - Dec 14
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.

Frontier Airlines
Sat, Nov 15 - Thu, Nov 20
ATL
Hartsfield-Jackson Atlanta Intl.
BDL
Bradley Intl.
$64 Roundtrip, found 2 days ago
$64
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, Nov 15 from Hartsfield-Jackson Atlanta Intl. to Bradley Intl., returning Thu, Nov 20, priced at $64 found 2 days ago
Breeze Airways
Tue, Nov 18 - Sat, Nov 22
MCO
Orlando Intl.
BDL
Bradley Intl.
$109 Roundtrip, found 4 days ago
$109
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Tue, Nov 18 from Orlando Intl. to Bradley Intl., returning Sat, Nov 22, priced at $109 found 4 days ago
Breeze Airways
Thu, Dec 11 - Sun, Dec 14
TPA
Tampa Intl.
HVN
Tweed - New Haven Regional
$118 Roundtrip, found 1 day ago
$118
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Dec 11 from Tampa Intl. to Tweed - New Haven Regional, returning Sun, Dec 14, priced at $118 found 1 day ago
Breeze Airways
Thu, Nov 13 - Sun, Nov 16
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$125 Roundtrip, found 6 days ago
$125
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Nov 13 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Nov 16, priced at $125 found 6 days ago