Photo by Brian V. Rowe

Chester Gap Holiday Rentals

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Check prices for these dates

Tonight
4 Nov - 5 Nov
Tomorrow
5 Nov - 6 Nov
This weekend
7 Nov - 9 Nov
Next weekend
14 Nov - 16 Nov

Holiday Rentals in Chester Gap

Outdoor spa tub
Riverfront🏕A-Frame/HOT TUB/Fire Pit! FAST Wifi
Riverfront🏕A-Frame/HOT TUB/Fire Pit! FAST Wifi
9.8 out of 10, Exceptional, (70)
"Great time "
United States
Yana A.
Riverfront🏕A-Frame/HOT TUB/Fire Pit! FAST Wifi
Exterior
Falling Leaf Cabin - Rustic Charm With Modern Decor!
Falling Leaf Cabin - Rustic Charm With Modern Decor!
9.8 out of 10, Exceptional, (302)
"Fallong Lead cabin is just the perfect little cabin. Everything you need to relax and unwind with gorgeous views and a wonderful hot tub. Looking forward to staying here again!!"
United States
Melissa R.
Falling Leaf Cabin - Rustic Charm With Modern Decor!
Exterior
Amazing Grace log cabin home with 3 bedrooms, WiFi and AC in breathtaking Luray
Amazing Grace log cabin home with 3 bedrooms, WiFi and AC in breathtaking Luray
2.0 star property
10.0 out of 10, Exceptional, (40)
"Wonderful vacation home in a great location. We visited Shenandoah NP and Luray Caverns both just 10-15 min away. Clean spacious and well equipped home. Would definitely stay here again. "
United States
Amy M.
The price is HK$1,224
HK$2,899 total
includes taxes & fees
10 Nov - 11 Nov
Amazing Grace log cabin home with 3 bedrooms, WiFi and AC in breathtaking Luray
Outdoor spa tub
"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub
"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub
10.0 out of 10, Exceptional, (343)
"Well appointed home. Location is gorgeous, extremely private, quiet, close to the river with 2 seating areas by the water, one with a fire pit and grill. Owners quick to respond. "
United States
Diane B.
The price is HK$1,224
HK$2,120 total
includes taxes & fees
6 Nov - 7 Nov
"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub
Terrace/patio
River Access Cabin w Hot Tub, Deck, Grill, & Wifi
River Access Cabin w Hot Tub, Deck, Grill, & Wifi
8.8 out of 10, Excellent, (22)
"This a beautiful place to explore the Shenandoah area. Close to Luray and wonderful hikes. The cabin has a great kitchen and outdoor grill that we used to cook every night. Beds were incredibly comfortable and the hot tub was very clean & relaxing. The host was very considerate, checking in on us and helping with ideas on activities."
United States
sue r.
The price is HK$1,145
HK$2,008 total
includes taxes & fees
11 Nov - 12 Nov
River Access Cabin w Hot Tub, Deck, Grill, & Wifi
Property grounds
Bear Mountain Lodge Shenandoah Mountains Skyline Drive / Front Royal (hottub)<br>
Bear Mountain Lodge Shenandoah Mountains Skyline Drive / Front Royal (hottub)<br>
10.0 out of 10, Exceptional, (48)
"My wife and wanted a short and sweet trip for the weekend and this was the perfect place. Loved the views. Sunrise from the wall of windows was beautiful. Place was beautiful."
United States
Michael R.
Bear Mountain Lodge Shenandoah Mountains Skyline Drive / Front Royal (hottub)<br>
Exterior
Beautiful Private Cabin, adjacent to the National Forest
Beautiful Private Cabin, adjacent to the National Forest
9.8 out of 10, Exceptional, (136)
"Everything we hoped for in a weekend trip! The house smelled like cedar, was clean and very ample space. The hot tub was easy to operate; kitchen appliances helped cut down on eating out costs - would highly recommend and plan on making a reservation again!"
United States
Brieona C.
Beautiful Private Cabin, adjacent to the National Forest
2 bedrooms, WiFi, bed sheets
Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo
Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo
9.6 out of 10, Exceptional, (329)
"Been staying here for years. Great spot"
United States
Nicholas D.
Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo
Terrace/patio
Rustic Mountain Log Cabin Perched on a cliff side above the Shenandoah River
Rustic Mountain Log Cabin Perched on a cliff side above the Shenandoah River
9.2 out of 10, Wonderful, (241)
"The tranquility and peacefulness was just what we were looking for. We have already inquired about the other cabins and dates available. We will definitely book again! We hated to leave! 10 out of 10 stars!"
United States
Rebecca M.
Rustic Mountain Log Cabin Perched on a cliff side above the Shenandoah River
Outdoor spa tub
Charming 3-bedroom cabin with Moutain Views, Hottub, WiFi in Shenandoah.
Charming 3-bedroom cabin with Moutain Views, Hottub, WiFi in Shenandoah.
2.0 star property
9.8 out of 10, Exceptional, (29)
"Comfy and clean accomodations! Loved the pet and kid friendly vibe. Close to lots of local attractions. Host is very responsive and welcoming"
United States
Diane L.
The price is HK$1,259
HK$2,572 total
includes taxes & fees
11 Nov - 12 Nov
Charming 3-bedroom cabin with Moutain Views, Hottub, WiFi in Shenandoah.
2 bedrooms, WiFi, bed sheets
Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River
Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River
9.6 out of 10, Exceptional, (373)
"So quiet and access to hikes, trails, towns and other amenities all within 5-8miles. "
United States
Rob S.
Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River
Property grounds
Luxury mountain cabin W/ hot tub & majestic views
Luxury mountain cabin W/ hot tub & majestic views
9.8 out of 10, Exceptional, (30)
"The views were amazing. It was very quiet and relaxing to sit out by the fire pit and in the hot tub. The house was clean, and the owner was responsive. We plan to come back."
United States
Lisa H.
Luxury mountain cabin W/ hot tub & majestic views
Terrace/patio
Cute Riverside Cabin w Hot Tub, Fire Pit, & Kayaks
Cute Riverside Cabin w Hot Tub, Fire Pit, & Kayaks
10.0 out of 10, Exceptional, (13)
"Everything you need in this little space with easy access to deck with grill, fire pit and hot tub."
United States
Traci M.
The price is HK$1,162
HK$1,938 total
includes taxes & fees
12 Nov - 13 Nov
Cute Riverside Cabin w Hot Tub, Fire Pit, & Kayaks
Pool
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.
10.0 out of 10, Exceptional, (336)
"Place was beautiful and lived up to the name Solitude. Spent our honeymoon in perfect bliss. Great location to get away. "
United States
Sumcountryguy
The price is HK$1,329
HK$2,258 total
includes taxes & fees
25 Nov - 26 Nov
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.
Outdoor dining
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.
10.0 out of 10, Exceptional, (98)
"We enjoyed our weekend at Whiskey Hill Cabin. The cabin was beautiful and very clean. We were looking for quiet and found it there. Beautiful view and scenic drive to get there!"
United States
Heather G.
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.
Exterior
Enjoy Secluded Starry Nights! Near Luray, HotTub, FastWiFi, Handicap, Fireplace
Enjoy Secluded Starry Nights! Near Luray, HotTub, FastWiFi, Handicap, Fireplace
10.0 out of 10, Exceptional, (205)
"Both the host and property are great. "
United States
Nicolete M.
Enjoy Secluded Starry Nights! Near Luray, HotTub, FastWiFi, Handicap, Fireplace
Outdoor dining
Dog Friendly Cabin near River on Nearly 5 acres w/Strong WiFi + Robust Amenities
Dog Friendly Cabin near River on Nearly 5 acres w/Strong WiFi + Robust Amenities
9.6 out of 10, Exceptional, (67)
"Such a nice place! Clean, charming and nice views. Will definitely stay again!"
United States
scott D.
The price is HK$1,020
HK$2,447 total
includes taxes & fees
6 Nov - 7 Nov
Dog Friendly Cabin near River on Nearly 5 acres w/Strong WiFi + Robust Amenities
Outdoor spa tub
Adorable river front cabin ,with hot tub on the River
Adorable river front cabin ,with hot tub on the River
9.0 out of 10, Wonderful, (9)
"Pictures don’t do justice to the cozyness and tranquility of this place. Very pleased"
United States
Mauro F.
Adorable river front cabin ,with hot tub on the River
Dining
Spectacular Views, Swimming Pool, Hot Tub, Real Log Fires, Mountain Getaway
Spectacular Views, Swimming Pool, Hot Tub, Real Log Fires, Mountain Getaway
9.4 out of 10, Exceptional, (148)
"Enjoyable. 4wd required"
United States
Kathy M.
Spectacular Views, Swimming Pool, Hot Tub, Real Log Fires, Mountain Getaway
Outdoor dining
Waterfront, Luxury Panoramic View, Fast Wi-Fi, Private River Access Steps Away!
Waterfront, Luxury Panoramic View, Fast Wi-Fi, Private River Access Steps Away!
10.0 out of 10, Exceptional, (57)
"Hosts are very attentive and the property is a perfect family getaway."
United States
Renee R.
Waterfront, Luxury Panoramic View, Fast Wi-Fi, Private River Access Steps Away!
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

10/10 Excellent
"Good people attending guest"
Edgardo 1-night trip
Posted 1 day ago
Quality Inn Stephens City - Winchester South

Find out more about Chester Gap

Search for holiday rentals in Chester Gap on Expedia! You can easily find your home rentals, villas, holiday apartments in Chester Gap using one of the methods below:

  • View our selection of featured holiday rentals in Chester Gap
  • Use the map to find apartments and other holiday homes in the Chester Gap neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chester Gap while they last

Look no further and take a look at our great range of rental properties in Chester Gap!

Frequently asked questions

Are there holiday rentals in Chester Gap?

Yes, there are holiday rentals close to the most popular sights in Chester Gap, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Chester Gap has to offer?

Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly: This holiday home rental outside of Chester Gap is located on a river, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Chester Gap?

Choose from 3 Expedia holiday rentals in Chester Gap for a memorable holiday.

What can I see and do in Chester Gap?

While exploring the area, visit family-friendly sights like Dinosaur Land, or get outside and enjoy nature at Shenandoah National Park. Dickey Ridge Visitor Center and Linden Vineyards are a couple of places you'll find in the wider area.

What are holiday rentals like in Chester Gap?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chester Gap. Holiday rentals feature extras like kitchens and laundry facilities so your stay will be comfortable. If you're concerned about cleanliness, a holiday rental can provide a sense of seclusion away from shared hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for a family trip or a small group gathering.