Search Deals onCheshire Vacation Packages
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Cheshire Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Graduate by Hilton New Haven
Price was $381, price is now $322 per person
$322
per person
Dec 5 - Dec 7
found 1 day ago
Roundtrip non-stop 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.
Beechmont - Perfect for Family Retreat!
Save 100% on your flight
Price was $1,660, price is now $973 per person
$973
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
Madison Beach Hotel
Price was $1,244, price is now $971 per person
$971
per person
Dec 21 - Dec 25
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to New Haven (HVN)
Stay at this 4-star beach hotel in Madison. Enjoy free WiFi, a full-service spa, and a private beach. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Deacon John Grave House and Anna Mia's are located nearby.
Hyatt Place Milford / New Haven
Price was $776, price is now $644 per person
$644
per person
Nov 20 - Nov 24
found 20 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Stay at this 3-star business-friendly hotel in Milford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Westfield Connecticut Post Mall and Milford Plaza Shopping Center are located nearby.
Holiday Inn Express Southington by IHG
Price was $740, price is now $626 per person
$626
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Hyatt Place Uncasville - Casino Area
Price was $473, price is now $400 per person
$400
per person
Dec 6 - Dec 8
found 1 day ago
Roundtrip flight included
Jacksonville (JAX) to New Haven (HVN)
Stay at this 3-star business-friendly hotel in Montville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Mohegan Sun Casino and Mohegan Sun Arena are located nearby.
Hilton Garden Inn Hartford North/Bradley Int'l Airport
Price was $800, price is now $679 per person
$679
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area
Price was $486, price is now $418 per person
$418
per person
Dec 6 - Dec 8
found 1 day ago
Roundtrip flight included
Jacksonville (JAX) to New Haven (HVN)
Stay at this 3-star business-friendly hotel in Montville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Mohegan Sun Casino and Mohegan Sun Arena 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.
Mon, Oct 27 - Fri, Oct 31
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$98 Roundtrip, found 6 days ago
$98
Roundtrip
found 6 days ago
Fri, Oct 24 - Mon, Oct 27
MCO
Orlando Intl.
BDL
Bradley Intl.
$117 Roundtrip, found 15 hours ago
$117
Roundtrip
found 15 hours ago
Tue, Dec 23 - Thu, Jan 1
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$122 Roundtrip, found 2 days ago
$122
Roundtrip
found 2 days ago
Sat, Nov 1 - Sat, Nov 8
ATL
Hartsfield-Jackson Atlanta Intl.
BDL
Bradley Intl.
$128 Roundtrip, found 15 hours ago
$128
Roundtrip
found 15 hours ago
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