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Chester Gap Vacation Rentals

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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Chester Gap Vacation Homes

Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly
Property grounds

Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly

9.6 out of 10, Exceptional, (188)
"We had a great time sitting on the porch relaxing. "
Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly
Secluded River Cabin Getaway (Masten Cabin)
Fridge, microwave, oven, stovetop

Secluded River Cabin Getaway (Masten Cabin)

9.8 out of 10, Exceptional, (157)
"Beautiful and convenient location for a short getaway!"
Secluded River Cabin Getaway (Masten Cabin)
Waterfront, Luxury Panoramic View, Fast Wi-Fi, Private River Access Steps Away!
Outdoor dining

Waterfront, Luxury Panoramic View, Fast Wi-Fi, Private River Access Steps Away!

10.0 out of 10, Exceptional, (49)
"We had a wonderful weekend, just what we needed. Relaxing and beautiful house and scenery. Diana was very communicative and responsive and gave great recommendations for things to do in the area. Hope to go back again."
Waterfront, Luxury Panoramic View, Fast Wi-Fi, Private River Access Steps Away!
Mountain View Bungalow in Front Royal
Fridge, microwave, oven, stovetop

Mountain View Bungalow in Front Royal

"Excelente propiedad "
The price is CA $206
CA $328 total
includes taxes & fees
Aug 25 - Aug 26
Mountain View Bungalow in Front Royal
Rivers Edge Retreat with spectacular water views, Full kitchen, Games, Fishing
Outdoor dining

Rivers Edge Retreat with spectacular water views, Full kitchen, Games, Fishing

10.0 out of 10, Exceptional, (2)
"Easy check-in, excellent communication. Home was very clean with quality furnishings and bedding. Lots of thoughtful touches and extras. Located along Shenandoah River makes it picturesque."
Rivers Edge Retreat with spectacular water views, Full kitchen, Games, Fishing
Lone Bear Cabin: Lv2 EV, WiFi, River Access, Mountain Views, fireplace, hot tub
Pool

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

10.0 out of 10, Exceptional, (94)
"Clean and nice place to stay to visit Shenandoah "
The price is CA $248
CA $595 total
includes taxes & fees
Aug 11 - Aug 12
Lone Bear Cabin: Lv2 EV, WiFi, River Access, Mountain Views, fireplace, hot tub
On the river ~ hot tub ~ serene river views ~ fire pit
Outdoor spa tub

On the river ~ hot tub ~ serene river views ~ fire pit

10.0 out of 10, Exceptional, (21)
"We enjoyed our stay!"
On the river ~ hot tub ~ serene river views ~ fire pit
Linden Family Home w/ Yard < 5 Mi to Wineries!
TV, books

Linden Family Home w/ Yard < 5 Mi to Wineries!

2.0 star property
8.6 out of 10, Excellent, (12)
"Great place to stay on a nice mountain my family and dogs loved itMike was great and answered any questions we had will definitely book again in the future"
Linden Family Home w/ Yard < 5 Mi to Wineries!
Modern Mountain Retreat w/ Deck + Hot Tub!
Fridge, microwave, stovetop, dishwasher

Modern Mountain Retreat w/ Deck + Hot Tub!

9.8 out of 10, Exceptional, (74)
"Very comfortable and spacious place with all the comforts of home. We wanted to get away and just relax for a few days and this was perfect!"
Modern Mountain Retreat w/ Deck + Hot Tub!
Waterfront Log Home Hot Tub Flat yard w/ Volleyball Fire Pit & Tubes for Floating
Smart TV, fireplace

Waterfront Log Home Hot Tub Flat yard w/ Volleyball Fire Pit & Tubes for Floating

8.6 out of 10, Excellent, (30)
"location by the river was beautiful. House is roomy and great for our family of 12. "
The price is CA $516
CA $1,091 total
includes taxes & fees
Aug 13 - Aug 14
Waterfront Log Home Hot Tub Flat yard w/ Volleyball Fire Pit & Tubes for Floating
Cozy mountain retreat minutes to the river, Luray, and 25 to Shenandoah NP!
Property grounds

Cozy mountain retreat minutes to the river, Luray, and 25 to Shenandoah NP!

10.0 out of 10, Exceptional, (9)
"My friends and I had an amazing time at the cabin, everything was nicely placed and organized. The view and the cabin itself was perfect with the addition of the hot tub."
The price is CA $193
CA $464 total
includes taxes & fees
Sep 1 - Sep 2
Cozy mountain retreat minutes to the river, Luray, and 25 to Shenandoah NP!
Tranquil mountainhouse w/hot tub, super close to trails & wineries- pet friendly
Fridge, microwave, oven, stovetop

Tranquil mountainhouse w/hot tub, super close to trails & wineries- pet friendly

10.0 out of 10, Exceptional, (45)
"The home is super clean and well maintained! "
Tranquil mountainhouse w/hot tub, super close to trails & wineries- pet friendly
5-bedroom Farmhouse In Heart Of Virginia Horse Country- Private Trail To Wine
Terrace/patio

5-bedroom Farmhouse In Heart Of Virginia Horse Country- Private Trail To Wine

9.8 out of 10, Exceptional, (57)
"WE HAD A NICE WEEKEND AT THE HOUSE .THE KITCHEN UTENSILS HAS SEEN BETTER DAYS. FYI THE HOUSE IS RIGHT N3XT TL A BUSY ROAD.WE ENJOYED THE HOTTUB AND TV COUCH AREA. THE QINERY NEXT DOOR WAS REALLY NICE"
5-bedroom Farmhouse In Heart Of Virginia Horse Country- Private Trail To Wine
Shenandoah Mountain Cabin
Interior

Shenandoah Mountain Cabin

10.0 out of 10, Exceptional, (14)
"This place is amazing! So clean and comfortable. Drive up to the cabin is very bumpy but so very worth it. "
The price is CA $259
CA $508 total
includes taxes & fees
Aug 11 - Aug 12
Shenandoah Mountain Cabin
Secluded Mountain Retreat with Stunning Views, Hot Tub, Wifi and more
Outdoor spa tub

Secluded Mountain Retreat with Stunning Views, Hot Tub, Wifi and more

9.8 out of 10, Exceptional, (32)
"Loved the property and having space for the kids to run and play. Perfect location for visiting Luray and Shenandoah. Hosts were great and super responsive. Would stay again!"
Secluded Mountain Retreat with Stunning Views, Hot Tub, Wifi and more
Mystic Pines log home in Shenandoah with hot tub and spectacular views!
Exterior

Mystic Pines log home in Shenandoah with hot tub and spectacular views!

10.0 out of 10, Exceptional, (2)
"Property was wonderful and just what we needed for a short weekend away! Clean, well organized, and friendly host make it a 5/5."
Mystic Pines log home in Shenandoah with hot tub and spectacular views!
NEW! The Hilltop Station
Exterior

NEW! The Hilltop Station

6.0 out of 10, (1)
"A train came past the house at 7am in the morning. There is no mention of early morning train activity in the description. The mattresses were extremely soft and the blankets were very thin…so we were chilly. The house is beautiful…just these details are something to consider."
The price is CA $498
CA $974 total
includes taxes & fees
Sep 2 - Sep 3
NEW! The Hilltop Station
Warm, Welcoming Retreat on Shenandoah River and Stunning views
Terrace/patio

Warm, Welcoming Retreat on Shenandoah River and Stunning views

10.0 out of 10, Exceptional, (125)
"Great property and nice house"
Warm, Welcoming Retreat on Shenandoah River and Stunning views
#CozyCleanCabin#HotTub#WoodStove#PetsOK#near BMLodge&Skyline D&Wineries
Property grounds

#CozyCleanCabin#HotTub#WoodStove#PetsOK#near BMLodge&Skyline D&Wineries

10.0 out of 10, Exceptional, (14)
"Wonderful hosts and a great home! Lots of extra special touches."
#CozyCleanCabin#HotTub#WoodStove#PetsOK#near BMLodge&Skyline D&Wineries
Valley Vista-Mins to Skyline Drive-HOT TUB- King-Queen Beds, Great location.
Fridge, microwave, oven, stovetop

Valley Vista-Mins to Skyline Drive-HOT TUB- King-Queen Beds, Great location.

7.4 out of 10, Good, (3)
"A delightful home that has plenty of room to run and play outside. Tucked into the woods, but surrounded by lots of open grass around the house with a fire pit and even room for a volleyball net or other activities. Great hot tub on the screened in patio, easy to get to, close to Front Royal, quiet property, lovely place to relax and super nice host! "
Valley Vista-Mins to Skyline Drive-HOT TUB- King-Queen Beds, Great location.
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

Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley

10/10 Excellent
"Clean, spacious room located near highway. Nice and friendly staff."
Mohammadreza 1-night trip
Posted 22 hours ago
Ramada by Wyndham Strasburg/Shenandoah Valley