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Holiday Homes in Chester Gap

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Chester Gap holiday homes

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

1. Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (37 reviews)
"Perfect place- would stay here again."
United States
HEMANT S.
The price is AU$310
includes taxes & fees
30 Aug - 31 Aug
Mountain View Bungalow in Front Royal
A modern kitchen with white cabinets, stainless steel appliances, and a central island with stools.

2. Greek Spa • Private Acreage • Stonefire pizza oven

Greek Spa • Private Acreage • Stonefire pizza oven
Front Royal
6.0 out of 10, (2 reviews)
"Wonderful!"
United States
jmichaelcopas
The price is AU$438
includes taxes & fees
1 Sept - 2 Sept
Greek Spa • Private Acreage • Stonefire pizza oven

3. Entire home in Apple Mountain Lake, Virginia,

Entire home in Apple Mountain Lake, Virginia,
Apple Mountain Lake
The price is AU$474
includes taxes & fees
9 Sept - 10 Sept
Entire home in Apple Mountain Lake, Virginia,
A stone fireplace with a glass front, a wooden mantel shelf, and a cozy knitted throw on a chair.

4. 4BR Golf Retreat | 3 Courses | Pool Table

4BR Golf Retreat | 3 Courses | Pool Table
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.
The price is AU$716
includes taxes & fees
17 Sept - 18 Sept
4BR Golf Retreat | 3 Courses | Pool Table
A hallway with a white door, a large mirror, a coat rack, and a patterned rug.

5. 1-Min Walk to The Inn • Private Suite, Tub & Full Kitchen.

1-Min Walk to The Inn • Private Suite, Tub & Full Kitchen.
Washington
10.0 out of 10, Exceptional, (20 reviews)
"Perfect location in town"
United States
Mona T.
The price is AU$321
includes taxes & fees
31 Aug - 1 Sept
1-Min Walk to The Inn • Private Suite, Tub & Full Kitchen.
A garden with a wooden swing set and a circular seating area.

6. Newly renovated Farm cottage with Mountain views

Newly renovated Farm cottage with Mountain views
Strasburg
10.0 out of 10, Exceptional, (50 reviews)
"What an absolutely lovely and peaceful place to stay! We had a wonderful visit. "
United States
Stephanie T.
The price is AU$423
includes taxes & fees
31 Aug - 1 Sept
Newly renovated Farm cottage with Mountain views
A small, single-story wooden cabin with a white-framed door and a small porch.

7. 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, (11 reviews)
"Host and everything was very accommodating! Very nice stay"
United States
James G.
The price is AU$317
includes taxes & fees
29 Aug - 30 Aug
Charming tiny home only 15 mins from Town of Warrenton & Town of Culpeper
A spacious loft bedroom with a large window, a cozy seating area, and a flat-screen TV.

8. ⭐️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, (15 reviews)
"Roomy, well stocked kitchen, and great view. Appreciated the chopsticks!"
United States
Brian T.
The price is AU$928
includes taxes & fees
8 Sept - 9 Sept
⭐️Lunar Lookout ⭐️ Geodesic Dome on 8 acres with HOT TUB!
A living room with a brick fireplace, a sofa, a television, and a window with a view of greenery.

9. Mountain home w/ hot tub & sunroom

Mountain home w/ hot tub & sunroom
Front Royal
9.0 out of 10, Wonderful, (32 reviews)
The price is AU$416
includes taxes & fees
8 Sept - 9 Sept
Mountain home w/ hot tub & sunroom
A modern kitchen with stainless steel appliances, a wooden countertop, and a large sliding glass door leading to a backyard.

10. Bend of Brothers’ | Riverfront Cottage Shenandoah

Bend of Brothers’ | Riverfront Cottage Shenandoah
Front Royal
8.0 out of 10, Very good, (1 review)
"This is a new place and owners have done great work . Excellent value for the money ."
United States
Dave B.
Bend of Brothers’ | Riverfront Cottage Shenandoah

11. 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)
The price is AU$523
includes taxes & fees
24 Sept - 25 Sept
Mountain Views w/Hot Tub, 95” TV & Trail Access
A conservatory with a glass ceiling, wicker furniture, and potted plants.

12. 1min walk to The Inn • Entire Colonial 3BR House Fast WiFi, tub & full kitchen .

1min walk to The Inn • Entire Colonial 3BR House Fast WiFi, tub & full kitchen .
Washington
10.0 out of 10, Exceptional, (128 reviews)
The price is AU$378
includes taxes & fees
7 Sept - 8 Sept
1min walk to The Inn • Entire Colonial 3BR House Fast WiFi, tub & full kitchen .
A spacious log cabin with a stone fireplace, large windows, a television, and a cozy seating area.

13. River Woods Retreat: Hot Tub, Hikes, 2 Fireplaces, EV

River Woods Retreat: Hot Tub, Hikes, 2 Fireplaces, EV
Bentonville
10.0 out of 10, Exceptional, (69 reviews)
"Lovely home in quiet, rustic setting. Very relaxing stay. Great communication with owner."
United States
Mary W.
The price is AU$567
includes taxes & fees
9 Sept - 10 Sept
River Woods Retreat: Hot Tub, Hikes, 2 Fireplaces, EV
A two-story house with a porch, surrounded by trees and grass.

14. 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)
The price is AU$529
includes taxes & fees
1 Sept - 2 Sept
1910 Farmhouse on 6 Acres • VA Wine Country
A wooden table with a vase of flowers, two glasses, and a bottle.

15. Valley View Farmhouse · Hot Tub, Fenced Pasture

Valley View Farmhouse · Hot Tub, Fenced Pasture
Amissville
The price is AU$551
includes taxes & fees
31 Aug - 1 Sept
Valley View Farmhouse · Hot Tub, Fenced Pasture
A covered porch with wooden railings, a ceiling fan, and a view of a green landscape.

16. 2BR home w/ BBQ grill & backyard

2BR home w/ BBQ grill & backyard
Luray
9.6 out of 10, Exceptional, (4 reviews)
"Enjoyed the stay!"
United States
Eric I.
The price is AU$464
includes taxes & fees
7 Sept - 8 Sept
2BR home w/ BBQ grill & backyard
A cabin interior with wooden walls, a dining table, a sofa, and mounted animal heads.

17. Antler Ridge - surrounded by nature & wildlife!

Antler Ridge - surrounded by nature & wildlife!
Page County
10.0 out of 10, Exceptional, (4 reviews)
"Nature lovers will love the Amazing property views and abundant opportunities to see wildlife. Deer, bears. Turkey were all seen while outside or viewed on the game cameras around the property from the comfort of relaxing inside and watching on the TV monitors. All aspects of our stay were above our expectations. Very clean, full kitchen with everything needed to cook inside or on grill while enjoying hot tub. Host and owners were awesome and great to communicate with . Complimentary local honey...
United States
Larry R.
The price is AU$497
includes taxes & fees
30 Aug - 31 Aug
Antler Ridge - surrounded by nature & wildlife!
A spacious living room with a wooden ceiling, a large sliding glass door leading to a deck, a comfortable sofa, and a fireplace.

18. Clouds Mountain Cabin

Clouds Mountain Cabin
Rileyville
9.6 out of 10, Exceptional, (17 reviews)
"We had a very quiet nice stay it was nice to have the woods where we could walk the dogs. The drive up was a little difficult even with four wheel drive but definitely worth the view "
United States
Jessica S.
The price is AU$468
includes taxes & fees
30 Aug - 31 Aug
Clouds Mountain Cabin
A hot tub with a view of a forest and mountains.

19. Cozy Cabin near Shenandoah · Hot Tub & Valley Views · Couples Retreat

Cozy Cabin near Shenandoah · Hot Tub & Valley Views · Couples Retreat
Rileyville
10.0 out of 10, Exceptional, (12 reviews)
"We had a great time. Quite and away from the hussle and bussle of the city. Enjoyed the views around."
United States
ItsMeBuknoy
The price is AU$490
includes taxes & fees
30 Aug - 31 Aug
Cozy Cabin near Shenandoah · Hot Tub & Valley Views · Couples Retreat
A balcony with a hot tub, wooden deck, and a view of a mountainous landscape.

20. Bear Ridge Cabin-Views & Hot tub

Bear Ridge Cabin-Views & Hot tub
Page County
The price is AU$457
includes taxes & fees
8 Sept - 9 Sept
Bear Ridge Cabin-Views & Hot tub
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

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

8/10 Good
"Great location love the space super clean only thing super close to the highway very loud"
Marque 4-night trip
Posted less than an hour ago
Comfort Inn & Suites Winchester

Find out more about Chester Gap

Chester Gap Holiday Homes information

Number of reviews
372
Accommodation
152 Holiday Homes
Lowest Price
AU$310
Highest Price
AU$928