Photo by Brian V. Rowe

Holiday Rentals in Chester Gap

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Holiday Rentals in Chester Gap

Modern Mountain Retreat w/ Deck + Hot Tub!

10.0 out of 10, Exceptional, (66)
"The owner communicated well and was very responsive. The fireplace stove was great and we used the hot tub every day. Kitchen was well stocked. We cooked almost every meal and had everything we needed. The office space is a nice, private, comfortable space, as well. "
Modern Mountain Retreat w/ Deck + Hot Tub!

Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River

9.6 out of 10, Exceptional, (340)
"My friend and I spent the weekend in John's Cozy Cabin to enjoy some time away from our urban settings and focus on writing in a quiet, secluded place. This cabin was just what we were seeking because it was tranquil, isolated, in serene settings in the forest along the Shenandoah River, and it had everything we needed. John was proactive in his approach, taking the time to discuss our needs and preferences before our stay. His thorough communication and attention to detail ensured that my...
Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River

Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo

9.6 out of 10, Exceptional, (300)
"Beautiful view, really nice wood burning fireplace, clean and cozy. Nice accommodations. Rustic in appearance and feel, with modern amenities."
Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo

Magical Riverfront Retreat in Luray – Cozy Getaway with Stunning Views!

9.8 out of 10, Exceptional, (179)
"Wonderful property I hope to be back during warmer weather"
Magical Riverfront Retreat in Luray – Cozy Getaway with Stunning Views!

"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA

9.8 out of 10, Exceptional, (280)
"Beautiful setting"
The price is €300
includes taxes & fees
17 Feb - 18 Feb
"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA

Whiskey Hill Cabin in Virginia Wine country. Close to Fox Meadow & Capstone!

10.0 out of 10, Exceptional, (79)
"My husband and I had a lovely stay in this cabin for Thanksgiving. We had everything we needed to cook our Thanksgiving meal, stay cozy, and enjoy the views around the cabin. Thank you!"
Whiskey Hill Cabin in Virginia Wine country. Close to Fox Meadow & Capstone!

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

9.2 out of 10, Wonderful, (23)
"location by the river was beautiful. House is roomy and great for our family of 12. "
The price is €646
includes taxes & fees
17 Feb - 18 Feb
Waterfront Log Home Hot Tub Flat yard w/ Volleyball Fire Pit & Tubes for Floating

Cute cabin retreat near Shenandoah National Park and pet friendly!

9.2 out of 10, Wonderful, (10)
"Fun location near tons of wineries, bowling, trails, and mountain living. Place is really nice with a grill, solo stove, kfantastic kitchen"
The price is €322
includes taxes & fees
16 Mar - 17 Mar
Cute cabin retreat near Shenandoah National Park and pet friendly!

Brand New Cabin, Romantic, Private,Adjacent to George Washington National Forest

9.8 out of 10, Exceptional, (117)
"Everything we hoped for in a weekend trip! The house smelled like cedar, was clean and very ample space. The hot tub was easy to operate; kitchen appliances helped cut down on eating out costs - would highly recommend and plan on making a reservation again!"
Brand New Cabin, Romantic, Private,Adjacent to George Washington National Forest

Mountain Views, River Frontage & HotTub + Country!

10.0 out of 10, Exceptional, (26)
"We loved it! Thank you for sharing one of your wonderful cabins with us!!"
Mountain Views, River Frontage & HotTub + Country!

Riverfront, pet friendly ! Log cabin with 2 bedrooms and loft!

10.0 out of 10, Exceptional, (259)
"While there was a miscommunication between the owner and the cleaning crew resulting in us arriving to a dirty cabin at the beginning of our stay, Andy was very responsive and got someone out to get the place spotless within an hour. This is a very secluded spot and very quiet. The cabin was cozy and well-kept as well as the dog run. Our favorite feature was the gas fireplace! Just note that there are a LOT of muddy areas on the property near the river due to recent flooding in the area, so we...
Riverfront, pet friendly ! Log cabin with 2 bedrooms and loft!

"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.

10.0 out of 10, Exceptional, (304)
"Quiet and the hot tub was popular. Nice winter trip through Shen Nat Park, but no snowshoeing."
The price is €255
includes taxes & fees
17 Feb - 18 Feb
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.

Riverfront Retreat

10.0 out of 10, Exceptional, (26)
"We made a great choice in choosing the Riverfront Retreat for our Thanksgiving celebration. The large dining table fit our group and its close proximity to the kitchen made serving and cleanup a breeze. One bedroom is set apart from the others which worked perfectly for one couple who ducked out at 5am to catch a flight out of Dulles (about an hours drive) without disturbing others in the group. We enjoyed hiking in Seven Bends State Park and even toured the Shenandoah Caverns (a short drive)....
Riverfront Retreat

Star view cabin-Riverfront

9.8 out of 10, Exceptional, (304)
"We experienced the beauty of a mountain snowstorm and it was awesome! We enjoyed the gorgeous view sitting by the fireplace and feeling super cozy. Nina the owner was so thoughtful, checking on us, suggesting a good place for our car during the storm so that we wouldn’t get stuck when it came time to go home, even cleaning our car off for us! That was above and beyond—thank you, Nina. The cabin is as pictured and well appointed. We plan to return here. "
Star view cabin-Riverfront

Captain's Lodge 15 Acres w/300 Meters Of Private Shenandoah Riverfront property

9.6 out of 10, Exceptional, (51)
"Had our new year party here. Beautiful location, direct access to Shenandoah river."
Captain's Lodge 15 Acres w/300 Meters Of Private Shenandoah Riverfront property

Front Royal Hilltop Cabin w/ Panoramic Views!

10.0 out of 10, Exceptional, (30)
"Five of us really enjoyed our weekend. Beautiful home with a great views. Greg made sure we had everything we needed. Would love to stay again. "
Front Royal Hilltop Cabin w/ Panoramic Views!

The Perch Riverfront Cabin - Starlink Satellite Wi-Fi

9.4 out of 10, Exceptional, (29)
"Great getaway with 2 adults, tween and child. There was enough room for all. The nook was a hit with the kids. The area was very quiet and relaxing. It snowed while we were there and the roads were plowed fast. House was very clean and well stocked. There was plenty of cookware and spices available. Would definitely come back. "
The Perch Riverfront Cabin - Starlink Satellite Wi-Fi

Bear Mountain Lodge Shenandoah Mountains Skyline Drive / Front Royal (hottub)<br>

10.0 out of 10, Exceptional, (36)
"Great and communicative host. Very accommodating. Spent a few hours in the hot tub enjoying the stars. Great kitchen to cook a lovely meal. Would stay again!"
Bear Mountain Lodge Shenandoah Mountains Skyline Drive / Front Royal (hottub)<br>

Riverfront Cabin, Ideal Location - Family and Pet Friendly w/ Hot Tub!

10.0 out of 10, Exceptional, (8)
"Great location for the family. Proximity to Luray 20 mins, great river front location with a hot tub which the kids loved. Nightly fires were a plus. Small but all you need. Beautiful mountain view. Close to several hikes and not too far from Shenandoah Park as well."
Riverfront Cabin, Ideal Location - Family and Pet Friendly w/ Hot Tub!

Enjoy Secluded Starry Nights! Near Luray, HotTub, FastWiFi, Handicap, Fireplace

10.0 out of 10, Exceptional, (188)
"We had a great time celebrating New Years at the cabin. We made use of all amenities, said hi to the horses, and enjoyed our stay. "
Enjoy Secluded Starry Nights! Near Luray, HotTub, FastWiFi, Handicap, Fireplace
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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Other types of properties in Chester Gap you may be interested in

Modern Mountain Retreat w/ Deck + Hot Tub!

10.0 out of 10, Exceptional, (66)
"The owner communicated well and was very responsive. The fireplace stove was great and we used the hot tub every day. Kitchen was well stocked. We cooked almost every meal and had everything we needed. The office space is a nice, private, comfortable space, as well. "
Modern Mountain Retreat w/ Deck + Hot Tub!

Ramada by Wyndham Strasburg/Shenandoah Valley

2.5 star property
8.0 out of 10, Very good, (1002)
"I need accessibility bathroom with bathtub grab bars. The bathtub drain would not stay closed. Had to rig it with a washcloth. It was very to get luggage into hotel from car, but there was no one to help so I struggled a bit. I have my luggage split across several bags so I don’t lift too much. I mean, if you see a man wearing a back brace … offer to help? I would have tipped. Idk. Really great built in Mexican restaurant on lower floor. Good think because this town very small, I drove in the...
The price is €77
includes taxes & fees
2 Mar - 3 Mar
Ramada by Wyndham Strasburg/Shenandoah Valley

Hampton Inn Front Royal

2.5 star property
8.8 out of 10, Excellent, (1001)
"Nice"
The price is €94
includes taxes & fees
23 Feb - 24 Feb
Hampton Inn Front Royal
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.

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.