Cheshire Vacations

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Your Cheshire Vacation

There's no better way to travel than with one of our vacation packages to Cheshire. The spectacular views and rich history are just two of the compelling reasons to spend some time in this captivating city. If a sightseeing tour is on the agenda during your trip to Cheshire, check out major attractions like Toyota Presents Oakdale Theatre, Choate Rosemary Hall and Sleeping Giant State Park. Browse Expedia's extensive range of travel options and start planning your ultimate vacation to Cheshire today.

Cheshire Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Tweed - New Haven Regional Airport (HVN)
Population
29,400
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Lake Compounce, Toyota Presents Oakdale Theatre and Powder Ridge Mountain Park and Resort

Cheshire Hotel Deals

Holiday Inn Cheshire - Southington, an IHG Hotel
Holiday Inn Cheshire - Southington, an IHG Hotel
3 out of 5
64 Knotter Dr, Cheshire, CT
Fully refundable
The price is $125 per night from Jun 23 to Jun 24
$125
$144 total
includes taxes & fees
Jun 23 - Jun 24
8.2/10 Very Good! (871 reviews)
"Nice room"

Reviewed on Jun 16, 2024

Holiday Inn Cheshire - Southington, an IHG Hotel
Cheshire Welcome Inn
Cheshire Welcome Inn
2.5 out of 5
1106 S Main St., Cheshire, CT
The price is $76 per night from Jun 30 to Jul 1
$76
$88 total
includes taxes & fees
Jun 30 - Jul 1
8.4/10 Very Good! (565 reviews)
"The staff is wonderful and smiling. Never wanted anything. They were great!"

Reviewed on Jun 9, 2024

Cheshire Welcome Inn
New Haven Hotel
New Haven Hotel
3.5 out of 5
229 George Street, New Haven, CT
Fully refundableReserve now, pay when you stay
The price is $149 per night from Jun 30 to Jul 1
$149
$171 total
includes taxes & fees
Jun 30 - Jul 1
8.8/10 Excellent! (1,251 reviews)
"The lobby looks very nice, however rooms are quite outdated, furniture with dust, need some renovations"

Reviewed on Jun 19, 2024

New Haven Hotel
See all 1,089 properties in Cheshire
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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Cheshire vacation package cost?
We make it simple to travel the world, with Cheshire vacation packages starting from just . You’ll have the flexibility to combine your favorite airlines, hotels and car rental. For the ultimate getaway, why not add a couple of experiences and tours to your travel itinerary?
How do I get a cheap travel package to Cheshire?
Track down flights that suit your busy schedule, add a hotel to your booking and watch the savings grow with a Cheshire vacation package. It’s as easy as that! From flights and hotels to tours and rental cars, Expedia is your gateway to cheap travel. And with over 550 air carriers and 1,000,000 hotel options around the world to choose from, you’ll never be short of choice.
Where should I stay in Cheshire?
With so much to do in Cheshire, it makes sense to book a hotel close to its attractions. Cheshire Golf Course, Cheshire Hollow Farm and Bartlem Park are some popular ones to put on your must-see list.
What are the top hotels in Cheshire?
Whether you plan to stay for just one night or a week in Cheshire, you’ll get a good night’s sleep at Cheshire Welcome Inn. This place is a top pick for plenty of travelers.
How far in advance should I book my Cheshire vacation?
It all depends on the airline, but you can usually compare international fares on Expedia up to 12 months in advance. While it’s generally a good idea to book ahead of time, lucky travelers occasionally find a cheaper flight just weeks prior to the date of departure.
What does an Expedia Cheshire travel package include?
Hotels, flights and rental cars — we have them covered. With Expedia, you can shape your Cheshire travel package just how you like it. All you have to do is work out just what you need. Once you’ve made your booking, you can add extras like tours and activities. The more you bundle, the greater the savings!
What should I know before booking a Cheshire travel package?
When you book your hotels, flights and car rentals together, you’ll score terrific discounts. Whether you’re organizing a beach break in a villa or want to stay in a fancy hotel in the city, Expedia will make it happen for less.
Can I choose my airline with a Cheshire Expedia vacation package?
Yes — that’s one of the best things about an Expedia package. You get to decide. We have access to more than 550 airline partners all over the world, so you have lots of choice when creating your Cheshire trip.
If I'm not able to travel, can I cancel my Cheshire vacation package?
Yes, you can. We realize life happens, so we’re happy to help if you need to make changes to your Cheshire vacation package. It may be possible to cancel or amend your itinerary for free if you’ve booked within 24 hours. Your hotel, airline or car rental company may charge you a fee if you booked more than 24 hours ago. Take a look at our Customer Service Portal for more information. Also, be sure to check your itinerary for the finer details on change fees.

Discover the most popular places to visit in Cheshire

Image for Cheshire Golf Course

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
Image for Cheshire Hollow Farm

Cheshire Hollow Farm

Enjoy a stop at Cheshire Hollow Farm, an entertaining place to visit in Cheshire. Take in the theater scene in this romantic area.

Cheshire Hollow Farm
Image for Quinnipiac Recreation Area

Quinnipiac Recreation Area

Explore the great outdoors at Quinnipiac Recreation Area, a lovely green space in Cheshire. Experience the entertainment venues and theater scene in this romantic area.

Quinnipiac Recreation Area

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.