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.
Omni New Haven Hotel at Yale
Downtown New Haven
Price was $554, price is now $449 per person
$449
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip flight included
Chicago (ORD) to New Haven (HVN)
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.
New Haven Hotel
Downtown New Haven
Price was $607, price is now $469 per person
$469
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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.
Madison Beach Hotel
Madison Center
Save 100% on your flight
Price was $1,491, price is now $1,158 per person
$1,158
per person
Jul 7 - Jul 10
found 1 day ago
Roundtrip flight included
Chicago (ORD) to New Haven (HVN)
This smoke-free 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.
Pier Blue Inn Old Saybrook - Essex
Saybrook Manor
Price was $595, price is now $468 per person
$468
per person
Aug 19 - Aug 22
found 21 hours ago
Roundtrip flight included
Houston (IAH) to New Haven (HVN)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including an off-leash area. A picnic area and barbecue grills are also provided.
Beechmont - Perfect for Family Retreat!
North End
Save 100% on your flight
Price was $1,341, price is now $1,113 per person
$1,113
per person
Jul 14 - Jul 16
found 12 hours ago
Roundtrip flight included
Chicago (ORD) 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.
Top Cheshire hotels deals
Cheshire Welcome Inn
1106 S Main St. Cheshire CT
Free Cancellation
Reserve now, pay when you stay
$99 nightly
The price is $114 total per night
$114 total
Jun 7 - Jun 8
Total with 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
$106 nightly
The price is $122 total per night
$122 total
Jun 7 - Jun 8
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
$94 nightly
The price is $108 total per night
$108 total
Jul 5 - Jul 6
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
Motel 6 Wethersfield, CT - Hartford
1341 Silas Deane Hwy Wethersfield CT
Free Cancellation
Reserve now, pay when you stay
$71 nightly
The price is $82 total per night
$82 total
Jun 7 - Jun 8
Total with 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.
Pet friendly
Parking included
Omni New Haven Hotel at Yale
155 Temple St New Haven CT
Free Cancellation
Reserve now, pay when you stay
$142 nightly
The price is $163 total per night
$163 total
Jul 2 - Jul 3
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
New Haven Hotel
229 George Street New Haven CT
Free Cancellation
Reserve now, pay when you stay
$124 nightly
The price is $143 total per night
$143 total
Jun 14 - Jun 15
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
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
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.
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.
Frequently asked questions
Photos of local treasures
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