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Chester Gap Holiday Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Chester Gap holiday rentals

A spacious loft bedroom with a large window, a cozy seating area, and a flat-screen TV.

1. ⭐️Lunar Lookout ⭐️ Geodesic Dome on 8 acres with HOT TUB!

⭐️Lunar Lookout ⭐️ Geodesic Dome on 8 acres with HOT TUB!
Front Royal
10.0 out of 10, Exceptional, (15 reviews)
"Taylor was great to work with! Nice property and wonderful view ."
United States
Christine H.
The price is HK$2,471
HK$5,305 total
includes taxes & fees
23 Sept - 24 Sept
⭐️Lunar Lookout ⭐️ Geodesic Dome on 8 acres with HOT TUB!
A covered outdoor seating area with wicker furniture, a patterned floor, and a view of autumn trees.

2. Hidden Gem on Hidden Valley Lane

Hidden Gem on Hidden Valley Lane
Linden
9.6 out of 10, Exceptional, (32 reviews)
"Great location and communication from the host. All the comforts of home and more! Thanks for a great stay!"
United States
Jen T.
The price is HK$1,804
HK$4,327 total
includes taxes & fees
4 Oct - 5 Oct
Hidden Gem on Hidden Valley Lane
A wooden cabin with a garage, surrounded by trees and a gravel driveway.

3. The Pond Cabin

The Pond Cabin
2.0 star property
Linden
The price is HK$2,032
HK$3,756 total
includes taxes & fees
29 Sept - 30 Sept
The Pond Cabin
A hot tub with a view of a forest and a sunset.

4. 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.
A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub
A modern kitchen with a black countertop, wooden dining table, and a view of the outdoors through large sliding glass doors.

5. 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 HK$1,483
HK$3,331 total
includes taxes & fees
23 Sept - 24 Sept
Mountain cabin near national park & wineries
A hot tub area with a view of a lake and trees, surrounded by ornate black metal railings and decorative lanterns.

6. Riverfront! Shenandoah River! Sleeps 4! New Hot Tub

Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
Front Royal
9.8 out of 10, Exceptional, (16 reviews)
"Unique and adorable little place on the river. Perfectly clean and comfortable. We would definitely book again!"
United States
Hailey
The price is HK$2,295
HK$3,418 total
includes taxes & fees
23 Sept - 24 Sept
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
A wooden cabin with a porch, surrounded by trees and a gravel path.

7. 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.
The price is HK$1,030
HK$2,131 total
includes taxes & fees
24 Sept - 25 Sept
The Grape Escape - A-Frame Cabin
A cozy living room with a stone fireplace, leather sofas, and a large TV.

8. Delicious Cabin • Wine Country Retreat w/ Hot Tub

Delicious Cabin • Wine Country Retreat w/ Hot Tub
Linden
10.0 out of 10, Exceptional, (18 reviews)
"Property and cabin was very clean and well stocked. Location was great to get to wineries. We saw deer and fox in the back yard, very peaceful."
United States
Edward
The price is HK$1,193
HK$3,202 total
includes taxes & fees
23 Sept - 24 Sept
Delicious Cabin • Wine Country Retreat w/ Hot Tub
A house with a deck, outdoor hot tub, and a staircase leading to a covered porch.

9. The Juniper Cabin • Cozy Hideaway w/ Hot Tub

The Juniper Cabin • Cozy Hideaway w/ Hot Tub
Linden
10.0 out of 10, Exceptional, (23 reviews)
"We had a fantastic time staying at this property for the weekend."
United States
Colin N.
The price is HK$1,255
HK$3,245 total
includes taxes & fees
23 Sept - 24 Sept
The Juniper Cabin • Cozy Hideaway w/ Hot Tub
A living room with a leather sofa, a bookshelf, a desk with a chair, and a staircase.

10. The Pond Cabin: Hot Tub & Stocked Pond

The Pond Cabin: Hot Tub & Stocked Pond
Linden
10.0 out of 10, Exceptional, (36 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.
The price is HK$2,032
HK$4,102 total
includes taxes & fees
29 Sept - 30 Sept
The Pond Cabin: Hot Tub & Stocked Pond
A wooden deck with a hot tub, outdoor furniture, and a view of trees.

11. 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.
The price is HK$1,153
HK$3,210 total
includes taxes & fees
27 Sept - 28 Sept
Skyland Hideaway | Mountain Cabin w/ Hot Tub
A cozy living room with a grey sofa, patterned cushions, a small side table with a lamp, and decorative vases.

12. 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.
The price is HK$1,165
HK$1,770 total
includes taxes & fees
29 Sept - 30 Sept
Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
A wooden deck with white railings and a covered porch area.

13. Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (41 reviews)
"Perfect place- would stay here again."
United States
HEMANT S.
The price is HK$1,059
HK$1,746 total
includes taxes & fees
4 Oct - 5 Oct
Mountain View Bungalow in Front Royal
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, (44 reviews)
"Beautiful, relaxing and quiet cabin, exceeded expectations."
United States
Johnathan B.
The price is HK$1,341
HK$1,696 total
includes taxes & fees
4 Oct - 5 Oct
Blue Mountain Cabin, secluded, perfect for couples, near main road
A hot tub on an outdoor deck with a view of trees and hills.

15. Mountain View Cottage | Hot Tub & Game Room

Mountain View Cottage | Hot Tub & Game Room
Front Royal
9.8 out of 10, Exceptional, (17 reviews)
"The stay was amazing! Breathtaking views, clean home, and wonderful amenities!!"
United States
Katia R.
The price is HK$2,495
HK$5,452 total
includes taxes & fees
23 Sept - 24 Sept
Mountain View Cottage | Hot Tub & Game Room

16. Sunset Haven - 10 min from Skyline Drive. Hot Tub

Sunset Haven - 10 min from Skyline Drive. Hot Tub
Front Royal
9.6 out of 10, Exceptional, (8 reviews)
"Really enjoyed our stay. The house was lovely with amazing views. The bar and game room were fun. Lots of detail and thought were put into making this house feel like home. We will definitely be back!"
United States
Laura D.
The price is HK$2,550
HK$4,612 total
includes taxes & fees
29 Sept - 30 Sept
Sunset Haven - 10 min from Skyline Drive. Hot Tub
A stone fireplace with a glass front, a wooden mantel shelf, and a cozy knitted throw on a chair.

17. Golfers' Paradise: 3 Courses Nearby + Pool Table

Golfers' Paradise: 3 Courses Nearby + Pool Table
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.
The price is HK$2,016
HK$4,855 total
includes taxes & fees
23 Sept - 24 Sept
Golfers' Paradise: 3 Courses Nearby + Pool Table
A balcony with a view of a valley and distant mountains.

18. Wilderness Ridge | Private Cabin w/ Mountain Views

Wilderness Ridge | Private Cabin w/ Mountain Views
Linden
9.6 out of 10, Exceptional, (11 reviews)
"We had a great time and experience. "
United States
Adriane B.
The price is HK$1,491
HK$4,257 total
includes taxes & fees
4 Oct - 5 Oct
Wilderness Ridge | Private Cabin w/ Mountain Views

19. 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.
The price is HK$2,132
HK$3,302 total
includes taxes & fees
24 Sept - 25 Sept
Mountain Views w/Hot Tub, 95” TV & Trail Access
A wooden deck with a hot tub, a wooden bench, and a pair of shoes.

20. Getaway Cabin Retreat in Shenandoah Valley - Hot Tub, Sauna, Cold Plunge

Getaway Cabin Retreat in Shenandoah Valley - Hot Tub, Sauna, Cold Plunge
Shenandoah Farms
10.0 out of 10, Exceptional, (1 review)
The price is HK$1,961
HK$3,687 total
includes taxes & fees
23 Sept - 24 Sept
Getaway Cabin Retreat in Shenandoah Valley - Hot Tub, Sauna, Cold Plunge
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

Wayside Inn

Wayside Inn

10/10 Excellent
"We love staying at Wayside Inn. This is our third or fourth stay. The place is such a treasure! The food in the restaurant is good and the bar is fun. The only thing we noticed this time is that the bar closed at 9 p.m. on a Saturday night. We came in from dinner at 9:15 and planned to have a night cap and were told the bar closed at 9:00! The previous times we stayed there the bar was open until 10 or 11 on Saturday. We though such an early closing time was odd for the weekend."
James 2-night trip
Posted 2 hours ago
Wayside Inn

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?

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. 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.