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.
Pier Blue Inn Old Saybrook - Essex
Saybrook Manor
Price was $551, price is now $423 per person
$423
per person
Jun 19 - Jun 21
found 16 hours ago
Roundtrip flight included
Fort Myers (RSW) 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 $4,256, price is now $2,540 per person
$2,540
per person
Jul 1 - Jul 8
found 24 hours ago
Roundtrip flight included
Miami (MIA) 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
Save 100% on your flight
Price was $1,445, price is now $1,048 per person
$1,048
per person
Jun 19 - Jun 21
found 16 hours ago
Roundtrip flight included
Fort Myers (RSW) 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.
Hyatus Luxury Residences City Crossing
The Hill
Save 100% on your flight
Price was $1,660, price is now $1,367 per person
$1,367
per person
May 15 - May 17
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to New Haven (HVN)
This aparthotel features a 24-hour gym and a seasonal outdoor pool. Traveling for business? Take advantage of the free WiFi in public areas, laundry service, and conference center. Enjoy the a rooftop terrace and perks like free self parking and a free area shuttle.
Clarion Inn North Haven - New Haven North
Price was $632, price is now $562 per person
$562
per person
Jun 11 - Jun 15
found 1 day ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)
A restaurant and a 24-hour gym are featured at this hotel. 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.
Top Cheshire hotels deals
New Haven Hotel
229 George Street New Haven CT
Free Cancellation
Reserve now, pay when you stay
$105 nightly
The price is $121 total per night
$121 total
May 3 - May 4
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
Holiday Inn Express Southington by IHG
120 Laning St Southington CT
Free Cancellation
Reserve now, pay when you stay
$100 nightly
The price is $115 total per night
$115 total
Apr 19 - Apr 20
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
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
Apr 21 - Apr 22
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
Omni New Haven Hotel at Yale
155 Temple St New Haven CT
Free Cancellation
Reserve now, pay when you stay
$163 nightly
The price is $187 total per night
$187 total
Apr 22 - Apr 23
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
Hyatt Place Milford / New Haven
190 Old Gate Lane Milford CT
Free Cancellation
Reserve now, pay when you stay
$118 nightly
The price is $136 total per night
$136 total
Apr 26 - Apr 27
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
Hampton Inn & Suites Hartford/East Hartford
351 Pitkin Steet East Hartford CT
Free Cancellation
Reserve now, pay when you stay
$114 nightly
The price is $131 total per night
$131 total
Apr 26 - Apr 27
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. There's no skimping on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. A 24-hour business center, a lobby fireplace, and express check-in are also on offer.
Pool
Breakfast included
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.
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.
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
Browse Cheshire vacation photos for more inspiration
