Book Exclusive Cheshire Vacation Packages
Cheshire flight + hotel packages
Price found within the past 48 hours. Click for updated prices.
Pier Blue Inn Old Saybrook - Essex
Saybrook Manor
per person
Jun. 19 - Jun. 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New Haven (HVN)
Stay at this hotel in Old Saybrook. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chalker Beach and Crystal Lake Town Park are located nearby.
Residence Inn by Marriott Hartford/Windsor
per person
Jun. 13 - Jun. 15
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to New Haven (HVN)
Stay at this 3-star business-friendly hotel in Windsor. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions XL Center and Windsor Arts Center are located nearby.
Hilton Garden Inn Hartford North/Bradley Int'l Airport
per person
Jun. 13 - Jun. 15
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to New Haven (HVN)
Stay at this 3-star business-friendly hotel in Windsor. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Vintage Radio and Communications Museum of Connecticut and Windsor Historical Society are located nearby.
Marriott Hartford/Windsor Airport
per person
Jun. 13 - Jun. 15
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to New Haven (HVN)
Stay at this 3.5-star business-friendly hotel in Windsor. Enjoy free parking, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Vintage Radio and Communications Museum of Connecticut and Windsor Historical Society are located nearby.
Top Cheshire hotels deals
Holiday Inn Cheshire - Southington by IHG
64 Knotter Dr, Cheshire, CT
Free cancellation
The price is CA $153 per night
CA $153
CA $176 total
May 26 - May 27
includes taxes & fees
Stay at this 3-star business-friendly hotel in Cheshire. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Panthorn Park and Cheshire Hollow Farm are located nearby.
Pool
Parking included
Cheshire Welcome Inn
1106 S Main St., Cheshire, CT
The price is CA $137 per night
CA $137
CA $157 total
May 25 - May 26
includes taxes & fees
Stay at this motel in Cheshire. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Lock 12 Historical Park and Bartlem Park are located nearby.
Parking included
Free WiFi
New Haven Hotel
229 George Street, New Haven, CT
Free cancellation
Reserve now, pay when you stay
The price is CA $188 per night
CA $188
CA $217 total
Jun 2 - Jun 3
includes taxes & fees
Stay at this 3.5-star business-friendly hotel in New Haven. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff and the convenient parking in our reviews. Popular attractions Shubert Theater and Schubert Performing Arts Center are located nearby.
Pet-friendly
Free WiFi
Clarion Inn
201 Washington Avenue, North Haven, CT
Free cancellation
Reserve now, pay when you stay
The price is CA $134 per night
CA $134
CA $154 total
May 27 - May 28
includes taxes & fees
Book a stay at this business-friendly hotel in North Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Quinnipiac River State Park and Tradition Golf Club at Wallingford are located nearby.
Pool
Breakfast included
Holiday Inn Express Southington by IHG
120 Laning St, Southington, CT
Free cancellation
The price is CA $148 per night
CA $148
CA $170 total
Jun 1 - Jun 2
includes taxes & fees
Book a stay at this business-friendly hotel in Southington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Crystal Bees and Hawks Landing Country Club are located nearby.
Pool
Breakfast included
Omni New Haven Hotel at Yale
155 Temple St, New Haven, CT
Free cancellation
Reserve now, pay when you stay
The price is CA $211 per night
CA $211
CA $242 total
May 26 - May 27
includes taxes & fees
Stay at this 4-star business-friendly hotel in New Haven. Enjoy 2 restaurants, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Schubert Performing Arts Center and Shubert Theater are located nearby.
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.
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 Vacations
Even if you're the most impulsive adventurer, it's still good to study up on a couple of things about Cheshire before you take off. Pinpoint it on your map, discover the sights on offer and let the good times roll!
To help you find your feet, Cheshire is 75 miles (121 kilometers) to the northeast of the significant city of New York.
Love meeting the locals when you're on vacation? This corner of Connecticut is home to around 29,000 residents.
Places to visit in Cheshire
Are the kids getting bored with parks and swings? Let their imaginations run wild at Barker Museum. Jam-packed with interesting exhibits and hands-on experiences, getting your youngsters to learn about the world has never been more fun! Need some more ideas? Bartlem Park is a lovely place to hang out in if you're tired of trudging around town. Find a seat, sit yourself down and rest your weary legs. But there's more. Drazen Orchards is an ideal setting to learn firsthand about animal husbandry and agricultural methods. In case you have to help out, it might be wise to wear some sturdy boots!Where do you fly into for Cheshire?
Prepare for some unforgettable new experiences! The heart of Cheshire is only 30 miles (48 kilometers) south of Bradley International Airport (BDL).Photos of local treasures
Browse Cheshire vacation photos for more inspiration
