Caldwell Vacations from $863

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Your Caldwell Vacation

From its rich history to its rural countryside and beyond, there's plenty to love about Caldwell. Discover the delights of this captivating city with a Caldwell vacation package that's customized for you. Greenbrier Golf Course, West Virginia State Fair Fairgrounds and The Greenbrier Falconry are just a few of the sights you'll want to explore during your trip to Caldwell. Don't put off your visit to this destination any longer. The ultimate Caldwell vacation is a couple of clicks away with Expedia.

The Latest Caldwell vacation packages

Price found within the past 48 hours. Click for updated prices.
Washington Street Quarters

Washington Street Quarters

3 out of 5
Price was $951, price is now $863 per person
$863
per person
Sep 7 - Sep 12
found 23 hours ago
Roundtrip non-stop flight included
Portland (PDX) to Lewisburg (LWB)
9.8/10 Exceptional! (42 reviews)
Beautiful property, everything was in perfect order. Good coffee and she even had creamer. She thought of everything we needed, bar of soap, dish soap , extra towels and good coffee mugs. Location is excellent, if back in the area, we would definitely stay here again. Very Classy Place!!!

Reviewed on Jun 25, 2026

Motel M Lewisburg

Motel M Lewisburg

2 out of 5
Price was $1,124, price is now $1,029 per person
$1,029
per person
Sep 7 - Sep 12
found 23 hours ago
Roundtrip non-stop flight included
Portland (PDX) to Lewisburg (LWB)
5.8/10 (23 reviews)
It wasn't great it was ok. The price was the best part . There were no bugs it was definitely what you pay for

Reviewed on Jun 23, 2026

Thomas Rose Inn

Thomas Rose Inn

4 out of 5
Price was $1,215, price is now $1,128 per person
$1,128
per person
Sep 7 - Sep 12
found 23 hours ago
Roundtrip non-stop flight included
Portland (PDX) to Lewisburg (LWB)
9.8/10 Exceptional! (64 reviews)
We couldn't have been more pleased with our stay. Our room and amenities were exactly as they were shown and reviewed. There's so much thought and detail in every area. We will definitely be back again!

Reviewed on Jun 21, 2026

Historic General Lewis Inn

Historic General Lewis Inn

2 out of 5
Price was $1,097, price is now $1,032 per person
$1,032
per person
Sep 7 - Sep 12
found 23 hours ago
Roundtrip non-stop flight included
Portland (PDX) to Lewisburg (LWB)
9.6/10 Exceptional! (30 reviews)
Nicely maintained. Restaurant on the grounds. Good location.

Reviewed on Jun 22, 2026

Quality Inn Lewisburg

Quality Inn Lewisburg

2.5 out of 5
Price was $910, price is now $877 per person
$877
per person
Sep 7 - Sep 12
found 23 hours ago
Roundtrip non-stop flight included
Portland (PDX) to Lewisburg (LWB)
8.2/10 Very Good! (1,007 reviews)
Breakfast was all right - everything else about the stay was great :)

Reviewed on Jun 28, 2026

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Caldwell Hotel Deals

The Barn House: Caldwell Mtn Retreat w/ Hot Tub!

The Barn House: Caldwell Mtn Retreat w/ Hot Tub!

Caldwell WV
10/10 Exceptional! (67 reviews)
"Great Place- we enjoyed the Barn and the view-Worked well for our visit to WV.-Would book again/"

Reviewed on Jun 9, 2026

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The Barn House: Caldwell Mtn Retreat w/ Hot Tub!
Creek side Log Cabin with hot tub in White Sulphur Springs WV

Creek side Log Cabin with hot tub in White Sulphur Springs WV

Caldwell WV
10/10 Exceptional! (8 reviews)
"We had an excellent weekend. Stay at Creekside. The location was very convenient. Just 1 mile off the highway, a five minute drive to the Greenbrier, and a 10 minute drive to old town, Lewisburg. The cabin was immaculate. The beds were extremely comfortable. The shower was hot with good water pressure. ..."

Reviewed on May 10, 2026

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Creek side Log Cabin with hot tub in White Sulphur Springs WV
Mtn Views & Spacious Deck! Modern Caldwell Getaway

Mtn Views & Spacious Deck! Modern Caldwell Getaway

Caldwell WV
9.6/10 Exceptional! (4 reviews)
"Yes, the fireplace was great and we had everything we needed in the kitchen"

Reviewed on Apr 2, 2026

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Mtn Views & Spacious Deck! Modern Caldwell Getaway
See all 148 properties in Caldwell
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 Caldwell Vacation Packages

Caldwell Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Greenbrier Valley Airport (LWB)
Top Sights
The Greenbrier Falconry, Organ Cave and Greenbrier Golf Course

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Frequently asked questions

How much does a Caldwell vacation package cost?
You'll find cheap prices from $863 on Expedia for your Caldwell escape. However, factors like the season, choice of hotel and length of stay will determine how much your vacation to Caldwell costs.
What are the cheapest months to go to Caldwell?
You can typically find lower rates and better availability in February, November and December. Explore our cheap Caldwell vacation packages and you could get some great off-season discounts.
How many days is enough for Caldwell?
The ideal duration for your Caldwell vacation depends on what you'd like to see. Typically, a handful of days to a week will give you enough time to tick off all the leading sights and explore some hidden treasures along the way.
How to find the best Caldwell package deals?
Finding a cheap Caldwell package deal is a cinch with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your budget, apply a few filters and see what's available. You can tweak your search by "Amenities," "Property type," "Traveler experience" and more. Sort the results by "Price: low to high" to discover the most economical Caldwell package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Caldwell vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your car rental, flight and hotel into one great-value price and enjoy significant savings. You'll usually land a better deal than booking each component separately. And you'll still enjoy the flexibility to create a customized Caldwell vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Caldwell?
Enjoy incredible discounts by reserving your flights ahead of time with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Caldwell adventure.
Does Expedia offer Book Now, Pay Later Caldwell vacation packages?
Your Caldwell trip should be a relaxing escape from your busy life, not a source of money-related stress. So to allow you a little more flexibility, we've partnered with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the total 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.