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.

HK$3,107 total

includes taxes & fees

12 Oct - 13 Oct

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.

HK$5,912 total

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.

HK$5,990 total

includes taxes & fees

9 Nov - 10 Nov

4. Mountaintop Cottage | Private Hot Tub

Front Royal

Sara Z.

HK$4,901 total

includes taxes & fees

15 Oct - 16 Oct

A two-story house with a wooden deck, surrounded by lush greenery.

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

Front Royal

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

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

Boyce

Felice N.

HK$5,534 total

includes taxes & fees

22 Oct - 23 Oct

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

7. Peaceful Lakefront Cottage with Mountain Views!

Harpers Ferry

Lisa h.

HK$4,007 total

includes taxes & fees

20 Oct - 21 Oct

A hot tub area with a view of a lake and trees, surrounded by ornate black metal railings and decorative lanterns.

8. Riverfront! Shenandoah River! Sleeps 4! New Hot Tub

Front Royal

Hailey

HK$3,420 total

includes taxes & fees

12 Oct - 13 Oct

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Top Upperville Hotel Reviews

Travelodge by Wyndham Winchester

8/10 Good

"Very nice and convenient location. The rooms were very clean and well maintained. A lot of free parking available."

Comfort Inn & Suites Winchester

10/10 Excellent

"It’s in a very nice shopping plaza next to a grocery store restaurant in movie theater, so it was perfect for me. It’s been relatively recently renovated, but besides that it was very very clean and the staff was excellent from front desk to the night audit and even the woman who did breakfast was really lovely and the door to breakfast prep was open so I could see how clean it was in there."

Country Inn & Suites by Radisson, Winchester, VA

10/10 Excellent

"This facility is excellent. The breakfast was excellent with many extras including honey packets. It has a very good selection 8 plus to add to yogurt, etc. I had a very nice cream cheese bagel with honey drizzled. They also had eggs and sausage. It also has a coffee/herbal tea station in the lobby. The pool was spotless. Perfectly clean. Perfect. The room was spacious. There were plenty of spaces to congregate both inside and outside. The seasonal fall decor was a very nice touch. It was very full and impressive. I very highly reccomend this facility. Superb."

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