Photo by Brian V. Rowe

Book a Chester Gap Cottage

Start date: Check-in selected.
To Date
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
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
3 Oct - 5 Oct
In one month
17 Oct - 19 Oct
In two months
14 Nov - 16 Nov
In three months
12 Dec - 14 Dec

Featured Cottages in Chester Gap

Our top choices for Chester Gap cottages

Hunt Country cottage in Upperville!
Exterior

Hunt Country cottage in Upperville!

10.0 out of 10, Exceptional, (21)
"Beautiful cottage!! Incredibly comfortable! Loved it!!"
Hunt Country cottage in Upperville!
Historical cottage in the town of Paris
Exterior

Historical cottage in the town of Paris

9.8 out of 10, Exceptional, (47)
"This is a nice home near sky meadow park. A great place to see the stars... Very close to DC. "
Historical cottage in the town of Paris
Secluded Cottage on 10 Acres. Close to Shen. Natl. Park and Luray Caverns
Exterior

Secluded Cottage on 10 Acres. Close to Shen. Natl. Park and Luray Caverns

9.6 out of 10, Exceptional, (217)
"After several weeks of camping in the cold and rain, we looked forward to a quiet and comfortable stay and we found it on Old Mine Road."
Secluded Cottage on 10 Acres. Close to Shen. Natl. Park and Luray Caverns
The Vue - Mountain top hot tub overlooking the Shenandoah River
Property grounds

The Vue - Mountain top hot tub overlooking the Shenandoah River

2.0 star property
9.8 out of 10, Exceptional, (6)
"Love the view and beautiful appointed decor throughout the home…"
The price is NZ$607
includes taxes & fees
22 Sept - 23 Sept
The Vue - Mountain top hot tub overlooking the Shenandoah River
Weekend getaway short distance from DC/Northern Virginia
Property grounds

Weekend getaway short distance from DC/Northern Virginia

10.0 out of 10, Exceptional, (87)
"This place was cozy and welcoming, exactly what we were looking for on a weekend away."
Weekend getaway short distance from DC/Northern Virginia
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
Outdoor spa tub

Riverfront! Shenandoah River! Sleeps 4! New Hot Tub

9.8 out of 10, Exceptional, (13)
"What a beautiful little house!! And can’t beat the magnificent view of the river! "
The price is NZ$641
includes taxes & fees
22 Sept - 23 Sept
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi
Outdoor spa tub

Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi

9.8 out of 10, Exceptional, (28)
"So much to do in the area, cute little cottage, very clean and comfortable "
Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi
'black Walnut Cabin' on 2 Acres in Luray!
House (2 Bedrooms) | Interior

'black Walnut Cabin' on 2 Acres in Luray!

3.0 star property
'black Walnut Cabin' on 2 Acres in Luray!
Chic Front Royal Retreat Near Shenandoah River!
House (2 Bedrooms) | Interior

Chic Front Royal Retreat Near Shenandoah River!

3.0 star property
10.0 out of 10, Exceptional, (5)
"Nice place near skyline drive"
Chic Front Royal Retreat Near Shenandoah River!
Alpacas, Rolling Hills & Starry Nights – Peaceful 3-Bedroom Farm Retreat
Exterior

Alpacas, Rolling Hills & Starry Nights – Peaceful 3-Bedroom Farm Retreat

10.0 out of 10, Exceptional, (45)
"Incredibly comfortable and peaceful. Surrounded by animals of all kinds and great hiking on the property."
Alpacas, Rolling Hills & Starry Nights – Peaceful 3-Bedroom Farm Retreat
Modern Mountain Retreat w/ Deck + Hot Tub!
House (3 Bedrooms) | Interior

Modern Mountain Retreat w/ Deck + Hot Tub!

3.0 star property
Modern Mountain Retreat w/ Deck + Hot Tub!
Mountain Town Adventures Home w/ Fire Pit!
House (3 Bedrooms) | Interior

Mountain Town Adventures Home w/ Fire Pit!

3.0 star property
10.0 out of 10, Exceptional, (1)
"It was fantastic"
Mountain Town Adventures Home w/ Fire Pit!
Romantic Cottage with Private Hot Tub
Exterior

Romantic Cottage with Private Hot Tub

9.8 out of 10, Exceptional, (67)
"Stayed here as we planned to hike old rag and everything about this place is great. Will definitely plan to return for future stay !"
Romantic Cottage with Private Hot Tub
Country Elegance overlooking the Shenandoah River
Outdoor spa tub

Country Elegance overlooking the Shenandoah River

10.0 out of 10, Exceptional, (105)
"It was so relaxing & beautiful! We loved the views from every room , even the bathroom upstairs! "
Country Elegance overlooking the Shenandoah River
Front Royal Hilltop Cabin w/ Panoramic Views!
House (4 Bedrooms) | Interior

Front Royal Hilltop Cabin w/ Panoramic Views!

3.0 star property
Front Royal Hilltop Cabin w/ Panoramic Views!
Sunny Front Royal Vacation Rental w/ Hot Tub!
House (1 Bedroom) | Interior

Sunny Front Royal Vacation Rental w/ Hot Tub!

3.0 star property
Sunny Front Royal Vacation Rental w/ Hot Tub!
Home w/ Hot Tub Near Shenandoah Nat'l Park!
House (3 Bedrooms) | Interior

Home w/ Hot Tub Near Shenandoah Nat'l Park!

3.0 star property
Home w/ Hot Tub Near Shenandoah Nat'l Park!
Front Royal Retreat ~ 1 Mi to National Park!
House (3 Bedrooms) | Interior

Front Royal Retreat ~ 1 Mi to National Park!

3.0 star property
Front Royal Retreat ~ 1 Mi to National Park!
Spectacular Cottage with Shenandoah River Views
Terrace/patio

Spectacular Cottage with Shenandoah River Views

10.0 out of 10, Exceptional, (208)
"We loved our stay here. Came here to escape DC. Very easy to get to. Still close to civilization but still feels remote on the property. 20 minutes from Skyline Drive."
Spectacular Cottage with Shenandoah River Views
Cottage Getaway for Two with Private Hot Tub
Exterior

Cottage Getaway for Two with Private Hot Tub

9.8 out of 10, Exceptional, (50)
"We booked this cabin as a last minute trip to hike old rag and also bring our pup along and it was more than I could've imagined!! Have stayed in this area before and this place knocked all others out of the park we will definitely be back!"
Cottage Getaway for Two with Private Hot Tub
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chester Gap Hotel Reviews

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

10/10 Excellent
"Excellent staff every time we stay!!"
Leslie 5-night trip
Posted 3 days ago
Comfort Inn & Suites Winchester

Find out more about Chester Gap

Find out more about Chester Gap

Chester Gap Cottages information

Number of reviews
831
Accommodation
51 Cottages
Lowest Price
NZ$607
Highest Price
NZ$641

Explore a world of travel with Expedia

Explore a world of travel with Expedia