Search Chalets in Upperville from CA $233

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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Upperville Chalets

Bear Mountain Lodge Shenandoah Mountains Skyline Drive / Front Royal (hottub)<br>
Property grounds

Bear Mountain Lodge Shenandoah Mountains Skyline Drive / Front Royal (hottub)<br>

10.0 out of 10, Exceptional, (46)
"We had a nice stay at this location. The property managers were extremely quick to respond and helpful pointing out must visit locations while at the property."
Bear Mountain Lodge Shenandoah Mountains Skyline Drive / Front Royal (hottub)<br>
Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI
Outdoor dining

Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI

9.2 out of 10, Wonderful, (25)
"We came for a two-night getaway and loved our stay. The cabin is clean, quiet, quaint, and well-appointed. We particularly enjoyed the hot tub!"
The price is CA $288
CA $488 total
includes taxes & fees
Sep 1 - Sep 2
Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI
Modern Harpers Ferry Cabin w Hot Tub, Deck, WiFi!
Outdoor spa tub

Modern Harpers Ferry Cabin w Hot Tub, Deck, WiFi!

10.0 out of 10, Exceptional, (7)
"My group of friends enjoyed our stay at the cabin after a day of light hiking and visiting nearby Harper's Ferry. The property manager/owner was great with communicating to make sure we were checked in and very quick at answering a question we had. I would stay again when visiting the area. "
The price is CA $462
CA $713 total
includes taxes & fees
Sep 3 - Sep 4
Modern Harpers Ferry Cabin w Hot Tub, Deck, WiFi!
Cozy w Fire Pit, Grill, Deck, Screened Porch, WiFi
Property grounds

Cozy w Fire Pit, Grill, Deck, Screened Porch, WiFi

10.0 out of 10, Exceptional, (1)
"Our family had a cozy weekend at the cabin. Tony was super helpful and a great host. Thank you for sharing your lovely property with us!"
The price is CA $233
CA $430 total
includes taxes & fees
Sep 2 - Sep 3
Cozy w Fire Pit, Grill, Deck, Screened Porch, WiFi
Whitetail Summit - Shenandoah/hot tub/wineries
Outdoor dining

Whitetail Summit - Shenandoah/hot tub/wineries

10.0 out of 10, Exceptional, (41)
"Really enjoyed our stay and all the little touches - like labeled drawers and clear instructions. Very comfortable beds, pillows, and all the amenities you could want. Perfect for an uninterrupted girls weekend getaway."
Whitetail Summit - Shenandoah/hot tub/wineries
Timber frame chalet with incredible views minutes from Shenandoah National Park.
Outdoor dining

Timber frame chalet with incredible views minutes from Shenandoah National Park.

9.8 out of 10, Exceptional, (7)
"I would recommend this property to anyone looking to visit Virginia wineries with friends, go hiking in the beautiful mountains, or just unwind. It is close to so many wineries, restaurants, hiking trails, and is a quiet spot to just relax. We will definitely be back!"
Timber frame chalet with incredible views minutes from Shenandoah National Park.
"Charming 3-Bedroom Chalet in Harpers Ferry, WV: Perfect Escape"
Property grounds

"Charming 3-Bedroom Chalet in Harpers Ferry, WV: Perfect Escape"

10.0 out of 10, Exceptional, (33)
"Great place to stay, peaceful and quiet"
"Charming 3-Bedroom Chalet in Harpers Ferry, WV: Perfect Escape"
The Cuckoo Chalet, Get-Away Cabin near Historic Harpers Ferry, West Virginia
Outdoor dining

The Cuckoo Chalet, Get-Away Cabin near Historic Harpers Ferry, West Virginia

9.0 out of 10, Wonderful, (2)
"Adorable chalet. I’d love to come back! Clean and well stocked. "
The Cuckoo Chalet, Get-Away Cabin near Historic Harpers Ferry, West Virginia
River Retreat-modern luxury 5 min to Skyline Drive
Terrace/patio

River Retreat-modern luxury 5 min to Skyline Drive

9.6 out of 10, Exceptional, (16)
"This house was new, clean, well stocked in the kitchen and bathrooms with essentials which was very nice. . Quick responses with the owner when I had questions. Enjoyed our stay!!"
River Retreat-modern luxury 5 min to Skyline Drive
Emberwood | Modern Chalet + Nature Spa + Trails, & Wineries
Property grounds

Emberwood | Modern Chalet + Nature Spa + Trails, & Wineries

The price is CA $328
CA $802 total
includes taxes & fees
Aug 5 - Aug 6
Emberwood | Modern Chalet + Nature Spa + Trails, & Wineries
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.
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Top Upperville Hotel Reviews

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

10/10 Excellent
"Friendly staff. Good location. Lots of places to eat. Within walking distance. Property was clean. And well maintained. "
Frank 1-night trip
Posted 2 days ago
Comfort Inn & Suites Winchester