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Top Cheshire hotels deals

Holiday Inn Cheshire - Southington, an IHG Hotel

Holiday Inn Cheshire - Southington, an IHG Hotel

3 out of 5
64 Knotter Dr, Cheshire, CT
Free cancellation
The price is CA $115 per night
CA $115
CA $133 total
includes taxes & fees
5 Jan - 6 Jan 2025
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.
Cheshire Welcome Inn

Cheshire Welcome Inn

2.5 out of 5
1106 S Main St., Cheshire, CT
The price is CA $132 per night
CA $132
CA $152 total
includes taxes & fees
19 Dec - 20 Dec
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 Maplecroft Plaza Shopping Center are located nearby.
Best Western Hartford Hotel & Suites

Best Western Hartford Hotel & Suites

2.5 out of 5
185 Brainard Rd, Hartford, CT
Free cancellation
Reserve now, pay when you stay
The price is CA $144 per night
CA $144
CA $166 total
includes taxes & fees
26 Dec - 27 Dec
Stay at this hotel in Hartford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions XL Center and Wethersfield Cove Park are located nearby.
New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street, New Haven, CT
Free cancellation
Reserve now, pay when you stay
The price is CA $184 per night
CA $184
CA $211 total
includes taxes & fees
19 Dec - 20 Dec
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 White Space Gallery are located nearby.
Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

2 out of 5
320 E Main St, Branford, CT
Free cancellation
The price is CA $104 per night
CA $104
CA $121 total
includes taxes & fees
23 Dec - 24 Dec
Stay at this motel in Branford. 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 Orchard Hill Plaza Shopping Center and Polished are located nearby.
The Capitol Hotel, Ascend Hotel Collection

The Capitol Hotel, Ascend Hotel Collection

3 out of 5
440 Asylum St, Hartford, CT
Free cancellation
The price is CA $120 per night
CA $120
CA $139 total
includes taxes & fees
29 Dec - 30 Dec
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.
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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 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 Golf Course

Lock 12 Historical Park

Explore the great outdoors at Lock 12 Historical Park, a lovely green space in Cheshire. While in this family-friendly area, you can enjoy the restaurants.

Lock 12 Historical Park

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.

Maplecroft Plaza Shopping Center

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

How much are vacation packages to Cheshire?
You’ll find an amazing hotel + flight bundle for as little as . With one of our Travelocity vacation packages, a stay in Cheshire has never looked more irresistible! Save both time and money and then get a start on packing those bags.
How long should my Cheshire vacation be?
There are no firm rules when it comes to how long you should spend in Cheshire, but most people stay around 3 nights. Got some wiggle room in your departure date? Consider treating yourself to an extra night or two. Then you’ll have enough time to check out the area’s hidden treasures as well.
Where can I get the best vacation package deals for Cheshire?
For an amazing package deal to Cheshire, nothing compares to Travelocity. Pick from as many as 400 partner airlines and 1,000,000 properties worldwide to create the ultimate escape — it couldn’t be easier than that.
Why should I book my Cheshire vacation bundle with Travelocity?
We offer experiences to suit every type of globetrotter, top-quality service and 24/7 customer support. And to top all that off, we’ll match any better price you find with our Price Match Guarantee.
Can I save on my Cheshire car rental if I combine it with a hotel or flight?
With a Cheshire vacation package, you can bundle your car, flight and hotel bookings and save a ton. If you’d love to explore the best of this wonderful location, why not check out Times Square? This popular sight is 121 kilometers from Cheshire. With your own wheels, you’ll be there in the blink of an eye.
Which airport is best for Cheshire?
Many visitors choose to fly into Bradley Intl. Airport (BDL), 48 kilometers north of downtown Cheshire. Others prefer MacArthur Airport (ISP) (80 kilometers away from central Cheshire) or Tweed - New Haven Regional Airport (HVN) (27 kilometers away from central Cheshire).
What is there to do in Cheshire?
Cheshire is overflowing with things to see and do, including Cheshire Golf Course and Cheshire Hollow Farm. These two popular attractions are at the top of most tourists’ must-see lists.
Where should I stay when visiting Cheshire?
Many travelers spend their nights at the Holiday Inn Cheshire - Southington, an IHG Hotel. It’s a great base for your Cheshire escape.

Photos of local treasures

Browse Cheshire vacation photos for more inspiration

Photo by Tai Bui
Photo by Tai Bui