The Overlook

Winchester, Virginia
$218 avg/night Minimum Stay 2 Nights
Bed 4

Bed

Bath 2

Bath

Home Cabin

Property Type

Sleep 11

Max Sleeps

Night 2 nights

Min Stay

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.

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    1 Total Pets Pet Friendly Welcoming Dogs Only
  • DINING

    Dining Table
  • SAFETY

    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)
  • BEDROOM

    4 Bedrooms Sofa Bed
  • KITCHEN

    Blender Coffee/tea Maker Cookware/dishes/utensils Dishwasher Microwave Refrigerator Spices Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • INTERNET

    Free WiFi
  • OUTDOORS

    Firepit Outdoor Furniture Porch Or Lanai
  • BATHROOMS

    2 Bathrooms Bathtub Or Shower Soap
  • THINGS TO DO

    Hiking Nearby
  • ENTERTAINMENT

    Games Smart TV
  • LIVING SPACES

    Living Room
  • CLIMATE CONTROL

    Air Conditioning
  • LOCATION HIGHLIGHTS

    In The Mountains
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 11:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 11

Map Map

School District Rates & Availability

Review Review

  • Kris M.

    Submitted Dec 30, 2025

    Stayed Dec 27, 2025

    Lovely home with spectacular views! As some people have mentioned there are lots of ladybugs, the toaster is broken and the upstairs shower doesn’t drain properly. That being said, we truly enjoyed our stay. Plenty of towels and blankets.

  • Jayne W.

    Submitted Nov 11, 2025

    Stayed Oct 10, 2025

    I typically leave only 5 stars reviews (I know it affects future renting). However, this stay only gets a generous 3 due to communication from Abby.All information to get inside referred to a lock box. The door had a Schlage KEYPAD and there was a lockbox affixed to the side of the house. Neither was working with the code we were given. Because it was dark/cold (w/ small children), we tried to call Abby. 10 mins later, as a response from her, we received a video on YouTube- how to open a masterlock box (the one on the house, not door itself). We told her it wasn’t working, and we’d like her to call, and got a response that she’d call in 5 mins “if we couldn’t figure it out.” At the time she said she’d call she didn’t, so a few minutes later I called her, went straight to VM. Then I received a call from a man (co-owner?) and at the exact same time suddenly the door worked. Over 25 minutes we were calling/texting Abby pictures/videos to show nothing was working and THEN she told us to NOT use the master lockbox on the house, only the Schlage door keypad (despite the tutorial she sent on the masterlock box which is what was on the side of the house).Abby was snarky in her messages. She didn’t call when she said she would and we ultimately never locked the door again while we were there. The price is decent, but just beware the kitchen is bare (no coffee, 15 mins from town) and one of the bathroom doors was coming off hinges. I’d look for somewhere else to stay next time.

  • D E.

    Submitted Oct 27, 2025

    Stayed Oct 24, 2025

    Alas, the property had not been cleaned when we arrived: dirty sheets, debris on the floor, no clean towels. We complained, and a cleaning crew arrived the next morning. But they only cleaned the floors (we had already run two washing machine cycles) and the bathrooms. Kitchen utensils remained grimy, piles of dirty towels from he previous renters were left untouched, and most of the plates and glassware weren't cleaned either. We received half of our money back, which is fair. But we would not recommend this place unless it is professionally cleaned, top to bottom, and all sheets, towels, blankets are replaced. We also noted a missing remote control for the large TV, an unhinged cabinet that needs to be fixed, and no kettle in the kitchen.

  • Angela S.

    Submitted Oct 19, 2025

    Stayed Oct 17, 2025

    Just needs a little tlcThe pictures posted are when the property was freshly updated.

  • Sharon D.

    Submitted Oct 16, 2025

    Stayed Oct 14, 2025

    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!

  • Brian L.

    Submitted Jun 7, 2025

    Stayed Jun 2, 2025

    Very comfortable, great location.

  • Brian L.

    Submitted Jun 1, 2025

    Stayed May 27, 2025

    Very nice. Quiet neighborhood. Great location.

  • Megan J.

    Submitted Dec 1, 2024

    Stayed Nov 24, 2024

    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.

  • Brenda L.

    Submitted Oct 15, 2024

    Stayed Sep 5, 2024

    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.

  • Lori G.

    Submitted Aug 26, 2024

    Stayed Aug 22, 2024

    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.

  • Haylee L.

    Submitted Jul 14, 2024

    Stayed Jul 11, 2024

    We had a mini family surprise reunion for my grandparents the house was great location and met all our families needs

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Total

Includes taxes and fees
$218+
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