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
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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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    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
The price is NZ$181 per night from 28 May to 29 May
NZ$181
per night
28 May - 29 May
9/10 Wonderful! (243 reviews)
"Love the lobby (even smells great!) Love the decor and the outdoor patio. Happy with entire stay."

Reviewed on 16 May 2024

Life House Berkshires
The Red Lion Inn
The Red Lion Inn
3.5 out of 5
30 Main Street, Stockbridge, MA
Fully refundableReserve now, pay when you stay
The price is NZ$312 per night from 30 May to 31 May
NZ$312
per night
30 May - 31 May
8.8/10 Excellent! (885 reviews)
"Very comfortable beds. Quiet with very friendly staff. Wasn’t too thrilled with the antique bathtub, too high to step into safely for seniors."

Reviewed on 18 May 2024

The Red Lion Inn
Hotel Downstreet
Hotel Downstreet
3 out of 5
40 Main St, North Adams, MA
The price is NZ$273 per night from 29 May to 30 May
NZ$273
per night
29 May - 30 May
8.4/10 Very Good! (922 reviews)
"A great place to stay in North Adams. Clean, friendly and located just a couple of miles from an outstanding breakfast restaurant."

Reviewed on 15 May 2024

Hotel Downstreet
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.