Chester Gap Holiday Homes from £172: Search Holiday Homes in Chester Gap

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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

Front Royal

includes taxes & fees

3 Nov - 4 Nov

A wooden deck with white railings and a covered porch area.

2. Mountain View Bungalow in Front Royal

Front Royal

HEMANT S.

includes taxes & fees

21 Oct - 22 Oct

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

Apple Mountain Lake

includes taxes & fees

26 Oct - 27 Oct

A single-story brick building with a front porch, a picnic table, and a barbecue grill.

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

Front Royal

includes taxes & fees

19 Oct - 20 Oct

A stone fireplace with a glass front, a wooden mantel shelf, and a cozy knitted throw on a chair.

5. Pool Table, Fireplace & Deck near Shenandoah Park

Front Royal

"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...

Crystal H.

includes taxes & fees

22 Oct - 23 Oct

A garden with a central fountain, surrounded by neatly trimmed hedges and a brick pathway.

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

Washington

Mona T.

includes taxes & fees

27 Oct - 28 Oct

Local wineries, breweries, and small-town charm in Front Royal

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

Shenandoah Farms

"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...

Joshua J.

includes taxes & fees

28 Oct - 29 Oct

8. The River Bungalow at Shenandoah Haven

Bentonville

includes taxes & fees

3 Nov - 4 Nov

A garden with a wooden swing set and a circular seating area.

9. Newly renovated Farm cottage with Mountain views

Strasburg

Marsha N.

includes taxes & fees

20 Oct - 21 Oct

A living room with a brick fireplace, a sofa, a television, and a window with a view of greenery.

10. Mountain home w/ hot tub & sunroom

Front Royal

Mollie S.

includes taxes & fees

3 Nov - 4 Nov

A spacious living room with a wooden coffee table, two leather sofas, a hanging light fixture, and a view of the adjacent kitchen.

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

Front Royal

includes taxes & fees

28 Oct - 29 Oct

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

Front Royal

Nick G.

includes taxes & fees

3 Nov - 4 Nov

A spacious loft bedroom with a large window, a cozy seating area, and a flat-screen TV.

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

Front Royal

Christine H.

includes taxes & fees

19 Oct - 20 Oct

A small, single-story wooden cabin with a white-framed door and a small porch.

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

Rixeyville

Debbie G.

includes taxes & fees

19 Oct - 20 Oct

A balcony with a hot tub, wooden deck, and a view of a mountainous landscape.

15. Bear Ridge Cabin-Views & Hot tub

Page County

includes taxes & fees

16 Nov - 17 Nov

A brick pathway leading to a fountain, surrounded by neatly trimmed hedges and a variety of plants.

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

Washington

Daniel R.

includes taxes & fees

2 Nov - 3 Nov

A two-story house with a porch, surrounded by trees and grass.

17. 1910 Farmhouse on 6 Acres • VA Wine Country

Marshall

Erick U.

includes taxes & fees

17 Nov - 18 Nov

A hot tub with a view of a mountainous landscape.

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

Page County

includes taxes & fees

18 Nov - 19 Nov

A cabin interior with wooden walls, a dining table, a sofa, and mounted animal heads.

19. Antler Ridge - surrounded by nature & wildlife!

Page County

"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...

kristin c.

includes taxes & fees

16 Nov - 17 Nov

20. Sunset Haven - 10 min from Skyline Drive. Hot Tub

Front Royal

Laura D.

includes taxes & fees

20 Oct - 21 Oct

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Top Chester Gap Hotel Reviews

Hillside

8/10 Good

"The location is beautiful. Enough picnic benches to sit outside and enjoy gorgeous evenings. The main issue was thin walls. I could hear talking from both sides (left & right) of the room. Rooms with queen beds are a tight fit getting in from the door."

Baymont by Wyndham Front Royal Near Shenandoah National Park

10/10 Excellent

"My room was very clean. Bed was comfortable and I loved having a coffee maker, microwave and refrigerator. Also had a safe for valuables. I will definitely stay again. Plus was the elevator. I had reserved a night at the Motel 6 but they didn't have elevators and no rooms available on the first floor. I told them I couldn't carry my luggage up so I wouldn't be able to stay there. I still got charged."

TownePlace Suites by Marriott Front Royal

10/10 Excellent

"The hotel is really nice, seems new. The decor is lovely and the rooms are big. The breakfast isn't as fancy as some but was very good. I did have a problem with the dishwasher beeping and a staff member came right over and reset it. I would certainly stay again."

"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub

10/10 Excellent

"The cabin is very secluded and very relaxing. The field with the trails was fantastic nice quiet hang out by the water was beautiful. It's an excellent place to unplug from the world."

Find out more about Chester Gap

Chester Gap Holiday Homes information

Number of reviews	340
Accommodation	179 Holiday Homes
Lowest Price	£172
Highest Price	£518

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Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chester Gap holiday homes

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

2. Mountain View Bungalow in Front Royal

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

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

5. Pool Table, Fireplace & Deck near Shenandoah Park

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

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

8. The River Bungalow at Shenandoah Haven

9. Newly renovated Farm cottage with Mountain views

10. Mountain home w/ hot tub & sunroom

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

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

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

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

15. Bear Ridge Cabin-Views & Hot tub

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

17. 1910 Farmhouse on 6 Acres • VA Wine Country

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

19. Antler Ridge - surrounded by nature & wildlife!

20. Sunset Haven - 10 min from Skyline Drive. Hot Tub

Find holiday rentals that suit your style

Top Chester Gap Hotel Reviews

Hillside

Baymont by Wyndham Front Royal Near Shenandoah National Park

Wayside Inn

Super 8 by Wyndham Front Royal Near Shenandoah National Park

Fairfield Inn & Suites Strasburg Shenandoah Valley

Hampton Inn Front Royal

Holiday Inn Express Winchester South-Stephens City by IHG

TownePlace Suites by Marriott Front Royal

"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub

Find out more about Chester Gap

Chester Gap Holiday Homes information

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