Book Exclusive Cheshire Vacation Packages
Cheshire flight + hotel packages
Price found within the past 48 hours. Click for updated prices.
Quality Suites
per person
Apr. 25 - Apr. 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New Haven (HVN)
Book a stay at this golf hotel in Stratford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Stratford Historical Society Capt David Judson House and Academy Hill are located nearby.
Saybrook Point Resort & Marina
Old Saybrook Center
per person
Apr. 17 - Apr. 21
found 6 hours ago
Roundtrip flight included
Toronto (YTO) to New Haven (HVN)
Stay at this 3.5-star spa hotel in Old Saybrook. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions General William Hart House and Katharine Hepburn Cultural Arts Center are located nearby.
Pier Blue Inn Old Saybrook - Essex
Saybrook Manor
per person
Apr. 17 - Apr. 21
found 6 hours 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.
Motel 6 Niantic, CT - New London
per person
Mar. 30 - Apr. 3
found 3 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to New Haven (HVN)
Stay at this motel in Niantic. 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 Flanders Plaza Shopping Center and Cedar Ridge Golf Course are located nearby.
Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area
per person
Mar. 30 - Apr. 3
found 3 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to New Haven (HVN)
Stay at this 3-star business-friendly hotel in Montville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Mohegan Sun Casino and Mohegan Sun Arena are located nearby.
Top Cheshire hotels deals
Holiday Inn Cheshire - Southington, an IHG Hotel
64 Knotter Dr, Cheshire, CT
Free cancellation
The price is CA $128 per night
CA $128
CA $147 total
includes taxes & fees
9 Mar - 10 Mar
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 Mount Southington Ski Area are located nearby.
Pool
Parking included
New Haven Hotel
229 George Street, New Haven, CT
Free cancellation
Reserve now, pay when you stay
The price is CA $168 per night
CA $168
CA $193 total
includes taxes & fees
2 Mar - 3 Mar
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
Omni New Haven Hotel at Yale
155 Temple St, New Haven, CT
Free cancellation
Reserve now, pay when you stay
The price is CA $215 per night
CA $215
CA $247 total
includes taxes & fees
9 Mar - 10 Mar
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
The Capitol Hotel, Ascend Hotel Collection
440 Asylum St, Hartford, CT
Free cancellation
The price is CA $129 per night
CA $129
CA $148 total
includes taxes & fees
26 Feb - 27 Feb
Stay at this 3-star business-friendly hotel in Hartford. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions XL Center and Soldiers and Sailors Memorial Arch are located nearby.
Breakfast included
Pet-friendly
Cambria Hotel New Haven University Area
20 Dwight Street, New Haven, CT
Free cancellation
Reserve now, pay when you stay
The price is CA $156 per night
CA $156
CA $179 total
includes taxes & fees
16 Mar - 17 Mar
Stay at this 3-star business-friendly hotel in New Haven. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Art Plus Studio and Yale University Art Gallery are located nearby.
Pet-friendly
Free WiFi
Hampton Inn & Suites Hartford/East Hartford
351 Pitkin Steet, East Hartford, CT
Free cancellation
Reserve now, pay when you stay
The price is CA $146 per night
CA $146
CA $168 total
includes taxes & fees
2 Mar - 3 Mar
Stay at this hotel in East Hartford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Connecticut River and Mortensen Riverfront Plaza are located nearby.
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
Barker Character, Comic and Cartoon Museum
You can take time to visit Barker Character, Comic and Cartoon Museum during your travels to Cheshire. Experience the entertainment venues and theater scene in this romantic area.
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.
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).Frequently asked questions
Photos of local treasures
Browse Cheshire vacation photos for more inspiration
