Chester Gap Vacation Rentals from $223: Search Short-Term Rentals

Q: What are some of the best vacation rentals in Chester Gap?

Peaceful with Firepit, Hiking & River Access Pet Friendly! : This vacation home rental near Chester Gap is located near skiing and has a patio, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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In two weeks

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Our top choices for Chester Gap vacation rentals

Smart TV, fireplace, video games, foosball

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

Front Royal

Christine H.

$620 nightly

Sep 2 - Sep 3

Total with taxes and fees

2. Hidden Gem on Hidden Valley Lane

Linden

Jen T.

$514 nightly

Sep 2 - Sep 3

Total with taxes and fees

3. A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub

Linden

Scott M.

$349 nightly

Sep 22 - Sep 23

Total with taxes and fees

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

Linden

Edward

$369 nightly

Sep 7 - Sep 8

Total with taxes and fees

5. The Pond Cabin: Hot Tub & Stocked Pond

Linden

Mary S.

$473 nightly

Sep 2 - Sep 3

Total with taxes and fees

Cabin, Private Bathroom (The Pond Cabin) | Exterior

6. The Pond Cabin

Linden

$414 nightly

Sep 2 - Sep 3

Total with taxes and fees

7. Mountain cabin near national park & wineries

Linden

Chynna V.

8. Skyland Hideaway | Mountain Cabin w/ Hot Tub

Linden

Patricia B.

$374 nightly

Sep 23 - Sep 24

Total with taxes and fees

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

Linden

Colin N.

$349 nightly

Sep 7 - Sep 8

Total with taxes and fees

10. Wilderness Ridge | Private Cabin w/ Mountain Views

Linden

Adriane B.

$492 nightly

Sep 2 - Sep 3

Total with taxes and fees

11. 4BR Shenandoah Golf Retreat | Pool Table | Pets

Front Royal

"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...

Crystal H.

$472 nightly

Sep 2 - Sep 3

Total with taxes and fees

12. Mountain Views w/Hot Tub, 95” TV & Trail Access

Shenandoah Farms

"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...

Joshua J.

$365 nightly

Sep 30 - Oct 1

Total with taxes and fees

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

Front Royal

Hailey

$392 nightly

Sep 2 - Sep 3

Total with taxes and fees

14. Events and Concierge! 6BR Heated Pool Near Wineries

Hume

$1,412 nightly

Sep 2 - Sep 3

Total with taxes and fees

3 bedrooms, desk, iron/ironing board, WiFi (free)

15. 3 bedroom cabin with an exclusive view of the Shenandoah Mountains and RIver

Front Royal

$407 nightly

Sep 7 - Sep 8

Total with taxes and fees

16. Mountain View Bungalow in Front Royal

Front Royal

HEMANT S.

$200 nightly

Sep 2 - Sep 3

Total with taxes and fees

17. Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View

Front Royal

Jake M.

$205 nightly

Sep 9 - Sep 10

Total with taxes and fees

18. Skyline Yurt: Hot Tub~Wood Stove~WiFi~EVcharger

Front Royal

Paul S.

$472 nightly

Sep 8 - Sep 9

Total with taxes and fees

19. Timber Creek Falls - a Shenandoah cabin with a private waterfall

Bentonville

Brent R.

$477 nightly

Sep 2 - Sep 3

Total with taxes and fees

20. Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6

Linden

$394 nightly

Sep 2 - Sep 3

Total with taxes and fees

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Top Chester Gap Hotel Reviews

Hampton Inn Front Royal

8/10 Good

"The pool filter was broken and not open. When its this hot out the pool must be open. The breakfast was top notch though!"

DoubleTree by Hilton Front Royal Blue Ridge Shadows

10/10 Excellent

"The rooms were clean and well-maintained. The hotel has a convenient location to shopping and dining options. The public spaces are beautiful and comfortable. I rented a meeting room for a Celebration of Life gathering and used the hotel's catering service. The food was excellent and the staff was professional and helpful. The hotel restaurant wasn't great for breakfast, as the service was slow and the oatmeal was served undercooked. However, dinner was fine."

Mystic Mountain-Secluded Log Cabin with Pool, Hot Tub & Amazing Views!

10/10 Excellent

"Firstly, the road to get to the property is a little bit rough for the last half mile or so, but thats stated clearly in the listing; If you don't have AWD/4X4 or are NOT familiar with how to drive on slightly rocky/rain-washed backroads with a decent incline , I would avoid. A steady pace & good tires will do the trick no issue. Very clean property, good morning view of the mountains and spacious in the family areas. Good sized bedrooms and plenty of room for the family. 5 people and a 9 month old slept comfortably, with a crib we brought ourselves.Only downfalls were the backdoor was a little rough to close;the air-conditioning vent door kept falling of the master bedrooms air conditioning unit, and there were a few bulbs burnt out in the upstairs bathroom making it a little harder to see. Kitchen area is a little small, but it's a cabin; so what do you expect realistically?The pool was nice and was a perfect end to the day after being out all day with the family, the hottub was good to relax in but was missing the adjustment knob for the side closest too the pool. So the jets weren't as strong on that side, but it's not a major issue. But other than that, it was a good experience. Host was quick and easy to communicate with, and we enjoyed the property for the weekend."

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.

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?

Peaceful with Firepit, Hiking & River Access Pet Friendly!: This vacation home rental near Chester Gap is located near skiing and has a patio, a barbecue grill, and air-conditioning to put you at ease 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. 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.

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Check prices for these dates

Our top choices for Chester Gap vacation rentals

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

2. Hidden Gem on Hidden Valley Lane

3. A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub

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

5. The Pond Cabin: Hot Tub & Stocked Pond

6. The Pond Cabin

7. Mountain cabin near national park & wineries

8. Skyland Hideaway | Mountain Cabin w/ Hot Tub

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

10. Wilderness Ridge | Private Cabin w/ Mountain Views

11. 4BR Shenandoah Golf Retreat | Pool Table | Pets

12. Mountain Views w/Hot Tub, 95” TV & Trail Access

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

14. Events and Concierge! 6BR Heated Pool Near Wineries

15. 3 bedroom cabin with an exclusive view of the Shenandoah Mountains and RIver

16. Mountain View Bungalow in Front Royal

17. Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View

18. Skyline Yurt: Hot Tub~Wood Stove~WiFi~EVcharger

19. Timber Creek Falls - a Shenandoah cabin with a private waterfall

20. Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6

Find vacation rentals that suit your style

Top Chester Gap Hotel Reviews

Hampton Inn Front Royal

Holiday Inn Express Winchester South-Stephens City by IHG

Ramada by Wyndham Strasburg/Shenandoah Valley

Hillside

DoubleTree by Hilton Front Royal Blue Ridge Shadows

Quality Inn Stephens City - Winchester South

Mystic Mountain-Secluded Log Cabin with Pool, Hot Tub & Amazing Views!

Whiskey Hill Cabin a mountain escape in Virginia wine country

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

Find out more about Chester Gap

Frequently asked questions

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