The Overlook | Cabin in Winchester, VA

8.0 (14 Reviews) |   Pet Friendly   4 Bedrooms  2 Bathrooms  11 Guests
Winchester Cabin | The Overlook

4 Bedroom Cabin with Air Conditioner, Security and Entertainment

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 Overlook is located in Winchester. The Overlook provides accommodation, featuring Entertainment, Laundry, Pet Friendly, among other amenities. This Cabin features Entertainment, Laundry, Pet Friendly, to make your stay a comfortable one.

The Overlook has 4 Bedrooms , 2 Bathrooms, and max occupancy of 11 persons. The minimum rental for this property is 1 night, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated Cabin because of the excellent services rendered by the owner or manager of this Cabin, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. Cabin has a friendly neighborhood, and the Winchester has interesting places to visit. If you want to learn more about the Cabin in Winchester, such as places to visit and things to do nearby, you can check below to learn more.

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Winchester, 22602, USA

Amenities

Air ConditionerAir Conditioner
Pet FriendlyPet Friendly
TVTV
Balcony/TerraceBalcony/Terrace
Security/SafetySecurity/Safety
Sports/ActivitiesSports/Activities
EntertainmentEntertainment
Barbecue/Outdoor CookingBarbecue/Outdoor Cooking
Child FriendlyChild Friendly
InternetInternet
KitchenKitchen
LaundryLaundry

Facility Overview

Air ConditionerAir Conditioner
  • Air conditioningAir conditioning
BathroomsBathrooms
  • 2 bathrooms2 bathrooms
  • Bathtub or showerBathtub or shower
  • SoapSoap
BedroomBedroom
  • Sofa bedSofa bed
  • 4 bedrooms4 bedrooms
  • Dining tableDining table
  • Living roomLiving room
KitchenKitchen
  • Cookware/dishes/utensilsCookware/dishes/utensils
  • DishwasherDishwasher
  • Coffee/tea makerCoffee/tea maker
  • MicrowaveMicrowave
  • BlenderBlender
  • RefrigeratorRefrigerator
  • ToasterToaster
  • SpicesSpices
  • StovetopStovetop
LaundryLaundry
  • Laundry facilitiesLaundry facilities
  • Washing machine and dryerWashing machine and dryer
Pet FriendlyPet Friendly
  • Pet friendlyPet friendly
  • Welcoming dogs onlyWelcoming dogs only
  • 1 total pets1 total pets
AccessibilityAccessibility
  • Smoke-free propertySmoke-free property
ActivitiesActivities
  • Hiking nearbyHiking nearby
EntertainmentEntertainment
  • Smart TVSmart TV
  • GamesGames
GeneralGeneral
  • In the mountainsIn the mountains
InternetInternet
  • Free WiFiFree WiFi
OutdoorsOutdoors
  • Outdoor furnitureOutdoor furniture
  • Porch or lanaiPorch or lanai
  • FirepitFirepit
Security/SafetySecurity/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)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)Smoke detector not reported (host has not indicated whether there is a smoke detector on the property)

Policies

Check-in
Check-in
Check-in time starts at 4:00 pm minimum check-in age: 21
Check-out
Check-out
Check-out before 11:00 am
Child Policy
Child Policy
Children are welcome.
Event Policy
Event Policy
No events allowed
Pet Policy
Pet Policy
1 total pets note from host: we only allow up to 1 dog pets allowed service animals are welcome, and are exempt from fees welcoming dogs only
Smoking Policy
Smoking Policy
Smoking is not permitted
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 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 onsite parties or group events are strictly prohibited special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed 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

Reviews

Brian L.
Jun 7, 2025 09:41:51 PM
Review Score:   10
Summary: Very comfortable, great location.
See All Reviews

FAQ's

Is this The Overlook pet-friendly for guests?

Yes, pets are allowed at this property. Check the guest reviews to learn what guests had to share.

Does the The Overlook have a swimming pool?

No, this The Overlook does not have a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in The Overlook?

Best-rates for the The Overlook starts from $218 per night with includes Sports/Activities, Barbecue/Outdoor Cooking, Child Friendly, Internet, Kitchen, Air Conditioner, Security/Safety, Entertainment, Laundry, Pet Friendly, TV, Balcony/Terrace with all other facilities. Casai.ca matches every traveler with their perfect accommodation, whether you are traveling with a group, friends, family, or pets.

Is The Overlook a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this cabin good or guests have recommended them suitable for families. As reported by the owner or manager, the cabin has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the The Overlook wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the The Overlook has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the The Overlook?

Based on the information reported by the owner or manager, the The Overlook indicates 1 day stay policy at this cabin. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for The Overlook?

Based on the information reported by the owner or manager, details for the cancellation policy for the The Overlook are as follows: Cancellation policy Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

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