Cheshire Vacations from $341

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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.
Saratoga Casino Hotel

Saratoga Casino Hotel

4 out of 5
Price was $433, price is now $341 per person
$341
per person
Apr 3 - Apr 5
found 6 hours ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
9.2/10 Wonderful! (1,001 reviews)
Clean room and facility. Friendly staff

Reviewed on Feb 6, 2026

The Perch Hotel

The Perch Hotel

2 out of 5
Price was $1,062, price is now $766 per person
$766
per person
Apr 9 - Apr 13
found 1 hour ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Albany (ALB)
9.4/10 Exceptional! (22 reviews)
This place is great!! Awesome view with a pool table and fireplace in the common area. Very home feeling with the decor, place was clean and tidy.

Reviewed on Jan 3, 2026

The Old Catskill Game Farm Inn

The Old Catskill Game Farm Inn

3.5 out of 5
Price was $4,220, price is now $3,201 per person
$3,201
per person
Apr 9 - Apr 13
found 1 hour ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Albany (ALB)
9.6/10 Exceptional! (26 reviews)
This Inn was amazing. We booked the Giraffe room for the weekend, and it was a great escape. Our room was super clean, a large jacuzzi tub, and very private. There was also a sauna room, gourmet kitchen, pantry with another stove, refrigerator, dish washer, fully stock with plates, and utensils. Additionally, there is a coffee bar and mini fridge stocked with bottled water. There is also a large common area with several leather sofa, and plenty of games. Another great feature is there is a bar area with a wine fridge. Shawn was amazing, he was very attentive and accommodating, he was right out front to greet us on arrival and gave a tour of the Inn. The decor was very nostalgic with decor from the original Catskill Game Farm. It was a great stay and looking forward to returning again.

Reviewed on Jan 19, 2026

Hutton Brickyards Riverfront Hotel + Venue

Hutton Brickyards Riverfront Hotel + Venue

3.5 out of 5
Price was $1,185, price is now $998 per person
$998
per person
Apr 9 - Apr 13
found 1 hour ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Albany (ALB)
8.8/10 Excellent! (93 reviews)
This was our 1st time at Hutton Brickyards, it was amazing! The staff was so nice and accommodating. The room and the amenities were amazing. We will definitely be back.

Reviewed on Feb 2, 2026

Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

2 out of 5
Price was $1,249, price is now $1,058 per person
$1,058
per person
Apr 9 - Apr 13
found 1 hour ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Albany (ALB)
8.8/10 Excellent! (3 reviews)
The room was modern, clean, and perfect for two. I highly recommend the hotel if you are visiting Hudson. Unfortunately the Expedia picture and description did not match what was actually booked. This was not the fault of the hotel as their website accurately depicted the booking. Expedia needs to do better....

Reviewed on Feb 3, 2026

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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
Fully refundableReserve now, pay when you stay
$126 nightly
The price is $141 total per night from Feb 22 to Feb 23
$141 total
Feb 22 - Feb 23
Total with taxes and fees
8.6/10 Excellent! (2,227 reviews)
Spacious 2 bed 2 bath!

Reviewed on Feb 3, 2026

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
$121 nightly
The price is $136 total per night from Mar 8 to Mar 9
$136 total
Mar 8 - Mar 9
Total with taxes and fees
9/10 Wonderful! (826 reviews)
Room was clean and nicely equipped with kitchen. Will return if the future.

Reviewed on Feb 1, 2026

Berkshire Mountain Lodge
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street Williamstown MA
Fully refundableReserve now, pay when you stay
$208 nightly
The price is $233 total per night from Mar 1 to Mar 2
$233 total
Mar 1 - Mar 2
Total with taxes and fees
9.6/10 Exceptional! (572 reviews)
Clean

Reviewed on Jan 31, 2026

The Williams Inn
See all 1,006 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 $341 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.