Deals on vacations and trips to Cheshire
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Cheshire flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Hartford North/Bradley Int'l Airport
per person
Jul 3 - Jul 6
found 13 hours ago
Roundtrip flight included
Detroit (DTW) to New Haven (HVN)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy free perks like free self parking and an area shuttle.
Hilton Garden Inn Milford
per person
Jun 27 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) to New Haven (HVN)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like free self parking and free WiFi. A 24-hour business center, a lobby fireplace, and express check-out are also on offer.
Luxury Apartments by Hyatus at Pierpont
The Hill
per person
Jun 27 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) to New Haven (HVN)
This aparthotel features a 24-hour gym and a seasonal outdoor pool. Enjoy the a rooftop terrace and perks like free self parking and a free area shuttle. Free WiFi in public areas, a garden, and a lobby fireplace are also on offer.
New Haven Hotel
Downtown New Haven
per person
Jun 27 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) to New Haven (HVN)
A gym, self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the 2 conference rooms, along with dry cleaning/laundry services.
Top Cheshire hotels deals
Holiday Inn Cheshire - Southington by IHG
64 Knotter Dr, Cheshire, CT
Free Cancellation
The price is $114 per night
$114
includes taxes & fees
$99 per night
May 11 - May 12
This hotel features an indoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the in-room fitness and perks like free self parking.
Pool
Parking included
Cheshire Welcome Inn
1106 S Main St., Cheshire, CT
The price is $125 per night
$125
includes taxes & fees
$109 per night
May 11 - May 12
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. The front desk is staffed around-the-clock and laundry facilities are on offer.
Parking included
Free WiFi
New Haven Hotel
229 George Street, New Haven, CT
The price is $136 per night
$136
includes taxes & fees
$118 per night
May 11 - May 12
A gym, self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the 2 conference rooms, along with dry cleaning/laundry services.
Pet friendly
Free WiFi
Clarion Inn
201 Washington Avenue, North Haven, CT
The price is $110 per night
$110
includes taxes & fees
$95 per night
May 14 - May 15
This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the business center, free WiFi in public areas, and airport shuttle. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
Holiday Inn Express Southington by IHG
120 Laning St, Southington, CT
Free Cancellation
The price is $122 per night
$122
includes taxes & fees
$106 per night
Jun 1 - Jun 2
This hotel features a 24-hour gym and a seasonal outdoor pool. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
Cambria Hotel New Haven University Area
20 Dwight Street, New Haven, CT
The price is $146 per night
$146
includes taxes & fees
$127 per night
May 11 - May 12
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a lobby fireplace, and a computer station are also offered.
Pet friendly
Free WiFi
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Popular places to visit
Cheshire Hollow Farm
Enjoy a stop at Cheshire Hollow Farm, an entertaining place to visit in Cheshire. Take in the theater scene in this romantic area.
Roaring Brook Park
Explore the great outdoors at Roaring Brook Park, a lovely green space in Cheshire. Experience the area's entertainment venues and theater scene.
Maplecroft Plaza Shopping Center
You can search for that perfect souvenir at Maplecroft Plaza Shopping Center during your visit to Cheshire. Experience the area's entertainment venues and theater scene.
Photos of local treasures
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