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

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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

Luxury tiny home farm stay on historic property with hot tub in Stephens City
Stephens City
10.0 out of 10, Exceptional, (14 reviews)
"The house was wonderfully situated and stocked for our needs. It is very well kept and decorated. We enjoyed our stay very much!"
United States
Shawn P.
The price is CA $206
CA $260 total
includes taxes & fees
Oct 6 - Oct 7
Luxury tiny home farm stay on historic property with hot tub in Stephens City
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

Peaceful mountain cabin in charming Berryville VA - next to river and brewery
Berryville
10.0 out of 10, Exceptional, (3 reviews)
"Loved the place, the log cabin has the old world charm and beautiful settings. "
United States
Anonymous traveller
The price is CA $106
CA $348 total
includes taxes & fees
Oct 7 - Oct 8
Peaceful mountain cabin in charming Berryville VA - next to river and brewery
A two-story house with a balcony, string lights, and a swing.

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

Cozy A frame cabin in quaint Front Royal. Dog friendly
Front Royal
10.0 out of 10, Exceptional, (7 reviews)
"Had a good time during my stay and loved seeing Shenandoah"
United States
Kye Y.
The price is CA $237
CA $443 total
includes taxes & fees
Oct 5 - Oct 6
Cozy A frame cabin in quaint Front Royal. Dog friendly
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

Blue Mountain Cabin, secluded, perfect for couples, near main road
Front Royal
10.0 out of 10, Exceptional, (44 reviews)
"Beautiful, relaxing and quiet cabin, exceeded expectations."
United States
Johnathan B.
The price is CA $268
CA $337 total
includes taxes & fees
Oct 14 - Oct 15
Blue Mountain Cabin, secluded, perfect for couples, near main road
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.

Your Peaceful Getaway in the Blue Ridge.
Bluemont
8.0 out of 10, Very good, (5 reviews)
"Great experience booking and staying. Would absolutely book again!"
United States
Blake S.
The price is CA $213
CA $308 total
includes taxes & fees
Oct 1 - Oct 2
Your Peaceful Getaway in the Blue Ridge.
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

Secluded Couples Retreat Cabin: Hot Tub, Pets Welcome, Beautiful Valley Views
Strasburg
The price is CA $204
CA $488 total
includes taxes & fees
Oct 26 - Oct 27
Secluded Couples Retreat Cabin: Hot Tub, Pets Welcome, Beautiful Valley Views
A two-story wooden cabin with a balcony, a staircase, and a driveway.

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

Delicious Cabin • Wine Country Retreat w/ Hot Tub
Linden
10.0 out of 10, Exceptional, (18 reviews)
"Property and cabin was very clean and well stocked. Location was great to get to wineries. We saw deer and fox in the back yard, very peaceful."
United States
Edward
The price is CA $216
CA $612 total
includes taxes & fees
Oct 5 - Oct 6
Delicious Cabin • Wine Country Retreat w/ Hot Tub
A cabin with a gravel driveway, surrounded by trees and potted plants.

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

The Juniper Cabin • Cozy Hideaway w/ Hot Tub
Linden
10.0 out of 10, Exceptional, (23 reviews)
"We had a fantastic time staying at this property for the weekend."
United States
Colin N.
The Juniper Cabin • Cozy Hideaway w/ Hot Tub
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

The Honeymoon Cabin | Private Couple's Retreat w/ hot tub
Front Royal
9.6 out of 10, Exceptional, (8 reviews)
"Absolutely perfect spot for a leaf-peeping getaway. Clean, charming, romantic! Close to antiques, vineyards and Shenandoah!"
United States
Paul B.
The price is CA $297
CA $657 total
includes taxes & fees
Oct 1 - Oct 2
The Honeymoon Cabin | Private Couple's Retreat w/ hot tub
A log cabin with a porch, stone foundation, and a gravel driveway.

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

Custom Log Cabin•Hot Tub• Friendly•Close to River,Wineries,Breweries
Front Royal
10.0 out of 10, Exceptional, (1 review)
"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!"
United States
Laura B.
The price is CA $241
CA $501 total
includes taxes & fees
Oct 4 - Oct 5
Custom Log Cabin•Hot Tub• Friendly•Close to River,Wineries,Breweries
A two-story house with a deck, large windows, and a covered outdoor area.

11. Mountain cabin near national park & wineries

Mountain cabin near national park & wineries
Linden
9.8 out of 10, Exceptional, (36 reviews)
"It was a great place to stay and very clean."
United States
Chynna V.
The price is CA $268
CA $604 total
includes taxes & fees
Oct 1 - Oct 2
Mountain cabin near national park & wineries
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

Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6
Linden
10.0 out of 10, Exceptional, (1 review)
"Great location. Great quiet atmosphere. Just one little thing - the steps are steep; so just something to be aware of."
United States
David S.
The price is CA $206
CA $617 total
includes taxes & fees
Oct 27 - Oct 28
Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6
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!

Cozy Bear Cabin | Hot Tub, Fenced Yard, Game & Theatre Rooms + THREE KING BEDS!
Front Royal
10.0 out of 10, Exceptional, (7 reviews)
"We had a wonderful time staying there during our time at upperville. The quiet nights in the hot tub were just what we needed! Matthew was a wonderful host and so helpful ! We hope to come back again "
United States
grace g.
The price is CA $349
CA $895 total
includes taxes & fees
Oct 20 - Oct 21
Cozy Bear Cabin | Hot Tub, Fenced Yard, Game & Theatre Rooms + THREE KING BEDS!
A cabin with a hot tub, wooden deck, and a staircase leading to the entrance.

14. Shenandoah Twilight | Hot Tub & Golden Hour Mountain Views

Shenandoah Twilight | Hot Tub & Golden Hour Mountain Views
Front Royal
9.0 out of 10, Wonderful, (2 reviews)
"Shenandoah Twilight is a beautiful spot tgats beautifully appointed. I really enjoyed my time there. "
United States
Wilson (Wally) W.
The price is CA $199
CA $537 total
includes taxes & fees
Oct 5 - Oct 6
Shenandoah Twilight | Hot Tub & Golden Hour Mountain Views
A house with a sloped roof, surrounded by a well-maintained lawn and trees.

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

Chalet w/Hot Tub, Deck, Game Room & EV Charger
Stephens City
10.0 out of 10, Exceptional, (10 reviews)
"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...
United States
Brian F.
The price is CA $341
CA $620 total
includes taxes & fees
Oct 7 - Oct 8
Chalet w/Hot Tub, Deck, Game Room & EV Charger
A wooden cabin with large windows, a deck, and a staircase leading to the entrance.

16. The Foxwood Cabin | Hot Tub, Screened Porch, Grill

The Foxwood Cabin | Hot Tub, Screened Porch, Grill
Front Royal
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful, quiet place to stay. Beds are very comfortable. Every room was very clean. "
United States
Alex H.
The price is CA $234
CA $689 total
includes taxes & fees
Oct 7 - Oct 8
The Foxwood Cabin | Hot Tub, Screened Porch, Grill
A two-story house with a covered porch, a garage, and a driveway.

17. Mountain Cabin Retreat | Hot Tub & Foosball |

Mountain Cabin Retreat | Hot Tub & Foosball |
Front Royal
8.8 out of 10, Excellent, (11 reviews)
"Amazing house in an amazing place. The deck, view and sunsets are great stress reducers. Hope to visit again!"
United States
Christine T.
The price is CA $404
CA $935 total
includes taxes & fees
Oct 27 - Oct 28
Mountain Cabin Retreat | Hot Tub & Foosball |
A two-story house with a balcony, a hot tub, and a stone pathway leading to the entrance.

18. Far View Shenandoah | Hot Tub, Movie & Game Room, Valley Views | 3BR & Sleeps 6

Far View Shenandoah | Hot Tub, Movie & Game Room, Valley Views | 3BR & Sleeps 6
Front Royal
10.0 out of 10, Exceptional, (18 reviews)
"We loved this house and will definitely use it again. That said, the bathroom "
United States
Margaret S.
The price is CA $233
CA $634 total
includes taxes & fees
Oct 5 - Oct 6
Far View Shenandoah | Hot Tub, Movie & Game Room, Valley Views | 3BR & Sleeps 6
A wooden cabin with a garage, surrounded by trees and a gravel driveway.

19. The Pond Cabin

The Pond Cabin
2.0 star property
Linden
The price is CA $339
CA $648 total
includes taxes & fees
Oct 26 - Oct 27
The Pond Cabin
A wooden cabin with a sloped roof, a front door, and a small set of steps leading to the entrance.

20. Getaway Cabin Retreat in Shenandoah Valley - Hot Tub, Sauna, Cold Plunge

Getaway Cabin Retreat in Shenandoah Valley - Hot Tub, Sauna, Cold Plunge
Shenandoah Farms
10.0 out of 10, Exceptional, (1 review)
The price is CA $355
CA $636 total
includes taxes & fees
Oct 4 - Oct 5
Getaway Cabin Retreat in Shenandoah Valley - Hot Tub, Sauna, Cold Plunge
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winchester Hotel Reviews

TRU By Hilton Winchester

TRU By Hilton Winchester

10/10 Excellent
"Convenient location. Clean and very comfortable beds and bedding. Staff was friendly and helpful. We left before breakfast was served. Lots of parking space"
Nancy 1-night trip
Posted 1 hour ago
TRU By Hilton Winchester

Find out more about Winchester

Winchester Cabin Rentals information

Number of reviews
215
Accommodation
564 Cabin Rentals
Lowest Price
CA $260
Highest Price
CA $935

Frequently asked questions

What are the best cabins near Winchester?
Get cozy at one of our 892 cabins in Winchester and you'll be rewarded with beautiful scenery, outdoor adventure and long-lasting memories. A Luxurious Cabin Quietly Tucked Away In The Woods is the place to put your bags down and your feet up. Cabin - 3 King Master Suites ~ Dog Friendly is another popular option if you need time out in nature.
Are there cheap cabins in Winchester?
For a nicely priced escape in the great outdoors, check out our cheap cabins in Winchester. Wake up to the sound of birds singing from one of our cozy retreats priced from CA $260 to CA $935 per night.These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best luxury cabins near Winchester?
After spending your day having adventures in nature, come home to the high-end comfort and style of a Winchester luxury cabin. Romantic Couples Log Cabin #9 Escape Hot Tub Fireplace Mountain Views Luray is an excellent option if you're in the mood to spoil yourself. You'll appreciate the top touches here, such as a spa tub and a firepit. Cabin - The White Pine Loft: Perfect For Couples is another enticing stay. Make use of a deck, a spa tub and a good deal more.
What are the best river cabins near Winchester?
When you think of the word relaxing, a river cabin near Winchester should jump to mind. Cabin - Stunning, Modern Mountain Getaway An Unbelievable Experience is the ideal place to enjoy some calm. In addition to its pretty surroundings, it offers amenities such as snowsport activities and winery tours. Shenandoah Shores Waterfront Log Cabin is another top choice. On-site watersports and snowsport activities are just some of the conveniences you'll have at hand here.
What are the best cabins with pools near Winchester?
If you love the thought of every day being a pool day, make a break for Acorn Lodge, The Perfect Log Cabin Get Away. It's one of our most popular cabin rentals with a pool near Winchester and offers amenities like on-site watersports and a swimming pool. Custom Family Log Cabin 1 Mi To Massanutten Resort is another popular place to spend relaxing days poolside. A swimming pool, a porch and good times are up for grabs here.
Can I find beach cabins near Winchester?
Enjoy a dose of sunshine and salty air at Shenandoah Shores Waterfront Log Cabin. One of our most impressive Winchester beach cabins, it offers on-site watersports and children's activities. You can also spend worry-free days by the shore at Cozy Cabin Hidden Away On A Lake. Parking facilities and children's activities will help make your visit nice and comfy.
What are the best weekend cabin rentals in Winchester?
Whether you're planning a quick escape with your darling or your close friends, we'll help you find the best weekend cabin getaway. One awesome example? Cabin - Stunning, Modern Mountain Getaway An Unbelievable Experience. Featuring a firepit and massage services, you'll love the natural surroundings here. Shenandoah Shores Waterfront Log Cabin is another fantastic place where you can slow down for a while. Enjoy a few nights at this retreat which offers on-site watersports and a patio.
What are the best cabin prices in Winchester?
Whether you're counting your pennies or want to splash out on your next trip away, you'll find what you're looking for on Expedia. At the moment, you can get a Winchester cabin from only CA $260 a night.
Can I find log cabins in Winchester?
If you find yourself craving a slower pace of life, you'll find it at one of our log cabins in Winchester. For example, Shenandoah Shores Waterfront Log Cabin. Spend your days here shore fishing and swimming and then come home to kick back among its comforts. Time also seems to go slower at Acorn Lodge, The Perfect Log Cabin Get Away. When you're in the mood to venture beyond your front door, quad biking and horse riding opportunities are nearby.
What are the top things to see and do in Winchester?
Laze about in your charming cabin one day and then explore the next. Shenandoah University and Museum of the Shenandoah Valley are some of the best attractions around Winchester. Other crowd-pleasers to tick off your itinerary include The Kernstown Battlefield and Rocking S Ranch. Find yourself a set of wheels with Expedia and visit them whenever you want.
Why should I book a cabin in Winchester?
For a getaway in nature that won't cost the earth, nothing beats a cabin. Imagine waking to the sounds of chirping birds and having breakfast on your deck surrounded by stunning views. Rent a cabin in Winchester to escape the busyness of the city. Whether they're by a lake, river, beach or mountain, cabins offer a relaxing, rustic experience that makes them the perfect choice.
What are the top nature cabins in Winchester?
Offering plenty of charm and creature comforts, Cabin - Stunning, Modern Mountain Getaway An Unbelievable Experience is among our most popular nature cabins in Winchester. But with a big range of things to do and see nearby, you won't want to spend all your time kicking back indoors. Activities including water tubing and nearby windsurfing are on the to-do list here. Shenandoah Shores Waterfront Log Cabin is another getaway where you can get back to nature. Nearby water skiing and nearby mountain biking are a couple of fun ways to do it.
What are some of the best cabins near Museum of the Shenandoah Valley in Winchester?
Escape the city and spend time in nature at a Museum of the Shenandoah Valley cabin. Get up close to wildlife, get some fresh air and then settle in at Spacious Cabin On Cedar Creek, Shenandoah's Hidden Getaway. Activities like nearby motor boating and nearby fishing are waiting for you here. Another place where you'll be nice and comfortable is Cabin - Peaceful Mountain Retreat Near Appalachian Trail. Nearby hiking and biking trails and water tubing are a couple of things to keep you busy during your break.

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