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Entire cabin

The Overlook

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Smart TV - The Overlook (Winchester)
Terrace/patio - The Overlook (Winchester)
Dining - The Overlook (Winchester)
Interior - The Overlook (Winchester)
Fridge, microwave, stovetop, dishwasher - 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
  • Washer
  • Dryer
  • Pet friendly
  • Free WiFi
  • Air conditioning

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About this property

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.

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/lanai

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)

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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 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
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 has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm 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 travelers 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 an opportunity to explore the area for outdoor excitement like hiking. Visit our Winchester travel guide
View more Cabin rentals in Winchester
Map
Winchester, VA

What's nearby

  • Museum of the Shenandoah Valley
    Museum of the Shenandoah Valley
    19 min drive - 21.3 km
  • Rock Harbor Golf Course
    18 min drive - 20.8 km
  • Winchester Little Theater
    22 min drive - 22.3 km
  • Bright Box Theater
    23 min drive - 22.7 km
  • Shenandoah University
    25 min drive - 25.0 km

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
  • Patti’s Place
    15 min drive
  • J&J Estates
    13 min drive
  • Nino’s
    16 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?

Check-out is at 11:00 AM.

Where is The Overlook located?

Situated in the mountains, this cabin is within 12 mi (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 mi (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. 8 out of 16 reviews
Rating 8 - Good. 1 out of 16 reviews
Rating 6 - Okay. 6 out of 16 reviews
Rating 4 - Poor. 1 out of 16 reviews
Rating 2 - Terrible. 0 out of 16 reviews

7.2

Cleanliness

8.8

Location

Reviews

Verified

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
Verified

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
Verified

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
Verified

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
Verified

10/10 Excellent

Brian L.

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

6/10 Okay

Kris M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 3 nights in Dec 2025
Verified

6/10 Okay

Angela S.

Liked: Check-in, communication
Just needs a little tlcThe pictures posted are when the property was freshly updated.
Stayed 2 nights in Oct 2025
Verified

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
Verified

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
Verified

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
Verified

6/10 Okay

D E.

Liked: Listing accuracy
Disliked: Cleanliness
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.
Stayed 2 nights in Oct 2025
Verified

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
Verified

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
Verified

6/10 Okay

Jayne W.

Liked: Location
Disliked: Check-in, communication
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.
Stayed 2 nights in Oct 2025
Verified

10/10 Excellent

Connie E.

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