Title: The Overlook - Latest Reviews, Deals & Photos 2026 - Expedia.ca [See all properties](http://www.expedia.ca/Hotel-Search?regionId=&selected=89816618&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire cabin # The Overlook Cabin in Winchester with kitchen ## Photo gallery for The Overlook ![Smart TV - The Overlook (Winchester)](https://images.trvl-media.com/lodging/90000000/89820000/89816700/89816618/d1ae7905.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Dining - The Overlook (Winchester)](https://images.trvl-media.com/lodging/90000000/89820000/89816700/89816618/be519012.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Fridge, microwave, stovetop, dishwasher - The Overlook (Winchester)](https://images.trvl-media.com/lodging/90000000/89820000/89816700/89816618/641d9f75.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Property grounds - The Overlook (Winchester)](https://images.trvl-media.com/lodging/90000000/89820000/89816700/89816618/a8acdcf4.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Interior - The Overlook (Winchester)](https://images.trvl-media.com/lodging/90000000/89820000/89816700/89816618/fb57ee0e.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Location - Amenities - Policies 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 Very good ### Entire cabin 4 bedrooms2 bathroomsSleeps 11 ## Popular amenities - Kitchen - Washer - Dryer - Pet friendly - Free WiFi - Air conditioning ## Add dates for prices Check-in Check-out Travellers ## 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. ## 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) ## Similar properties ![Property grounds](https://images.trvl-media.com/lodging/111000000/110450000/110443500/110443456/ef1e59b0.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Slice of Heaven on Highview! 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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](https://www.expedia.ca/Winchester.dx6056879) [View more Cabin rentals in Winchester](https://www.expedia.ca/Winchester-Cabins.d6056879-aaCabins.Travel-Guide-Accommodation) ![Map](https://maps.googleapis.com/maps/api/staticmap?&size=660x330&map_id=3b266eb50d2997c6¢er=39.202244,-78.34195&zoom=13&channel=expedia-HotelInformation&maptype=roadmap&scale=1&path=color:0xFFFFF|weight:2|fillcolor:0x005AEB7F|enc:cqhnFddd%7DM%3FS%3FU%40S%3FS%40Q%40S%3FU%40SBS%40S%40SBSBSBQBS%40SDQBSDSBQDSDSDQDQDQFQDQFQDSFOFQHQFOFOHQFOHQFMHQHMJOHMHOHMJOHKJMJMJMJKJMJKJKJKLKJKLKLIJKLGLILILIJGNILGLGLGNGLELGNELENELCNENCLENALENANCNANALAN%3FNANAN%3FN%3FN%3FL%3FN%40N%40N%3FN%40N%40L%40NBN%40NDL%40NDLBNDNBLDNDLDLFNDLFLFLFNFLHLFLHJHLHLFLJLHJJLJJJJJLJJJHLLJJLHLJLHJJNHLJNHLHNHNHNHLFPHNFPHNFNFPFPFNDRFPFPDPFPDPDPBRDRDPBRDRBPBRBRBPBR%40R%40RBR%40R%40R%40T%40R%3FP%40R%3FR%3FT%3FR%3FR%3FR%3FRAR%3FRARATARARCRARAPCRCRCRCRCPERCREPEPCREPERGPEPGPGPEPGPGPGNGPINGPINGNININININILKNILKLILKLILKLMJILKJMJKJKJMJKJMHMHMHMHKHMFMHMHOFMFMFMFODMDMFODMDOBODMBODM%40OBOBO%40MBO%40O%3FO%40O%40O%40M%3FO%3FO%3FO%3FOAOAOAM%3FOAOCOAOCMCOAMEOCOEMCOEMEOGMEMEOGMGMGMGOIKIMGMIMIMIKIMIMKKKMKKKKKKKKMKKKMKMKMIMKMIMIOIMKOIOIOGOIOGOIQGOGQIOGQGQEQGQEQGQEQESEQESEQCQESCSEQASCSCSCSCQASASCSAS%3FUASAS%3FSAS%3FS%3FS&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=bxJf5FxnsiMH8d42nIh9i5wONqY=) 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? ### What time is check-in at The Overlook? ### What time is check-out at The Overlook? ### Where is The Overlook located? ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. Ask a question ## 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 information](https://www.expedia.ca/lp/b/content-guidelines) 10 - Excellent 7 8 - Good 1 6 - Okay 6 4 - Poor 1 2 - Terrible 0 ### 7.0 Cleanliness ### 8.8 Location ## Reviews ### 10/10 Excellent #### Haylee L. Jul 14, 2024 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 ##### Haylee L. Stayed 3 nights in Jul 2024 ### 10/10 Excellent #### Lori G. Aug 26, 2024 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. ##### Lori G. Stayed 3 nights in Aug 2024 ### 6/10 Okay #### Megan J. Dec 1, 2024 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. ##### Megan J. Stayed 4 nights in Nov 2024 ### 10/10 Excellent #### Caroline B. Sep 24, 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! ##### Caroline B. Stayed 3 nights in Sep 2023 ### 10/10 Excellent #### Brian L. Jun 7, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy Very comfortable, great location. ##### Brian L. Stayed 4 nights in Jun 2025 ### 10/10 Excellent #### Brian L. Jun 1, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Peaceful and relaxing Very nice. Quiet neighborhood. Great location. ##### Brian L. Stayed 3 nights in May 2025 ### 10/10 Excellent #### Courtney R. Jan 22, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Amazing I loved everything about this place. Very very nice. ##### Courtney R. Stayed 2 nights in Jan 2024 ### 8/10 Good #### Kim B. Jun 22, 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. ##### Kim B. Stayed 2 nights in Jun 2023 ### 6/10 Okay #### Brenda L. Oct 15, 2024 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. ##### Brenda L. Stayed 3 nights in Sep 2024 ### 4/10 Poor #### Sharon D. Oct 16, 2025 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! ##### Sharon D. Stayed 2 nights in Oct 2025 ### 10/10 Excellent #### Connie E. Jul 31, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy ##### Connie E. 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