Search Deals onCheshire 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
Price was $225, price is now $184 per person
$184
per person
Dec 5 - Dec 7
found 1 day ago
Roundtrip non-stop 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.
Hyatt Place Milford / New Haven
Price was $1,035, price is now $726 per person
$726
per person
Nov 23 - Nov 30
found 4 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.
Graduate by Hilton New Haven
Price was $1,068, price is now $793 per person
$793
per person
Nov 23 - Nov 30
found 4 hours 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.
Luxury Furnished Apartments by Hyatus Downtown at Yale
Save 100% on your flight
Price was $1,343, price is now $1,029 per person
$1,029
per person
Nov 23 - Nov 30
found 4 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Enjoy free WiFi, free parking, and a rooftop terrace. Popular attractions Shubert Theater and White Space Gallery are located nearby.
Omni New Haven Hotel at Yale
Price was $1,092, price is now $864 per person
$864
per person
Nov 23 - Nov 30
found 4 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Stay at this 4-star business-friendly hotel in New Haven. Enjoy 2 restaurants, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Shubert Theater and New Haven Green are located nearby.
Cambria Hotel New Haven University Area
Price was $813, price is now $656 per person
$656
per person
Nov 23 - Nov 30
found 4 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Stay at this 3-star business-friendly hotel in New Haven. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions White Space Gallery and Shubert Theater are located nearby.
Hilton Garden Inn Hartford North/Bradley Int'l Airport
Price was $256, price is now $209 per person
$209
per person
Dec 5 - Dec 7
found 1 day ago
Roundtrip non-stop 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.
Holiday Inn Cheshire - Southington by IHG
Price was $546, price is now $453 per person
$453
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
Stay at this 3-star business-friendly hotel in Southington. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Panthorn Park and Cheshire Hollow Farm 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.
Fri, Oct 31 - Mon, Nov 3
MCO
Orlando Intl.
BDL
Bradley Intl.
$64 Roundtrip, found 3 hours ago
$64
Roundtrip
found 3 hours ago
Fri, Oct 24 - Mon, Oct 27
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$112 Roundtrip, found 5 days ago
$112
Roundtrip
found 5 days ago
Thu, Dec 11 - Sun, Dec 14
TPA
Tampa Intl.
HVN
Tweed - New Haven Regional
$118 Roundtrip, found 3 days ago
$118
Roundtrip
found 3 days ago
Thu, Dec 4 - Thu, Dec 11
DEN
Denver Intl.
BDL
Bradley Intl.
$120 Roundtrip, found 5 days ago
$120
Roundtrip
found 5 days ago
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