Photo by Brian V. Rowe

Chester Gap Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Nov 22 - Nov 23
Tomorrow
Nov 23 - Nov 24
Next weekend
Nov 28 - Nov 30
In two weeks
Dec 5 - Dec 7

Vacation Rentals in Chester Gap

Cookware/dishes/utensils
The Pond Cabin: Hot Tub & Stocked Pond

Cabin in Linden

10.0 out of 10, Exceptional, (33)
"It was the perfect home away from home in a place that allowed our little family to take a breath of nature and just be. Close enough to many fun adventures. The amenities provided on the property also kept us very busy!"
United States
Brena H.
The price is ￥37,382
￥78,843 total
includes taxes & fees
Dec 1 - Dec 2
The Pond Cabin: Hot Tub & Stocked Pond
Fridge, microwave, oven, stovetop
Cozy 1BR Apt Minutes From Skyline Drive!!

Apartment in Amissville

9.6 out of 10, Exceptional, (35)
"My wife and I enjoyed our stay at this cute and cozy spot. Very convenient for exploring Northern Virginia, from Shenandoah National Park, to Leesburg, Culpeper, Manassas, and beyond. Check-in was very easy and Jimmie, our host, was very friendly and responsive. "
United States
John P.
The price is ￥19,004
￥36,483 total
includes taxes & fees
Nov 24 - Nov 25
Cozy 1BR Apt Minutes From Skyline Drive!!
Exterior
Private Cabin in the woods w/ firepit right next to Shenandoah River

Cabin in Bentonville

10.0 out of 10, Exceptional, (30)
"We had a great time. Close to national park and an hour and a half commute to Washington DC.We enjoyed the property and the quietness."
United States
Scott H.
The price is ￥29,561
￥60,555 total
includes taxes & fees
Nov 24 - Nov 25
Private Cabin in the woods w/ firepit right next to Shenandoah River
Property grounds
Nestled Among Majestic Trees, Hilltop Hideaway is a Woodland Sanctuary

Vacation Home in Amissville

9.8 out of 10, Exceptional, (88)
"Great place that works well for Rixey Manor weddings "
United States
Gregory
The price is ￥32,064
￥64,234 total
includes taxes & fees
Nov 24 - Nov 25
Nestled Among Majestic Trees, Hilltop Hideaway is a Woodland Sanctuary
Terrace/patio
Cute cabin retreat near Shenandoah National Park and pet friendly!

Cabin in Linden

9.4 out of 10, Exceptional, (12)
"Fun location near tons of wineries, bowling, trails, and mountain living. Place is really nice with a grill, solo stove, kfantastic kitchen"
United States
Bret L.
Cute cabin retreat near Shenandoah National Park and pet friendly!
Outdoor dining
Dog Friendly Cabin near River on Nearly 5 acres w/Strong WiFi + Robust Amenities

Cabin in Luray

9.6 out of 10, Exceptional, (69)
"Check in was easy and I loved that they used my last four of my phone as the door code- made it easy to remember!"
United States
Kathy M.
The price is ￥20,529
￥47,794 total
includes taxes & fees
Nov 24 - Nov 25
Dog Friendly Cabin near River on Nearly 5 acres w/Strong WiFi + Robust Amenities
Fridge, microwave, oven, stovetop
Blue Mountain Cabin, secluded, perfect for couples, near main road

Cabin in Front Royal

10.0 out of 10, Exceptional, (25)
"Great place to relax"
United States
Judy
The price is ￥28,154
￥35,540 total
includes taxes & fees
Nov 24 - Nov 25
Blue Mountain Cabin, secluded, perfect for couples, near main road
Outdoor dining
Newly renovated Farm cottage with Mountain views

Vacation Home in Strasburg

10.0 out of 10, Exceptional, (38)
"Fantastic property. Clean, well-stocked, and peaceful. "
United States
Robert M.
The price is ￥25,026
￥50,895 total
includes taxes & fees
Nov 30 - Dec 1
Newly renovated Farm cottage with Mountain views
Terrace/patio
Hidden Gem on Hidden Valley Lane

Cabin in Linden

9.6 out of 10, Exceptional, (27)
"The house was ready to have guests. Very well prepared, clean, enough beds & baths. Beautiful scenary from porch. We would like to visit again when we have another chance. thank you so much!"
United States
Don
The price is ￥29,561
￥69,480 total
includes taxes & fees
Nov 24 - Nov 25
Hidden Gem on Hidden Valley Lane
Smart TV, fireplace, stereo
Escape to Shenandoah River, Hot Tub after a Hike!

Cabin in Front Royal

10.0 out of 10, Exceptional, (54)
"Very nice updated home in a beautiful peaceful setting. I would highly recomend it!"
United States
Kathy L.
The price is ￥16,673
￥50,307 total
includes taxes & fees
Dec 1 - Dec 2
Escape to Shenandoah River, Hot Tub after a Hike!
Fridge, microwave, oven, stovetop
🔥 Hottub + 🐕 friendly + 🏔️ view + Skyline Dr + Wineries

Vacation Home in Linden

10.0 out of 10, Exceptional, (20)
"View was great, was pretty isolated from other houses in the area, and cute decor. Very comfortable stay. "
United States
Andrew G.
The price is ￥22,101
￥52,326 total
includes taxes & fees
Dec 1 - Dec 2
🔥 Hottub + 🐕 friendly + 🏔️ view + Skyline Dr + Wineries
Pool
Lone Bear Cabin: Lv2 EV, WiFi, River Access, Mountain Views, fireplace, hot tub

Vacation Home in Rileyville

10.0 out of 10, Exceptional, (101)
"Very easy check in and great communication with the owners. We saw so many deer and the view of the mountains was great. "
United States
Kim D.
The price is ￥26,590
￥65,103 total
includes taxes & fees
Nov 24 - Nov 25
Lone Bear Cabin: Lv2 EV, WiFi, River Access, Mountain Views, fireplace, hot tub
Property grounds
"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA

Cabin in Rileyville

9.8 out of 10, Exceptional, (307)
"We really enjoyed our stay! The Chalet was peaceful, clean, and perfect in every way. We enjoyed the hot tub and the view.Location was perfect, near Luray caverns and Shenandoah Park.Thank you for allowing us to stay there. It was a wonderful getaway."
United States
Amy A.
The price is ￥25,260
￥43,732 total
includes taxes & fees
Dec 2 - Dec 3
"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA
Outdoor spa tub
Fox Den — Hot Tub, Fire Pit, Steps to River

Cabin in Luray

10.0 out of 10, Exceptional, (8)
"Great time. Really comfortable place."
United States
Joshua E.
The price is ￥18,688
￥51,321 total
includes taxes & fees
Nov 24 - Nov 25
Fox Den — Hot Tub, Fire Pit, Steps to River
Terrace/patio
"Sundance" Spectacular Views on 54 Acres along Shenandoah River w/ Hot Tub

Cabin in Rileyville

10.0 out of 10, Exceptional, (315)
"House is very clean with amazing views! Kitchen stocked with everything you need. Water access is private with only a couple of shared cabins. Enjoyed fishing, canoeing and relaxing over three days. This was our second stay here and we look forward to coming back!Dan"
United States
Daniel P.
The price is ￥25,221
￥43,507 total
includes taxes & fees
Nov 24 - Nov 25
"Sundance" Spectacular Views on 54 Acres along Shenandoah River w/ Hot Tub
Outdoor spa tub
Lookout Cabin in the mountains, Amazing Views!

Cabin in Page County

9.8 out of 10, Exceptional, (29)
"Charming, picturesque, cozy!"
United States
Bill B.
The price is ￥27,966
￥59,339 total
includes taxes & fees
Nov 24 - Nov 25
Lookout Cabin in the mountains, Amazing Views!
Pool
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.

Cabin in Rileyville

10.0 out of 10, Exceptional, (338)
"Excellent experience! The cabin was great, the location was great, the sights and people were great!"
United States
Tom A.
The price is ￥22,288
￥39,585 total
includes taxes & fees
Nov 25 - Nov 26
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.
Terrace/patio
River Access Cabin w Hot Tub, Deck, Grill, & Wifi

Cabin in Luray

8.8 out of 10, Excellent, (22)
"As it is described. Clean and peaceful. "
United States
Anna A.
The price is ￥23,039
￥40,418 total
includes taxes & fees
Nov 30 - Dec 1
River Access Cabin w Hot Tub, Deck, Grill, & Wifi
Outdoor spa tub
Charming 3-bedroom cabin with Moutain Views, Hottub, WiFi in Shenandoah.

Cabin in Rileyville

2.0 star property
9.8 out of 10, Exceptional, (31)
"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 ￥26,746
￥53,200 total
includes taxes & fees
Nov 24 - Nov 25
Charming 3-bedroom cabin with Moutain Views, Hottub, WiFi in Shenandoah.
Dining
Cozy Farmhouse by Shenandoah with Mountain Views

Vacation Home in 2, East Luray

10.0 out of 10, Exceptional, (14)
"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.
Cozy Farmhouse by Shenandoah with Mountain Views
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chester Gap Hotel Reviews

Holiday Inn Express Winchester South-Stephens City by IHG

Holiday Inn Express Winchester South-Stephens City by IHG

10/10 Excellent
"Good"
Ken 1-night trip
Posted 2 days ago
Holiday Inn Express Winchester South-Stephens City by IHG

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 vacation rentals in Chester Gap?

Yes, we offer vacation rentals close to popular points of interest in Chester Gap, or you can select a secluded option if you're looking for a relaxing stay.

What are some of the best vacation rentals in Chester Gap?

Waterfront, Luxury Panoramic View, Fast Wi-Fi, Private River Access Steps Away!: This vacation home near Chester Gap is located on a river and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals will I find in Chester Gap?

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

What can I see and do in Chester Gap?

While exploring the area, visit family-friendly sights like Secret Passage Ranch, 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 larger area.

What are vacation rentals like in Chester Gap?

Vacation rentals are privately owned accommodations you can book for several days or more in Chester Gap. Vacation rentals provide amenities such as hot tubs, fire pits, and patios so you'll have all the comforts of home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from shared hotel elevators and busy front desks while still allowing you to travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for family gatherings.