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

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In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Winchester cabin rentals

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

1. 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.
$210 nightly
The price is $232
Sep 17 - Sep 18
Total with taxes and fees
Blue Mountain Cabin, secluded, perfect for couples, near main road
A two-story wooden cabin with a balcony, a staircase, and a driveway.

2. 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
$371 nightly
The price is $409
Sep 23 - Sep 24
Total with taxes and fees
Delicious Cabin • Wine Country Retreat w/ Hot Tub
A hot tub with a view of a forest and a sunset.

3. A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub

A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub
Linden
9.4 out of 10, Exceptional, (13 reviews)
"Great place to stay to catch the northern entrance to Shenandoah. Comfortable beds, great furniture, and easy drive to Front Royal for dining. "
United States
Scott M.
$331 nightly
The price is $365
Sep 23 - Sep 24
Total with taxes and fees
A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub
A house with a covered porch, surrounded by lush greenery and a trampoline.

4. Hidden Gem on Hidden Valley Lane

Hidden Gem on Hidden Valley Lane
Linden
9.6 out of 10, Exceptional, (32 reviews)
"Great location and communication from the host. All the comforts of home and more! Thanks for a great stay!"
United States
Jen T.
$511 nightly
The price is $548
Sep 20 - Sep 21
Total with taxes and fees
Hidden Gem on Hidden Valley Lane
A wooden staircase leading to a building with a green carpet and a red heart decoration on the door.

5. 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.
$383 nightly
The price is $422
Sep 23 - Sep 24
Total with taxes and fees
The Honeymoon Cabin | Private Couple's Retreat w/ hot tub
A house with a deck, outdoor hot tub, and a staircase leading to a covered porch.

6. 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.
$357 nightly
The price is $394
Sep 23 - Sep 24
Total with taxes and fees
The Juniper Cabin • Cozy Hideaway w/ Hot Tub
A wooden cabin with a garage, surrounded by trees and a gravel driveway.

7. The Pond Cabin: Hot Tub & Stocked Pond

The Pond Cabin: Hot Tub & Stocked Pond
Linden
10.0 out of 10, Exceptional, (35 reviews)
"We always love staying here. We have stayed at The Pond Cabin multiple times and will continue doing so as long as it is available!"
United States
Mary S.
$473 nightly
The price is $522
Sep 28 - Sep 29
Total with taxes and fees
The Pond Cabin: Hot Tub & Stocked Pond
A two-story house with a balcony, outdoor seating, and a hot tub.

8. 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, (17 reviews)
"We loved this house and will definitely use it again. That said, the bathroom "
United States
Margaret S.
$379 nightly
The price is $418
Sep 23 - Sep 24
Total with taxes and fees
Far View Shenandoah | Hot Tub, Movie & Game Room, Valley Views | 3BR & Sleeps 6
A rustic log cabin with a covered porch, a stone pathway, and a welcoming 'WELCOME' sign.

9. Skyland Hideaway | Mountain Cabin w/ Hot Tub

Skyland Hideaway | Mountain Cabin w/ Hot Tub
Linden
9.6 out of 10, Exceptional, (21 reviews)
"We had a wonderful stay! The house was lovely and accommodating. We will definitely be back!"
United States
Amanda B.
$371 nightly
The price is $409
Sep 27 - Sep 28
Total with taxes and fees
Skyland Hideaway | Mountain Cabin w/ Hot Tub
A two-story house with a balcony, string lights, and a swing.

10. 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.
$248 nightly
The price is $274
Sep 21 - Sep 22
Total with taxes and fees
Cozy A frame cabin in quaint Front Royal. Dog friendly
A stone house with a metal roof, a front porch, and a well-maintained lawn.

11. 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, (13 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.
$165 nightly
The price is $184
Sep 28 - Sep 29
Total with taxes and fees
Luxury tiny home farm stay on historic property with hot tub in Stephens City
A two-story wooden house with a balcony, large windows, and a visible basketball hoop.

12. Wilderness Ridge | Private Cabin w/ Mountain Views

Wilderness Ridge | Private Cabin w/ Mountain Views
Linden
9.6 out of 10, Exceptional, (11 reviews)
"We had a great time and experience. "
United States
Adriane B.
$467 nightly
The price is $515
Sep 23 - Sep 24
Total with taxes and fees
Wilderness Ridge | Private Cabin w/ Mountain Views
A wooden cabin with two windows and a door, a porch with benches, and purple flowers in the foreground.

13. 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 traveler
$212 nightly
The price is $234
Oct 5 - Oct 6
Total with taxes and fees
Peaceful mountain cabin in charming Berryville VA - next to river and brewery
A wooden cabin with large windows, a deck, and a staircase leading to the entrance.

14. 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)
"Excellent stay. Very quiet and private. The property was very clean, had all of the amenities needed. Very comfortable and homey. The only thing you need to be aware of is that the USPS does not deliver to the address, Amazon will have the post office hold it in Front Royal."
United States
Roland C.
$413 nightly
The price is $456
Sep 29 - Sep 30
Total with taxes and fees
The Foxwood Cabin | Hot Tub, Screened Porch, Grill
A two-story cabin with a porch, a staircase, and a flag.

15. 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.
$479 nightly
The price is $528
Sep 23 - Sep 24
Total with taxes and fees
Cozy Bear Cabin | Hot Tub, Fenced Yard, Game & Theatre Rooms + THREE KING BEDS!
A cabin with a deck, a covered outdoor area, and a gravel path leading to the entrance.

16. 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.
$376 nightly
The price is $414
Sep 23 - Sep 24
Total with taxes and fees
Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6
A wooden cabin with a garage, surrounded by trees and a gravel driveway.

17. The Pond Cabin

The Pond Cabin
2.0 star property
Linden
$414 nightly
The price is $457
Sep 28 - Sep 29
Total with taxes and fees
The Pond Cabin
A large house with a covered porch, a fenced yard, and a view of a hilly landscape.

18. Luxury Mountain Retreat w/ Valley Views, Hot Tub

Luxury Mountain Retreat w/ Valley Views, Hot Tub
Front Royal
9.4 out of 10, Exceptional, (3 reviews)
"Gorgeous views!!"
United States
Charlie R.
$643 nightly
The price is $709
Sep 22 - Sep 23
Total with taxes and fees
Luxury Mountain Retreat w/ Valley Views, Hot Tub
A two-story house with a covered porch, a garage, and a driveway.

19. Mountain Cabin Retreat | Hot Tub & Foosball |

Mountain Cabin Retreat | Hot Tub & Foosball |
Front Royal
8.8 out of 10, Excellent, (11 reviews)
"Great property. Location is perfect with amazing view. Great house and amenities. "
United States
Michael M.
$535 nightly
The price is $590
Sep 22 - Sep 23
Total with taxes and fees
Mountain Cabin Retreat | Hot Tub & Foosball |
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

Skyland

Skyland

10/10 Excellent
"The rooms were very comfortable and clean. Area around was safe. Staff was very helpful and welcoming."
Larry 2-night trip
Posted 5 hours ago
Skyland

Find out more about Winchester

Winchester Cabin Rentals information

Number of reviews
261
Accommodation
570 Cabin Rentals
Lowest Price
$184
Highest Price
$709

Frequently asked questions

What are the best cabins near Winchester?
Ranging from rustic and small to roomy and luxurious, you have 891 cabins on offer in and around Winchester. Top options include A Luxurious Cabin Quietly Tucked Away In The Woods and Cabin - 3 King Master Suites ~ Dog Friendly.
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 $184 to $709 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?
Get set to treat yourself to an escape you'll always remember at one of our Winchester luxury cabins. Romantic Couples Log Cabin #9 Escape Hot Tub Fireplace Mountain Views Luray is one place where you can spend a couple of days or so indulging your passion for the finer things in life. It features a spa tub and a firepit. Alternatively, use Cabin - The White Pine Loft: Perfect For Couples as a base to explore the natural splendors around you. Quality touches here include a deck and a spa tub.
What are the best river cabins near Winchester?
Spend your waking hours enjoying the water and your nights listening to it flowing past at a river cabin near Winchester. Our top pick — Cabin - Stunning, Modern Mountain Getaway An Unbelievable Experience. This riverside retreat offers snowsport activities and winery tours. Or, make yourself at home at Shenandoah Shores Waterfront Log Cabin. Along with its gorgeous location, it features on-site watersports and snowsport activities.
What are the best cabins with pools near Winchester?
Put on your swimsuit and enjoy a few laps whenever the mood strikes when you opt for one of our cabin rentals with a pool. Acorn Lodge, The Perfect Log Cabin Get Away is a hit with travelers. On-site watersports and a swimming pool are some of the other amenities that'll help make your stay comfortable. Or, escape to Custom Family Log Cabin 1 Mi To Massanutten Resort. In addition to a pool, this cabin comes with a swimming pool and a porch.
Can I find beach cabins near Winchester?
Pack your board shorts and enjoy a more relaxed pace of life at Shenandoah Shores Waterfront Log Cabin. This Winchester beach cabin has amenities including on-site watersports and children's activities. Cozy Cabin Hidden Away On A Lake also delivers a sun-drenched stay. Featuring parking facilities and children's activities, it was made for easygoing days by the shore.
What are the best weekend cabin rentals in Winchester?
If you're eager to spend two or so restful days in nature, Spacious Log Villa 6700sf Hot Tub is calling your name. Kick back here for a long weekend and enjoy access to amenities including a patio and a firepit. Another superb choice is Cozy Cabin In The Woods, With A Wood Fireplace. Offering a patio, a firepit and plenty of chill vibes, you'll go home feeling all brand new.
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 $184 a night.
Can I find log cabins in Winchester?
If you crave a quieter pace of life, you'll discover it at one of our log cabins in Winchester. For example, Shenandoah Shores Waterfront Log Cabin. Spend your days here parasailing and quad biking and then return home to enjoy its rustic charms. You can also hit the brakes at Acorn Lodge, The Perfect Log Cabin Get Away. When you're ready to explore beyond your front door, picnicking and fishing 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 travel experience that's big on character, affordability and comfort, a cabin is the best choice. Ditch your city blues for the greenery of nature. From fun-filled days to restful nights cuddled up by the fire, cabins offer the perfect mix of excitement and relaxation. You'll find all the best Winchester options right here on Expedia.
What are the top nature cabins in Winchester?
Settle in at Cabin - Stunning, Modern Mountain Getaway An Unbelievable Experience and let all your troubles float away. Activities such as mountain climbing and nearby water skiing help make this river cabin in Winchester a top choice. Shenandoah Shores Waterfront Log Cabin is another retreat where you can hang out in Mother Nature. If it's adventure you're seeking here, go nearby hiking and biking trails and hiking.
What are some of the best cabins near Shenandoah Valley Discovery Museum in Winchester?
You'll have Mother Nature as a neighbor at a Shenandoah Valley Discovery Museum cabin. Spacious Cabin On Cedar Creek, Shenandoah's Hidden Getaway is a top pick. This retreat also opens the door to big adventure, with nearby hiking and biking trails and nearby motor boating among the things to do in the area. Guests also love Cabin - Peaceful Mountain Retreat Near Appalachian Trail. Get active and then head back to your cabin to appreciate its comforts.

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