Cheshire Holidays from £559
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Your Cheshire Holiday
When an adventure in the city is calling your name, answer it with a Cheshire holiday package. With all your travel needs taken care of before you go, all you have to do here is focus on enjoying yourself. Like to explore your new surroundings? Mount Greylock, Mount Greylock State Reservation and East Hoosac Quaker Meetinghouse are just a few of the best places to visit during a trip to Cheshire. Don't delay visiting this destination any longer. The ultimate Cheshire holiday is a few quick clicks away with Expedia.
Top Cheshire Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Hideaway Inn Lenox
£723
per person
17 Nov - 22 Nov
found 1 day ago
Return flight included
London (LHR) to Albany (ALB)
7.8/10 Good! (60 reviews)
Easy check in, but a bit different since there is no staff to help check in. Had to find things on your own, but that was not difficult. Outside furniture could use and upgrade as our friends almost fell through the chair. But is was wonderful being able to sit outside, have appetizers, and play a game or just relax. All other guests we ran into were nice. I would return.
Reviewed on 18 Sept 2026
The Whitlock
£696
per person
17 Nov - 22 Nov
found 1 day ago
Return flight included
London (LHR) to Albany (ALB)
8.4/10 Very good! (385 reviews)
The hotel staff were very friendly and helpful. There is ample parking and the location in town is great for walking to shops and restaurants. This is a very nice property.
Reviewed on 25 Sept 2026
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 |
Top hotels in Cheshire
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
£89
30 Sept - 1 Oct
includes taxes & fees
8.8/10 Excellent! (2,685 reviews)
"This was an amazing property with a lot to offer"
Reviewed on 28 Sept 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
£84
1 Oct - 2 Oct
includes taxes & fees
9/10 Wonderful! (1,160 reviews)
"The problem with the suites is that the cooking smell of the adjoining kitchen can really permeate throughout the entire space. So whoever cooked like a tomato sauce or something before I was there, I could really smell it in the bedroom. The bed was very comfortable though. The room was clean. The ..."
Reviewed on 28 Sept 2026
The Yankee Inn
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
£91
27 Oct - 28 Oct
includes taxes & fees
9.2/10 Wonderful! (1,016 reviews)
"Nice room. Exceptionally clean. Great staff"
Reviewed on 28 Sept 2026
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.
Stay near popular Cheshire attractions
St Mary's of the Assumption Church
10.0/10 (1 review)
This historic Catholic parish has served Cheshire's community since 1879, offering a serene space for reflection. Visit during religious holidays to experience special services in its traditional architectural setting.
Frequently asked questions
How much does a Cheshire travel package cost?
Be ready to book, because a getaway to Cheshire starts from an enticing £559. When you bundle your flights, hotels and car rentals into a package, you'll score the lowest prices.
If I'm not able to travel, can I cancel my Cheshire travel package?
You sure can, and we're here to help. You may be able to cancel or change your Cheshire travel package at no cost within 24 hours of booking. However, you may be charged a fee by your airline, hotel or car rental company if you booked more than 24 hours ago. If your circumstances unexpectedly change, visit our Customer Service Portal for further information.
How do I get a cheap travel package to Cheshire?
Just think of all the fun things you could do in Cheshire with a wad of extra cash in your wallet. Watch your savings stack up when you combine your travel bookings into a Cheshire travel package. You have plenty of choice with Expedia too. In fact, you can take your pick of more than 550 airlines and 1,000,000 hotels globally. Whether you're heading off with the family or travelling solo, planning a trip to Cheshire is better with a package.
Does Expedia offer Book Now, Pay Later Cheshire holidays?
We certainly do. Expedia has joined forces with online lender Klarna to help you easily pay for your trip in instalments. Simply click on the payment plan that suits best during checkout and take the stress out of budgeting for your next trip. Remember to bundle your flights, hotel and car hire with Expedia to get the biggest bang for your holiday buck. Consider these flexible payment options below:
- Pay monthly holidays: Klarna has easy monthly payment plans that fit all budgets, so you can book that well-deserved holiday now.
- Pay in instalments holidays: If you'd like to pay off your getaway in multiple transactions, holidays paid in instalments might be the right option for your Book Now, Pay Later holiday through Klarna.
- Low deposit holidays: When you come across an awesome deal but your budget doesn't quite cover it yet, Klarna's low deposit holiday plan will help you lock in your escape.
Where should I stay in Cheshire?
There's plenty to do in Cheshire, so spend your nights close to its top sights and allow yourself more time sightseeing. Mount Greylock State Reservation Visitor Centre is one spot to put on your must-see list.
What are the top hotels in Cheshire?
Reserve a room at Boston Park Plaza. It's one of this area's most popular hotels. Another great option in Cheshire is Embassy Suites Boston Logan Airport.
How far in advance should I book my Cheshire holiday?
It can be tricky to know when the best time is to book your Cheshire trip. But generally the earlier you book, the lower the prices. In some cases, you can book your flights and hotels up to a year before departure. If you're considering a last-minute getaway, no need to panic! There are unbeatable deals posted on Expedia every day.
What does an Expedia Cheshire travel package include?
From flights and hotels to car rentals, Expedia can help you shape a Cheshire package that fits you. Holidaying for a week or two? Give some thought to a hotel, rental car and flight bundle. If you can only manage a quick getaway, an airfare and hotel deal could suit you better. Activities can also be added once you've made your booking. Our packages make it simple to plan and save.
What should I know before booking a Cheshire travel package?
Discover deals that match your budget with an Expedia package. Hotels, airfares, rental cars — we're a one-stop shop for all of them. You'll save precious cash just by bundling your bookings. Whether you're taking off on an adventure in the snow or sipping cocktails on a beach, your dream getaway is just a few clicks away.
Can I choose my airline with a Cheshire Expedia travel package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines throughout the world. Our travel packages give you the freedom to pick from available flights, hotels and activities that suit you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
