Cheshire Holidays

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Your Cheshire Holiday

When you choose a Cheshire holiday package, it's all about letting go and enjoying your getaway to the fullest. Discover the sights and sounds of this vibrant city knowing that everything has been taken care of before you go. Make your trip to Cheshire even more fun by going sightseeing. Mount Greylock, Mount Greylock State Reservation and Wahconah Falls State Park are among the big attractions worth exploring. Stop dreaming and start doing. Browse the wide range of options on Expedia today and put your Cheshire holiday plans into action!

Cheshire Holiday

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

Harbour House Inn

Harbour House Inn

3.5 out of 5
725 North State Road, Cheshire, MA
The price is AU$384 per night from 9 Sept to 10 Sept
AU$384
9 Sept - 10 Sept
includes taxes & fees
9.6/10 Exceptional! (37 reviews)
"We had a wonderful stay! Brandi is a wonderful host, super friendly and full of helpful information! The afternoon cookies and morning breakfast were delicious! Will definitely stay again next time we’re in the area!!"

Reviewed on 4 Jul. 2025

Harbour House Inn
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
Fully refundableReserve now, pay when you stay
The price is AU$203 per night from 1 Sept to 2 Sept
AU$203
1 Sept - 2 Sept
includes taxes & fees
8.6/10 Excellent! (1,966 reviews)
"Our family of 6 had a wonderful time here! The front desk staff were so friendly and helpful. The pool was clean, with a children’s area and playground right nearby. The rooms were spacious and comfortable. Beautiful scenic views and area."

Reviewed on 23 Aug. 2025

Vacation Village in the Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (589 reviews)
"I stayed here for a work trip to a remote project site. This place was very impressive for the money. The rooms were large and had everything. The place was clean and staff very pleasant and accommodating. I didn’t expect a lot for what I paid but was pleasantly surprised."

Reviewed on 23 Aug. 2025

Get rates
Berkshire Mountain Lodge
See all 996 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
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All Inclusive Holidays
Cheap Holidays
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Beach Holidays
Beach Holidays

Frequently asked questions

How much does a Cheshire holiday package cost?
You'll find cheap prices on Expedia for your Cheshire getaway. However, factors like your choice of hotel, the season and length of stay will determine how much your holiday to Cheshire costs.
What are the cheapest months to go to Cheshire?
To pick up cheap Cheshire holiday packages, organise your getaway outside of peak periods like public holidays and major events. You'll typically find better availability and lower prices when it's less busy.
How many days is enough for Cheshire?
The ideal length for your Cheshire holiday depends on what you'd like to see and do. Usually, a few days to a week will give you time to hit all the leading attractions and discover some hidden treasures along the way.
How to find the best Cheshire package deals?
Use Expedia's handy filters to find some fabulous Cheshire package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your escape for midweek, or search for Cheshire package deals in the off-peak season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to lock in your holiday package as early as possible.
Is it cheaper to book a Cheshire holiday as a package?
Expedia holiday packages are designed to help you keep more cash in your pocket. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You'll generally snag a better deal than booking each component individually. And you'll still enjoy the freedom to create a tailored Cheshire holiday by choosing your preferred accommodation type, airline and car class.
When to book a holiday package to Cheshire?
Score amazing discounts by reserving your flights ahead of time with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for an impromptu Cheshire escape.
How to plan a trip to Cheshire?

  1. Choose your travel dates: What you plan to do in Cheshire and your favourite season will help you decide when to get away.
  2. Work out your budget: Make sure you have enough money to pay for everything from meals and transportation to activities and airfares. Your hotel will likely be the biggest expense during your trip to Cheshire.
  3. Decide how many days away: Start by making a list of all the attractions and activities you'd like to experience in Cheshire. Then, estimate how long you'll need for each, including any travel time.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to find a Cheshire holiday package that brings all your bookings together.

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