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.
Hilton Garden Inn Hartford North/Bradley Int'l Airport
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
San Juan (SJU) 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.
Saybrook Point Resort & Marina
Old Saybrook Center
Save 100% on your flight
per person
Sep 20 - Sep 23
found 1 day ago
Roundtrip flight included
Raleigh (RDU) 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.
Hampton Inn Hartford/Airport
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Guests will appreciate freebies like buffet breakfast and free self parking.
Courtyard by Marriott Southington
per person
Oct 5 - Oct 8
found 17 hours ago
Roundtrip non-stop flight included
Houston (IAH) to New Haven (HVN)
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 garden, and dry cleaning are also offered.
James Pharmacy Bed & Breakfast
Old Saybrook Center
Save 100% on your flight
per person
Sep 20 - Sep 23
found 1 day ago
Roundtrip flight included
Raleigh (RDU) 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
$107 nightly
The price is $123 total per night
$123 total
Sep 7 - Sep 8
Total includes taxes and fees
This hotel features an indoor pool, a hot tub, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.
Pool
Hot Tub
Cheshire Welcome Inn
1106 S Main St., Cheshire, CT
$109 nightly
The price is $125 total per night
$125 total
Aug 17 - Aug 18
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
The Capitol Hotel
440 Asylum St, Hartford, CT
Free Cancellation
Reserve now, pay when you stay
$76 nightly
The price is $88 total per night
$88 total
Aug 27 - Aug 28
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.
Holiday Inn Express Southington by IHG
120 Laning St, Southington, CT
Free Cancellation
$112 nightly
The price is $129 total per night
$129 total
Aug 31 - Sep 1
Total includes taxes and fees
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.
Cambria Hotel New Haven University Area
20 Dwight Street, New Haven, CT
Free Cancellation
Reserve now, pay when you stay
$118 nightly
The price is $136 total per night
$136 total
Sep 1 - Sep 2
Total includes taxes and fees
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
Best Western Executive Hotel Of New Haven - West Haven
490 Saw Mill Rd, West Haven, CT
Free Cancellation
Reserve now, pay when you stay
$105 nightly
The price is $120 total per night
$120 total
Aug 18 - Aug 19
Total includes taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like full breakfast and free self parking.
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.
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 Golf Course
Enjoy a round of golf in Cheshire at Cheshire Golf Course. Experience the entertainment venues and theater scene in this romantic area.
Frequently asked questions
Photos of local treasures
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