Cheshire Holidays

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Top hotels in Cheshire

Hotel Downstreet
Hotel Downstreet
3 out of 5
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
The price is €126 per night from 2 Feb to 3 Feb
€126
includes taxes & fees
2 Feb - 3 Feb
8.6/10 Excellent! (999 reviews)
"The Hotel Downstreet is the best hotel. We always enjoy our stay here and never hesitate to stay again when in the area."

Reviewed on 6 Jan 2025

Hotel Downstreet
Life House Berkshires
Life House Berkshires
3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is €106 per night from 20 Jan to 21 Jan
€106
includes taxes & fees
20 Jan - 21 Jan
9/10 Wonderful! (477 reviews)
"Great place! Beautiful room and dining area very aesthetic. The bed was so comfortable. No microwaves and the bathroom floor could’ve been a little cleaner but other than that it was great for a roadside motel!"

Reviewed on 15 Jan 2025

Life House Berkshires
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
2.5 out of 5
461 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is €109 per night from 20 Jan to 21 Jan
€109
includes taxes & fees
20 Jan - 21 Jan
9/10 Wonderful! (1,001 reviews)
"It was a clean and nice place. The wall must be a little thin since we could hear next door person’s conversations. The breakfast was decent and a variety of choices. I enjoyed the swimming pool and jet. I wish that there could be a sauna. Over all, it was a good place to stay!"

Reviewed on 16 Jan 2025

The Yankee, Trademark Collection by Wyndham
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.

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