Chester Gap Cottages

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Our top choices for Chester Gap cottages

A single-story house with a porch, a stone pathway leading to the entrance, and a clear sky.

1. Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View

Front Royal

Jake M.

includes taxes & fees

29 Sept - 30 Sept

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

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

Front Royal

Hailey

includes taxes & fees

29 Sept - 30 Sept

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

29 Sept - 30 Sept

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

4. 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

30 Sept - 1 Oct

5. Mountaintop Cottage | Private Hot Tub

Front Royal

Sara Z.

includes taxes & fees

27 Sept - 28 Sept

An outdoor patio with Adirondack chairs and a fire pit, surrounded by a forested area.

6. Luray 'black Walnut Cabin' on 2 Acres w/ Fire Pit!

Luray

includes taxes & fees

27 Sept - 28 Sept

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

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

Boyce

Felice N.

includes taxes & fees

22 Oct - 23 Oct

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Top Chester Gap Hotel Reviews

Country Inn & Suites by Radisson, Winchester, VA

10/10 Excellent

"Good bed, nice size room, desk clerk was very helpful in getting us on the non-highway side of the property (which was then very quiet). Breakfast OK, lots of restaurants around the property and a movie theatre. Good location for Winchester"

Wayside Inn

10/10 Excellent

"We love staying at Wayside Inn. This is our third or fourth stay. The place is such a treasure! The food in the restaurant is good and the bar is fun. The only thing we noticed this time is that the bar closed at 9 p.m. on a Saturday night. We came in from dinner at 9:15 and planned to have a night cap and were told the bar closed at 9:00! The previous times we stayed there the bar was open until 10 or 11 on Saturday. We though such an early closing time was odd for the weekend."

Holiday Inn Express Winchester South-Stephens City by IHG

8/10 Good

"The hotel and all amenities were fine. When I went to check in I was told I had gone through a search site to book the room, which I had not. I booked directly with them, I had to get that clear before I could use my AAA discount."

Find out more about Chester Gap