15 Best Cabins in Winchester, VA - Cabins for Rent from SAR 690

A white neoclassical building with columns and a clock tower, surrounded by brick buildings and a clear blue sky.

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Our top choices for Winchester cabin rentals

A stone house with a metal roof, a front porch, and a well-maintained lawn.

1. Luxury tiny home farm stay on historic property with hot tub in Stephens City

Stephens City

Shawn P.

SAR 690 total

includes taxes & fees

6 Oct - 7 Oct

A wooden cabin with two windows and a door, a porch with benches, and purple flowers in the foreground.

2. Peaceful mountain cabin in charming Berryville VA - next to river and brewery

Berryville

Anonymous traveler

SAR 919 total

includes taxes & fees

5 Oct - 6 Oct

A two-story house with a balcony, string lights, and a swing.

3. Cozy A frame cabin in quaint Front Royal. Dog friendly

Front Royal

Kye Y.

SAR 1,160 total

includes taxes & fees

5 Oct - 6 Oct

A wooden staircase leading to a deck with a lattice railing, surrounded by dense foliage.

4. Blue Mountain Cabin, secluded, perfect for couples, near main road

Front Royal

Johnathan B.

SAR 886 total

includes taxes & fees

14 Oct - 15 Oct

A small, single-story house with a gray exterior and a dark roof. It features a front porch with a white railing and a small deck area.

5. Your Peaceful Getaway in the Blue Ridge.

Bluemont

Blake S.

SAR 820 total

includes taxes & fees

4 Oct - 5 Oct

A cabin with a hot tub, deck, and outdoor seating area surrounded by trees.

6. Secluded Couples Retreat Cabin: Hot Tub, Pets Welcome, Beautiful Valley Views

Strasburg

SAR 1,292 total

includes taxes & fees

26 Oct - 27 Oct

A two-story wooden cabin with a balcony, a staircase, and a driveway.

7. Delicious Cabin • Wine Country Retreat w/ Hot Tub

Linden

Edward

SAR 1,603 total

includes taxes & fees

5 Oct - 6 Oct

A cabin with a gravel driveway, surrounded by trees and potted plants.

8. The Juniper Cabin • Cozy Hideaway w/ Hot Tub

Linden

Colin N.

A wooden staircase leading to a building with a green carpet and a red heart decoration on the door.

9. The Honeymoon Cabin | Private Couple's Retreat w/ hot tub

Front Royal

Paul B.

SAR 1,839 total

includes taxes & fees

25 Oct - 26 Oct

A log cabin with a porch, stone foundation, and a gravel driveway.

10. Custom Log Cabin•Hot Tub• Friendly•Close to River,Wineries,Breweries

Front Royal

"This beautifully new cabin in the mountains was the perfect getaway location! So serene and beautiful! The front porch and back deck areas were the perfect setting to catch up with family! We will definitely be booking again. Rex and Meredith communicated with us perfectly before and during our stay. The indoors were just as beautiful as the outside with gorgeous bathrooms and unbelievably comfortable beds! Even our pooch loved the getaway!"

Laura B.

SAR 1,330 total

includes taxes & fees

4 Oct - 5 Oct

A two-story house with a deck, large windows, and a covered outdoor area.

11. Mountain cabin near national park & wineries

Linden

Chynna V.

SAR 1,607 total

includes taxes & fees

4 Oct - 5 Oct

A cabin with a deck, a covered outdoor area, and a gravel path leading to the entrance.

12. Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6

Linden

David S.

SAR 1,611 total

includes taxes & fees

27 Oct - 28 Oct

A two-story cabin with a porch, a staircase, and a flag.

13. Cozy Bear Cabin | Hot Tub, Fenced Yard, Game & Theatre Rooms + THREE KING BEDS!

Front Royal

grace g.

SAR 2,377 total

includes taxes & fees

20 Oct - 21 Oct

A cabin with a hot tub, wooden deck, and a staircase leading to the entrance.

14. Shenandoah Twilight | Sunset Views w/ Hot Tub + Fire Table, Near Skyline Drive

Front Royal

Wilson (Wally) W.

A house with a sloped roof, surrounded by a well-maintained lawn and trees.

15. Chalet w/Hot Tub, Deck, Game Room & EV Charger

Stephens City

"We had a wonderful 10-day stay with our dogs at this beautiful property. The area is great, with quick access to many things. There are many really nice, small details about the home that we enjoyed. The large table was great for our 3000-piece puzzle, and the dogs enjoyed running around the property and down by the creek. Everything was very clean, and the kitchen, although low on cooking supplies, was very nice for cooking our meals. Sadly, it rained almost every day, but we were able to enjoy...

Brian F.

SAR 1,754 total

includes taxes & fees

6 Oct - 7 Oct