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Cabin holiday rentals in Winchester

Find and book unique cabins on Airbnb

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Popular amenities for Winchester cabin rentals

Cabin rentals with a hot tub

Top Guest favourite
Cabin in Rileyville
4.98 out of 5 average rating, 203 reviews

Charming, cozy cabin on the ridge.

NicholasRating, 5 stars1 week ago
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
Top Guest favourite
Cabin in Berkeley Springs
5 out of 5 average rating, 284 reviews

+ The Cabin + @ Camp Potomac Peak

RamseyRating, 5 stars1 week ago
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.
Guest favourite
Cabin in Gerrardstown
4.89 out of 5 average rating, 228 reviews

Hot Tub - Fishing - Private Creek Access

DougRating, 5 stars3 weeks ago
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.
Guest favourite
Cabin in Berkeley Springs
4.91 out of 5 average rating, 149 reviews

The Hideaway~Remote Cabin ~Hot Tub~Fast Internet!

JenniferRating, 5 stars1 week ago
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.
Guest favourite
Cabin in Rileyville
4.98 out of 5 average rating, 139 reviews

Mtn. Escape! Hot Tub, Firepit, Stargazing, SNP!

BrittanyRating, 5 stars2 weeks ago
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!
Guest favourite
Cabin in Lost City
4.97 out of 5 average rating, 202 reviews

Modern Mountain Retreat, Hot Tub & Views

ErikRating, 5 stars2 weeks ago
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.
Guest favourite
Cabin in Woodstock
4.92 out of 5 average rating, 103 reviews

Luxury Cabin: Pool, Hot Tub, Romance & Family Fun

MichaelRating, 5 stars1 week ago
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.
Guest favourite
Cabin in Rileyville
4.94 out of 5 average rating, 154 reviews

A+ Privacy & Views | HotTub + Firepit + BBQ | Pets

RonRating, 5 stars1 month ago
This is an amazing home on a mountain side. You have a spectacular view of the mountains and the sunsets were incredible. The home is well furnished and tasteful. The beds very comfortable. It is a restful location and no need to go driving around. I would stay anytme.

Pet-friendly cabin rentals

Guest favourite
Cabin in Mount Jackson
4.92 out of 5 average rating, 315 reviews

Peaceful Chalet 2 Kings 2 BA Firepit Mins to Bryce

JenniferRating, 5 stars1 day ago
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.
Guest favourite
Cabin in Great Cacapon
4.99 out of 5 average rating, 168 reviews

Secluded Cabin w/VIEWS | River Access | Game Room

StephanieRating, 5 stars1 week ago
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!
Top Guest favourite
Cabin in Bentonville
4.99 out of 5 average rating, 136 reviews

Venture Cabin in Shenandoah Valley

JulieRating, 5 stars1 day ago
THIS is a great house and property!! It’s a beautiful modern feeling cabin. And this place is super clean!!!! I can’t stress this enough. The bedrooms are so comfortable. The kitchen had everything we needed. We used the laundry area and all. Living room is very comfy with great seating. Outside on the back is a patio sofa, fun lighting and a swing. The front entry is very easy to get into. Great gravel driveway and just a few steps to the door. There is a great fire pit with a huge swing. It is private. It felt very safe. And the pool table room was so fun! We spent lots of time there. Plenty of towels, blankets, throws, etc. We highly recommend this property and would love to come back.
Guest favourite
Cabin in Upperville
4.94 out of 5 average rating, 154 reviews

Island cabin

WilliamRating, 5 stars1 month ago
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.
Top Guest favourite
Cabin in Star Tannery
4.99 out of 5 average rating, 122 reviews

Double Spur Outfitters' Brook Cabin

ShirleyRating, 5 stars3 weeks ago
We love staying at Levi’s with friends. We usually take over the place with some of us in the cabin and others camping along the creek. The kids run feral and the adults hang out around the fire. It’s a great break from real life. Just do me a favor and don’t tell too many people about this gem.
Superhost
Cabin in Strasburg
4.74 out of 5 average rating, 221 reviews

Deer Rapids Retreat

LelandRating, 5 stars1 week ago
The location is supreme and the house is charming. The ride into town is easy and as to be expected quite beautiful. Perfect house to unplug, unwind, relax and enjoy family time or reconnecting as a couple.
Guest favourite
Cabin in Paw Paw
4.96 out of 5 average rating, 230 reviews

Easygoing

SydneyRating, 5 stars2 weeks ago
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!! 🤤
Guest favourite
Cabin in Upper Tract
4.96 out of 5 average rating, 378 reviews

potomac overlook log cabin at Smoke hole with wifi

KimRating, 5 stars1 day ago
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

Superhost
Cabin in Winchester
4.86 out of 5 average rating, 90 reviews

Kona's Cabin — Walk to Lake, Firepit, Pet Friendly

PattyRating, 5 stars4 weeks ago
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.
Top Guest favourite
Cabin in Great Cacapon
5 out of 5 average rating, 38 reviews

Trofton Solace - River View

WesleyRating, 5 stars1 month ago
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.
Top Guest favourite
Cabin in Hedgesville
5 out of 5 average rating, 90 reviews

Cozy A-Frame Cabin In The Woods

AustinRating, 5 stars2 weeks ago
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.
Top Guest favourite
Cabin in Swanton
5 out of 5 average rating, 41 reviews

Chalet in the Orchard; Romance, Luxury, Relaxation

KristiRating, 5 stars1 week ago
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!!
Guest favourite
Cabin in Front Royal
5 out of 5 average rating, 7 reviews

New! Zen Cabin in the Clouds

MalarieRating, 5 stars5 days ago
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!
Top Guest favourite
Cabin in Dayton
4.99 out of 5 average rating, 423 reviews

Serenity by the Stream

AlexRating, 5 stars3 days ago
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.
Top Guest favourite
Cabin in Culpeper
5 out of 5 average rating, 25 reviews

Campo Cibola - Breeze

AlexandraRating, 5 stars1 week ago
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.
Guest favourite
Cabin in Capon Bridge
4.96 out of 5 average rating, 75 reviews

Mountain Top Cabin

JustinRating, 5 stars1 week ago
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.

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