Book Exclusive Cheshire Vacation Packages

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Cheshire flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Heritage Hotel, Golf & Conference Center

Heritage Hotel, Golf & Conference Center

3.5 out of 5
Price was CA $712, price is now CA $621 per person
CA $621
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to New Haven (HVN)
Book a stay at this boutique hotel in Southbury. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Vicinanza Studios & Gallery and Hollow Park are located nearby.
Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

3 out of 5
Newhallville
Price was CA $2,354, price is now CA $1,993 per person
CA $1,993
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Regina (YQR) to New Haven (HVN)
Stay at this apartment in New Haven. Enjoy an in-room coffeemaker and air conditioning. Popular attractions Peabody Museum of Natural History and Grove Street Cemetery are located nearby.
Landing Furnished Apartment Near Yale University

Landing Furnished Apartment Near Yale University

3 out of 5
Downtown New Haven
Price was CA $892, price is now CA $775 per person
CA $775
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to New Haven (HVN)
Stay at this apartment in New Haven. Enjoy free WiFi, a fitness center, and laundry facilities. Popular attractions Schubert Performing Arts Center and Shubert Theater are located nearby.
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
Downtown New Haven
Price was CA $1,945, price is now CA $1,699 per person
CA $1,699
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Regina (YQR) to New Haven (HVN)
Book a stay at this business-friendly hotel in New Haven. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. 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.
Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Price was CA $892, price is now CA $784 per person
CA $784
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to New Haven (HVN)
Stay at this hotel in New Haven. Enjoy free WiFi, breakfast (surcharge), and free bicycles on site. Our guests praise the helpful staff and the comfy rooms in our reviews. Popular attractions Harkness Tower and Schubert Performing Arts Center are located nearby.

Top Cheshire hotels deals

Cheshire Welcome Inn

Cheshire Welcome Inn

2.5 out of 5
1106 S Main St. Cheshire CT
Free cancellation
Reserve now, pay when you stay
The price is CA $126 per night
CA $126
CA $145 total
Nov 1 - Nov 2
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 Roaring Brook Park and Maplecroft Plaza Shopping Center are located nearby.
Parking included
Free WiFi
The Capitol Hotel

The Capitol Hotel

3 out of 5
440 Asylum St Hartford CT
Free cancellation
Reserve now, pay when you stay
The price is CA $118 per night
CA $118
CA $136 total
Nov 1 - Nov 2
includes taxes & fees
Book a stay at this 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 PeoplesBank Arena and Bushnell Park are located nearby.
Breakfast included
Pet-friendly
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 $194 per night
CA $194
CA $223 total
Oct 26 - Oct 27
includes taxes & fees
Book a stay at this business-friendly hotel in New Haven. Enjoy free WiFi, breakfast (surcharge), and a fitness center. 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
Motel 6 Wethersfield, CT - Hartford

Motel 6 Wethersfield, CT - Hartford

2 out of 5
1341 Silas Deane Hwy Wethersfield CT
Free cancellation
The price is CA $88 per night
CA $88
CA $101 total
Nov 6 - Nov 7
includes taxes & fees
Stay at this motel in Wethersfield. 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 PeoplesBank Arena and Rocky Hill - Glastonbury Ferry are located nearby.
Pet-friendly
Parking included
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 $93 per night
CA $93
CA $108 total
Nov 1 - Nov 2
includes taxes & fees
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 Branford Supply Pond and Stony Creek Brewery are located nearby.
Pet-friendly
Parking included
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 $140 per night
CA $140
CA $161 total
Nov 1 - Nov 2
includes taxes & fees
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 PeoplesBank Arena and Webster Theater are located nearby.
Pool
Breakfast included
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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.

Stay near popular Cheshire attractions

Roaring Brook Park

8.4/10 (12 reviews)
Explore the great outdoors at Roaring Brook Park, a lovely green space in Cheshire. Experience the area's entertainment venues and theater scene.
See properties

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 CA $621. 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

A stone tower with a metal gate, surrounded by trees and a stone wall.
A frozen lake with a solitary tree in the foreground and a sunset in the background.
A wooden bridge over a river with a forested area in the background.
A stone tower with American flags in front.
A road flanked by autumn trees with sunlight filtering through.