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.
New Haven Hotel
Downtown New Haven
Price was $468, price is now $365 per person
$365
per person
Apr 30 - May 3
found 1 day ago
Roundtrip flight included
Raleigh (RDU) 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.
Beechmont - Perfect for Family Retreat!
North End
Save 100% on your flight
Price was $1,942, price is now $1,286 per person
$1,286
per person
Apr 10 - Apr 13
found 21 hours ago
Roundtrip flight included
Raleigh (RDU) 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.
Graduate by Hilton New Haven
Downtown New Haven
Save 100% on your flight
Price was $865, price is now $620 per person
$620
per person
Apr 30 - May 3
found 1 day ago
Roundtrip flight included
Raleigh (RDU) 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.
Luxury Apartments by Hyatus at Pierpont
The Hill
Save 100% on your flight
Price was $888, price is now $667 per person
$667
per person
Apr 30 - May 3
found 1 day ago
Roundtrip flight included
Raleigh (RDU) 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.
Luxury Furnished Apartments by Hyatus Downtown at Yale
The Hill
Save 100% on your flight
Price was $705, price is now $549 per person
$549
per person
Apr 10 - Apr 13
found 21 hours ago
Roundtrip flight included
Raleigh (RDU) to New Haven (HVN)
This aparthotel features a gym and a rooftop terrace. Guests will appreciate free perks like free self parking and WiFi in public areas. A garden, express check-out, and dry cleaning are also on offer.
Top Cheshire hotels deals
New Haven Hotel
229 George Street New Haven CT
Free Cancellation
Reserve now, pay when you stay
$118 nightly
The price is $136 total per night
$136 total
Feb 22 - Feb 23
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
Mar 1 - Mar 2
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
Cambria Hotel New Haven University Area
20 Dwight Street New Haven CT
Free Cancellation
$119 nightly
The price is $137 total per night
$137 total
Mar 15 - Mar 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
Hampton Inn & Suites Hartford/East Hartford
351 Pitkin Steet East Hartford CT
Free Cancellation
Reserve now, pay when you stay
$100 nightly
The price is $115 total per night
$115 total
Feb 22 - Feb 23
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.
Omni New Haven Hotel at Yale
155 Temple St New Haven CT
Free Cancellation
Reserve now, pay when you stay
$152 nightly
The price is $175 total per night
$175 total
Feb 22 - Feb 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
Holiday Inn Express Southington by IHG
120 Laning St Southington CT
Free Cancellation
$82 nightly
The price is $94 total per night
$94 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.
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
Browse Cheshire vacation photos for more inspiration
