Cheshire Vacations

Book a Hotel + Flight or Car together to unlock savings

Photo by Ed Gaffny
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    Better together

    Save up to ₩234,741 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Plan, book, and manage your trip all in one place

Find the Best Cheshire Vacation Packages

Cheshire Hotel Deals

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 ₩119,667 per night from Jul 17 to Jul 18
₩119,667
₩148,888 total
Jul 17 - Jul 18
includes taxes & fees
8.6/10 Excellent! (1,874 reviews)
"Great stay with all plenty of things to do…"

Reviewed on Jul 14, 2025

Vacation Village in the Berkshires
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street, Williamstown, MA
The price is ₩373,363 per night from Aug 10 to Aug 11
₩373,363
₩417,046 total
Aug 10 - Aug 11
includes taxes & fees
9.6/10 Exceptional! (466 reviews)
"Hrwat"

Reviewed on Jul 11, 2025

The Williams Inn
Hotel Downstreet, Ascend Hotel Collection

Hotel Downstreet, Ascend Hotel Collection

3 out of 5
40 Main St, North Adams, MA
The price is ₩211,031 per night from Aug 4 to Aug 5
₩211,031
₩235,722 total
Aug 4 - Aug 5
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
"Very convenient hotel close to all attractions. It also has a wonderful view of the mountains"

Reviewed on Jul 14, 2025

Hotel Downstreet, Ascend Hotel Collection
See all 994 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 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 many days is enough for Cheshire?
The ideal length for your Cheshire vacation 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 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.

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