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Chester Gap Holiday Rentals

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Chester Gap holiday 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.
The price is AU$451
includes taxes & fees
9 Nov - 10 Nov
NEW! Historic Schoolhouse HotTub+FirePit+Wineries
A hot tub with a view of a forest and a sunset.

2. 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.
The price is AU$500
includes taxes & fees
9 Nov - 10 Nov
A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub
A wooden deck with white railings and a covered porch area.

3. 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.
The price is AU$323
includes taxes & fees
29 Oct - 30 Oct
Mountain View Bungalow in Front Royal
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.
The price is AU$323
includes taxes & fees
27 Oct - 28 Oct
Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
A wooden table with two chairs and a bowl of fruit, set against a backdrop of trees and a view through large windows.

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.
The price is AU$568
includes taxes & fees
28 Oct - 29 Oct
The Juniper Cabin | Cozy Hideaway w/ Hot Tub, Screened Porch + Fire Pit
A cabin with a deck, a covered outdoor area, and a gravel path leading to the entrance.

6. 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, (2 reviews)
"Really wonderful cabin. Everything was very clean and the house was super cute. Amenities were great. Would stay here again!!"
United States
Andrew G.
The price is AU$644
includes taxes & fees
27 Oct - 28 Oct
Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6
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.
The price is AU$344
includes taxes & fees
27 Oct - 28 Oct
The Inn 1-Min Walk to Private Suite with Full Kitchen in 3BR Colonial House
A wooden cabin with a porch, surrounded by trees and a gravel path.

8. The Grape Escape - A-Frame Cabin

The Grape Escape - A-Frame Cabin
Linden
10.0 out of 10, Exceptional, (28 reviews)
"This property was great for a weekend of relaxation!"
United States
Steven B.
The price is AU$415
includes taxes & fees
25 Oct - 26 Oct
The Grape Escape - A-Frame Cabin
A deck with outdoor furniture, a grill, and a cozy interior with a fireplace.

9. Skyland Hideaway | Mountain Cabin w/ Hot Tub + Fire Table | 3BR, Sleeps 6

Skyland Hideaway | Mountain Cabin w/ Hot Tub + Fire Table | 3BR, Sleeps 6
Linden
9.6 out of 10, Exceptional, (22 reviews)
"We had a wonderful stay! The house was lovely and accommodating. We will definitely be back!"
United States
Amanda B.
The price is AU$612
includes taxes & fees
3 Nov - 4 Nov
Skyland Hideaway | Mountain Cabin w/ Hot Tub + Fire Table | 3BR, Sleeps 6
A two-story house with a balcony, string lights, and a swing.

10. 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.
The price is AU$402
includes taxes & fees
2 Nov - 3 Nov
Cozy A frame cabin in quaint Front Royal. Dog friendly
A covered outdoor seating area with wicker furniture, a patterned floor, and a view of autumn trees.

11. 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.
The price is AU$761
includes taxes & fees
25 Oct - 26 Oct
Hidden Gem on Hidden Valley Lane
A spacious living room with a fireplace, a dining area with a bench, and a large sliding glass door leading to an outdoor patio.

12. The Honeymoon Cabin | Private Couple's Retreat w/ hot tub

The Honeymoon Cabin | Private Couple's Retreat w/ hot tub
Front Royal
9.6 out of 10, Exceptional, (8 reviews)
"Great little hideout! We loved this little place, accurately described and the communication was superb!"
United States
P H.
The price is AU$542
includes taxes & fees
28 Oct - 29 Oct
The Honeymoon Cabin | Private Couple's Retreat w/ hot tub
A modern kitchen with a black countertop, wooden dining table, and a view of the outdoors through large sliding glass doors.

13. 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.
The price is AU$596
includes taxes & fees
26 Oct - 27 Oct
Mountain cabin near national park & wineries
A cozy living room with a stone fireplace, leather sofas, and a large TV.

14. 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.
Delicious Cabin | Wine Country Hot Tub, Game Room + Screened Porch
A wooden deck with a swing, surrounded by trees.

15. 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, (41 reviews)
"Had a great stay, host was quick to answer questions, available for communication and extremely kind. Cabin was clean and comfortable, it’s going on our list of places to come back to."
United States
Isaac S.
Private Cabin in the woods w/ firepit right next to Shenandoah River
A stone fireplace with a glass front, a wooden mantel shelf, and a cozy knitted throw on a chair.

16. Pool Table, Fireplace & Deck near Shenandoah Park

Pool Table, Fireplace & Deck near Shenandoah Park
Front Royal
10.0 out of 10, Exceptional, (2 reviews)
"Great location. Very quiet neighborhood good for walking"
United States
tom c.
The price is AU$721
includes taxes & fees
26 Oct - 27 Oct
Pool Table, Fireplace & Deck near Shenandoah Park
A small, single-story wooden cabin with a white-framed door and a small porch.

17. 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, (16 reviews)
"Very comfortable and clean space. Plenty of room for 1 or 2 people. Check in and out instructions were very detailed. Price was very affordable compared to the nicer hotels in town who were charging $200 to $300 a night. Kind of out in the country but its easy to get to and from town, pretty straight stretch. I was only there in the evenings and everything was very quiet and peaceful."
United States
emily
The price is AU$324
includes taxes & fees
25 Oct - 26 Oct
Charming tiny home only 15 mins from Town of Warrenton & Town of Culpeper
A wooden cabin with a garage, surrounded by trees and a gravel driveway.

18. The Pond Cabin

The Pond Cabin
2.0 star property
Linden
The price is AU$855
includes taxes & fees
26 Oct - 27 Oct
The Pond Cabin
A balcony with a table, two wine glasses, and a view of a fenced area with a truck and a building in the background.

19. "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.
The price is AU$371
includes taxes & fees
25 Oct - 26 Oct
"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country
A wooden staircase leading to a deck with a lattice railing, surrounded by dense foliage.

20. 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.
The price is AU$372
includes taxes & fees
29 Oct - 30 Oct
Blue Mountain Cabin, secluded, perfect for couples, near main road
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

8/10 Good
"Ok stay, free breakfast was good ( just there for a transit)."
Maria 1-night trip
Posted 1 hour ago
Ramada by Wyndham Strasburg/Shenandoah Valley

Find out more about Chester Gap

Everything you need to know about Chester Gap holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chester Gap holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Chester Gap holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chester Gap holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chester Gap holiday rentals we have selected for you start as low as AU$323 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Chester Gap rentals

At Expedia, we put the best Chester Gap holiday 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 holiday.

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 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?

Mountain View Bungalow in Front Royal: This holiday home rental outside of 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 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. Rappahannock Cellars and Dickey Ridge Visitor Center 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.