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Chester Gap Vacation Rentals

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Nov 30 - Dec 1
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Dec 1 - Dec 2
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Dec 5 - Dec 7
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Dec 12 - Dec 14

Vacation Rentals in Chester Gap

Terrace/patio
Rivah Retreat -River Front- Fishing -Hot tub

Cabin in Woodstock

10.0 out of 10, Exceptional, (17)
"Fantastic as always, wonderful place and wonderful host!"
United States
Milton W.
$225 nightly
The price is $228
Dec 2 - Dec 3
Total with taxes and fees
Rivah Retreat -River Front- Fishing -Hot tub
Outdoor spa tub
Fox Den — Hot Tub, Fire Pit, Steps to River

Cabin in Luray

10.0 out of 10, Exceptional, (8)
"Great time. Really comfortable place."
United States
Joshua E.
$308 nightly
The price is $333
Dec 2 - Dec 3
Total with taxes and fees
Fox Den — Hot Tub, Fire Pit, Steps to River
Outdoor spa tub
The Honeymoon Cabin | Private Retreat w/ hot tub

Cabin in Front Royal

10.0 out of 10, Exceptional, (2)
"Absolutely perfect spot for a leaf-peeping getaway. Clean, charming, romantic! Close to antiques, vineyards and Shenandoah!"
United States
Paul B.
$320 nightly
The price is $353
Dec 1 - Dec 2
Total with taxes and fees
The Honeymoon Cabin | Private Retreat w/ hot tub
TV, fireplace, offices
Skyland Hideaway • Relaxing Cabin w/ Hot Tub, Deck, Grill, & Fire table

Cabin in Linden

10.0 out of 10, Exceptional, (15)
"Quiet with amenities to support R&R, enjoying nature, and togetherness."
United States
Patricia B.
$331 nightly
The price is $365
Dec 4 - Dec 5
Total with taxes and fees
Skyland Hideaway • Relaxing Cabin w/ Hot Tub, Deck, Grill, & Fire table
Exterior
The Foxwood Cabin: Cozy Retreat w/ Hot Tub, Screened Porch, Firepit & Grill

Cabin in Front Royal

10.0 out of 10, Exceptional, (5)
"Beautiful, quiet place to stay. Beds are very comfortable. Every room was very clean. "
United States
Alex H.
$344 nightly
The price is $379
Dec 7 - Dec 8
Total with taxes and fees
The Foxwood Cabin: Cozy Retreat w/ Hot Tub, Screened Porch, Firepit & Grill
Outdoor dining
Shenandoah Twilight | Cozy Cabin w/ hot tub

Cabin in Front Royal

9.0 out of 10, Wonderful, (2)
"Shenandoah Twilight is a beautiful spot tgats beautifully appointed. I really enjoyed my time there. "
United States
Wilson (Wally) W.
$305 nightly
The price is $336
Dec 1 - Dec 2
Total with taxes and fees
Shenandoah Twilight | Cozy Cabin w/ hot tub
Exterior
Mountain retreat w/hot tub, sauna, projector, close to river and 25 to NP!

Vacation Home in Luray

9.6 out of 10, Exceptional, (12)
"Great stay, very quiet. Everything was in place to ensure a comfortable stay. Perfect getaway for a couple of days and within 15 minutes to town. "
United States
Derek B.
$246 nightly
The price is $284
Dec 8 - Dec 9
Total with taxes and fees
Mountain retreat w/hot tub, sauna, projector, close to river and 25 to NP!
Pool
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.

Cabin in Rileyville

10.0 out of 10, Exceptional, (339)
"Excellent experience! The cabin was great, the location was great, the sights and people were great!"
United States
Tom A.
$207 nightly
The price is $239
Dec 1 - Dec 2
Total with taxes and fees
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.
Terrace/patio
The Zen Garden by Zen Living

Cabin in Page County

9.6 out of 10, Exceptional, (15)
"King size bed, fenced yard for our dog, and good mid-week price are what made us choose this place for a short get away. It really suited our needs and we'll be back! Bed was comfortable. House was clean, nicely decorated, and felt welcoming. Could not get WiFi to work, but our cell phone reception was fine."
United States
Joyce F.
$249 nightly
The price is $287
Dec 1 - Dec 2
Total with taxes and fees
The Zen Garden by Zen Living
Exterior
The Juniper Cabin • Private Hideaway w/ Hot Tub, Grill & Screened Porch

Cabin in Linden

10.0 out of 10, Exceptional, (22)
"We had a fantastic time staying at this property for the weekend."
United States
Colin N.
$305 nightly
The price is $337
Dec 1 - Dec 2
Total with taxes and fees
The Juniper Cabin • Private Hideaway w/ Hot Tub, Grill & Screened Porch
Terrace/patio
Cabin Retreat in Virginia Wine Country • Hot Tub, Theatre & Game Room, & More

Cabin in Linden

9.8 out of 10, Exceptional, (10)
"The cabin was impressive both inside and out. We loved the location and proximity to skyline drive. We would definitely stay here again as it made our trip so much more enjoyable. "
United States
Bill A.
$359 nightly
The price is $396
Dec 3 - Dec 4
Total with taxes and fees
Cabin Retreat in Virginia Wine Country • Hot Tub, Theatre & Game Room, & More
Fridge, microwave, oven, stovetop
Cozy 1BR Apt Minutes From Skyline Drive!!

Apartment in Amissville

9.6 out of 10, Exceptional, (37)
"My wife and I enjoyed our stay at this cute and cozy spot. Very convenient for exploring Northern Virginia, from Shenandoah National Park, to Leesburg, Culpeper, Manassas, and beyond. Check-in was very easy and Jimmie, our host, was very friendly and responsive. "
United States
John P.
$223 nightly
The price is $234
Dec 1 - Dec 2
Total with taxes and fees
Cozy 1BR Apt Minutes From Skyline Drive!!
Exterior detail
Charming 1-bedroom house with WiFi, AC in Pleasant Rixeyville, VA on 13 acres!

Vacation Home in Rixeyville

9.6 out of 10, Exceptional, (5)
"Great place. Great people!"
United States
Brian
$216 nightly
The price is $228
Dec 2 - Dec 3
Total with taxes and fees
Charming 1-bedroom house with WiFi, AC in Pleasant Rixeyville, VA on 13 acres!
Property grounds
"Prima BnB" a Superb 4-bedroom cottage on the mountain near Front Royal

Cottage in Front Royal

10.0 out of 10, Exceptional, (2)
"My family and I had a wonderful stay! The property and surrounding views are beautiful. The house was very clean and the host was very responsive when I had a question or two to ask. I highly recommend staying here!"
United States
Jay L.
$357 nightly
The price is $393
Dec 3 - Dec 4
Total with taxes and fees
"Prima BnB" a Superb 4-bedroom cottage on the mountain near Front Royal
Terrace/patio
"Sundance" Spectacular Views on 54 Acres along Shenandoah River w/ Hot Tub

Cabin in Rileyville

10.0 out of 10, Exceptional, (316)
"We absolutely loved Sundance! Perfect property for a couple wanting to reconnect. Great location and amenities were outstanding. I would highly recommend it."
United States
Anthony V.
$216 nightly
The price is $249
Dec 1 - Dec 2
Total with taxes and fees
"Sundance" Spectacular Views on 54 Acres along Shenandoah River w/ Hot Tub
Outdoor dining
Modern Riverside Cabin w Hot Tub, Fire Pit, Kayaks

Cabin in Rileyville

9.4 out of 10, Exceptional, (3)
"We had an absolute wonderful time! It was so relaxing and the descriptions were spot on. After reading the reviews, we brought our foam mattress cover for the bed and it made a big difference. The public fishing spot near the cabin is also a boat launch spot so we had some traffic while fishing but we still caught some fish! Rivers Edge is also on the corner lot so we felt it was very private and highly recommend! The hot tub was also a perfect touch. 10/10 vacation! Thanks Tony! "
United States
Allison S.
$243 nightly
The price is $267
Dec 3 - Dec 4
Total with taxes and fees
Modern Riverside Cabin w Hot Tub, Fire Pit, Kayaks
Smart TV, fireplace, stereo
Escape to Shenandoah River, Hot Tub after a Hike!

Cabin in Front Royal

10.0 out of 10, Exceptional, (54)
"Very nice updated home in a beautiful peaceful setting. I would highly recomend it!"
United States
Kathy L.
$267 nightly
The price is $294
Dec 1 - Dec 2
Total with taxes and fees
Escape to Shenandoah River, Hot Tub after a Hike!
Property grounds
"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA

Cabin in Rileyville

9.8 out of 10, Exceptional, (308)
"We really enjoyed our stay! The Chalet was peaceful, clean, and perfect in every way. We enjoyed the hot tub and the view.Location was perfect, near Luray caverns and Shenandoah Park.Thank you for allowing us to stay there. It was a wonderful getaway."
United States
Amy A.
$216 nightly
The price is $249
Dec 1 - Dec 2
Total with taxes and fees
"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA
Outdoor dining
Dog Friendly Cabin near River on Nearly 5 acres w/Strong WiFi + Robust Amenities

Cabin in Luray

9.6 out of 10, Exceptional, (70)
"Check in was easy and I loved that they used my last four of my phone as the door code- made it easy to remember!"
United States
Kathy M.
$276 nightly
The price is $316
Dec 1 - Dec 2
Total with taxes and fees
Dog Friendly Cabin near River on Nearly 5 acres w/Strong WiFi + Robust Amenities
Terrace/patio
The Cozy Bear Cabin | Hot Tub, Fenced Yard, Games

Cabin in Front Royal

10.0 out of 10, Exceptional, (4)
"We had a wonderful time staying there during our time at upperville. The quiet nights in the hot tub were just what we needed! Matthew was a wonderful host and so helpful ! We hope to come back again "
United States
grace g.
$479 nightly
The price is $528
Dec 14 - Dec 15
Total with taxes and fees
The Cozy Bear Cabin | Hot Tub, Fenced Yard, Games
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

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

10/10 Excellent
"Great overnight stay. Clean, easy parking, & good food around."
Steve 1-night trip
Posted 2 days ago
Comfort Inn & Suites Winchester

Find out more about Chester Gap

Everything you need to know about Chester Gap vacation rentals

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

Chester Gap vacation 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 low season months. For more hustle and bustle, you may prefer to visit Chester Gap in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $223 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chester Gap rentals

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

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.

Explore a world of travel with Expedia

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?

Secluded River Cabin Getaway (Masten Cabin): This vacation home rental near Chester Gap is located in the mountains and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

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. Dickey Ridge Visitor Center and Linden Vineyards 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.