The Overlook

4 bedrooms2 bathroomsSleeps 11

Popular amenities

Pet-friendly

Free WiFi

Air conditioning

Washer

Dryer

Kitchen

Enjoy the area

Winchester, VA

Winchester Medical Center20 min drive
Museum of the Shenandoah Valley21 min drive
Shenandoah University25 min drive
Washington, DC (IAD-Washington Dulles Intl.)78 min drive

Rooms & beds

4 bedrooms (sleeps 11)

Bedroom 1

1 Queen Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 Double Bed

Bedroom 4

1 Single Bed, 1 Single Bunk Bed and 1 Double Sofa Bed

2 bathrooms

Bathroom 1

Bathtub or shower · Toilet

Bathroom 2

Bathtub or shower · Toilet

Spaces

Porch or lanai

Kitchen

About this property

Cozy up and get away to our tranquil A framed Cabin we affectionately call The Overlook; where you'll enjoy a 360-degree view of the Shenandoah Mountains. Soak in our breathtaking views no matter the season and escape to the peace and quiet our cabin provides.
Relax by the fire at night, hike the beautiful trails nearby, enjoy our famous wineries/breweries, and rest easy in our fully stocked home equipped with everything you could need to get the vacation you deserve!
The space
Our cabin is fully stocked home with everything you'll need for a comfortable stay. Enjoy our fast wifi speed and spacious living room and porch to enjoy the breathtaking scenery around you. Wake up in the morning to a stunning sunrise view of the mountains and feel free to bring lots of friends and family with you as our home has not only three bedrooms upstairs, but a fully finished basement with sleeping arrangements for up to 5 guests!
Don't worry about bringing your supplies from home because we provide it all! Our kitchen is equipped with all cooking supplies, dinnerware, spices, a coffee maker, and more! Enjoy a hot bath or shower fully stocked with soaps and bathroom necessities. Cozy up at night and sit by the fire pit with a glass of wine or lounge inside with reading materials or board games we provide!
Guest access
The Overlook is nestled on the mountain overlooking the Shenandoah Valley with 100+ mile views. Guests have access to the whole home with no shared spaces. This is the only house on that section of the road. The top of the driveway can be a little tricky, but there is plenty of parking for guests. In winter conditions you may need AWD or 4WD. When you book you will receive a personal door code that you can enter on your arrival.
Other things to note
Our stay allows you to be removed from the hustle and bustle, but be close to enjoying the local wineries, and breweries. You are 20min from historic downtown Winchester VA. Please make sure you keep your trash picked up outside and the trash can locked as we have been known to be visited by bears on several occasions. Please also do not use the fire pits if it is windy as you could start a forest fire.

Property manager

Abby Joy

Amenities

Kitchen

Washer

Dryer

Pet-friendly

Free WiFi

Air conditioning

Kitchen

Pet-friendly

Free WiFi

Air conditioning

House Rules

Check in after 4:00 PM

Minimum age to rent: 21

Check out before 11:00 AM

Children

Children allowed: ages 0–17

Events

No events allowed

Pets

Pets allowed: dogs (limit 1 total)

We only allow up to 1 dog

Smoking

Smoking is not permitted

Damage and incidentals

You will be responsible for any damage to the rental property caused by you or your party during your stay.

Important information

You need to know

Extra-person charges may apply and vary depending on property policy

Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges

Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed

On-site parties or group events are strictly prohibited

Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip

Host has not indicated whether there is a smoke detector on the property

About the area

Winchester

Located in Winchester, this cabin is in the mountains. George Washington's Office and Stonewall Jackson's Headquarters are local landmarks, and the area's natural beauty can be seen at George Washington National Forest and Jim Barnett Park. Shenandoah Valley Discovery Museum and Nalls Farm Market are also worth visiting. Take the opportunity to explore the area for outdoor excitement like hiking/biking trails.

Winchester, VA

What's nearby

Winchester Medical Center - 20 min drive
Museum of the Shenandoah Valley - 21 min drive
Rock Harbor Golf Course - 24 min drive
Shenandoah University - 25 min drive
Apple Blossom Mall - 26 min drive

Getting around

Martinsburg, WV (MRB-Eastern West Virginia Regional) - 43 min drive

Restaurants

Hayfield Family Restaurant - 13 min drive
Jo Gails Family Restaurant - 14 min drive
Anthony's Pizza IV - 16 min drive
Sheila's Sweets - 15 min drive
Jogail's Country Cookin - 14 min drive

Frequently asked questions

Is The Overlook pet-friendly?

Yes, this property allows dogs (limit 1 total).

What time is check-in at The Overlook?

Check-in begins at 4:00 PM.

What time is check-out at The Overlook?

Checkout is at 11:00 AM.

Where is The Overlook located?

Situated in the mountains, this cabin is within 12 miles (20 km) of Winchester Medical Center, Museum of the Shenandoah Valley and Winchester Little Theater. Handley Regional Library and Bright Box Theater are also within 12 miles (20 km).

9.4

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.

Learn more

8.0/10

Cleanliness

10/10

Check-in

10/10

Communication

8.8/10

Location

9.4/10

Listing accuracy

10/10 Excellent

Courtney R.

22 January 2024

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing

I loved everything about this place. Very very nice.

Stayed 2 nights in Jan 2024

10/10 Excellent

Caroline B.

24 September 2023

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect for us.

We stayed at Abby’s house with 2 other couples and between 3 families we had 4 kids under 2, the house worked out wonderfully. A pack n play fit in every room and the basement was massive. The temperature in the basement is ideal for people that like sleeping on the cooler side and upstairs is definitely quite a bit warmer but it wasn’t too warm for anyone. Overall, the house was perfect for our group and we would consider staying again if we find ourselves in Winchester. The roads were steep and lots of turns but all paved so very doable. We approached the house from different roads each time but we were able to easily pull into the driveway or back in if we didn’t want to do an 8 point turn on the road. Abby was very responsive before and during our trip. My only suggestion would be to bring your own corkscrew!

Stayed 3 nights in Sep 2023

8/10 Good

Kim B.

22 June 2023

Liked: Check-in, communication, listing accuracy

Charming-Well Decorated

The house was very charming...the roads were a bit of an adventure...mother nature's roller coaster for sure. Very nicely decorated. There was a few of nature's creatures(a house mouse and some indoor bugs) but when in a forest-wooded area I guess that comes with the territory a bit but would definitely been a better stay without them. The hosts were very accommodating and easy to contact. Overall a nicely updated cottage with great owners...only complaint was the mouse and bugs.

Stayed 2 nights in Jun 2023