Cheshire Vacations from $290

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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 Clocktower Hotel at Century House, an Ascend Collection Hotel

The Clocktower Hotel at Century House, an Ascend Collection Hotel

2.5 out of 5
Price was $347, price is now $290 per person
$290
per person
Jan 15 - Jan 18
found 21 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Albany (ALB)
8.4/10 Very Good! (1,022 reviews)
Fresh breakfast items, immaculate hotel, polite staff

Reviewed on Nov 8, 2025

Holiday Inn Express and Suites Albany Airport- Wolf Road by IHG

Holiday Inn Express and Suites Albany Airport- Wolf Road by IHG

2.5 out of 5
Price was $361, price is now $298 per person
$298
per person
Jan 15 - Jan 18
found 21 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Albany (ALB)
8.6/10 Excellent! (1,024 reviews)
We spent one night here. The welcome water and snacks were lovely after a long drive. I would stay here again .

Reviewed on Nov 1, 2025

Marriott Albany

Marriott Albany

3.5 out of 5
Price was $412, price is now $347 per person
$347
per person
Jan 15 - Jan 18
found 21 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Albany (ALB)
8.2/10 Very Good! (724 reviews)
Nice front desk lady

Reviewed on Nov 1, 2025

Hampton Inn Albany-Wolf Road (Airport)

Hampton Inn Albany-Wolf Road (Airport)

2.5 out of 5
Price was $354, price is now $299 per person
$299
per person
Jan 15 - Jan 18
found 21 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Albany (ALB)
8.6/10 Excellent! (1,023 reviews)
Nice, spacious room, very comfortable

Reviewed on Nov 6, 2025

Hilton Garden Inn Albany Medical Center

Hilton Garden Inn Albany Medical Center

3 out of 5
Price was $403, price is now $341 per person
$341
per person
Jan 15 - Jan 18
found 21 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Albany (ALB)
8.6/10 Excellent! (1,006 reviews)
The room could have been in better condition.

Reviewed on Nov 4, 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
$244 nightly
The price is $258 total per night from Dec 9 to Dec 10
$258 total
Dec 9 - Dec 10
Total with taxes and fees
9.6/10 Exceptional! (38 reviews)
The owner Brandi was outstanding, friendly, she made us fresh homemade breakfast each morning, which the best. Will differently stay there again. Wonderful place and people.

Reviewed on Sep 12, 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
$112 nightly
The price is $125 total per night from Nov 12 to Nov 13
$125 total
Nov 12 - Nov 13
Total with taxes and fees
8.6/10 Excellent! (2,117 reviews)
The amenities are great. The pool and hot tub are very comfortable temperatures, pool tables, ping pong, foosball, arcade games, movie theater, and more.

Reviewed on Nov 2, 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
$144 nightly
The price is $161 total per night from Dec 9 to Dec 10
$161 total
Dec 9 - Dec 10
Total with taxes and fees
8.6/10 Excellent! (1,001 reviews)
Very clean and inviting Hotel located in downtown area. Very walkable area. Parking was free. Front desk very friendly and helpful. Would stay again.

Reviewed on Nov 3, 2025

Hotel Downstreet, an Ascend Collection Hotel
See all 998 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 $290 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.