Cheshire Holidays from £699

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Your Cheshire Holiday

The rich history and spectacular views are just the beginning of the things Cheshire has going for it. Enjoy the sights and sounds of this captivating city your way with a customized Cheshire holiday package. Choate Rosemary Hall, Toyota Presents Oakdale Theatre and Sleeping Giant State Park are just some of the attractions worth checking out during your trip to Cheshire. A few quick clicks is all it takes to put together the perfect Cheshire holiday on Expedia.

The Latest Cheshire Holiday Deals

Prices and availability subject to change. Additional terms may apply.
Motel 6 Niantic, CT - New London

Motel 6 Niantic, CT - New London

2 out of 5
per person
1 Jul - 7 Jul
Return flight included
London (LON) to New Haven (HVN)
7.2/10 Good! (1,000 reviews)
You get what you pay for.. not the cleaniest.. also seems like monthly rentals. No fridge or microwaves in rooms

Reviewed on 14 Apr 2024

Cheshire Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Tweed - New Haven Regional Airport (HVN)
Population
29,400
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
Lake Compounce, Toyota Presents Oakdale Theatre and Powder Ridge Mountain Park and Resort

Our pick of the best Cheshire Hotel Deals

Cheshire Welcome Inn
Cheshire Welcome Inn
2.5 out of 5
1106 S Main St., Cheshire, CT
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 convenient parking in their ...
8.4/10 Very Good! (548 reviews)
"We only stayed 1 night, the check in was easy it took less than 5 minutes. We arrived a few hours prior to stated check in time and they checked s in and gave us key to our room no questions asked. The room is large with a small attached room with counter, chair, and coffe maker. There is a Sushi ..."

Reviewed on 14 Apr 2024

Cheshire Welcome Inn
Holiday Inn Cheshire - Southington, an IHG Hotel
Holiday Inn Cheshire - Southington, an IHG Hotel
3 out of 5
64 Knotter Dr, Cheshire, CT
Stay at this business-friendly hotel in Cheshire. Enjoy free WiFi, free parking and breakfast. Our guests praise the helpful staff and the clean rooms in their ...
8.2/10 Very Good! (850 reviews)
"Staff was wonderful."

Reviewed on 21 Apr 2024

Holiday Inn Cheshire - Southington, an IHG Hotel
New Haven Hotel
New Haven Hotel
3.5 out of 5
229 George Street, New Haven, CT
Stay at this business-friendly hotel in New Haven. Enjoy free WiFi, a fitness centre and on-site parking. Our guests praise the helpful staff and the clean rooms ...
8.8/10 Excellent! (1,221 reviews)
"#"

Reviewed on 22 Apr 2024

New Haven Hotel
See all 1,104 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 Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

How much does a Cheshire travel package cost?
Choose from any combination of hotels, flights and car rentals, and you can be holidaying in Cheshire from just £699. And the more you bundle, the more money you save. Your dream escape has never been more affordable.
If I'm not able to travel, can I cancel my Cheshire travel package?
If your holiday plans in Cheshire have been upended, it’s good to know that you can cancel your booking. If you made your booking in the last 24 hours, you may be eligible to receive a refund. If your booking was made more than 24 hours ago, your hotel, airline or car rental company may charge a fee. For more details, visit our Customer Service Portal.
How do I get a cheap travel package to Cheshire?
Bundle your hotel and flight bookings, throw in extras such as a rental car or activities, and save with a Cheshire travel package. You won’t just enjoy superb discounts on your escape — you’ll have a world of choice too. When you book through Expedia, you can select from more than 550 air carriers and 1,000,000 properties globally. Your next affordable adventure begins right here, right now!
Does Expedia offer Book Now, Pay Later Cheshire holidays?
Your bank balance shouldn’t get in the way of taking a holiday, so Expedia has come up with a solution to help. Now that we’ve teamed up with online lender Klarna, it’s easier than ever to book a dream getaway without drying up your savings. Klarna offers flexible payment options at checkout that take the stress out of budgeting for your break. Check out these flexible payment options:

  • Pay monthly holidays: Klarna offers convenient monthly payment plans that work for all budget sizes, so you can lock in that well-earned holiday sooner.
  • Pay in instalments holidays: Into the idea of paying down your holiday in multiple transactions? Then select this Book Now, Pay Later option with Klarna.
  • Low deposit holidays: If paying a small percentage of your getaway (rather than the full total upfront) makes it easier to hit that “book now” button, go for a low deposit holiday payment plan from Klarna.

Where should I stay in Cheshire?
With popular attractions such as Cheshire Golf Course and Cheshire Hollow Farm in this area, look for a hotel situated near either of them. Bartlem Park is another Cheshire sight that lures the crowds.
What are the top hotels in Cheshire?
Hilton Stamford Hotel & Executive Meeting Centre and Howard Johnson by Wyndham Mystic are two of the most sought-after properties in Cheshire. Why not look up the amenities and rates at each and then make up your mind?
How far in advance should I book my Cheshire holiday?
Smart travellers often book early. You can generally compare international fares on Expedia up to a year before your flight. If you’re purchasing tickets last minute, don’t stress. Cheap prices sometimes occur in the last weeks before departure.
What does an Expedia Cheshire travel package include?
It all boils down to what type of getaway you’re contemplating. Cheshire travel deals can include flights, hotels and car rentals. You can mix and match to find the bundle that suits your needs. You can also add on activities and experiences after you’ve booked to land even bigger discounts.
What should I know before booking a Cheshire travel package?
Bundling your bookings into a Cheshire travel package is the easiest way to organise your trip. Not only that, you’ll save when you combine your flights, hotels and car rentals. Once you’ve booked, why not add on an activity or a tour?
Can I choose my airline with a Cheshire Expedia travel package?
Yes, definitely. Expedia has more than 550 partner airlines to choose from around the globe. With all that choice at your fingertips, finding the perfect carrier to get you to Cheshire will be easy.

Discover the most popular places to visit in Cheshire

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 theatre scene in this romantic area.

Cheshire Hollow Farm
Image for Cheshire Golf Course

Cheshire Golf Course

Enjoy a round of golf in Cheshire at Cheshire Golf Course. Experience the entertainment venues and theatre scene in this romantic area.

Cheshire Golf Course
Image for Roaring Brook Park

Roaring Brook Park

Explore the great outdoors at Roaring Brook Park, a lovely green space in Cheshire. Experience the area's entertainment venues and theatre scene.

Roaring Brook Park

Unmissable things to do in Cheshire

Image for Waterbury City Scavenger Hunt Excursion by Zombie Scavengers

Waterbury City Scavenger Hunt Excursion by Zombie Scavengers

£16
Per adult
Waterbury City Scavenger Hunt Excursion by Zombie Scavengers
See all activities in Cheshire

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.