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Check prices for these dates

In two weeks
1 May - 3 May
In two months
12 Jun - 14 Jun
In three months
10 Jul - 12 Jul
In four months
7 Aug - 9 Aug

Our top choices for Chester Gap holiday homes

Exterior detail

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
9.6 out of 10, Exceptional, (8 reviews)
"Host and everything was very accommodating! Very nice stay"
United States
James G.
The price is £168
includes taxes & fees
19 Apr - 20 Apr
Charming tiny home only 15 mins from Town of Warrenton & Town of Culpeper
Terrace/patio

Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (20 reviews)
"We enjoyed our stayed so much! This location is perfect. This property is so clean. "
United States
Nicole Z.
The price is £165
includes taxes & fees
21 Apr - 22 Apr
Mountain View Bungalow in Front Royal
Terrace/patio

Sunset Mountain Cabin

Sunset Mountain Cabin
Rileyville
9.8 out of 10, Exceptional, (38 reviews)
"Absolutely enjoyed our time here! So peaceful and beautiful! The host was amazing and very responsive! Loved the hot tub and how very open the space was. Definitely would come back!"
United States
Kim B.
The price is £297
includes taxes & fees
21 Apr - 22 Apr
Sunset Mountain Cabin
Fireplace, DVD player

Ridgeview Mountain Cabin

Ridgeview Mountain Cabin
Rileyville
9.4 out of 10, Exceptional, (43 reviews)
"We had a great stay at this cabin! Host was responsive and gave many ideas of what to do. The cabin was cozy and it was a perfect stay! A must see is the caverns about 20-30 min away. We drove a Subaru Outback suv and had no problem with the road going up to the cabin, if it snows it can be slippery and icy going down, drive very slow. Overall 5 star stay! Thanks "
United States
Stephanie C.
The price is £308
includes taxes & fees
19 Apr - 20 Apr
Ridgeview Mountain Cabin
Property grounds

Newly renovated Farm cottage with Mountain views

Newly renovated Farm cottage with Mountain views
Strasburg
10.0 out of 10, Exceptional, (40 reviews)
"Beautiful place; very friendly hosts. We enjoyed our stay very much! We will visit again! "
United States
Shannon H.
The price is £242
includes taxes & fees
26 Apr - 27 Apr
Newly renovated Farm cottage with Mountain views
Interior

Cozy Farmhouse by Shenandoah with Mountain Views

Cozy Farmhouse by Shenandoah with Mountain Views
2, East Luray
10.0 out of 10, Exceptional, (14 reviews)
"Thank you so much for a great stay. It is an outstanding house in a great location. Close to all local restaurants and activities."
United States
Scott H.
The price is £295
includes taxes & fees
19 Apr - 20 Apr
Cozy Farmhouse by Shenandoah with Mountain Views
Interior

Bear Ridge Cabin-Views & Hot tub

Bear Ridge Cabin-Views & Hot tub
Page County
The price is £274
includes taxes & fees
20 Apr - 21 Apr
Bear Ridge Cabin-Views & Hot tub
Terrace/patio

The Apple Mountain House

The Apple Mountain House
Front Royal
9.8 out of 10, Exceptional, (11 reviews)
"The stay was amazing! Breathtaking views, clean home, and wonderful amenities!!"
United States
Katia R.
The price is £355
includes taxes & fees
22 Apr - 23 Apr
The Apple Mountain House
Outdoor spa tub

Overlook Mountain Cabin

Overlook Mountain Cabin
Page County
9.8 out of 10, Exceptional, (165 reviews)
"We loved this little cabin. It’s extremely comfortable and the view is spectacular (and you can enjoy it from the hot tub !) Unless you have a4-wheel drive with good clearance, we recommend taking one of the Jeeps the owner offers up to the house. "
United States
sara r.
The price is £319
includes taxes & fees
19 Apr - 20 Apr
Overlook Mountain Cabin
Interior

Spacious & Fun Family Oasis ~ Games ~ Hot Tub ~ View

Spacious & Fun Family Oasis ~ Games ~ Hot Tub ~ View
Rileyville
10.0 out of 10, Exceptional, (4 reviews)
"The property is lovely. It has all the needs for a family, and is very well located for hikes and visits to vineyards in the area. Will definitely visit again (this is our second stay)."
United States
Jonathan H.
The price is £274
includes taxes & fees
29 Apr - 30 Apr
Spacious & Fun Family Oasis ~ Games ~ Hot Tub ~ View
Pool

Lone Bear Cabin: Lv2 EV, WiFi, River Access, Mountain Views, fireplace, hot tub

Lone Bear Cabin: Lv2 EV, WiFi, River Access, Mountain Views, fireplace, hot tub
Rileyville
10.0 out of 10, Exceptional, (113 reviews)
"Beautiful cabin, amazing view."
United States
noah w.
The price is £320
includes taxes & fees
26 Apr - 27 Apr
Lone Bear Cabin: Lv2 EV, WiFi, River Access, Mountain Views, fireplace, hot tub
TV, offices

Shenandoah mountain cottage w/hot tub & fire pit

Shenandoah mountain cottage w/hot tub & fire pit
Front Royal
9.0 out of 10, Wonderful, (31 reviews)
"The house itself was clean, the beds are comfortable, and it is in a nice, quiet, and private location. The property manager was very pleasant and responsed to any questions or concerns quickly. "
United States
Elissa S.
The price is £253
includes taxes & fees
28 Apr - 29 Apr
Shenandoah mountain cottage w/hot tub & fire pit
Property grounds

Nestled Among Majestic Trees, Hilltop Hideaway is a Woodland Sanctuary

Nestled Among Majestic Trees, Hilltop Hideaway is a Woodland Sanctuary
Amissville
9.8 out of 10, Exceptional, (89 reviews)
"Hilltop Hideaway is a very charming house out in the middle of beautiful country by itself. We only stayed one night but we were very impressed with how clean the house is."
United States
Lisa S.
The price is £329
includes taxes & fees
19 Apr - 20 Apr
Nestled Among Majestic Trees, Hilltop Hideaway is a Woodland Sanctuary
Property grounds

🔥 Hottub + 🐕 friendly + 🏔️ view + Skyline Dr + Wineries

🔥 Hottub + 🐕 friendly + 🏔️ view + Skyline Dr + Wineries
Linden
10.0 out of 10, Exceptional, (26 reviews)
"Very nice stay! A peaceful, quiet little place. Cozy beds! We enjoyed our time. "
United States
Katelyn E.
The price is £291
includes taxes & fees
28 Apr - 29 Apr
🔥 Hottub + 🐕 friendly + 🏔️ view + Skyline Dr + Wineries
Dining

Completely private suite with tub,kitchen, living room, & private entrance

Completely private suite with tub,kitchen, living room, & private entrance
Washington
10.0 out of 10, Exceptional, (19 reviews)
"Very nice well kept property"
United States
Anonymous traveller
The price is £168
includes taxes & fees
4 May - 5 May
Completely private suite with tub,kitchen, living room, & private entrance
Interior

Family Friendly Farmhouse on FENCED 16 Acres with Trails

Family Friendly Farmhouse on FENCED 16 Acres with Trails
Luray
10.0 out of 10, Exceptional, (10 reviews)
"Such a wonderful stay! Our dogs loved the completely fenced in property. Hosts were incredibly welcoming and set up a treasure hunt across the property. Super fun, we will be back!"
United States
Palak G.
The price is £477
includes taxes & fees
20 Apr - 21 Apr
Family Friendly Farmhouse on FENCED 16 Acres with Trails
TV, fireplace, ping pong, stereo

Escape the city to this Spacious and Clean 5BR / 3.5BA home with a Heated Pool and Spa on 8 Acres in Horse & Wine Country

Escape the city to this Spacious and Clean 5BR / 3.5BA home with a Heated Pool and Spa on 8 Acres in Horse & Wine Country
Marshall
9.8 out of 10, Exceptional, (29 reviews)
"Everything was great "
United States
James A.
The price is £423
includes taxes & fees
21 Apr - 22 Apr
Escape the city to this Spacious and Clean 5BR / 3.5BA home with a Heated Pool and Spa on 8 Acres in Horse & Wine Country
Outdoor spa tub

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

Mountain Summit Views Hot Tub-Fire Pit-BBQ, Pets
Page County
The price is £267
includes taxes & fees
21 Apr - 22 Apr
Mountain Summit Views Hot Tub-Fire Pit-BBQ, Pets
Exterior

Mountain retreat w/hot tub, sauna, projector, close to river and 25 to NP!

Mountain retreat w/hot tub, sauna, projector, close to river and 25 to NP!
Luray
9.6 out of 10, Exceptional, (12 reviews)
"Great stay, very quiet. Everything was in place to ensure a comfortable stay. Perfect getaway for a couple of days and within 15 minutes to town. "
United States
Derek B.
The price is £252
includes taxes & fees
21 Apr - 22 Apr
Mountain retreat w/hot tub, sauna, projector, close to river and 25 to NP!
Private kitchen

Greek Spa on private acreage! Stonefire pizza oven

Greek Spa on private acreage! Stonefire pizza oven
Front Royal
The price is £221
includes taxes & fees
20 Apr - 21 Apr
Greek Spa on private acreage! Stonefire pizza oven
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

Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA

8/10 Good
"Stayed with family. Overall, nice place to stay for few days. "
scott 3-night trip
Posted 16 hours ago
Country Inn & Suites by Radisson, Winchester, VA

Find out more about Chester Gap

Chester Gap Holiday Homes information

Number of reviews
495
Accommodation
162 Holiday Homes
Lowest Price
£165
Highest Price
£477