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Cabin Rentals in Upperville

Whiskey Hill Cabin a Mountain escape in Virginia Wine country.
Outdoor dining

Whiskey Hill Cabin a Mountain escape in Virginia Wine country.

10.0 out of 10, Exceptional, (90)
"This beautiful cabin has everything you need for a wonderful stay. My husband and I stayed here for our 44th anniversary while visiting local wineries. It was a perfect location."
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.
Rustic Mountain Log Cabin Perched on a cliff side above the Shenandoah River
Terrace/patio

Rustic Mountain Log Cabin Perched on a cliff side above the Shenandoah River

9.2 out of 10, Wonderful, (232)
"Quiet, cozy cabin in serene setting. "
Rustic Mountain Log Cabin Perched on a cliff side above the Shenandoah River
Blue Ridge Getaway - Sunset Views, A.T. Access
Exterior

Blue Ridge Getaway - Sunset Views, A.T. Access

10.0 out of 10, Exceptional, (54)
"Perfect house for a trip to the mountains!"
$424 nightly
The price is $472
Aug 24 - Aug 25
Total includes taxes and fees
Blue Ridge Getaway - Sunset Views, A.T. Access
Escape to Shenandoah River, Hot Tub after a Hike!
Smart TV, fireplace, stereo

Escape to Shenandoah River, Hot Tub after a Hike!

10.0 out of 10, Exceptional, (47)
"We had a great overnight stay. The house was very clean, and the hot tub was a nice bonus!"
Escape to Shenandoah River, Hot Tub after a Hike!
Relaxing log home on a private mountainside in Rappahannock County, Virginia
Property grounds

Relaxing log home on a private mountainside in Rappahannock County, Virginia

10.0 out of 10, Exceptional, (55)
"The cabin was fantastic, and perfect space for our family. Brian went above and beyond to accommodate us, and he provided everything we could possibly need. Next time we are visiting family in the area, we hope to book the cabin again!"
Relaxing log home on a private mountainside in Rappahannock County, Virginia
Cozy Mountain Cabin w/ Steam Shower. Family Friendly!
Dining

Cozy Mountain Cabin w/ Steam Shower. Family Friendly!

10.0 out of 10, Exceptional, (73)
"We had such a relaxing visit. The views were incredible. We can’t wait to go back!"
$300 nightly
The price is $333
Aug 5 - Aug 6
Total includes taxes and fees
Cozy Mountain Cabin w/ Steam Shower. Family Friendly!
Silo Tiny House Cabin
1 bedroom, iron/ironing board, free WiFi, bed sheets

Silo Tiny House Cabin

9.2 out of 10, Wonderful, (5)
"Heated mattress was the best. Thank you! "
$269 nightly
The price is $299
Aug 13 - Aug 14
Total includes taxes and fees
Silo Tiny House Cabin
Lakefront Log Cabin w/ Dreamy Waterfront Patio!
3 bedrooms, free WiFi, bed sheets

Lakefront Log Cabin w/ Dreamy Waterfront Patio!

2.0 star property
9.4 out of 10, Exceptional, (3)
"We loved the location and the property itself was decorated very cute. Would be awesome to have kayaks or something to take on the water but that is the only thing I would change! "
$349 nightly
The price is $388
Aug 6 - Aug 7
Total includes taxes and fees
Lakefront Log Cabin w/ Dreamy Waterfront Patio!
Whitetail Cabin | Couple's Retreat w/ Hot Tub
Fridge, microwave, stovetop, coffee/tea maker

Whitetail Cabin | Couple's Retreat w/ Hot Tub

10.0 out of 10, Exceptional, (19)
"We had a fantastic time staying at this property for the weekend."
$290 nightly
The price is $320
Aug 25 - Aug 26
Total includes taxes and fees
Whitetail Cabin | Couple's Retreat w/ Hot Tub
Secluded Cabin a Stone's Throw From the A.T.!
Fridge, microwave, oven, stovetop

Secluded Cabin a Stone's Throw From the A.T.!

9.8 out of 10, Exceptional, (28)
"We had an amazing time staying in this beautiful home. Communication and pre-trip information was outstanding, and the house was exactly as described. We didn’t even need to leave the property, we had everything we needed right there. Loved seeing a wild turkey and a baby deer with its mama, and the view from the kitchen and dining area was so serene. We would definitely stay here again!"
$354 nightly
The price is $394
Aug 12 - Aug 13
Total includes taxes and fees
Secluded Cabin a Stone's Throw From the A.T.!
Mountain Cabin in the Woods, Near Wineries & More!
Property grounds

Mountain Cabin in the Woods, Near Wineries & More!

8.6 out of 10, Excellent, (17)
"Lovely for short getaway with adult family. Games, hot tub, roomy with great bathrooms and little extras. "
Mountain Cabin in the Woods, Near Wineries & More!
Riverbend Retreat
Living area

Riverbend Retreat

10.0 out of 10, Exceptional, (1)
"Well done newly renovated cabin. I will definitely stay here again if I am in the area."
Riverbend Retreat
Blue Mountain Cabin, secluded, perfect for couples, near main road
Fridge, microwave, oven, stovetop

Blue Mountain Cabin, secluded, perfect for couples, near main road

10.0 out of 10, Exceptional, (21)
"Great place to relax"
Blue Mountain Cabin, secluded, perfect for couples, near main road
The Cozy Bear Cabin | Hot Tub, Fenced Yard, Games
Terrace/patio

The Cozy Bear Cabin | Hot Tub, Fenced Yard, Games

10.0 out of 10, Exceptional, (2)
"The house is amazing. Settled up on a hill. Nice and quiet. The house is big lots of room for a family. Big fenced back yard. My husband and I just need to rest. And we did just that. My dogs really enjoyed the back yard. It was both of their first time seeing deers and if they could the chase would be on. You will not be disappointed with this house it is amazing. Oh the kitchen has everything you need. I was able to bake our anniversary cake in the kitchen. Matt the host is amazing. ...
$408 nightly
The price is $450
Aug 26 - Aug 27
Total includes taxes and fees
The Cozy Bear Cabin | Hot Tub, Fenced Yard, Games
The Oculus - Huge Cabin with a Hot Tub!
Outdoor spa tub

The Oculus - Huge Cabin with a Hot Tub!

9.8 out of 10, Exceptional, (20)
"The property is well maintained. The surroundings are peaceful. It was conveniently located near the casino and winery we visited. The house only has one TV; but that gave us more time to make new memories. "
$396 nightly
The price is $441
Aug 21 - Aug 22
Total includes taxes and fees
The Oculus - Huge Cabin with a Hot Tub!
Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!
Property grounds

Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!

10.0 out of 10, Exceptional, (15)
"Great location. Great house. Could not have asked for more. "
$375 nightly
The price is $417
Aug 11 - Aug 12
Total includes taxes and fees
Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!
Peaceful Mountain Retreat Near Appalachian Trail, Wineries, Breweries and More
4 bedrooms, in-room safe, desk, iron/ironing board

Peaceful Mountain Retreat Near Appalachian Trail, Wineries, Breweries and More

10.0 out of 10, Exceptional, (16)
"A group of us stayed here while in town for a horse show. The property is clean and comfortable. Would definitely recommend!!"
Peaceful Mountain Retreat Near Appalachian Trail, Wineries, Breweries and More
The Foxwood Cabin | Hot Tub, Screened Porch, Grill
Terrace/patio

The Foxwood Cabin | Hot Tub, Screened Porch, Grill

10.0 out of 10, Exceptional, (3)
"The house was perfect! It was clean, updated, and was in a great location near multiple wineries and hiking spots. The bed was comfortable, we liked the layout, and enjoyed the hot tub. We would definitely book this place again. The communication was great as well. "
$359 nightly
The price is $396
Aug 20 - Aug 21
Total includes taxes and fees
The Foxwood Cabin | Hot Tub, Screened Porch, Grill
Rebels Rest - Cabin with Enchanting Sunset Views!
TV, DVD player, offices

Rebels Rest - Cabin with Enchanting Sunset Views!

9.8 out of 10, Exceptional, (30)
"Would come back anytime, very scenic and easy check-in process"
$377 nightly
The price is $419
Aug 20 - Aug 21
Total includes taxes and fees
Rebels Rest - Cabin with Enchanting Sunset Views!
Hilltop Retreat
Smart TV

Hilltop Retreat

Hilltop Retreat
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

Red Roof Inn Leesburg, VA

Red Roof Inn Leesburg, VA

10/10 Excellent
"Helpful staff"
julian 1-night trip
Posted 1 day ago
Red Roof Inn Leesburg, VA