Cheshire Holidays

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Top hotels in Cheshire

The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is Rp2.277.770 per night from 6 Jul to 7 Jul
Rp2.277.770
Rp2.544.269 total
6 Jul - 7 Jul
includes taxes & fees
9.2/10 Wonderful! (1,016 reviews)
"We love to snow shoe.. after a chilly day of trekking through the mountains. We grab dinner locally,and cozy up to our romantic ,fully loaded room. Fire roaring,bubbles in the hot tub.. an amazing ending to and amazing day."

Reviewed on 1 Jul 2026

The Yankee Inn
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
The price is Rp2.225.769 per night from 21 Jul to 22 Jul
Rp2.225.769
Rp2.682.623 total
21 Jul - 22 Jul
includes taxes & fees
8.8/10 Excellent! (2,413 reviews)
"Clean large room- some wear on the kitchen cabinets and the bathroom door stuck check in was a bit of a challenge. Otherwise good"

Reviewed on 1 Jul 2026

Vacation Village in the Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
The price is Rp2.854.107 per night from 12 Jul to 13 Jul
Rp2.854.107
Rp3.586.828 total
12 Jul - 13 Jul
includes taxes & fees
9/10 Wonderful! (1,005 reviews)
"Friendly staff, great coffee and very clean ."

Reviewed on 1 Jul 2026

Berkshire Mountain Lodge
See all 989 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.

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.
See properties

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.

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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.