Cheshire Trips (flight + hotel)

Photo by Ed Gaffny
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Top hotels in Cheshire

The Black Swan Lee - Lenox, Ascend Hotel Collection
The Black Swan Lee - Lenox, Ascend Hotel Collection
3 out of 5
435 Laurel St, Lee, MA
Fully refundableReserve now, pay when you stay
The price is P5,404 per night from 22 Apr to 23 Apr
P5,404
per night
22 Apr - 23 Apr
8.8/10 Excellent! (1,000 reviews)
"Excellent room with gas fireplace and jacuzzi tub! Clean and Quiet. Nice views of the lake. Would stay there again."

Reviewed on Apr 14, 2024

The Black Swan Lee - Lenox, Ascend Hotel Collection
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 P5,662 per night from 21 Apr to 22 Apr
P5,662
per night
21 Apr - 22 Apr
9/10 Wonderful! (222 reviews)
"Really nice place. Very nicely renovated, and a real bargain in the off season. My only issue was no shops/restaurants near to walk to and the highway it’s on is fast and busy making left turns out of the place a real challenge."

Reviewed on Apr 15, 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 P5,560 per night from 23 Apr to 24 Apr
P5,560
per night
23 Apr - 24 Apr
8.8/10 Excellent! (866 reviews)
"What a pleasure to have the opportunity to stay in an historic inn such as the Red Lion."

Reviewed on Apr 13, 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.

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