Photo by Brian V. Rowe

Search Chester Gap Cottages

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    one key icon
    Treat yourself
    Save instantly and earn perks with One Key
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 37 Cottages in Chester Gap with updated reviews, rates, and availability.

Historical cottage in the town of Paris
10.0 out of 10, Exceptional, (21)
"Cozy, small house that is close to the mountains & hiking. Sky Meadows State Park is very close; the ridge above includes the AT. Civilization vis a vis Middleburg, Marshall, and Purcellville are all within a pleasant, half-hour drive. Eating in the screened-in porch was great!"
The price is $169
$304 total
includes taxes & fees
Jun 17 - Jun 18
Historical cottage in the town of Paris
Alpacas & The Stars at night. Private Retreat. Fun & Peace
10.0 out of 10, Exceptional, (42)
"Very nice place to stay that is generally convenient to several towns and eating places. Hosts were very nice and helpful and we enjoyed getting to know them and their animals. Look forward to returning."
Alpacas & The Stars at night. Private Retreat. Fun & Peace
Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi
9.8 out of 10, Exceptional, (16)
"Came for my daughters wedding and this place was amazing. Awesome place to relax, firepit to chat around, outside table to enjoy a meal was amazing, comfy beds. Just awesome and amazing stay!!"
The price is $458
$844 total
includes taxes & fees
Jun 30 - Jul 1
Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi
Comfortable, one level cottage, within a 2000' hike to the Shenandoah River.
10.0 out of 10, Exceptional, (1)
"Convenient to any attractions, restaurants and things to do. The cottage was very comfortable. We all enjoyed it. Hope to book again."
Comfortable, one level cottage, within a 2000' hike to the Shenandoah River.
Hunt Country cottage in Upperville!
9.6 out of 10, Exceptional, (4)
"absolutely perfect house - close to upperville show grounds and host was awesome for communication"
Hunt Country cottage in Upperville!
Cottage Getaway for Two with Private Hot Tub
9.8 out of 10, Exceptional, (48)
"Your perfect escape from the city - clean, cozy, with a cute electric fireplace, and a Jacuzzi. Check in was easy and the farm is amazing! Highly recommend and we will be back."
Cottage Getaway for Two with Private Hot Tub
Romantic Cottage with Private Hot Tub
9.8 out of 10, Exceptional, (64)
"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
Homey Luray Cabin w/ Fire Pit & Deck!
3.5 star property
Homey Luray Cabin w/ Fire Pit & Deck!
Cozy Virginia Escape w/ Deck, Grill & Fire Pit!
2.0 star property
Cozy Virginia Escape w/ Deck, Grill & Fire Pit!
Chic Front Royal Retreat Near Shenandoah River!
3.0 star property
10.0 out of 10, Exceptional, (3)
"This was the perfect place for us to stay while visiting family. It was homey and comfortable. Owners were quick to respond to any questions we had. "
Chic Front Royal Retreat Near Shenandoah River!
Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
9.6 out of 10, Exceptional, (17)
"Nice place, comfortable bed. Close to hiking in the area."
The price is $165
$240 total
includes taxes & fees
Jun 17 - Jun 18
Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
Charming Rileyville Cottage on River w/ Fire Pit!
Charming Rileyville Cottage on River w/ Fire Pit!
Weekend getaway short distance from DC/Northern Virginia
10.0 out of 10, Exceptional, (79)
"Everything about this place was just perfect! It is truly a hidden gem and we really had a memorable stay here. The cottage is tastefully decorated and super clean, with beautiful views from every window. We had a welcome package waiting for us (wine/cheese/chocolates) and the owner gave the kids mini pumpkins as we were checking out. Very kind, thoughtful owner with excellent communication. Will definitely be coming back here again."
Weekend getaway short distance from DC/Northern Virginia
E & L's Mountain View Cottage. Front porch and deck. 7 miles N of Luray.
10.0 out of 10, Exceptional, (5)
"The cottage is facing a mountain range with spectacular sunset view and morning mist view. Cows, birds, deers, and squirrels are the only neighbors. The cottage is clean and new. The bed is comfy. We woke up early and hiked in the Shenandoah national park. Came back around 5. Enjoyed our dinner outside. Spent the rest of evening doing nothing but staring at the nature outside. It was wonderful. We will definitely come back."
E & L's Mountain View Cottage. Front porch and deck. 7 miles N of Luray.
Front Royal Retreat ~ 1 Mi to National Park!
3.5 star property
Front Royal Retreat ~ 1 Mi to National Park!
Cozy Cottage / Writers Retreat . Nestled in the woods . Private
Cozy Cottage / Writers Retreat . Nestled in the woods . Private
Beautiful Cottage on a Lavender Farm in the Blue Ridge Mountains
10.0 out of 10, Exceptional, (29)
"We stayed for a wedding nearby and we loved the house. The furniture and decor has been curated beautifully and the fairy theme was a magical touch, which our 2 yr old really enjoyed. Little Washington and Sperryville are idyllic little towns nearby and there is beautiful country all around. We enjoyed petting the horses next door and watching the fireflies in the evening. Would stay here again for sure."
Beautiful Cottage on a Lavender Farm in the Blue Ridge Mountains
Sunny Front Royal Vacation Rental w/ Hot Tub!
3.5 star property
Sunny Front Royal Vacation Rental w/ Hot Tub!
New! Modern family cottage oasis with fast WiFi and pet friendly.
9.0 out of 10, Wonderful, (8)
"We got to the home which sits on the side of a mountain the driveway is super steep. The pinpad door locks were really hard to open , once inside, the home smelled like wet dogs and had stains on the sofa and other furniture. The screen on the tv in the living room was covered with children’s handprints there was dog hair all around on the floor. The video arcade game’s downstairs had dried up cheese on them .. just nasty! The owner was very responsive and did refund my money back once I let him...
New! Modern family cottage oasis with fast WiFi and pet friendly.
Spacious Mountain Home: Family, Pet & WFH Friendly
3.5 star property
10.0 out of 10, Exceptional, (1)
"The property was exactly as advertised -- a spacious and well-equipped cottage on a working farm. This is a beautiful part of Virginia with plenty to do if you enjoy the outdoors. And a special bonus is the excellent restaurant, The Blue Door, in nearby Flint Hill. "
Spacious Mountain Home: Family, Pet & WFH Friendly
Don't see what you're looking for?
See all available properties in Chester Gap
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.

Other property types in Chester Gap

Star view cabin-Riverfront
9.8 out of 10, Exceptional, (278)
"I have to say the last two reviews made us a bit nervous but those people must have been self-proclaimed critics because we had a truly exceptional experience. Everything was perfect - the hot tub, the river access point, the fire pit(s). A dream come true. We will absolutely be back. Nina’s friendliness and attention to detail made this truly a one of a kind experience. Can’t wait to bring our whole family back!!"
Star view cabin-Riverfront
Mountain Views, River Frontage & HotTub + Country!
10.0 out of 10, Exceptional, (13)
"Took my kids 13 11 and 7 they had a great time at river and cooking out and s'mores over the fire and hot tub was a plus"
Mountain Views, River Frontage & HotTub + Country!
Bear Valley- Riverfront with hot tub!
9.8 out of 10, Exceptional, (101)
"We had a great time spending a long holiday weekend here. It was relaxing and peaceful and perfect for what we needed. However I would say the place needs some work and the owner should put some money back into it. The directv barely works and the internet is non existent but we made due without it. Cosmetically it needs some love. If it got some love we’d probably visit frequently however next time we’ll probably look for a more put together place. Location is fantastic so if you’re cool with...
Bear Valley- Riverfront with 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.

Chester Gap Cottages information

Number of reviews
335
Accommodation
37 Cottages
Lowest Price
$165
Highest Price
$458