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Chester Gap Vacation Rentals

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Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Chester Gap vacation rentals

Dining

Valley View Farmhouse · Hot Tub, Fenced Pasture

Valley View Farmhouse · Hot Tub, Fenced Pasture
Amissville
$355 nightly
The price is $409
Jul 21 - Jul 22
Total with taxes and fees
Valley View Farmhouse · Hot Tub, Fenced Pasture
Exterior

Mountain Views w/Hot Tub, 95” TV & Trail Access

Mountain Views w/Hot Tub, 95” TV & Trail Access
Shenandoah Farms
$354 nightly
The price is $381
Jul 19 - Jul 20
Total with taxes and fees
Mountain Views w/Hot Tub, 95” TV & Trail Access
Property grounds

Apple Mountain Retreat

Apple Mountain Retreat
Linden
10.0 out of 10, Exceptional, (26 reviews)
"Great place to stayed "
United States
Mike F.
$212 nightly
The price is $234
Jul 20 - Jul 21
Total with taxes and fees
Apple Mountain Retreat
Terrace/patio

Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (32 reviews)
"Perfect place- would stay here again."
United States
HEMANT S.
$199 nightly
The price is $221
Jul 21 - Jul 22
Total with taxes and fees
Mountain View Bungalow in Front Royal
Outdoor spa tub

The Juniper Cabin • Cozy Hideaway w/ Hot Tub

The Juniper Cabin • Cozy Hideaway w/ Hot Tub
Linden
10.0 out of 10, Exceptional, (22 reviews)
"We had a fantastic time staying at this property for the weekend."
United States
Colin N.
$330 nightly
The price is $363
Aug 6 - Aug 7
Total with taxes and fees
The Juniper Cabin • Cozy Hideaway w/ Hot Tub
TV, fireplace, foosball, offices

Delicious Cabin • Wine Country Retreat w/ Hot Tub

Delicious Cabin • Wine Country Retreat w/ Hot Tub
Linden
10.0 out of 10, Exceptional, (12 reviews)
"The cabin was impressive both inside and out. We loved the location and proximity to skyline drive. We would definitely stay here again as it made our trip so much more enjoyable. "
United States
Bill A.
$376 nightly
The price is $415
Aug 11 - Aug 12
Total with taxes and fees
Delicious Cabin • Wine Country Retreat w/ Hot Tub
Interior

Hidden Gem on Hidden Valley Lane

Hidden Gem on Hidden Valley Lane
Linden
9.6 out of 10, Exceptional, (31 reviews)
"Great place. Very clean, lots of comfortable rooms. Nice outside area for dogs. "
United States
Lisa W.
$460 nightly
The price is $494
Jul 27 - Jul 28
Total with taxes and fees
Hidden Gem on Hidden Valley Lane
Interior

Mountain cabin near national park & wineries

Mountain cabin near national park & wineries
Linden
10.0 out of 10, Exceptional, (31 reviews)
"It was a great place to stay and very clean."
United States
Chynna V.
$383 nightly
The price is $422
Jul 19 - Jul 20
Total with taxes and fees
Mountain cabin near national park & wineries
TV

Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View

Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
Front Royal
9.6 out of 10, Exceptional, (17 reviews)
"Nice place, comfortable bed. Close to hiking in the area."
United States
Jake M.
$203 nightly
The price is $223
Jul 20 - Jul 21
Total with taxes and fees
Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
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, (20 reviews)
"Perfect location in town"
United States
Mona T.
$208 nightly
The price is $224
Jul 20 - Jul 21
Total with taxes and fees
Completely private suite with tub,kitchen, living room, & private entrance
Outdoor dining

Skyland Hideaway | Mountain Cabin w/ Hot Tub

Skyland Hideaway | Mountain Cabin w/ Hot Tub
Linden
9.8 out of 10, Exceptional, (17 reviews)
"Quiet with amenities to support R&R, enjoying nature, and togetherness."
United States
Patricia B.
$377 nightly
The price is $416
Jul 29 - Jul 30
Total with taxes and fees
Skyland Hideaway | Mountain Cabin w/ Hot Tub
Coffee/tea maker, fridge, microwave, oven

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
$374 nightly
The price is $378
Aug 18 - Aug 19
Total with taxes and fees
Greek Spa • Private Acreage • Stonefire pizza oven
Exterior

Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6

Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6
Linden
$402 nightly
The price is $443
Jul 20 - Jul 21
Total with taxes and fees
Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6
Property grounds

Blue Mountain Cabin, secluded, perfect for couples, near main road

Blue Mountain Cabin, secluded, perfect for couples, near main road
Front Royal
10.0 out of 10, Exceptional, (37 reviews)
"Great stay! The place was clean, comfortable, and exactly as described. Host was responsive and helpful. Would definitely stay again."
United States
Wafaa L.
$215 nightly
The price is $237
Jul 19 - Jul 20
Total with taxes and fees
Blue Mountain Cabin, secluded, perfect for couples, near main road
Cookware/dishes/utensils

The Pond Cabin: Hot Tub & Stocked Pond

The Pond Cabin: Hot Tub & Stocked Pond
Linden
10.0 out of 10, Exceptional, (35 reviews)
"We always love staying here. We have stayed at The Pond Cabin multiple times and will continue doing so as long as it is available!"
United States
Mary S.
$469 nightly
The price is $517
Jul 20 - Jul 21
Total with taxes and fees
The Pond Cabin: Hot Tub & Stocked Pond
TV, offices

Mountain home w/ hot tub & sunroom

Mountain home w/ hot tub & sunroom
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.
$289 nightly
The price is $309
Jul 22 - Jul 23
Total with taxes and fees
Mountain home w/ hot tub & sunroom
Exterior

Cozy A frame cabin in quaint Front Royal. Dog friendly

Cozy A frame cabin in quaint Front Royal. Dog friendly
Front Royal
10.0 out of 10, Exceptional, (7 reviews)
"Had a good time during my stay and loved seeing Shenandoah"
United States
Kye Y.
$249 nightly
The price is $275
Aug 18 - Aug 19
Total with taxes and fees
Cozy A frame cabin in quaint Front Royal. Dog friendly
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
9.8 out of 10, Exceptional, (12 reviews)
"Great tiny home by the owner’s house. Beautiful area (but not super convenient to shopping or restaurants). I thought it was great."
United States
John Mark
$215 nightly
The price is $227
Aug 15 - Aug 16
Total with taxes and fees
Charming tiny home only 15 mins from Town of Warrenton & Town of Culpeper
Exterior

The Grape Escape - A-Frame Cabin

The Grape Escape - A-Frame Cabin
Linden
10.0 out of 10, Exceptional, (21 reviews)
"This property was great for a weekend of relaxation!"
United States
Steven B.
$391 nightly
The price is $431
Jul 25 - Jul 26
Total with taxes and fees
The Grape Escape - A-Frame Cabin
Property grounds

Private Cabin in the woods w/ firepit right next to Shenandoah River

Private Cabin in the woods w/ firepit right next to Shenandoah River
Bentonville
10.0 out of 10, Exceptional, (37 reviews)
"Awesome spot…clean, cozy, private. Hosts were very responsive- can’t ask for anything more "
United States
Asim K.
$317 nightly
The price is $350
Aug 4 - Aug 5
Total with taxes and fees
Private Cabin in the woods w/ firepit right next to Shenandoah River
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

Holiday Inn Express Winchester South-Stephens City by IHG

Holiday Inn Express Winchester South-Stephens City by IHG

10/10 Excellent
"Our first time here. Breakfast was very good, room was very clean as was entire building. Staff was polite and friendly. Will definitely stay again."
william 1-night trip
Posted 20 hours ago
Holiday Inn Express Winchester South-Stephens City by IHG

Find out more about Chester Gap

Everything you need to know about Chester Gap vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chester Gap vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chester Gap vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chester Gap vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chester Gap. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chester Gap in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $221 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chester Gap rentals

At Expedia, we put the best Chester Gap vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chester Gap rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chester Gap vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chester Gap. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

Mountain View Bungalow in Front Royal: This vacation home rental near Chester Gap offers a garden, a selection of games, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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 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 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.