Cheshire Vacation Packages 2026 from $1,750

Cheshire flight + hotel vacation packages

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

Beechmont - Perfect for Family Retreat!

North End

Save 100% on your flight

$1,750

per person

Dec 3 - Dec 7

found 4 hours ago

Roundtrip flight included

Austin (AUS) to New Haven (HVN)

This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a communal living room are also on offer.

Top Cheshire hotels deals

Cheshire Welcome Inn

1106 S Main St. Cheshire CT

Free Cancellation

Reserve now, pay when you stay

$91 nightly

$105 total

Nov 23 - Nov 24

Total with taxes and fees

This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. The front desk is staffed around-the-clock and laundry facilities are on offer.

Parking included

Free WiFi

The Capitol Hotel

440 Asylum St Hartford CT

Free Cancellation

Reserve now, pay when you stay

$90 nightly

$104 total

Nov 22 - Nov 23

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free full breakfast and free WiFi. Traveling on business? Take advantage of the 2 conference rooms, business center, and express check-out. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and laundry facilities.

Breakfast included

Pet friendly

New Haven Hotel

229 George Street New Haven CT

Free Cancellation

Reserve now, pay when you stay

$125 nightly

$144 total

Nov 22 - Nov 23

Total with taxes and fees

A gym, self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the 2 conference rooms, along with dry cleaning/laundry services.

Pet friendly

Free WiFi

Motel 6 Wethersfield, CT - Hartford

1341 Silas Deane Hwy Wethersfield CT

Free Cancellation

$62 nightly

$72 total

Nov 7 - Nov 8

Total with taxes and fees

This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. The front desk is staffed around-the-clock and laundry facilities are on offer.

Pet friendly

Parking included

Best Western Hartford Hotel & Suites

185 Brainard Rd Hartford CT

Free Cancellation

Reserve now, pay when you stay

$95 nightly

$109 total

Nov 8 - Nov 9

Total with taxes and fees

This hotel features a gym and a seasonal outdoor pool. There's no skimping on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. A 24-hour business center, a terrace, and a garden are also on offer.

Pool

Breakfast included

Hampton Inn & Suites Hartford/East Hartford

351 Pitkin Steet East Hartford CT

Free Cancellation

Reserve now, pay when you stay

$118 nightly

$136 total

Nov 1 - Nov 2

Total with taxes and fees

This hotel features an indoor pool and a 24-hour gym. There's no skimping on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. A 24-hour business center, a lobby fireplace, and express check-in are also on offer.

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

Frequently asked questions

How much are vacation packages to Cheshire?

You'll find an amazing hotel + flight bundle for as little as $1,750. 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 75 mi 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), 30 mi north of downtown Cheshire. Others prefer MacArthur Airport (ISP) (50 mi away from central Cheshire) or Tweed - New Haven Regional Airport (HVN) (17 mi 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.