Cheshire Vacations 2026 from CA $585

Cheshire flight + hotel packages

Price found within the past 48 hours. Click for updated prices.

Pier Blue Inn Old Saybrook - Essex

Saybrook Manor

CA $585

per person

Aug 10 - Aug 14

found 1 day ago

Roundtrip flight included

Detroit (DTT) 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.

Beechmont - Perfect for Family Retreat!

North End

CA $1,279

per person

Jul 19 - Jul 21

found 1 day ago

Roundtrip flight included

Toronto (YTO) to New Haven (HVN)

Book a stay at this luxury vacation home in Bridgeport. Enjoy free WiFi, free parking, and a garden. Popular attractions Total Mortgage Arena and Hartford HealthCare Amphitheater are located nearby.

Westbrook Inn B&B

Westbrook Center

CA $1,132

per person

Aug 10 - Aug 14

found 1 day ago

Roundtrip flight included

Detroit (DTT) to New Haven (HVN)

Stay at this B&B in Westbrook. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Hammonasset Beach State Park and Westbrook Town Beach are located nearby.

Water's Edge Resort & Spa

Westbrook Center

CA $1,431

per person

Aug 10 - Aug 14

found 1 day ago

Roundtrip flight included

Detroit (DTT) to New Haven (HVN)

Book a stay at this beach resort in Westbrook. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Tanger Outlets and Westbrook Town Beach are located nearby.

Top Cheshire hotels deals

Cheshire Welcome Inn

1106 S Main St. Cheshire CT

Free cancellation

Reserve now, pay when you stay

CA $126

CA $144 total

Jul 1 - Jul 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.

New Haven Hotel

229 George Street New Haven CT

Free cancellation

Reserve now, pay when you stay

CA $167

CA $192 total

Jul 5 - Jul 6

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 White Space Gallery are located nearby.

Motel 6 New Haven - Branford, CT

320 E Main St Branford CT

Free cancellation

CA $100

CA $117 total

Jun 22 - Jun 23

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 Polished are located nearby.

The Capitol Hotel

440 Asylum St Hartford CT

Free cancellation

Reserve now, pay when you stay

CA $149

CA $171 total

Jun 28 - Jun 29

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 Xfinity Theatre are located nearby.

Motel 6 Wethersfield, CT - Hartford

1341 Silas Deane Hwy Wethersfield CT

Free cancellation

Reserve now, pay when you stay

CA $100

CA $115 total

Jul 15 - Jul 16

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.

Omni New Haven Hotel at Yale

155 Temple St New Haven CT

Free cancellation

Reserve now, pay when you stay

CA $202

CA $232 total

Jul 1 - Jul 2

includes taxes & fees

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 Shubert Theater and New Haven Green 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.

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 $585. 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.