Cheshire Vacations from $286

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The Latest Cheshire vacation packages

Price found within the past 48 hours. Click for updated prices.
Quality Inn

Quality Inn

2.5 out of 5
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Parkersburg (PKB)
6.2/10 (624 reviews)
Good for quick sleep but was definitely dirty and needs help.

Reviewed on Jul 21, 2025

Super 8 by Wyndham Ripley

Super 8 by Wyndham Ripley

2 out of 5
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Parkersburg (PKB)
7.8/10 Good! (870 reviews)
It served its purpose well, needed a room for the night. Conveniently located and close to restaurants and stores. Not fancy, not new, but clean. Mattresses are getting worn but sheets are clean. Smelled clean. Didn't eat breakfast, looked simple but once again, it was clean.

Reviewed on Jul 26, 2025

The Blennerhassett Hotel

The Blennerhassett Hotel

3.5 out of 5
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Parkersburg (PKB)
9.4/10 Exceptional! (1,005 reviews)
Liked the actual place. Room maybe should have been nicer. Mgr in restaurant should hv been friendlier.

Reviewed on Jul 21, 2025

Holiday Inn Express Hotel & Suites RIPLEY by IHG

Holiday Inn Express Hotel & Suites RIPLEY by IHG

2.5 out of 5
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Parkersburg (PKB)
8.8/10 Excellent! (522 reviews)
Best beds I have slept in at a hotel! Staff friendly. Everything was great. Will be back.

Reviewed on Jul 22, 2025

Wingate by Wyndham Vienna/Parkersburg/Marietta

Wingate by Wyndham Vienna/Parkersburg/Marietta

2.5 out of 5
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Parkersburg (PKB)
8.4/10 Very Good! (1,000 reviews)
The suite and room our family stayed in was absolutely fantastic! We could not have asked for more!

Reviewed on Jul 23, 2025

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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
$83 nightly
The price is $94 total per night from Aug 3 to Aug 4
$94 total
Aug 3 - Aug 4
Total includes taxes and fees
7.8/10 Good! (857 reviews)
"Quality service. Rooms were clean. Breakfast was well managed. Air conditioners work really well. The pool was small, but it did its job. Good thing about it was it inside. Would stay again."

Reviewed on Jul 23, 2025

Super 8 by Wyndham Gallipolis Pt Pleasant Area
Quality Inn

Quality Inn

2.5 out of 5
577 State Route 7 N, Gallipolis, OH
Fully refundableReserve now, pay when you stay
$84 nightly
The price is $92 total per night from Aug 17 to Aug 18
$92 total
Aug 17 - Aug 18
Total includes taxes and fees
7.6/10 Good! (1,004 reviews)
"I will definitely stay again the contenial breakfast was excellent all staff was great 👍"

Reviewed on Jul 27, 2025

Quality Inn
Beached houseboat with lots of character and deck jacuzzi

Beached houseboat with lots of character and deck jacuzzi

Langsville
9.6/10 Exceptional! (19 reviews)
I’m the Captain Now
"We had a really nice stay! My child loved the “no-grown-ups-allowed secret room” (lower bedroom) and playing Captain of the boat. The kitchen had everything you need; I was able to cook full meals using the griddle provided."

Reviewed on Jun 21, 2025

Get rates
Beached houseboat with lots of character and deck jacuzzi
See all 86 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 $286 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.