Cheshire Vacations from $373

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Your Cheshire Vacation

When an adventure in the city is calling your name, answer it with a Cheshire vacation package. With all your travel needs taken care of before you go, all you have to do here is focus on enjoying yourself. Like to explore your new surroundings? Mount Greylock, Mount Greylock State Reservation and East Hoosac Quaker Meetinghouse are just a few of the best places to visit during a trip to Cheshire. Don't delay visiting this destination any longer. The ultimate Cheshire vacation is a few quick clicks away with Expedia.

The Latest Cheshire vacation packages

Price found within the past 48 hours. Click for updated prices.
Valley Craft Ales

Valley Craft Ales

2 out of 5
per person
Oct 11 - Oct 14
found 1 day ago
Roundtrip flight included
Washington (DCA) to Albany (ALB)
8.6/10 Excellent! (132 reviews)
No tv No fridge no microwave No AC I know, it's my fault for not asking. I've gotten used to the "normal" amenities I will surely check from now on. The place was fairly clean.

Reviewed on Aug 4, 2025

Hampton Inn Schenectady Downtown

Hampton Inn Schenectady Downtown

2.5 out of 5
Seward Place
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Charleston (CHS) to Albany (ALB)
9/10 Wonderful! (940 reviews)
Our stay was very good. All staff were very helpful and friendly. The food was great and at breakfast the staff were very friendly and helpful. Our room was very clean, and our beds were very comfortable. We enjoyed our stay.

Reviewed on Jul 30, 2025

DoubleTree by Hilton Schenectady Downtown

DoubleTree by Hilton Schenectady Downtown

4 out of 5
Seward Place
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Charleston (CHS) to Albany (ALB)
8.4/10 Very Good! (669 reviews)
Comfortable and clean.

Reviewed on Aug 6, 2025

Hotel Vervana, Trademark Collection by Wyndham

Hotel Vervana, Trademark Collection by Wyndham

2.5 out of 5
per person
Oct 11 - Oct 14
found 1 day ago
Roundtrip flight included
Washington (DCA) to Albany (ALB)
8.2/10 Very Good! (1,001 reviews)
We chose this property because it had a pool. It was summer and the pool was full of dead leaves. We were told it was “seasonal”. Perhaps it opens in the winter?

Reviewed on Jul 31, 2025

Super 8 by Wyndham Albany

Super 8 by Wyndham Albany

2 out of 5
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Charleston (CHS) to Albany (ALB)
6.8/10 (1,006 reviews)
Good was terrible. You should advertise breakfast and give almost zero. Not even Apple Juice.

Reviewed on Aug 6, 2025

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Cheshire Hotel Deals

Harbour House Inn

Harbour House Inn

3.5 out of 5
725 North State Road, Cheshire, MA
$237 nightly
The price is $251 total per night from Aug 14 to Aug 15
$251 total
Aug 14 - Aug 15
Total includes taxes and 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 Jul 4, 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
$118 nightly
The price is $132 total per night from Aug 11 to Aug 12
$132 total
Aug 11 - Aug 12
Total includes taxes and fees
8.6/10 Excellent! (1,928 reviews)
"Nice and quiet also clean."

Reviewed on Aug 4, 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
$129 nightly
The price is $145 total per night from Sep 7 to Sep 8
$145 total
Sep 7 - Sep 8
Total includes taxes and fees
8.8/10 Excellent! (543 reviews)
"Very spacious room with full kitchen. Definitely worth the price. Would use again"

Reviewed on Aug 5, 2025

Berkshire Mountain Lodge
See all 997 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.

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Frequently asked questions

How much does a Cheshire vacation package cost?
You'll find cheap prices from $373 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?
November, December and January are the best times to look for cheap Cheshire vacation packages. Choosing to travel in less busy periods means you can usually find reduced prices on flights and accommodations.
How many days is enough for Cheshire?
The ideal length of your Cheshire vacation depends on what you'd like to do. Usually, a handful of days to a week will give you enough time to go to all the main sights and explore some hidden gems 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.
Does Expedia offer Book Now, Pay Later Cheshire vacation packages?
Jet off on your perfect trip to Cheshire with Expedia's Book Now, Pay Later vacations. No need to save up or wait until your next payday — we've joined forces with online lender Affirm to give you more flexibility with your finances. Our vacation packages with payment plans allow you to spread the cost over 3, 6 or 12 months. With no late payment fees or hidden charges, it's a breeze to stick to your budget and snag great deals before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.