Upperville Cottages

A sign for the Village of UPPERVILLE with a 'Please drive slowly' message.

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Our top choices for Upperville cottages

A stone house with a chimney, surrounded by a well-maintained lawn and trees.

1. 18th Century Stone Cottage minutes from historic Middleburg

Middleburg

Mary H.

includes taxes & fees

15 Nov - 16 Nov

A covered outdoor area with a fire pit, seating, and a view of the landscape.

2. Mountain View Cottage with Hot Tub and River Views

Front Royal

"We enjoyed our stay and certainly return. Our group was 2 couples and 2 children.Everyone had enough space to be comfortable. The view is beautiful so we enjoyed our time at the house. While in the area, we visited Skyline Caverns and the Shenandoah River. I did have a challenging time getting Door Dash to the house. After 30 minutes of seeing the driver in the neighborhood we got in the car to track down the driver. Her cell service was poor so we were unable to communicate. If I ordered...

MaryBeth C.

includes taxes & fees

9 Nov - 10 Nov

A hot tub on an outdoor deck with a view of trees and hills.

3. Mountain View Cottage | Hot Tub & Game Room

Front Royal

Katia R.

includes taxes & fees

3 Nov - 4 Nov

4. Cozy Cottage with Hot Tub, Fire Pit and Sunroom - Loaded with Modern Touches in Front Royal, VA

Front Royal

includes taxes & fees

3 Nov - 4 Nov

A hot tub under a wooden pergola with a grassy yard and trees in the background.

5. Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi

Boyce

Felice N.

6. Mountaintop Cottage | Private Hot Tub

Front Royal

Sara Z.

includes taxes & fees

9 Nov - 10 Nov

A modern building with large windows, a deck, and a stone wall.

7. Woodsy Retreat with a Hot Tub and Seasonal Views!

Harpers Ferry

Rebecca N.

includes taxes & fees

12 Nov - 13 Nov

A hot tub on a deck with a view of a lake and forest.

8. Peaceful Lakefront Cottage with Mountain Views!

Harpers Ferry

Lisa h.

includes taxes & fees

9 Nov - 10 Nov

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Top Upperville Hotel Reviews

Comfort Inn & Suites Winchester

10/10 Excellent

"This was a last minute stop and I wish we could have stayed longer. Check in was fast and easy. The room was immaculate, spacious and comfortable. Our room was facing the highway and I was worried that the noise would be an issue but I slept like a rock. The breakfast was good."

The George Washington Hotel, A Wyndham Grand Hotel

10/10 Excellent

"rooms are clean, spacious, and serviced everyday. Good breakfast on offer and the Bar is good too. Greal location and good parking. Staff very helpful and knowledgeable about the area. Shenandoah mountains are wonderful. Lots of wineries and farmers market near by"

Spark by Hilton Winchester

10/10 Excellent

"What a pleasure staying a night in such a new, sparkling clean hotel! Location was fantastic with lots of stores and restaurants and the Highway very close! Our room was extremely clean and comfy! The front desk clerk on the night of Oct 18 was fantastic and friendly! Breakfast was just Continental, but better than nothing!"

Salamander Middleburg

10/10 Excellent

"The Salamander resort is breathtaking! Spectacular property. The staff was always willing to answer questions or to help in any way possible. Our room was clean and very comfortable. I was so happy to see that it is pet friendly. My only complaint was that guests left their dogs in their rooms while they were out. I heard a few dogs that were clearly distressed at being left alone. As a dog owner, it really upset me. The guests should be required to not leave their pets alone."

Find out more about Upperville