Photo by Brian V. Rowe

Holiday Rentals in Chester Gap

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Holiday Rentals in Chester Gap

Colonial 3BR Home • Walk to The Inn • Great Location • Fast Wi-Fi

10.0 out of 10, Exceptional, (119)
"The house was comfy and well appointed. The owners have made every effort to cover whatever you might need while staying in the home. "
The price is €280
includes taxes & fees
4 Aug - 5 Aug
Colonial 3BR Home • Walk to The Inn • Great Location • Fast Wi-Fi

Lone Bear Cabin: Lv2 EV, WiFi, River Access, Mountain Views, fireplace, hot tub

10.0 out of 10, Exceptional, (89)
"Loved the view, such a relaxing weekend. Hist was very responsive and access was a breeze. Highly recommend "
The price is €380
includes taxes & fees
15 Jul - 16 Jul
Lone Bear Cabin: Lv2 EV, WiFi, River Access, Mountain Views, fireplace, hot tub

Overlook Mountain Cabin

9.8 out of 10, Exceptional, (160)
"Beautiful mountain view! The trip was nice and beautiful! I love a good cozy vibe in the mountains! Communication with property manger was very excellent customer service! "
The price is €323
includes taxes & fees
21 Jul - 22 Jul
Overlook Mountain Cabin

Nestled Among Majestic Trees, Hilltop Hideaway is a Woodland Sanctuary

9.8 out of 10, Exceptional, (86)
"Great place that works well for Rixey Manor weddings "
The price is €370
includes taxes & fees
15 Jul - 16 Jul
Nestled Among Majestic Trees, Hilltop Hideaway is a Woodland Sanctuary

Big Sunny Family House

10.0 out of 10, Exceptional, (35)
"The house was clean, the kitchen had sufficient utensils and supplies, the location was close to restaurants."
The price is €474
includes taxes & fees
14 Aug - 15 Aug
Big Sunny Family House

Charming Private Suite in Historic Colonial House – right beside from The Inn!

10.0 out of 10, Exceptional, (14)
"an excellent option if dining at the INN"
The price is €204
includes taxes & fees
4 Aug - 5 Aug
Charming Private Suite in Historic Colonial House – right beside from The Inn!

Ridgeview Mountain Cabin

9.4 out of 10, Exceptional, (41)
"This was the perfect little cabin for me and my husband. The location was perfect for us. We went to the Laray Caverns and hiked Old Rag. The owner was very helpful and has great communication! Planning another trip soon! "
The price is €315
includes taxes & fees
15 Jul - 16 Jul
Ridgeview Mountain Cabin

Stepping Stone Cabin

9.8 out of 10, Exceptional, (48)
"awesome stay we will love to go again"
Stepping Stone Cabin

Sunset Mountain Cabin

10.0 out of 10, Exceptional, (32)
"We loved this little getaway spot! The view was gorgeous and the cabin was so clean and cozy!"
The price is €415
includes taxes & fees
25 Jul - 26 Jul
Sunset Mountain Cabin

Newly renovated Farm cottage with Mountain views

9.8 out of 10, Exceptional, (30)
"The cottage was very charming and outfitted for maximum relaxation. We would definitely stay there again."
The price is €286
includes taxes & fees
16 Jul - 17 Jul
Newly renovated Farm cottage with Mountain views

River Woods Retreat:10min to River, L2 EV, Hikes, 2 Fireplaces, Hottub, SP 10mi

10.0 out of 10, Exceptional, (51)
"Very well maintained property. "
The price is €358
includes taxes & fees
23 Jul - 24 Jul
River Woods Retreat:10min to River, L2 EV, Hikes, 2 Fireplaces, Hottub, SP 10mi

🔥 Hottub + 🐕 friendly + 🏔️ view + Skyline Dr + Wineries

10.0 out of 10, Exceptional, (14)
"View was great, was pretty isolated from other houses in the area, and cute decor. Very comfortable stay. "
The price is €365
includes taxes & fees
12 Aug - 13 Aug
🔥 Hottub + 🐕 friendly + 🏔️ view + Skyline Dr + Wineries

Spacious home steps from Main St and Shenandoah NP with firepit & large backyard

10.0 out of 10, Exceptional, (13)
"We needed a place to stay for our golf foursome. Thisfour bedroom property met all of our needs."
The price is €333
includes taxes & fees
15 Jul - 16 Jul
Spacious home steps from Main St and Shenandoah NP with firepit & large backyard

Shenandoah Mountain Cabin

10.0 out of 10, Exceptional, (14)
"This place is amazing! So clean and comfortable. Drive up to the cabin is very bumpy but so very worth it. "
Shenandoah Mountain Cabin

Waterfront Log Home Hot Tub Flat yard w/ Volleyball Fire Pit & Tubes for Floating

9.0 out of 10, Wonderful, (28)
"location by the river was beautiful. House is roomy and great for our family of 12. "
The price is €599
includes taxes & fees
16 Jul - 17 Jul
Waterfront Log Home Hot Tub Flat yard w/ Volleyball Fire Pit & Tubes for Floating

Mint Cottage at Little Washington - a modern, spacious retreat with a view

10.0 out of 10, Exceptional, (6)
"Mint Cottage is a gem. Its spacious, beautifully furnished, and a great place to stay to explore Shenandoah National Park and its environs"
The price is €404
includes taxes & fees
17 Jul - 18 Jul
Mint Cottage at Little Washington - a modern, spacious retreat with a view

Cozy Cottage w Hot Tub, Fire Pit, WiFi & Sunroom!

9.0 out of 10, Wonderful, (24)
"Everything was as described. We had a lovely weekend relaxing under the stars in the hot tub and spending time with family in the Shenandoah Valley. We can't wait to come back to this oasis!"
The price is €265
includes taxes & fees
28 Jul - 29 Jul
Cozy Cottage w Hot Tub, Fire Pit, WiFi & Sunroom!

Pirate's Cove River Front Oasis, Group Adventure

10.0 out of 10, Exceptional, (4)
"The place is amazing and the host was quick with the response! Me and my family had a great time and will be returning guests!!!"
The price is €1,276
includes taxes & fees
23 Jul - 24 Jul
Pirate's Cove River Front Oasis, Group Adventure

Dream Dome - Romantic Retreat + Wifi A/C + Hot Tub

2.0 star property
10.0 out of 10, Exceptional, (2)
"This was a great place to stay for a change of setting. So much more fun than a hotel room. The hot tub was a nice extra and bed was super comfortable. Nice to be able to have a cup of coffee and sit outside at picnic table. Great place!"
The price is €302
includes taxes & fees
22 Jul - 23 Jul
Dream Dome - Romantic Retreat + Wifi A/C + Hot Tub

Hideaway Mountain Cabin

10.0 out of 10, Exceptional, (11)
"Hideaway cabin was the perfect mountain getaway. My husband and I stayed here with our two dogs and it was so cozy and had everything we needed. The cabin was clean, and had all the essentials for cooking. The views are amazing and we loved using the wood fire stove. We took our dogs to the waterfall hike and they had a blast. Definitely recommend staying here! "
The price is €344
includes taxes & fees
15 Jul - 16 Jul
Hideaway Mountain Cabin
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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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?

Modern Mountain Retreat w/ Deck + Hot Tub!: This highly rated holiday home rental in Chester Gap offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub.

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.