
Cabin holiday rentals in Winchester
Find and book unique cabins on Airbnb
Top-rated cabin rentals in Winchester
Guests agree: These cabins are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Winchester cabin rentals
Cabin rentals with a hot tub

Charming, cozy cabin on the ridge.
nice private cabin in the woods. very small but accurately described and it had a wonderful porch that wrapped around the house. kitchen and bathroom had everything needed. would definitely recommend

+ The Cabin + @ Camp Potomac Peak
Jeff and Sam have created something so special and so beautiful in Berkeley Springs. You will not be disappointed. This was a return visit for us and for sure, not our last visit.

Hot Tub - Fishing - Private Creek Access
Perfect for a weekend getaway (or longer). Very quiet and peaceful with beautiful surroundings. If you’re looking for a quiet place to stay with all the amenities, this is the place.

Mtn. Escape! Hot Tub, Firepit, Stargazing, SNP!
We traveled with our 2 kids (2 and 4) and like others mentioned this listing has everything you could need! The listing even had step stools my 4 year old to reach the sink to wash her own hands. The hot tub was fantastic, extremely clean and comfortable. We visited Shenendoah National Park and it was a great home base. Definitely bring your groceries as it is a very secluded area and it’s a great space to cook grill, relax and reset ! Very comfortable, clean and organized!

Timber Creek: Falls - A Shenandoah Cabin
We had a wonderful stay! The property was beautiful, exactly as pictured, clean, and thoughtfully maintained. The host was very responsive and made everything easy from check-in to check-out.

Views, hike, work remote, private, hottub & CTVs!
The house is on the top of a hill overlooking the valley...the view is amazing. Very private, very secluded, but only about 5 miles off the interstate. The host is very quick to respond to messages. This is a great house for a family trip, the layout was perfect. Everybody loved the basement most of all. The hot tub and the shuffleboard were big hits. The refrigerator and the coffee maker were excellent. I’m looking at getting the same coffee maker because we liked it so much. They could use a few more place settings of plates and silverware, a few more utensils. There’s plenty of seating and the WiFi is great. We would definitely stay there again!

Modern Mountain Retreat, Hot Tub & Views
This was an amazing place to stay. The pictures don't do the house or the surrounding nature justice. The place was spotless and the guidebook had great recommendations for hiking, food, etc. A great peaceful place to get away for a weekend.

Luxury Cabin: Pool, Hot Tub, Romance & Family Fun
Excellent stay, everything was as described and the location is beautiful and very peaceful. Highly recommend, we plan to return. Topac was very responsive and helpful.
Pet-friendly cabin rentals

Peaceful Chalet 2 Kings 2 BA Firepit Mins to Bryce
We had a wonderful weekend. The cabin is really nice and comfortable, and the surroundings are beautiful! It feels like you're in the middle of the woods. Lisa's communication was great, and she gave wonderful local recommendations. There's so much to see and do in the area, as well as great wineries and breweries.

Secluded Cabin w/VIEWS | River Access | Game Room
We had a fantastic stay at the Eagle’s Nest in Cacapon, West Virginia! The house was perfect for a relaxing getaway — the wooded lot and peaceful views made it feel like a true retreat. We especially enjoyed the fire pit in the evenings and the basement game room, which was a hit with our group — the pool table and other games kept everyone entertained. The amenities were excellent, the beds were super comfortable, and everything was clean and well-stocked. We felt right at home. Five stars all around — highly recommended, and we’d love to come back again!

Island cabin
Julia's place is an Idyllic setting - so tranquil, yet close enough to a great tavern for dinner. Amazing - we cannot wait to come back.

Wilderness Ridge | Private Cabin w/ Mountain Views
This house was the ultimate retreat! If you want a peaceful, secluded place to relax and recharge, this is the rental for you! Amazing views especially at sunrise and sunset. Wildlife abounds. Literally no urban noise at all, just quiet solitude. Don’t let the drive up to the property intimidate you, easily accessible as described with 2WD in the summer. Matt was an awesome host, very responsive! The house itself was spotless and included many welcoming touches. Pictures are completely accurate. Many nice extras included if you are bringing your small kids, including toys, pack and play and high chair. Convenient 15-20 min drive to Shenandoah National Park. We would definitely return to this property!

The Hideaway~Remote Cabin ~Hot Tub~Fast Internet!
We absolutely loved staying at this cozy cabin. It looked just like the pictures and even had a little welcome card when we arrived on the island. It had every appliance we needed and then some. The location although 20 mins from town was perfect and peaceful. Very private and relaxing. Perfect for a weekend getaway. The host was responsive and very helpful with any questions we needed. It was a great stay and would definitely stay there again.

Double Spur Outfitters' Brook Cabin
We had a fantastic stay at Levi’s place. The creek is clean and beautiful, Levi is very friendly and helpful, the cabin was very clean and neat and laid out as expected from the pictures. The front porch is a nice size. I loved hearing the stream in the evening and we all enjoyed the cows and horses in the field. It was not a problem at all but because we booked through Airbnb and had not checked out his outfitting site, I was not aware that there were also camping sites and it is possible you have will have RV’s and/or tent campers around you. We have a pop up ourselves so I don’t have a problem with that, but I wasn’t expecting it. We stayed mid week in April so only a couple camping sites were in use and weren’t next to us but I am sure it fills certain times of the year. Also, it is creek side but if there are paying fishers in the creek you need to be respectful of their space. We had a great time at the pond and appreciated the use of kayaks, paddle boat, and paddle board

Easygoing
This cabin is exactly what my fiance and I needed. It was extremely cozy and we felt right at home. Raymond ‘s listing is exactly what we expected and exactly what we got. The outdoor shower is DIVINE, and with nobody around we felt at peace. Besides Raymond’s house (which is right up the hill) there is nothing around except for trees. There’s two of the cutest little hammocks with the prettiest view and a huge outdoor fire pit. We brought our two dogs with us and I think they were more relaxed than us. It is super dog friendly and they even had some dog toys there for them to play with. There is a previous review that says cell service is spotty, but we had no problem with text messages sending or outgoing phone calls. The host is extremely friendly and does make sure that you have everything you need. If you’re looking for a getaway where you can unplug and unwind, this is your perfect place. Ps, the outdoor shower water gets really hot!! 🤤

potomac overlook log cabin at Smoke hole with wifi
This house was quaint, cute, and very comfortable! We had a small issue and our hosts were extremely responsive in ensuring all was well. The only thing I would change is the location to the primary road. It was extremely close and you could hear the intermittent traffic at night as they would drive past. We had an amazing thunderstorm and the metal roof made the sleeping cozy.
Private cabin rentals

Kona's Cabin — Walk to Lake, Firepit, Pet Friendly
This was the perfect place to stay for a family getaway. We hiked, enjoyed coffee out on the patio, had a fire in the fire pit and shared meals in the well appointed kitchen. The area has beautiful parks and some delicious food.

Trofton Solace - River View
This was a beautiful and peaceful place to stay. Gorgeous view overlooking the river! The place was well decorated and we loved listening to the rain on the skylights in the living room. The neighbors were a little closer than expected, but wasn’t really an issue. Power went out one night (area outage), and Alison was responsive and proactive to provide a location of various lamps and lights. We were already using the grill on the incredibly back deck, so we weren’t really inconvenienced by it. I do appreciate the host keeping us updated on power outage.

Cozy A-Frame Cabin In The Woods
We enjoyed our stay! The cabin was very nice. The surrounding area was peaceful, perfect for a restful weekend. Our host was very responsive. Thanks for the great weekend.

Chalet in the Orchard; Romance, Luxury, Relaxation
Anthony was an amazing host and was so helpful in the communication process and booking and assisting us with all of our questions. This air b and b is absolutely beautiful and so much thought and intention put into the design and the surroundings in the woods added to the aura. The hot tub, sauna, and all the wonderful amenities made this getaway a dream. Such a comfortable bed and we had everything we needed. Thank you so much for hosting us we made many unforgettable memories at your gorgeous chalet!!

New! Zen Cabin in the Clouds
We had a wonderful stay! Natasha was very proactive with communication and helped us with anything we needed every step of the way. I highly recommend this beautiful getaway!

Serenity by the Stream
Serenity was beautiful! We had a great time enjoying the sound of the water whenever we opened a window. Walked around the property and really felt the peacefulness of the area. Would definitely come back.

Campo Cibola - Brisa
From the moment I set foot on the property my heart skipped a beat. Everything about our stay was a perfect. The cabin was clean and cozy. All the practical things comfortable bed, cold ac, hot shower, well stocked kitchen, comfy couch, big windows for taking in the peaceful surroundings and watching the bison. Getting into town was an easy 15min drive if you wish. But I never wanted to leave. I could not have wished for a better view of the bison. I watched them come out into the pasture every morning, sun bathe, munch on grass, roll in the dirt, and retire up the hill each evening. This was the most amazingly relaxing couple of days and more than I could have dreamed. I cannot wait to return.

Mountain Top Cabin
We stayed for a quick half night on a trip further south. Very cool place, wish we had been able to spend more time there.
Destinations to explore
- Rappahannock River Holiday rentals
- Outer Banks Holiday rentals
- Washington Holiday rentals
- Philadelphia Holiday rentals
- Pocono Mountains Holiday rentals
- South Jersey Holiday rentals
- Jersey Shore Holiday rentals
- New York Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Plainview Holiday rentals
- Long Island Holiday rentals
- Rentals with a patio Winchester
- Pet-friendly rentals Winchester
- Rentals with a washing machine and dryer Winchester
- Family-friendly rentals Winchester
- Cottage rentals Winchester
- Condo rentals Winchester
- Apartment rentals Winchester
- House rentals Winchester
- Rentals with outdoor seating Winchester
- Cabin rentals Virginia
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Luray Caverns
- Cunningham Falls State Park
- Stone Tower Winery
- Cacapon Resort State Park
- Robert Trent Jones Golf Club
- Bryce Resort
- Whitetail Resort
- Gambrill State Park
- South Mountain State Park
- Whiskey Creek Golf Club
- Shenandoah Valley Golf Club
- Notaviva Vineyards
- Sly Fox Golf Club
- Creighton Farms
- Twin Lakes Golf Course
- Berkeley Springs State Park
- Bowling Green Country Club
- Reston National Golf Course
- JayDee's Family Fun Center
- River Creek Club
- Car and Carriage Caravan Museum
- Warden Lake
- Herndon Centennial Golf Course
- Dinosaur Land