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Chester Gap Vacation Rentals

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Chester Gap vacation rentals

A living room with a fireplace, a television mounted above it, and a large window with a view of trees.

1. NEW! Historic Schoolhouse HotTub+FirePit+Wineries

NEW! Historic Schoolhouse HotTub+FirePit+Wineries
Fauquier County
9.4 out of 10, Exceptional, (3 reviews)
"We were staying at the schoolhouse to go hiking and ride bikes. They house has been tastefully decorated. I enjoyed the quite community and the listening to the tree frogs at night. Front Royal has a few things you can enjoy such as the movie theatre, bakery and state park. I would highly recommend this propery."
United States
Suzanne J.
$302 nightly
The price is $332
Nov 3 - Nov 4
Total with taxes and fees
NEW! Historic Schoolhouse HotTub+FirePit+Wineries
A wooden deck with white railings and a covered porch area.

2. Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (46 reviews)
"Perfect place- would stay here again."
United States
HEMANT S.
$200 nightly
The price is $223
Oct 18 - Oct 19
Total with taxes and fees
Mountain View Bungalow in Front Royal
A hot tub with a view of a forest and a sunset.

3. A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub

A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub
Linden
9.6 out of 10, Exceptional, (14 reviews)
"Great place to stay to catch the northern entrance to Shenandoah. Comfortable beds, great furniture, and easy drive to Front Royal for dining. "
United States
Scott M.
$330 nightly
The price is $364
Nov 9 - Nov 10
Total with taxes and fees
A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub
A cozy living room with a grey sofa, patterned cushions, a small side table with a lamp, and decorative vases.

4. 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
9.0 out of 10, Wonderful, (18 reviews)
"Nice place, comfortable bed. Close to hiking in the area."
United States
Jake M.
$204 nightly
The price is $224
Oct 27 - Oct 28
Total with taxes and fees
Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
A bedroom with a bed, a mirror, a wall-mounted artwork, and a radiator.

5. The Juniper Cabin | Cozy Hideaway w/ Hot Tub, Screened Porch + Fire Pit

The Juniper Cabin | Cozy Hideaway w/ Hot Tub, Screened Porch + Fire Pit
Linden
10.0 out of 10, Exceptional, (24 reviews)
"We had a fantastic time staying at this property for the weekend."
United States
Colin N.
$368 nightly
The price is $406
Oct 28 - Oct 29
Total with taxes and fees
The Juniper Cabin | Cozy Hideaway w/ Hot Tub, Screened Porch + Fire Pit
A wooden cabin with a porch, surrounded by trees and a gravel path.

6. The Grape Escape - A-Frame Cabin

The Grape Escape - A-Frame Cabin
Linden
10.0 out of 10, Exceptional, (26 reviews)
"This property was great for a weekend of relaxation!"
United States
Steven B.
$307 nightly
The price is $339
Oct 25 - Oct 26
Total with taxes and fees
The Grape Escape - A-Frame Cabin
A garden with a central fountain, surrounded by neatly trimmed hedges and a brick pathway.

7. The Inn 1-Min Walk to Private Suite with Full Kitchen in 3BR Colonial House

The Inn 1-Min Walk to Private Suite with Full Kitchen in 3BR Colonial House
Washington
10.0 out of 10, Exceptional, (22 reviews)
"Perfect location in town"
United States
Mona T.
$229 nightly
The price is $247
Oct 27 - Oct 28
Total with taxes and fees
The Inn 1-Min Walk to Private Suite with Full Kitchen in 3BR Colonial House
A cabin with a deck, a covered outdoor area, and a gravel path leading to the entrance.

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

Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6
Linden
10.0 out of 10, Exceptional, (1 review)
"Great location. Great quiet atmosphere. Just one little thing - the steps are steep; so just something to be aware of."
United States
David S.
$418 nightly
The price is $461
Oct 27 - Oct 28
Total with taxes and fees
Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6
A two-story house with a balcony, string lights, and a swing.

9. Cozy A frame cabin in quaint Front Royal. Dog friendly

Cozy A frame cabin in quaint Front Royal. Dog friendly
Front Royal
9.4 out of 10, Exceptional, (9 reviews)
"Had a good time during my stay and loved seeing Shenandoah"
United States
Kye Y.
$256 nightly
The price is $282
Nov 1 - Nov 2
Total with taxes and fees
Cozy A frame cabin in quaint Front Royal. Dog friendly
A bedroom with a large bed, a desk with a chair, a TV, and a balcony with a view of trees.

10. Skyland Hideaway | Mountain Cabin w/ Hot Tub

Skyland Hideaway | Mountain Cabin w/ Hot Tub
Linden
9.6 out of 10, Exceptional, (21 reviews)
"We had a wonderful stay! The house was lovely and accommodating. We will definitely be back!"
United States
Amanda B.
$398 nightly
The price is $439
Nov 1 - Nov 2
Total with taxes and fees
Skyland Hideaway | Mountain Cabin w/ Hot Tub
A stone fireplace with a glass front, a wooden mantel shelf, and a cozy knitted throw on a chair.

11. Pool Table, Fireplace & Deck near Shenandoah Park

Pool Table, Fireplace & Deck near Shenandoah Park
Front Royal
10.0 out of 10, Exceptional, (1 review)
"Home was clean and looked like it had recently been remodeled/updated. The host was very responsive and when the oven wasn't working properly, they went to Lowes and purchased a new one immediately! Made our short trip much easier not having to eat out or find a last minute option for our kids/babysitter on Friday evening. We were only in town from Thursday-Sunday, and it was perfect for the 5 of us. The pool table was a fun addition for the kids. The only minor complaint I have is that I wish I...
United States
Crystal H.
$471 nightly
The price is $519
Oct 19 - Oct 20
Total with taxes and fees
Pool Table, Fireplace & Deck near Shenandoah Park
A small, single-story wooden cabin with a white-framed door and a small porch.

12. 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, (15 reviews)
"Perfect little house. Clean and very nice host."
United States
Debbie G.
$216 nightly
The price is $228
Oct 18 - Oct 19
Total with taxes and fees
Charming tiny home only 15 mins from Town of Warrenton & Town of Culpeper
A garden with a wooden swing set and a circular seating area.

13. Newly renovated Farm cottage with Mountain views

Newly renovated Farm cottage with Mountain views
Strasburg
10.0 out of 10, Exceptional, (56 reviews)
"We enjoyed our stay here. The property was lovely and the house was nicely stocked and decorated. We will definitely stay again when in the area!"
United States
Marsha N.
$296 nightly
The price is $326
Oct 19 - Oct 20
Total with taxes and fees
Newly renovated Farm cottage with Mountain views
A wooden staircase leading to a deck with a lattice railing, surrounded by dense foliage.

14. 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, (45 reviews)
"Nice cabin for couples. The bed was comfy and had all basic necessities for making meals. We will definitely stay again."
United States
Carla M.
$237 nightly
The price is $261
Oct 18 - Oct 19
Total with taxes and fees
Blue Mountain Cabin, secluded, perfect for couples, near main road
A covered outdoor seating area with wicker furniture, a patterned floor, and a view of autumn trees.

15. Hidden Gem on Hidden Valley Lane

Hidden Gem on Hidden Valley Lane
Linden
9.6 out of 10, Exceptional, (33 reviews)
"A little off the beaten path but a lovely property!! Found out my cousin’s friend lives on this same street! If you like a little adventure, I highly recommend this fun relaxing enjoyable place!!!"
United States
Kelly C.
$511 nightly
The price is $548
Oct 19 - Oct 20
Total with taxes and fees
Hidden Gem on Hidden Valley Lane
A modern kitchen with a black countertop, wooden dining table, and a view of the outdoors through large sliding glass doors.

16. Mountain cabin near national park & wineries

Mountain cabin near national park & wineries
Linden
9.8 out of 10, Exceptional, (36 reviews)
"It was a great place to stay and very clean."
United States
Chynna V.
$390 nightly
The price is $430
Oct 19 - Oct 20
Total with taxes and fees
Mountain cabin near national park & wineries
A cozy living room with a stone fireplace, leather sofas, and a large TV.

17. Delicious Cabin | Wine Country Hot Tub, Game Room + Screened Porch

Delicious Cabin | Wine Country Hot Tub, Game Room + Screened Porch
Linden
10.0 out of 10, Exceptional, (22 reviews)
"Beautiful property in a beautiful location! Great amenities!"
United States
Joan M.
$477 nightly
The price is $526
Nov 5 - Nov 6
Total with taxes and fees
Delicious Cabin | Wine Country Hot Tub, Game Room + Screened Porch
A balcony with a table, two wine glasses, and a view of a fenced area with a truck and a building in the background.

18. "The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country

"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country
Markham
10.0 out of 10, Exceptional, (4 reviews)
"Such a lovely stay. The property was peaceful and relaxing, and the night sky was absolutely beautiful. We loved our time here and would happily return. Great communication (and snacks) too :)"
United States
Melissa B.
$245 nightly
The price is $263
Oct 18 - Oct 19
Total with taxes and fees
"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country
A hot tub with a view of a snowy landscape and trees.

19. "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
Rileyville
10.0 out of 10, Exceptional, (375 reviews)
"Amazing location and perfect get away for two"
United States
Heather R.
$266 nightly
The price is $306
Oct 22 - Oct 23
Total with taxes and fees
"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub
Local wineries, breweries, and small-town charm in Front Royal

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

Mountain Views w/Hot Tub, 95” TV & Trail Access
Shenandoah Farms
10.0 out of 10, Exceptional, (1 review)
"We were looking for a comfortable home base to explore Front Royal and Skyline Plaza, and this was perfect! A modernized home with enough amenities that we were tempted every day to just stay “home!” The kids loved the reading nook and cozy sitting areas, and the fire pit and clean, working hot tub were big pluses as well. Kitchen was roomy, with great appliances and plenty of counter space. Beds were comfortable. Bathrooms were nice and modern. Lots of closet space, too. When we left, the kids...
United States
Joshua J.
$432 nightly
The price is $466
Oct 26 - Oct 27
Total with taxes and fees
Mountain Views w/Hot Tub, 95” TV & Trail Access
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

Super 8 by Wyndham Front Royal Near Shenandoah National Park

Super 8 by Wyndham Front Royal Near Shenandoah National Park

8/10 Good
"Clean room, nice staff, and everything was orderly. For the price, its ok."
Hyo Jun 1-night trip
Posted 10 hours ago
Super 8 by Wyndham Front Royal Near Shenandoah National Park

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 $223 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. Rappahannock Cellars and Dickey Ridge Visitor Center 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.