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.
Courtyard by Marriott New Haven Orange-Milford
Price was $316, price is now $298 per person
$298
per person
Apr 18 - Apr 20
found 11 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to New Haven (HVN)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and perks like free self parking.
Beechmont - Perfect for Family Retreat!
North End
Save 100% on your flight
Price was $1,704, price is now $898 per person
$898
per person
Mar 12 - Mar 15
found 1 day ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)
This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a communal living room are also on offer.
Madison Beach Hotel
Madison Center
Price was $819, price is now $713 per person
$713
per person
Mar 6 - Mar 8
found 13 hours ago
Roundtrip non-stop flight included
Burbank (BUR) to New Haven (HVN)
This hotel features a private beach, a full-service spa, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Enjoy the gym and perks like free WiFi.
Graduate by Hilton New Haven
Downtown New Haven
Price was $537, price is now $471 per person
$471
per person
Mar 6 - Mar 8
found 13 hours ago
Roundtrip non-stop flight included
Burbank (BUR) to New Haven (HVN)
A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. A coffee shop and luggage storage are also provided.
Cambria Hotel New Haven University Area
West River
Price was $465, price is now $433 per person
$433
per person
Mar 6 - Mar 8
found 13 hours ago
Roundtrip non-stop flight included
Burbank (BUR) 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 lobby fireplace, and a computer station are also offered.
Top Cheshire hotels deals
New Haven Hotel
229 George Street New Haven CT
Free Cancellation
Reserve now, pay when you stay
$103 nightly
The price is $119 total per night
$119 total
Feb 8 - Feb 9
Total with 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
The Capitol Hotel
440 Asylum St Hartford CT
Free Cancellation
Reserve now, pay when you stay
$88 nightly
The price is $102 total per night
$102 total
Jan 25 - Jan 26
Total with 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
Holiday Inn Express Southington by IHG
120 Laning St Southington CT
Free Cancellation
$80 nightly
The price is $92 total per night
$92 total
Feb 20 - Feb 21
Total with 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.
Pool
Breakfast included
Cambria Hotel New Haven University Area
20 Dwight Street New Haven CT
Free Cancellation
$103 nightly
The price is $119 total per night
$119 total
Feb 15 - Feb 16
Total with 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
Hyatt Place Milford / New Haven
190 Old Gate Lane Milford CT
Free Cancellation
Reserve now, pay when you stay
$91 nightly
The price is $105 total per night
$105 total
Jan 28 - Jan 29
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. 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.
Breakfast included
Pet friendly
Omni New Haven Hotel at Yale
155 Temple St New Haven CT
Free Cancellation
Reserve now, pay when you stay
$149 nightly
The price is $172 total per night
$172 total
Feb 11 - Feb 12
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Self parking, a coffee shop, and limo/town car service 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.
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.
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.
Frequently asked questions
Photos of local treasures
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