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Chester Gap Vacation Rentals

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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 covered outdoor seating area with wicker furniture, a patterned floor, and a view of autumn trees.

1. Hidden Gem on Hidden Valley Lane

Hidden Gem on Hidden Valley Lane
Linden
9.6 out of 10, Exceptional, (32 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 ￥36,411
￥86,801 total
includes taxes & fees
Oct 13 - Oct 14
Hidden Gem on Hidden Valley Lane
A wooden cabin with a garage, surrounded by trees and a gravel driveway.

2. The Pond Cabin

The Pond Cabin
2.0 star property
Linden
The price is ￥46,860
￥82,245 total
includes taxes & fees
Oct 26 - Oct 27
The Pond Cabin
A living room with a fireplace, a television mounted above it, and a large window with a view of trees.

3. 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 ￥19,789
￥56,392 total
includes taxes & fees
Nov 9 - Nov 10
NEW! Historic Schoolhouse HotTub+FirePit+Wineries
A spacious loft bedroom with a large window, a cozy seating area, and a flat-screen TV.

4. ⭐️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, (16 reviews)
"Taylor was great to work with! Nice property and wonderful view ."
United States
Christine H.
The price is ￥49,868
￥106,342 total
includes taxes & fees
Oct 13 - Oct 14
⭐️Lunar Lookout ⭐️ Geodesic Dome on 8 acres with HOT TUB!
A hot tub area with a view of a lake and trees, surrounded by ornate black metal railings and decorative lanterns.

5. 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 ￥46,306
￥68,984 total
includes taxes & fees
Oct 13 - Oct 14
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
A stainless steel barbecue grill with four burners, positioned against a concrete wall with a wooden staircase in the background.

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

The Juniper Cabin • Cozy Hideaway w/ Hot Tub
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 ￥27,388
￥62,164 total
includes taxes & fees
Nov 3 - Nov 4
The Juniper Cabin • Cozy Hideaway w/ 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 ￥20,778
￥44,919 total
includes taxes & fees
Oct 14 - Oct 15
The Grape Escape - A-Frame Cabin
A wooden deck with white railings and a covered porch area.

8. Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (44 reviews)
"Perfect place- would stay here again."
United States
HEMANT S.
The price is ￥21,372
￥34,889 total
includes taxes & fees
Oct 18 - Oct 19
Mountain View Bungalow in Front Royal
A cozy living room with a stone fireplace, leather sofas, and a large TV.

9. 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, (19 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 ￥39,261
￥82,942 total
includes taxes & fees
Nov 5 - Nov 6
Delicious Cabin | Wine Country Hot Tub, Game Room + Screened Porch
A cozy living room with a grey sofa, patterned cushions, a small side table with a lamp, and decorative vases.

10. 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 ￥23,509
￥35,188 total
includes taxes & fees
Oct 13 - Oct 14
Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
A wooden house with a garage, surrounded by lush greenery and a wooden fence.

11. 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 ￥46,385
￥92,198 total
includes taxes & fees
Oct 13 - Oct 14
The Pond Cabin: Hot Tub & Stocked Pond
A bedroom with a large bed, a desk with a chair, a TV, and a balcony with a view of trees.

12. 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 ￥25,171
￥67,228 total
includes taxes & fees
Oct 27 - Oct 28
Skyland Hideaway | Mountain Cabin w/ Hot Tub
A balcony with a table, two wine glasses, and a view of a fenced area with a truck and a building in the background.

13. "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 ￥34,353
￥41,957 total
includes taxes & fees
Oct 13 - Oct 14
"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country
A rustic interior with a wooden dining table, chairs, and a fireplace.

14. Historic Estate • 6BR Heated Pool Near Wineries

Historic Estate • 6BR Heated Pool Near Wineries
Hume
The price is ￥99,735
￥258,860 total
includes taxes & fees
Oct 13 - Oct 14
Historic Estate • 6BR Heated Pool Near Wineries
A cabin with a deck, a covered outdoor area, and a gravel path leading to the entrance.

15. 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.
The price is ￥24,855
￥70,895 total
includes taxes & fees
Oct 27 - Oct 28
Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6
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, (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 ￥34,583
￥89,656 total
includes taxes & fees
Oct 18 - Oct 19
Pool Table, Fireplace & Deck near Shenandoah Park
A modern kitchen with large windows, granite countertops, and stainless steel appliances.

17. 3 bedroom cabin with an exclusive view of the Shenandoah Mountains and RIver

3 bedroom cabin with an exclusive view of the Shenandoah Mountains and RIver
Front Royal
The price is ￥42,744
￥67,751 total
includes taxes & fees
Nov 6 - Nov 7
3 bedroom cabin with an exclusive view of the Shenandoah Mountains and RIver
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 ￥32,612
￥88,530 total
includes taxes & fees
Oct 26 - Oct 27
Wilderness Ridge | Private Cabin w/ Mountain Views
A wooden staircase leading to a deck with a lattice railing, surrounded by dense foliage.

19. 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 ￥33,245
￥41,035 total
includes taxes & fees
Oct 14 - Oct 15
Blue Mountain Cabin, secluded, perfect for couples, near main road
A bedroom with a large window, a bedside table, a lamp, and a wardrobe.

20. 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.
The price is ￥39,736
￥73,163 total
includes taxes & fees
Oct 13 - Oct 14
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

Wayside Inn

Wayside Inn

10/10 Excellent
"This is the oldest hotel in the US. An exceptionally unique property from the mid 1700’s."
Judy 1-night trip
Posted 1 hour 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:

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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?

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.