Cheshire Vacations

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Find the Best Cheshire Vacation Packages

Cheshire Hotel Deals

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 SAR 484 per night from Apr 17 to Apr 18
SAR 484
SAR 541 total
includes taxes & fees
17 Apr - 18 Apr
9/10 Wonderful! (552 reviews)
"Really great value and great vibe, atmosphere here. Drove by this place a million times. Never knew it was here."

Reviewed on 13 April 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
The price is SAR 364 per night from Apr 24 to Apr 25
SAR 364
SAR 406 total
includes taxes & fees
24 Apr - 25 Apr
9/10 Wonderful! (1,002 reviews)
"Most everything was good. They were doing major renovation! Beds were decent, shower was nice, free breakfast buffet was great, lots to choose from! Pool was nice, but only 5 feet, but jacuzzi was wonderful! Heat was very noisy, though. Just a couple things they could have explained better in the ..."

Reviewed on 10 April 2025

The Yankee, Trademark Collection by Wyndham
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 out of 5
190 Meadow Street, South Lee, MA
The price is SAR 402 per night from Apr 28 to Apr 29
SAR 402
SAR 501 total
includes taxes & fees
28 Apr - 29 Apr
9/10 Wonderful! (619 reviews)
"Great deal for villa resort suite. Lots of space, great condition, great amenities, great location."

Reviewed on 12 April 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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 vacation 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 vacation to Cheshire costs.
What are the cheapest months to go to Cheshire?
To pick up cheap Cheshire vacation packages, organize 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 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 vacation package as early as possible.
Is it cheaper to book a Cheshire vacation as a package?
Expedia vacation 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 vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation 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 favorite 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 vacation package that brings all your bookings together.

Discover the most popular places to visit in Cheshire