Deals on vacations and trips to Cheshire

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Cheshire flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

3 out of 5
Price was $678, price is now $551 per person
$551
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Chicago (CHI) to New Haven (HVN)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Price was $2,169, price is now $928 per person
$928
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Chicago (CHI) 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.
Head of Pond House

Head of Pond House

3 out of 5
Price was $1,074, price is now $832 per person
$832
per person
Oct 23 - Oct 26
found 13 hours ago
Roundtrip flight included
Chicago (CHI) to New Haven (HVN)
A seasonal outdoor pool is featured at this bed & breakfast, along with free self parking. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and a communal living room are also on offer.
Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

3 out of 5
Newhallville
Save 100% on your flight
Price was $981, price is now $765 per person
$765
per person
Nov 13 - Nov 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
This apartment includes free WiFi in public areas and a virtual front desk.
Hyatus Luxury Residences City Crossing

Hyatus Luxury Residences City Crossing

4 out of 5
The Hill
Save 100% on your flight
Price was $1,116, price is now $883 per person
$883
per person
Oct 17 - Oct 20
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
This aparthotel features a 24-hour gym and a seasonal outdoor pool. Traveling for business? Take advantage of the free WiFi in public areas, laundry service, and conference center. Enjoy the a rooftop terrace and perks like free self parking and a free area shuttle.

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.
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Frequently asked questions

How much are vacation packages to Cheshire?
You'll find an amazing hotel + flight bundle for as little as $551. 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.

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.