Cheshire Vacations from $1,450

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The Latest Cheshire vacation packages

Price found within the past 48 hours. Click for updated prices.
The Lafayette A grand Riverboat Era Hotel

The Lafayette A grand Riverboat Era Hotel

3 out of 5
Price was $1,567, price is now $1,450 per person
$1,450
per person
Dec 26 - Jan 2
found 10 hours ago
Roundtrip flight included
San Antonio (SAT) to Parkersburg (PKB)
8.8/10 Excellent! (1,002 reviews)
My room was small, but had a great view of the Ohio River. The room was filled with antique furnishings which added to the atmosphere. The restaurant had a cool old bar, the food and service were good, and they had a nice selection of single malt Scotches and bourbons.

Reviewed on Nov 11, 2026

Workspace Studio Ski-in Ski-out AC

Workspace Studio Ski-in Ski-out AC

3 out of 5
Save 100% on your flight
Price was $5,564, price is now $4,391 per person
$4,391
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip flight included
San Antonio (SAT) to Parkersburg (PKB)
8/10 Very Good! (5 reviews)
Room was clean, exactly as described, check in was super easy and hosts communicated wonderfully will definitely considers staying again for our next trip.

Reviewed on Jul 26, 2026

Top Property on Snowshoe Mountain North Westridge 32 is as Magnificent as its Western Views!

Top Property on Snowshoe Mountain North Westridge 32 is as Magnificent as its Western Views!

2 out of 5
Save 100% on your flight
Price was $19,046, price is now $17,531 per person
$17,531
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip flight included
San Antonio (SAT) to Parkersburg (PKB)
No reviews

Sanctuary Family Paradise Private Home With Hot tub Snowshoe Mtn Resort

Sanctuary Family Paradise Private Home With Hot tub Snowshoe Mtn Resort

2 out of 5
Save 100% on your flight
Price was $15,558, price is now $14,342 per person
$14,342
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip flight included
San Antonio (SAT) to Parkersburg (PKB)
No reviews

Summit 304c, Snow White Summit 3 Br Walk to Slopes & Village

Summit 304c, Snow White Summit 3 Br Walk to Slopes & Village

2 out of 5
Price was $7,913, price is now $7,341 per person
$7,341
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip flight included
San Antonio (SAT) to Parkersburg (PKB)
No reviews

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Cheshire Hotel Deals

Super 8 by Wyndham Gallipolis Pt Pleasant Area

Super 8 by Wyndham Gallipolis Pt Pleasant Area

2 out of 5
321 Upper River Road Gallipolis OH
Fully refundableReserve now, pay when you stay
$84 nightly
The price is $95 total per night from Dec 6 to Dec 7
$95 total
Dec 6 - Dec 7
Total with taxes and fees
8/10 Very Good! (1,005 reviews)
"There were pubic hair on the “clean” sheets, urine in the toilet, and breakfast was not ready at the time it was suppose to be ready."

Reviewed on Nov 10, 2026

Super 8 by Wyndham Gallipolis Pt Pleasant Area
Four Seasons Inn

Four Seasons Inn

2.5 out of 5
151 Upper River Rd Gallipolis OH
Fully refundableReserve now, pay when you stay
$80 nightly
The price is $91 total per night from Nov 24 to Nov 25
$91 total
Nov 24 - Nov 25
Total with taxes and fees
8.6/10 Excellent! (125 reviews)
"Clean and well kept. Just need more items for breakfast."

Reviewed on Nov 9, 2026

Four Seasons Inn
Quality Inn Gallipolis

Quality Inn Gallipolis

2.5 out of 5
577 State Route 7 N Gallipolis OH
Fully refundable
$108 nightly
The price is $119 total per night from Dec 3 to Dec 4
$119 total
Dec 3 - Dec 4
Total with taxes and fees
7.4/10 Good! (1,000 reviews)
"Rooms were clean, staff was sweet and helpful and had a good attitude the entire time. Breakfast was pretty amazing and I love the restaurant style ordering system."

Reviewed on Nov 10, 2026

Quality Inn Gallipolis
See all 107 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
130
Max Temp Winter
40ºF
Max Temp Summer
85ºF

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Frequently asked questions

How much does a Cheshire vacation package cost?
You'll find cheap prices from $1,450 on Expedia for your Cheshire escape. However, a range of factors like the season, length of stay and your choice of hotel will determine how much your vacation to Cheshire costs.
What are the cheapest months to go to Cheshire?
December, January and February are great times to look for cheap Cheshire vacation packages. Traveling in less busy months means you can typically find reduced prices on accommodations and flights.
How many days is enough for Cheshire?
Typically, a handful of days is enough to check out the main attractions during your Cheshire vacation. But if you prefer to have time to kick back or take day trips, consider extending your itinerary.
How to find the best Cheshire package deals?
Use Expedia's handy filters to find some terrific Cheshire package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or browse 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 book your vacation package well in advance.
Is it cheaper to book a Cheshire vacation as a package?
You can enjoy significant savings on your Cheshire break by booking a personalized vacation package. Check the "Package" heading, then select your travel dates and destination to view some great flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Cheshire?
Score incredible discounts by booking your flights in advance with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for an impromptu Cheshire getaway.
Does Expedia offer Book Now, Pay Later Cheshire vacation packages?
Your Cheshire trip is meant to be an escape from your daily routine, not a reason for money worries. So to allow you extra flexibility, we've partnered with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there are no hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.