Vacation Homes in Chester Gap, VA

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Top Vacation Homes in Chester Gap

Waterfront, Luxury Panoramic View, Fast Wi-Fi, Private River Access Steps Away!

Waterfront, Luxury Panoramic View, Fast Wi-Fi, Private River Access Steps Away!

Luray VA
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This vacation home features a water park, a garden, and laundry facilities. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site.
Kitchen
Washer
🔥 Hottub + 🐕 friendly + 🏔️ view + Skyline Dr + Wineries

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

Linden VA
$364 nightly
The price is $401 total per night
$401 total
Jan 20 - Jan 21, 2026
Total with taxes and fees
A hot tub is featured at this vacation home, along with a garden and barbecue grills.
Hot Tub
Kitchen
Pets? YES! Hot Tub ★ Gym ★ Firepit ★ Game Room ★ Path to Winery

Pets? YES! Hot Tub ★ Gym ★ Firepit ★ Game Room ★ Path to Winery

Delaplane VA
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This vacation home features a gym and a hot tub. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. A garden and barbecue grills are also provided.
Hot Tub
Kitchen
Escape the city to this Spacious and Clean 5BR / 3.5BA home with a Heated Pool and Spa on 8 Acres in Horse & Wine Country

Escape the city to this Spacious and Clean 5BR / 3.5BA home with a Heated Pool and Spa on 8 Acres in Horse & Wine Country

Marshall VA
Free Cancellation
$552 nightly
The price is $591 total per night
$591 total
Jan 6 - Jan 7, 2026
Total with taxes and fees
A hot tub is featured at this vacation home, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.
Hot Tub
Kitchen
Secluded River Cabin Getaway (Masten Cabin)

Secluded River Cabin Getaway (Masten Cabin)

Strasburg VA
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This vacation home featured laundry facilities and barbecue grills.
Kitchen
Washer
Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal

Front Royal VA
$197 nightly
The price is $219 total per night
$219 total
Dec 28 - Dec 29
Total with taxes and fees
This vacation home includes a garden and laundry facilities.
Kitchen
Washer
Sunset Mountain Cabin

Sunset Mountain Cabin

Rileyville VA
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A hot tub is featured at this vacation home, along with laundry facilities.
Hot Tub
Kitchen
On the river ~ hot tub ~ serene river views ~ fire pit

On the river ~ hot tub ~ serene river views ~ fire pit

Strasburg VA
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A hot tub is featured at this vacation home, along with laundry facilities and barbecue grills.
Hot Tub
Kitchen
Mountain Views in Buena Vista Farm - Unit A

Mountain Views in Buena Vista Farm - Unit A

Front Royal VA
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This vacation home features a water park, a garden, and laundry facilities. Barbecue grills are provided for your convenience.
Kitchen
Washer
Waterfront on The.Shenandoah River near Luray, VA highspeed WiFi

Waterfront on The.Shenandoah River near Luray, VA highspeed WiFi

Rileyville VA
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This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Charming 1-bedroom house with WiFi, AC in Pleasant Rixeyville, VA on 13 acres!

Charming 1-bedroom house with WiFi, AC in Pleasant Rixeyville, VA on 13 acres!

Rixeyville VA
$215 nightly
The price is $227 total per night
$227 total
Dec 26 - Dec 27
Total with taxes and fees
This vacation home features limo/town car service, laundry facilities, and barbecue grills.
Kitchen
Washer
Nestled Among Majestic Trees, Hilltop Hideaway is a Woodland Sanctuary

Nestled Among Majestic Trees, Hilltop Hideaway is a Woodland Sanctuary

Amissville VA
$390 nightly
The price is $411 total per night
$411 total
Jan 10 - Jan 11, 2026
Total with taxes and fees
This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
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See all available properties in Chester Gap
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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.

Top hotels in Chester Gap

Falling Leaf Cabin - Rustic Charm With Modern Decor!

Falling Leaf Cabin - Rustic Charm With Modern Decor!

Rileyville VA
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9.6/10 Exceptional! (280 reviews)

Find the Best Vacation Homes in Chester Gap

Why book a vacation home in Chester Gap?

Vacation homes in Chester Gap make for a different travel experience. Your holiday home will allow you to feel at home during your visit. You’ll usually have more space, more privacy, and extra amenities not typically included with hotel stays.

How much is a vacation home in Chester Gap?

Private Chester Gap rental homes range between $79 - $591 per night. Prices change based on seasonal demand, travel dates, property location, capacity, amenities, etc.

What are the cancellation and flexibility options on Travelocity?

To cancel your vacation home, you must reach out to the individual property manager. Their contact details are available in your itinerary. For more information, head over to our customer service portal. Use the ‘free cancellation’ or ‘reserve now, pay later’ filters to find the most flexible options for your bookings.

What amenities should I look out for in a vacation home?

There are some exciting amenities available in Chester Gap vacation home rentals. You might look for Chester Gap rental houses with a private pool or free Wi-Fi. Some popular amenities also include a private hot tub, air-conditioning, laundry facilities, and a games room. 

Vacation rentals in Chester Gap offer other accommodations that may interest you. Some have resort-like amenities such as a fitness center, bar/lounge, or swimming pool.

When is the best time to rent a vacation home in Chester Gap?

You’ll typically get cheaper rates when staying during the off-season, . Prices are usually at their lowest for stays in . are the most popular months to visit.

Why book a vacation home with Travelocity?

Travel smart with Travelocity. Search over 1 million properties worldwide and access an incredible selection of holiday homes in Chester Gap. Our members save 10% or more on select hotels, and if you find a lower price, we’ll match it with our Price Match Guarantee. Get started finding Chester Gap hotels and vacation homes that best suit your stay. We also have deals for flights, and Chester Gap car rentals. You’ll save even more when you bundle your items into a Chester Gap vacation package!

How many vacation homes are available to book in Chester Gap?

There are 158 rental homes in Chester Gap. Enter your travel dates to check availability.

How do I find the best price for a vacation home in Chester Gap?

Private vacation homes vary in price, and we’ll help you get the best deal possible. Use the map feature to compare rental house prices in different neighborhoods. Also, try adjusting your dates to compare nightly rates within a similar timeframe.

Chester Gap Vacation Homes essential information

Accommodation
158 Vacation Homes
Lowest Price
$79
Highest Price
$591
Popular accommodation
Waterfront, Luxury Panoramic View, Fast Wi-Fi, Private River Access Steps Away!, 🔥 Hottub + 🐕 friendly + 🏔️ view + Skyline Dr + Wineries, Pets? YES! Hot Tub ★ Gym ★ Firepit ★ Game Room ★ Path to Winery, Escape the city to this Spacious and Clean 5BR / 3.5BA home with a Heated Pool and Spa on 8 Acres in Horse & Wine Country, Secluded River Cabin Getaway (Masten Cabin), Mountain View Bungalow in Front Royal, Sunset Mountain Cabin, On the river ~ hot tub ~ serene river views ~ fire pit, Mountain Views in Buena Vista Farm - Unit A, Waterfront on The.Shenandoah River near Luray, VA highspeed WiFi, Charming 1-bedroom house with WiFi, AC in Pleasant Rixeyville, VA on 13 acres!, Nestled Among Majestic Trees, Hilltop Hideaway is a Woodland Sanctuary