Cheshire Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Ed Gaffny
    Plan, book, travel with confidence
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    Better together
    Save up to NZ$545 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy
    Plan, book, and manage your trip all in one place

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 NZ$248 per night from 9 Jul to 10 Jul
NZ$248
per night
9 Jul - 10 Jul
9/10 Wonderful! (273 reviews)
"Very pleasant place to stay rooms and nice and clean. Staff is very nice."

Reviewed on 21 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 NZ$278 per night from 10 Jul to 11 Jul
NZ$278
per night
10 Jul - 11 Jul
8.4/10 Very Good! (931 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 NZ$264 per night from 10 Jul to 11 Jul
NZ$264
per night
10 Jul - 11 Jul
9/10 Wonderful! (1,003 reviews)
"Employees were all super friendly, a very clean and pleasant property. There was nothing that I didn’t like about this place"

Reviewed on 22 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.