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The Overlook

Cabin in Winchester with kitchen

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Fridge, microwave, stovetop, dishwasher
Smart TV
Exterior
Interior
Dining

Reviews

9.0 out of 10
Wonderful

Entire cabin

4 bedrooms2 bathroomsSleeps 11

Popular amenities

  • Dryer
  • Washer
  • Pet friendly
  • Kitchen
  • Air conditioning
  • Free WiFi

Explore the area

View in a map
Winchester, VA
  • Place, Winchester Medical Center
    ‪20 min drive‬
  • Place, Museum of the Shenandoah Valley
    ‪21 min drive‬
  • Place, Shenandoah University
    ‪26 min drive‬
  • Airport, Martinsburg, WV (MRB-Eastern West Virginia Regional)
    ‪47 min drive‬

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About the neighborhood

Winchester

This cabin places you 10.5 mi (16.9 km) from Winchester Medical Center and 11.1 mi (17.8 km) from Museum of the Shenandoah Valley. The cabin includes a kitchen, a sofa bed, and a refrigerator.
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What's nearby

  • Winchester Medical Center - 20 min drive - 11.3 miles
  • Rock Harbor Golf Course - 21 min drive - 11.7 miles
  • Museum of the Shenandoah Valley - 21 min drive - 12.0 miles
  • Shenandoah University - 26 min drive - 14.1 miles
  • Apple Blossom Mall - 27 min drive - 15.2 miles

Getting around

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

Restaurants

  • ‪Nino’s - ‬16 min drive
  • ‪Hayfield Family Restaurant - ‬13 min drive
  • ‪Patti’s Place - ‬15 min drive
  • ‪Jo Gails Family Restaurant - ‬14 min drive
  • ‪Hot Tub Room at The Gritty - ‬16 min walk

About this property

Entire place

You'll have the entire cabin to yourself and will only share it with other guests in your party.

The Overlook

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.
The cabin is air-conditioned and features a kitchen and 2 bathrooms, and there's space to spread out with 4 bedrooms. Guests can enjoy a Smart TV and stay connected with free WiFi. Other standard amenities include a washing machine, a sofa bed, and a coffee maker.

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Property amenities

Internet

  • Available in the cabin: Free WiFi

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Microwave
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 4 bedrooms
  • Sofa bed

Bathroom

  • 2 bathrooms
  • Bathtub or shower
  • Soap

Living spaces

  • Dining table
  • Living room

Entertainment

  • Games
  • Smart TV

Outdoor areas

  • Firepit
  • Outdoor furniture
  • Porch

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning

Pets

  • Pet friendly
  • Welcoming dogs only
  • One pet total

Suitability/Accessibility

  • Smoking not allowed

Location highlights

  • In the mountains

Things to do

  • Hiking nearby

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector not reported (host has not indicated whether there is a smoke detector on the property)

Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age: 21

Check-out

Check-out before 11:00 AM

Special check-in instructions

Guests will receive an access code
You will receive an email from the host with check-in and check-out instructions

Access methods

Access code

Pets

  • This property welcomes pets
  • Dogs only
  • 1 total pets
  • Service animals exempt from fees
  • Note from host: We only allow up to 1 dog

Children and extra beds

Children allowed: ages 0-17

Events

No events allowed

Smoking

Smoking is not permitted

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
Onsite 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
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
  • Check-in: 4:00 PM
  • Check-out: 11:00 AM
  • Minimum check-in age: 21

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a private host, not a professional engaged in trade or business.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.

Frequently asked questions

Will I be able to park at this cabin?

No, this cabin doesn't offer parking.

Is this cabin associated with a casino?

No, this cabin is not connected to a casino.

Is there an indoor pool at this cabin?

No, there is no indoor pool at this cabin.

Is The Overlook a good place to stay for couples?

Couples staying at this cabin will appreciate amenities like a kitchen and a smart TV as well as a firepit.

Are there hot tubs at The Overlook?

No, this cabin doesn't have a spa tub.

Does this cabin offer breakfast?

No, this cabin doesn't offer breakfast.

Does this cabin allow pets to stay free of charge?

Although dogs can't stay for free, they are welcome at this cabin.

Does this cabin have connecting rooms?

No, this cabin doesn't feature connecting guestrooms.

What is the closest airport to this cabin?

The closest major airport to this cabin is Martinsburg, WV (MRB-Eastern West Virginia Regional), which is about 23.6 mi away.

Are there rooms with balconies at The Overlook?

Yes, every cabin at The Overlook comes with a porch.

Reviews

The Overlook Reviews

9.0

Wonderful

8.0/10

Cleanliness
Rating 10 - Excellent. 7 out of 10 reviews
Rating 8 - Good. 1 out of 10 reviews
Rating 6 - Okay. 2 out of 10 reviews
Rating 4 - Poor. 0 out of 10 reviews
Rating 2 - Terrible. 0 out of 10 reviews

Reviews

10/10 Excellent

Brian L.

Liked: Cleanliness
Very comfortable, great location.
Stayed 4 nights in Jun 2025

10/10 Excellent

Brian L.

Liked: Cleanliness

Peaceful and relaxing

Very nice. Quiet neighborhood. Great location.
Stayed 3 nights in May 2025

6/10 Okay

Megan J.

Disliked: Cleanliness

Not clean and welcoming

The beds didn’t have sheets, the house was dirty, tub still had dirty water. Mouse poop in the closet’s downstairs. The location was good the size was great with a large family. The house could have been more welcoming to guest tired arriving late and wanting to get into a clean bed and rest. Host refunded cleaning fee but wouldn’t refund stay so we could go someplace else.The house has a lot of potential with more care and attention to detail.
Stayed 4 nights in Nov 2024

6/10 Okay

Brenda L.

slightly disappointed at maintenance but am coming back

cute cabin not as advertised, no contact with management and we were given the wrong code for the door, no lights in basement, wasn't fully cleaned, we had to provide our own laundry detergent as well as batteries for the remotes that still remained, there were still dirty sheets in the closet from the previous occupants when we arrived.
Stayed 3 nights in Sep 2024

10/10 Excellent

Lori G.

Liked: Cleanliness

The location was perfect for the event we were attending .

Hello, The property was very clean. My (older) mother is a stickler for clean and she was pleasantly surprised. The outlet in the upstairs bathroom did not work. We tried the GFCI and no luck. Not a problem as the bedrooms had working outlets. We struggled with the front door keypad. Otherwise, had a wonderful stay.
Stayed 3 nights in Aug 2024

10/10 Excellent

Connie E.

Liked: Cleanliness
Stayed 4 nights in Oct 2023

10/10 Excellent

Haylee L.

Liked: Cleanliness

Weekend cabin

We had a mini family surprise reunion for my grandparents the house was great location and met all our families needs
Stayed 3 nights in Jul 2024

10/10 Excellent

Courtney R.

Liked: Cleanliness

Amazing

I loved everything about this place. Very very nice.
Stayed 2 nights in Jan 2024

10/10 Excellent

Caroline B.

Liked: Cleanliness

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.

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