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Holiday Homes in Chester Gap

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Chester Gap holiday homes

A two-story house with a porch, a small deck, and a gravel driveway.

1. Greek Spa - Frisbee Golf - Stone fire Pizza Oven

Greek Spa - Frisbee Golf - Stone fire Pizza Oven
Front Royal
Greek Spa - Frisbee Golf - Stone fire Pizza Oven
A wooden deck with white railings and a covered porch area.

2. Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (43 reviews)
"Perfect place- would stay here again."
United States
HEMANT S.
The price is €203
includes taxes & fees
18 Oct - 19 Oct
Mountain View Bungalow in Front Royal
A bedroom with a bed, a ceiling fan, a nightstand, a lamp, and a view of the outdoors through a sliding door.

3. Cozy 3BR Retreat | Perfect for Families & Groups

Cozy 3BR Retreat | Perfect for Families & Groups
Apple Mountain Lake
The price is €285
includes taxes & fees
25 Oct - 26 Oct
Cozy 3BR Retreat | Perfect for Families & Groups
A single-story brick building with a front porch, a picnic table, and a barbecue grill.

4. Shenandoah River House | 3BR - Private Dock - Pets

Shenandoah River House | 3BR - Private Dock - Pets
Front Royal
Shenandoah River House | 3BR - Private Dock - Pets
A garden with a central fountain, surrounded by neatly trimmed hedges and a brick pathway.

5. The Inn 1-Min Walk to Private Suite with Full Kitchen in 3BR Colonial House

The Inn 1-Min Walk to Private Suite with Full Kitchen in 3BR Colonial House
Washington
10.0 out of 10, Exceptional, (22 reviews)
"Perfect location in town"
United States
Mona T.
The price is €225
includes taxes & fees
27 Oct - 28 Oct
The Inn 1-Min Walk to Private Suite with Full Kitchen in 3BR Colonial House
A stone fireplace with a glass front, a wooden mantel shelf, and a cozy knitted throw on a chair.

6. Pool Table, Fireplace & Deck near Shenandoah Park

Pool Table, Fireplace & Deck near Shenandoah Park
Front Royal
10.0 out of 10, Exceptional, (1 review)
"Home was clean and looked like it had recently been remodeled/updated. The host was very responsive and when the oven wasn't working properly, they went to Lowes and purchased a new one immediately! Made our short trip much easier not having to eat out or find a last minute option for our kids/babysitter on Friday evening. We were only in town from Thursday-Sunday, and it was perfect for the 5 of us. The pool table was a fun addition for the kids. The only minor complaint I have is that I wish I...
United States
Crystal H.
Pool Table, Fireplace & Deck near Shenandoah Park
A living room with a brick fireplace, a sofa, a television, and a window with a view of greenery.

7. Mountain home w/ hot tub & sunroom

Mountain home w/ hot tub & sunroom
Front Royal
9.0 out of 10, Wonderful, (32 reviews)
"The cottage was amazing!! The hot tub was great and check in was super easy :) Internet and phone service were very good, and the cottage was stocked with all the kitchen utensils and linens we could have needed!"
United States
Mollie S.
Mountain home w/ hot tub & sunroom
Private kitchen

8. The River Bungalow at Shenandoah Haven

The River Bungalow at Shenandoah Haven
Bentonville
The price is €417
includes taxes & fees
26 Oct - 27 Oct
The River Bungalow at Shenandoah Haven
A spacious living room with a wooden coffee table, two leather sofas, a hanging light fixture, and a view of the adjacent kitchen.

9. Mountain Escape: Hottub + Fireplace + WiFi +PetsOK

Mountain Escape: Hottub + Fireplace + WiFi +PetsOK
Front Royal
The price is €355
includes taxes & fees
2 Nov - 3 Nov
Mountain Escape: Hottub + Fireplace + WiFi +PetsOK
Local wineries, breweries, and small-town charm in Front Royal

10. Mountain Views w/Hot Tub, 95” TV & Trail Access

Mountain Views w/Hot Tub, 95” TV & Trail Access
Shenandoah Farms
10.0 out of 10, Exceptional, (1 review)
"We were looking for a comfortable home base to explore Front Royal and Skyline Plaza, and this was perfect! A modernized home with enough amenities that we were tempted every day to just stay “home!” The kids loved the reading nook and cozy sitting areas, and the fire pit and clean, working hot tub were big pluses as well. Kitchen was roomy, with great appliances and plenty of counter space. Beds were comfortable. Bathrooms were nice and modern. Lots of closet space, too. When we left, the kids...
United States
Joshua J.
Mountain Views w/Hot Tub, 95” TV & Trail Access
A garden with a wooden swing set and a circular seating area.

11. Newly renovated Farm cottage with Mountain views

Newly renovated Farm cottage with Mountain views
Strasburg
10.0 out of 10, Exceptional, (56 reviews)
"We enjoyed our stay here. The property was lovely and the house was nicely stocked and decorated. We will definitely stay again when in the area!"
United States
Marsha N.
The price is €313
includes taxes & fees
23 Oct - 24 Oct
Newly renovated Farm cottage with Mountain views
Room

12. Trailside Retreat w/ Hot Tub, Sauna, Fireplace

Trailside Retreat w/ Hot Tub, Sauna, Fireplace
Front Royal
The price is €482
includes taxes & fees
25 Oct - 26 Oct
Trailside Retreat w/ Hot Tub, Sauna, Fireplace
A room with a large window, a round chair, a bar area with stools, and a dining table with chairs.

13. A-Frame Soak and Cedar near Skyline Drive and Wineries

A-Frame Soak and Cedar near Skyline Drive and Wineries
Front Royal
A-Frame Soak and Cedar near Skyline Drive and Wineries
A spacious loft bedroom with a large window, a cozy seating area, and a flat-screen TV.

14. ⭐️Lunar Lookout ⭐️ Geodesic Dome on 8 acres with HOT TUB!

⭐️Lunar Lookout ⭐️ Geodesic Dome on 8 acres with HOT TUB!
Front Royal
10.0 out of 10, Exceptional, (16 reviews)
"Taylor was great to work with! Nice property and wonderful view ."
United States
Christine H.
⭐️Lunar Lookout ⭐️ Geodesic Dome on 8 acres with HOT TUB!
A brick pathway leading to a fountain, surrounded by neatly trimmed hedges and a variety of plants.

15. The Inn 1 min walk to Entire Colonial 3BR House Fast WiFi

The Inn 1 min walk to Entire Colonial 3BR House Fast WiFi
Washington
10.0 out of 10, Exceptional, (131 reviews)
"Really enjoyed the stay—great house, clean, and perfect for a relaxing weekend."
United States
Daniel R.
The price is €251
includes taxes & fees
2 Nov - 3 Nov
The Inn 1 min walk to Entire Colonial 3BR House Fast WiFi
A balcony with a hot tub, wooden deck, and a view of a mountainous landscape.

16. Bear Ridge Cabin-Views & Hot tub

Bear Ridge Cabin-Views & Hot tub
Page County
Bear Ridge Cabin-Views & Hot tub
A two-story house with a porch, surrounded by trees and grass.

17. 1910 Farmhouse on 6 Acres • VA Wine Country

1910 Farmhouse on 6 Acres • VA Wine Country
Marshall
9.6 out of 10, Exceptional, (5 reviews)
"If we managed to do everything, sing, dance, play, we loved the comfortable place for us"
United States
Erick U.
1910 Farmhouse on 6 Acres • VA Wine Country
A cabin interior with wooden walls, a dining table, a sofa, and mounted animal heads.

18. Antler Ridge - surrounded by nature & wildlife!

Antler Ridge - surrounded by nature & wildlife!
Page County
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful well maintained mountain cabin. Everything was as described in the add and then some! A gift of local honey, coozies and bottled water labeled Antler Ridge was there when we arrived! The wildlife was incredible, lots of deer, a turkey with babies, raccoon, bullfrogs in pond, birds, fireflies, and a bear wandered by while we were enjoying our morning coffee. We heard coyotes in the distance at night! Property manager Brian was great with communication and quick to respond. Owner...
United States
kristin c.
The price is €348
includes taxes & fees
26 Oct - 27 Oct
Antler Ridge - surrounded by nature & wildlife!
A small, single-story wooden cabin with a white-framed door and a small porch.

19. Charming tiny home only 15 mins from Town of Warrenton & Town of Culpeper

Charming tiny home only 15 mins from Town of Warrenton & Town of Culpeper
Rixeyville
9.8 out of 10, Exceptional, (13 reviews)
"Perfect little house. Clean and very nice host."
United States
Debbie G.
The price is €208
includes taxes & fees
23 Oct - 24 Oct
Charming tiny home only 15 mins from Town of Warrenton & Town of Culpeper
A hot tub with a view of a mountainous landscape.

20. Mountain Summit Views Hot Tub-Fire Pit-BBQ, Pets

Mountain Summit Views Hot Tub-Fire Pit-BBQ, Pets
Page County
Mountain Summit Views Hot Tub-Fire Pit-BBQ, Pets
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 Chester Gap Hotel Reviews

Quality Inn Stephens City - Winchester South

Quality Inn Stephens City - Winchester South

8/10 Good
"Rooms updated for the most part. Curtains and doors need attention. Very clean tho. Cleaning lady T was very helpful! Breakfast was weak. It's maintained by desk manager who was nice and very busy. Need someone seperate for breakfast job. Beds comfy. Easy access off 81."
Rebecca 2-night trip
Posted 12 hours ago
Quality Inn Stephens City - Winchester South

Find out more about Chester Gap

Chester Gap Holiday Homes information

Number of reviews
325
Accommodation
155 Holiday Homes
Lowest Price
€203
Highest Price
€482