Cheshire Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Ed Gaffny

Top hotels in Cheshire

Harbour House Inn

Harbour House Inn

3.5 out of 5
725 North State Road, Cheshire, MA
The price is 6.891.146 ₫ per night from 18 Aug to 19 Aug
6.891.146 ₫
7.283.941 ₫ total
18 Aug - 19 Aug
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 2.845.757 ₫ per night from 27 Aug to 28 Aug
2.845.757 ₫
3.466.915 ₫ total
27 Aug - 28 Aug
includes taxes & fees
8.6/10 Excellent! (1,948 reviews)
"Very nice"

Reviewed on 15 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! (561 reviews)
Rest, relax, and repeat
"Great value for families! The welcoming staff, location (Lenox/Pittsfield border), spacious suite, and ample amenities made for a fantastic vacation. No free breakfast but there are several dining options and markets nearby. Gorgeous view of the sunset from the upper floors. There was a note of upcoming ..."

Reviewed on 14 Aug 2025

Get rates
Berkshire Mountain Lodge
See all 998 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.

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.