Cheshire Vacations from $421

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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.
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Save 100% on your flight
Price was $615, price is now $421 per person
$421
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Albany (ALB)
9/10 Wonderful! (1,002 reviews)
The Inn was very nice and the staff was super friendly and attentive.

Reviewed on Dec 12, 2025

Prospect Berkshires

Prospect Berkshires

3 out of 5
Save 100% on your flight
Price was $907, price is now $533 per person
$533
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Albany (ALB)
9.4/10 Exceptional! (13 reviews)
Wow, just wow! My high school friend and I met up at Prospect Berkshires for a girls weekend. We had an incredible time relaxing by using all the amenities. The staff are so helpful and profession.

Reviewed on Nov 29, 2025

Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

2 out of 5
Save 100% on your flight
Price was $992, price is now $666 per person
$666
per person
Feb 13 - Feb 16
found 12 hours ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
8.8/10 Excellent! (3 reviews)
This was a very cool new hotel. Easy walk into the cute town of Hudson. They are still working out some kinks, we didn’t have hot water but staff was very understanding and offered us

Reviewed on Dec 9, 2025

Gedney Farm

Gedney Farm

3.5 out of 5
Price was $702, price is now $482 per person
$482
per person
Feb 13 - Feb 16
found 22 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Albany (ALB)
9.2/10 Wonderful! (132 reviews)
My wife and I chose Gedney Farms at the last minute to enjoy a quick escape from the city. The staff was friendly and welcoming. The checkin and checkout experience was seamless. The room had a truly rustic charm, and clean and orderly. In the morning we took a nice walk on the grounds. For a quick and relaxing getaway, Gedney Farms is a great choice.

Reviewed on Nov 2, 2025

The Manchester View

The Manchester View

2.5 out of 5
Price was $856, price is now $595 per person
$595
per person
Feb 26 - Mar 1
found 23 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Albany (ALB)
9.4/10 Exceptional! (772 reviews)
Staff and room was clean

Reviewed on Dec 22, 2025

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Cheshire Hotel Deals

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
$126 nightly
The price is $141 total per night from Jan 4 to Jan 5
$141 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
8.6/10 Excellent! (2,179 reviews)
My stay was great with no problems.

Reviewed on Dec 19, 2025

Vacation Village in the Berkshires
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
Fully refundable
$125 nightly
The price is $139 total per night from Jan 6 to Jan 7
$139 total
Jan 6 - Jan 7, 2026
Total with taxes and fees
8.6/10 Excellent! (1,000 reviews)
Clean room, friendly staff.

Reviewed on Dec 12, 2025

Hotel Downstreet, an Ascend Collection Hotel
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street Williamstown MA
Fully refundableReserve now, pay when you stay
$191 nightly
The price is $214 total per night from Dec 24 to Dec 25
$214 total
Dec 24 - Dec 25
Total with taxes and fees
9.6/10 Exceptional! (550 reviews)
Room was very clean. Didn’t have breakfast. Staff was friendly and check in was quick.

Reviewed on Dec 7, 2025

The Williams Inn
See all 984 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.

Find the Best Cheshire Vacation Packages

Cheshire Essential Information

Language
English
Currency
U.S dollars
Population
510
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
Jiminy Peak Mountain Resort, Bousquet Ski Area and Natural Bridge State Park

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Frequently asked questions

How much does a Cheshire vacation package cost?
You'll find cheap prices from $421 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.

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