Deals on vacations and trips to Cheshire
Save when you book Cheshire package deals
Cheshire flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
Saybrook Point Resort & Marina
Old Saybrook Center
Save 100% on your flight
per person
Jul 11 - Jul 16
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
A full-service spa, a marina, and 2 outdoor pools are all featured at this smoke-free hotel. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and free train station pick-up. Unwind with a drink at one of the 2 bars/lounges and enjoy free perks like free self parking and a shopping center shuttle.
Hilton Garden Inn Hartford North/Bradley Int'l Airport
per person
Jul 8 - Jul 13
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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.
James Pharmacy Bed & Breakfast
Old Saybrook Center
Save 100% on your flight
per person
Jul 11 - Jul 16
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
This bed & breakfast features free self parking and free WiFi in public areas. Enjoy the free local cuisine breakfast each morning. A garden and express check-out are also provided.
Top Cheshire hotels deals
Holiday Inn Cheshire - Southington by IHG
64 Knotter Dr, Cheshire, CT
Free Cancellation
$101 nightly
The price is $116 total per night
$116 total
Jun 15 - Jun 16
Total includes taxes and fees
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
$98 nightly
The price is $113 total per night
$113 total
Jun 25 - Jun 26
Total includes taxes and fees
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
Free Cancellation
Reserve now, pay when you stay
$129 nightly
The price is $149 total per night
$149 total
Jun 30 - Jul 1
Total includes taxes and fees
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
Free Cancellation
Reserve now, pay when you stay
$93 nightly
The price is $107 total per night
$107 total
Jun 22 - Jun 23
Total includes taxes and fees
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
The Capitol Hotel
440 Asylum St, Hartford, CT
Free Cancellation
Reserve now, pay when you stay
$84 nightly
The price is $97 total per night
$97 total
Jun 20 - Jun 21
Total includes taxes and fees
This hotel doesn't skimp on freebies - guests receive free full breakfast and free WiFi. Traveling on business? Take advantage of the 2 conference rooms, business center, and express check-out. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and laundry facilities.
Breakfast included
Pet friendly
La Quinta Inn & Suites by Wyndham New Haven
400 Sargent Dr, New Haven, CT
Free Cancellation
Reserve now, pay when you stay
$96 nightly
The price is $111 total per night
$111 total
Jun 22 - Jun 23
Total includes taxes and fees
A restaurant and a bar/lounge are featured at this hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
Breakfast included
Pet friendly
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
Barker Character, Comic and Cartoon Museum
You can take time to visit Barker Character, Comic and Cartoon Museum during your travels to Cheshire. Experience the entertainment venues and theater scene in this romantic area.
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.
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Photos of local treasures
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