Cheshire Holidays

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Your Cheshire Holiday

Unforgettable adventures await when you lock in a Cheshire holiday package. Whether you're a history buff, foodie or just a traveller who appreciates new places, there's something for everyone in this awesome city. A trip to Cheshire is a great opportunity to go sightseeing. Be sure to stop by renowned attractions like Mount Greylock, Wahconah Falls State Park and Mount Greylock State Reservation. Browse Expedia's extensive range of travel options and start planning your ultimate holiday to Cheshire today.

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

Our pick of the best Cheshire Hotel Deals

The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
2.5 out of 5
461 Pittsfield Rd, Lenox, MA
Stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the pool in their reviews. ...
9/10 Wonderful! (1,004 reviews)
Pleasantly surprised
"We had a good experience here! The staff was AWESOME! They were very helpful in checking in and gave us good info. They have a bar but it was not open during the times we were in and out. The breakfast was good and we enjoyed the omelet. Its only on the weekend--wish it was every day! The pool was ..."

Reviewed on 15 Jun 2024

The Yankee, Trademark Collection by Wyndham
Hotel Downstreet
Hotel Downstreet
3 out of 5
40 Main St, North Adams, MA
Stay at this hotel in North Adams. Enjoy free Wi-Fi, free parking and a 24-hour fitness centre. Our guests praise the helpful staff and the clean rooms in their ...
8.4/10 Very Good! (930 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
Life House Berkshires
Life House Berkshires
3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Stay at this 3.5-star lodge in Lenox. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in their ...
9/10 Wonderful! (264 reviews)
Highly recommended
"Excellent stay. Clean, comfortable, and well designed hotel. My husband had stayed previously and recommended. Will be back when we visit the area"

Reviewed on 17 Jun 2024

Life House Berkshires
See all 876 properties in Cheshire
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.

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

How much does a Cheshire travel package cost?
Be ready to book, because a getaway to Cheshire starts from an enticing . 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.

Discover the most popular places to visit in Cheshire

Image for St Mary's of the Assumption Church

St Mary's of the Assumption Church

Learn about the local history of Cheshire with a stop at St Mary's of the Assumption Church. Discover the area's mountain views or seek out its ski slopes.

St Mary's of the Assumption Church

* 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.