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Compare 9 Chalets in Upperville with updated reviews, rates, and availability.
![Bear Mountain Lodge](https://images.trvl-media.com/lodging/58000000/57990000/57981800/57981735/ef573c60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Bear Mountain Lodge Shenandoah Mountains Skyline Drive / Front Royal (hottub)<br>
Bear Mountain Lodge Shenandoah Mountains Skyline Drive / Front Royal (hottub)<br>
10.0 out of 10, Exceptional, (36)
![Stream movies on our smart TV!](https://images.trvl-media.com/lodging/93000000/92170000/92168300/92168272/ee51b436.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Modern Harpers Ferry Cabin w Hot Tub, Deck, WiFi!
Modern Harpers Ferry Cabin w Hot Tub, Deck, WiFi!
10.0 out of 10, Exceptional, (5)
The price is AED 650
AED 1,200 total
includes taxes & fees
18 Feb - 19 Feb
![Welcome to Sky Island Chalet. Only 1 hour from DC area. 5 Bedrooms 4 Bathroom.](https://images.trvl-media.com/lodging/104000000/103850000/103846500/103846459/d27dd9bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Timber frame chalet with incredible views minutes from Shenandoah National Park.
Timber frame chalet with incredible views minutes from Shenandoah National Park.
10.0 out of 10, Exceptional, (3)
![Our living room seats 9; our dining room seats 8, plus 2 at the kitchen bar](https://images.trvl-media.com/lodging/88000000/87650000/87642600/87642509/8946b3fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Whitetail Summit - Shenandoah/hot tub/wineries
Whitetail Summit - Shenandoah/hot tub/wineries
10.0 out of 10, Exceptional, (37)
![Read a book in our living room by the fireplace](https://images.trvl-media.com/lodging/93000000/92170000/92168300/92168268/5ac5a09a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI
Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI
9.4 out of 10, Exceptional, (18)
The price is AED 864
AED 1,420 total
includes taxes & fees
23 Feb - 24 Feb
![Private kitchen](https://images.trvl-media.com/lodging/74000000/73650000/73642300/73642204/102560d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
"Charming 3-Bedroom Chalet in Harpers Ferry, WV: Perfect Escape"
"Charming 3-Bedroom Chalet in Harpers Ferry, WV: Perfect Escape"
10.0 out of 10, Exceptional, (33)
![](https://images.trvl-media.com/lodging/111000000/110990000/110988600/110988526/88c304d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Cozy w Fire Pit, Grill, Deck, Screened Porch, WiFi
Cozy w Fire Pit, Grill, Deck, Screened Porch, WiFi
10.0 out of 10, Exceptional, (1)
The price is AED 581
AED 1,112 total
includes taxes & fees
17 Feb - 18 Feb
![Amazing view from porch and windows](https://images.trvl-media.com/lodging/75000000/74690000/74681000/74680918/cb4d9419.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
River Retreat-modern luxury 5 min to Skyline Drive
River Retreat-modern luxury 5 min to Skyline Drive
9.6 out of 10, Exceptional, (15)
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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Other property types in Upperville
![Exterior](https://images.trvl-media.com/lodging/94000000/93520000/93510500/93510450/e5d7776a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
18th Century Stone Cottage minutes from historic Middleburg
18th Century Stone Cottage minutes from historic Middleburg
10.0 out of 10, Exceptional, (36)
The price is AED 1,010
AED 1,439 total
includes taxes & fees
17 Feb - 18 Feb
![Exterior](https://images.trvl-media.com/lodging/20000000/19660000/19651400/19651347/140d8a96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Breathtaking views with an indoor private pool, come escape with us
Breathtaking views with an indoor private pool, come escape with us
9.8 out of 10, Exceptional, (244)
![Exterior](https://images.trvl-media.com/lodging/100000000/99280000/99271200/99271141/6ea949fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Trailside Retreat in breathtaking Western Loudoun
Trailside Retreat in breathtaking Western Loudoun
10.0 out of 10, Exceptional, (43)
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.
Recent reviews of Upperville hotels
Recent reviews of Upperville hotels
![La Quinta Inn & Suites by Wyndham Winchester](http://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/3336c7bb_y.jpg)
La Quinta Inn & Suites by Wyndham Winchester
5/5 Excellent
"Clean room right off the Interstate with friendly staff and a better than normal breakfast. Perfect for a one night stay while traveling. "
A verified traveler stayed at La Quinta Inn & Suites by Wyndham Winchester
Posted 1 day ago
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