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Entire cabin

The Overlook

Cabin in Winchester with kitchen

Photo gallery for The Overlook

Smart TV - The Overlook (Winchester)
Interior - The Overlook (Winchester)
Property grounds - The Overlook (Winchester)
Fridge, microwave, stovetop, dishwasher - The Overlook (Winchester)
Dining - The Overlook (Winchester)
Nestled in the Shenandoah Mountains, The Overlook offers a serene retreat with 360-degree views. Relax by the fire pit at night, explore nearby trails and wineries, and unwind in this fully-stocked home featuring fast WiFi speed, a spacious living room, and three bedrooms upstairs plus a finished basement.

Reviews

8.0 out of 10
Very good

Entire cabin

4 bedrooms2 bathroomsSleeps 11

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
  • Free Wi-Fi
  • Air-conditioning

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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

Cabin in Winchester with kitchen
This smoke-free cabin features laundry facilities. The cabin has 4 bedrooms and offers free WiFi and a sofa bed. Guests will find a kitchen with a fridge, a stovetop, a microwave and a dishwasher.
Air-conditioned accommodation at this cabin offers coffee/tea makers. This accommodation is furnished with sofa beds and dining tables. Kitchens offer fridges, stovetops, microwaves and kitchenware and utensils. Bathrooms include baths or showers.

Guests can surf the web using complimentary wireless Internet access. Smart televisions are featured in guestrooms.

Property amenities

Internet

  • Available in the cabin: Free WiFi

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Microwave
  • Refrigerator
  • Spices
  • 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/lanai

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning

Pets

  • Pet friendly
  • Welcoming dogs only
  • One pet total

Suitability/Accessibility

  • Smoke-free property

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)

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Property grounds
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  • Washing machine
  • Dryer
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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
Information provided by the property may be translated using automated translation tools

Access methods

Access code

Pets

Pets are allowed
Service animals are welcome, and are exempt from fees
Welcoming dogs only
1 total pets
Note from host: We only allow up to 1 dog

Children and extra beds

Children are welcome

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
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
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
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

About the area

Located in Winchester, this cabin is in the mountains. Museum of the Shenandoah Valley and Winchester Little Theater are cultural highlights, and travellers looking to shop may want to visit Stonewall Plaza and Apple Valley Square Shopping Center. Shenandoah Valley Discovery Museum and Nalls Farm Market are also worth visiting. Take the opportunity to explore the area for outdoor excitement like hiking.
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Map
Winchester, VA

What's nearby

  • Rock Harbor Golf Course - 17 min drive - 18.8 km
  • ValleyHealth Winchester Medical Center - 17 min drive - 18.2 km
  • Museum of the Shenandoah Valley - 18 min drive - 19.3 km
  • Shenandoah Valley Discovery Museum - 20 min drive - 20.6 km
  • Shenandoah University - 22 min drive - 23.0 km

Getting around

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

Restaurants

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

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 ValleyHealth Winchester Medical Center, Museum of the Shenandoah Valley and Winchester Little Theater. Abrams Creek Wetlands Preserve and Handley Regional Library are also within 12 miles (20 km).

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The Overlook Reviews

Reviews

Very good

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens in a new window
Rating 10 - Excellent. 7 out of 15 reviews
Rating 8 - Good. 1 out of 15 reviews
Rating 6 - Okay. 6 out of 15 reviews
Rating 4 - Poor. 1 out of 15 reviews
Rating 2 - Terrible. 0 out of 15 reviews

7.0

Cleanliness

8.8

Location

Reviews

10/10 Excellent

Haylee L.

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

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

Lori G.

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

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

6/10 Okay

Megan J.

Liked: Communication, location
Disliked: Cleanliness, check-in

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

10/10 Excellent

Caroline B.

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

10/10 Excellent

Brian L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very comfortable, great location.
Stayed 4 nights in Jun 2025

10/10 Excellent

Brian L.

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

Peaceful and relaxing

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

10/10 Excellent

Courtney R.

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

Amazing

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

8/10 Good

Kim B.

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

6/10 Okay

Brenda L.

Liked: Location
Disliked: Check-in, communication, listing accuracy

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

4/10 Poor

Sharon D.

Liked: Location
Disliked: Cleanliness, check-in, communication, listing accuracy
The write up for this property is mostly fictional. Yes, it's an adorable cabin in the woods with breathtaking views with plenty of room to accommodate 11 people, but don't be fooled, there are very little amenities so plan on bringing literally everything, especially kitchen cooking supplies. The fire pit or what once was one, is located in the driveway with a couple broken chairs lying about. The photos of the property must have been taken years ago because the outside needs quite a bit of maintenance. Bathroom faucet is broken, lots outlets don't work, 2 TVs but no remotes, board games but all have missing pieces and you may or may not walk into a dirty house & have to do laundry from previous tenants plus pick up all the garbage scattered about, depends on if owner remembers to call cleaning company. We did have an amazing time and would recommend it but its also a renter-beware kinda situation- pack heavy!
Stayed 2 nights in Oct 2025

10/10 Excellent

Connie E.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 4 nights in Oct 2023