Cheshire Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Ed Gaffny
Choose two or more items and save on your trip:
    Plan, book, travel with confidence
    payments icon
    Better together
    Save up to AU$460 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Your Cheshire Holiday

When you choose a Cheshire holiday package, it's all about letting go and enjoying your getaway to the fullest. Discover the sights and sounds of this vibrant city knowing that everything has been taken care of before you go. Make your trip to Cheshire even more fun by going sightseeing. Mount Greylock, Mount Greylock State Reservation and Wahconah Falls State Park are among the big attractions worth exploring. Stop dreaming and start doing. Browse the wide range of options on Expedia today and put your Cheshire holiday plans into action!

Cheshire Essential Information

Language
English
Currency
U.S dollars
Population
510
Max Temp Winter
-1.11ºC
Max Temp Summer
24ºC
Top Sights
Jiminy Peak Mountain Resort, Bousquet Ski Area and Natural Bridge State Park

Our pick of the best Cheshire Hotel Deals

Life House Berkshires
Life House Berkshires
3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is AU$199 per night from 24 Jun to 25 Jun
AU$199
per night
24 Jun - 25 Jun
9/10 Wonderful! (268 reviews)
One night away with kids
"Wonderful little get away with the family - the hotel was lovely, we had a great breakfast and a hike across the street at Kennedy Park."

Reviewed on 20 Jun. 2024

Life House Berkshires
Hotel Downstreet
Hotel Downstreet
3 out of 5
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
The price is AU$249 per night from 26 Jun to 27 Jun
AU$249
per night
26 Jun - 27 Jun
8.4/10 Very Good! (930 reviews)
Nifty hotel in a great little town
"The room was clean and distinctive. Everything worked properly. The hotel is perfectly located for accessing anything in town by foot, including MassMOCA and various eateries."

Reviewed on 16 Jun. 2024

Hotel Downstreet
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
2.5 out of 5
461 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is AU$210 per night from 26 Jun to 27 Jun
AU$210
per night
26 Jun - 27 Jun
9/10 Wonderful! (1,000 reviews)
Pleasantly surprised
"We had a good experience here! The staff was AWESOME! They were very helpful in checking in and gave us good info. They have a bar but it was not open during the times we were in and out. The breakfast was good and we enjoyed the omelet. Its only on the weekend--wish it was every day! The pool was ..."

Reviewed on 15 Jun. 2024

The Yankee, Trademark Collection by Wyndham
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.

Frequently asked questions

How much does a Cheshire holiday package cost?
From just . Yes, you read that right. Our Cheshire holiday packages are a simple way to make your budget last longer. Bundle your favourite flights, hotels and rental car and discover this lively destination.
How do I get a cheap travel package to Cheshire?
Booking a flight and hotel together with Expedia won’t just save precious time — it’ll save you a pretty penny too. A Cheshire holiday package makes it a breeze to arrange your perfect trip. With more than 550 airlines all over the world to select from, finding convenient flights that suit your busy schedule won’t be a challenge. On top of that, we’ve got over 1 000 000 hotel options globally to select from. Now that’s what we call choice. Whatever your budget, Expedia puts the world within your reach.
Where should I stay in Cheshire?
A holiday in Cheshire wouldn’t be complete without seeing Mount Greylock State Reservation Visitor Centre. Why not stay close to this great attraction?
What are the top hotels in Cheshire?
Get your trip off to an excellent start by locking in a room at Harbour House Inn. It’s one of most sought-after properties in Cheshire. Another option is 19th C. Barn In The Berkshires.
How far in advance should I book my Cheshire holiday?
Be rewarded with the widest variety and the lowest prices by booking your trip to Cheshire nice and early. Air carriers typically sell tickets anywhere up to a year before departure, so start locking things in ASAP. That being said, Expedia is committed to providing you with the best deals around, so there’s never a bad time to book your dream holiday!
What does an Expedia Cheshire travel package include?
Expedia has all you need to plan your Cheshire trip, but what your package looks like is totally up to you. Pick from a combination of hotels, rental cars and flights. In search of some activities or tours to fill in your time? Once you’ve made your booking, you can add them too. No matter your budget or style, there’s a deal to suit your needs.
What should I know before booking a Cheshire travel package?
You’ll land amazing savings when you bundle your hotels, flights and rental cars into a travel package. Plus, booking everything in one place simply makes planning easier. So why waste your money or time? Whether you’re putting together a ritzy romantic getaway or an affordable family break, have a look at our package deals today.
Can I choose my airline with a Cheshire Expedia holiday package?
Yes — and it’s simple too. Expedia has access to more than 550 partner airlines throughout the world. Our packages give you the flexibility to pick from available flight, hotel or activity options that suit you.
If I'm not able to travel, can I cancel my Cheshire holiday package?
Yes, you can. We understand that even the best-laid plans can go awry, so we’re happy to help if you need to make changes to your Cheshire holiday package. It may be possible to change or cancel your itinerary at no cost if you’ve booked within 24 hours. Your hotel, airline or car rental company may impose a fee if your booking was made more than 24 hours ago. Take a look at our Customer Service Portal for further information. Also, check your itinerary for the finer details on change fees.

Discover the most popular places to visit in Cheshire

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