Photo by Brian V. Rowe

Holiday Rentals in Chester Gap

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Holiday Rentals in Chester Gap

Falling Leaf Cabin - Rustic Charm With Modern Decor!

9.8 out of 10, Exceptional, (297)
"20th Anniversary weekend getaway. Perfect setting, quiet and peaceful. Luray had enough to do, food, entertainment etc. Wonderful weekend. "
Falling Leaf Cabin - Rustic Charm With Modern Decor!

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

10.0 out of 10, Exceptional, (98)
"Clean and nice place to stay to visit Shenandoah "
The price is €356
includes taxes & fees
15 Sept - 16 Sept
Lone Bear Cabin: Lv2 EV, WiFi, River Access, Mountain Views, fireplace, hot tub

"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub

10.0 out of 10, Exceptional, (335)
"we were looking for a quiet get away, loved having our 16YO boy more interested in fishing and hiking then sitting on his Xbox! We all really loved how quiet and calm it was, definitely plan on going back"
"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub

Whiskey Hill Cabin a Mountain escape in Virginia Wine country.

10.0 out of 10, Exceptional, (92)
"Very nice relaxing getaway, quite how do you spell quiet and serene location. "
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.

Dog Friendly Cabin near River on Nearly 5 acres w/Strong WiFi + Robust Amenities

9.6 out of 10, Exceptional, (60)
"Very nice property out in the wilderness. I would stay here again when I’m in the area."
The price is €285
includes taxes & fees
10 Sept - 11 Sept
Dog Friendly Cabin near River on Nearly 5 acres w/Strong WiFi + Robust Amenities

Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly

9.6 out of 10, Exceptional, (191)
"We had a great time sitting on the porch relaxing. "
Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly

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

10.0 out of 10, Exceptional, (327)
"Place was beautiful and lived up to the name Solitude. Spent our honeymoon in perfect bliss. Great location to get away. "
The price is €239
includes taxes & fees
16 Sept - 17 Sept
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.

Mountain Views, River Frontage & HotTub + Country!

9.8 out of 10, Exceptional, (31)
"Great location and beautiful property. "
Mountain Views, River Frontage & HotTub + Country!

Secluded River Cabin Getaway (Masten Cabin)

9.8 out of 10, Exceptional, (160)
"A beautiful home and property. This is a wonderful weekend getaway home. Modern and comfortable, but especially quiet!"
Secluded River Cabin Getaway (Masten Cabin)

Beautiful Private Cabin, adjacent to the National Forest

9.8 out of 10, Exceptional, (131)
"Peaceful and wonderful. Well appointed and very clean"
Beautiful Private Cabin, adjacent to the National Forest

Star view cabin-Riverfront

9.8 out of 10, Exceptional, (327)
"I absolutely love everything about staying here"
Star view cabin-Riverfront

Spectacular Views, Swimming Pool, Hot Tub, Real Log Fires, Mountain Getaway

9.4 out of 10, Exceptional, (143)
"Enjoyable. 4wd required"
Spectacular Views, Swimming Pool, Hot Tub, Real Log Fires, Mountain Getaway

Rustic Mountain Log Cabin Perched on a cliff side above the Shenandoah River

9.2 out of 10, Wonderful, (237)
"Nice cabin to relax and unwind. "
Rustic Mountain Log Cabin Perched on a cliff side above the Shenandoah River

Pine Cone Cabin at Fort Valley

10.0 out of 10, Exceptional, (189)
"All was good and perfect "
Pine Cone Cabin at Fort Valley

Lookout Cabin in the mountains, Amazing Views!

10.0 out of 10, Exceptional, (22)
"Great spot - beautiful and laid back. Brian was very flexible which is greatly appreciated. "
The price is €307
includes taxes & fees
10 Sept - 11 Sept
Lookout Cabin in the mountains, Amazing Views!

Apple Mountain Retreat

10.0 out of 10, Exceptional, (16)
"Very nice place to stay within convenient distance to Front Royal and Shenandoah Natl Park. "
The price is €204
includes taxes & fees
16 Sept - 17 Sept
Apple Mountain Retreat

Historical cottage in the town of Paris

9.8 out of 10, Exceptional, (47)
"we enjoy our stay everytime"
Historical cottage in the town of Paris

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

9.6 out of 10, Exceptional, (325)
"Loved the view and the cozy nature of the cabin. Would be happy to stay here again. "
Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo

Adorable river front cabin ,with hot tub on the River

8.4 out of 10, Very good, (6)
"Place was as advertised. Beautiful location. Short walk down to a very pretty riverfront with a fire pit in addition to the fire pit right outside the cabin. Top bunk could use a mattress upgrade :) No wifi and limited cell service which was actually nice but just be prepared. "
Adorable river front cabin ,with hot tub on the River

Newly renovated Farm cottage with Mountain views

10.0 out of 10, Exceptional, (35)
"This cottage was magical! The trails and wildlife on the property as well as the beautiful outdoor patio and fire pit to watch the sunset were so amazing! It’s centrally located to Skyline caverns, hiking trails,parks and canoeing. The wineries and breweries in the area were fantastic!We’rgrateful we code mint Cottage!"
The price is €287
includes taxes & fees
15 Sept - 16 Sept
Newly renovated Farm cottage with Mountain views
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chester Gap Hotel Reviews

Find out more about Chester Gap

Find out more about Chester Gap

Everything you need to know about Chester Gap holiday rentals

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

Chester Gap holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chester Gap holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chester Gap holiday rentals we have selected for you start as low as €204 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chester Gap rentals

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

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 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.