Cheshire Vacations

Book a Hotel + Flight or Car together to unlock savings

Photo by Ed Gaffny
    Plan, book, travel with confidence
    payments icon
    Better together
    Save up to ¥9,995 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

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 ¥18,720 per night from Jun 4 to Jun 5
¥18,720
per night
Jun 4 - Jun 5
9/10 Wonderful! (252 reviews)
"Terrific renovation of two story motel. Great bedding and toiletries. Everything has a curated retro-hipster look. Spacious shower and bathroom, closet space, robes, plenty of charging outlets and a big TV, great if you use Apple. The only downside is noisy, bulky air conditioner. Be sure to ask ..."

Reviewed on May 28, 2024

Life House Berkshires
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 ¥19,923 per night from Jun 17 to Jun 18
¥19,923
per night
Jun 17 - Jun 18
9/10 Wonderful! (1,004 reviews)
"This is our go-to spot for short trips to the Berkshires. It's on a busy road, but set back from the street, and it's convenient to everything we need. Good breakfast (better than the one I had a much more expensive hotel in NYC last week) and it's clean and comfortable."

Reviewed on May 25, 2024

The Yankee, Trademark Collection by Wyndham
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 ¥32,838 per night from Jun 16 to Jun 17
¥32,838
per night
Jun 16 - Jun 17
8.8/10 Excellent! (889 reviews)
"Always a great HISTORIC INN"

Reviewed on Jun 2, 2024

The Red Lion Inn
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 vacation package cost?
From just . Yes, you read that right. Our Cheshire vacation packages are a simple way to make your budget last longer. Bundle your favorite 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 vacation 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 vacation in Cheshire wouldn’t be complete without seeing Mount Greylock State Reservation Visitor Center. 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 vacation?
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 vacation!
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 vacation 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 vacation 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 vacation 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.