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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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.
$157 nightly
The price is $175
Sep 28 - Sep 29
Total with taxes and fees
Luxury tiny home farm stay on historic property with hot tub in Stephens City
A wooden cabin with a porch, surrounded by trees and a gravel path.

2. The Grape Escape - A-Frame Cabin

The Grape Escape - A-Frame Cabin
Linden
10.0 out of 10, Exceptional, (26 reviews)
"This property was great for a weekend of relaxation!"
United States
Steven B.
$525 nightly
The price is $579
Oct 3 - Oct 4
Total with taxes and fees
The Grape Escape - A-Frame Cabin
A wooden cabin with two windows and a door, a porch with benches, and purple flowers in the foreground.

3. 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
$223 nightly
The price is $246
Oct 5 - Oct 6
Total with taxes and fees
Peaceful mountain cabin in charming Berryville VA - next to river and brewery
A modern, dark-colored house with a triangular roof, multiple windows, and a paved driveway.

4. 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.
$399 nightly
The price is $436
Oct 6 - Oct 7
Total with taxes and fees
Chalet w/Hot Tub, Deck, Game Room & EV Charger
A hot tub with a view of a forest and a sunset.

5. 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
9.6 out of 10, Exceptional, (14 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.
A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub
A wooden staircase leading to a deck with a lattice railing, surrounded by dense foliage.

6. 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.
$194 nightly
The price is $214
Sep 27 - Sep 28
Total with taxes and fees
Blue Mountain Cabin, secluded, perfect for couples, near main road
A wooden cabin with a garage, surrounded by trees and a gravel driveway.

7. The Pond Cabin

The Pond Cabin
2.0 star property
Linden
$434 nightly
The price is $479
Sep 29 - Sep 30
Total with taxes and fees
The Pond Cabin
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.

8. Your Peaceful Getaway in the Blue Ridge.

Your Peaceful Getaway in the Blue Ridge.
Bluemont
7.6 out of 10, Good, (4 reviews)
"Cozy, clean, private. We really enjoyed our stay!"
United States
Sonya S.
$198 nightly
The price is $218
Oct 1 - Oct 2
Total with taxes and fees
Your Peaceful Getaway in the Blue Ridge.
A cabin with a deck, a covered outdoor area, and a gravel path leading to the entrance.

9. 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.
$392 nightly
The price is $432
Sep 27 - Sep 28
Total with taxes and fees
Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6
A wooden cabin with large windows, a deck, and a staircase leading to the entrance.

10. 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.
$431 nightly
The price is $475
Sep 29 - Sep 30
Total with taxes and fees
The Foxwood Cabin | Hot Tub, Screened Porch, Grill
A modern wooden house with a deck, string lights, and a wooden staircase.

11. NEW Zen Cabin in the Clouds . Hot Tub, Wineries, Skyline

NEW Zen Cabin in the Clouds . Hot Tub, Wineries, Skyline
Front Royal
10.0 out of 10, Exceptional, (1 review)
"We stayed at this lovely cabin for a few days over the Thanksgiving holiday, and it was perfect. It was cozy, comfortable, and spotless…just the right size to feel at home. Natasha, the host, was wonderful. Even while traveling abroad, she communicated quickly and clearly, and we never had any issues reaching her.The kitchen was fully equipped for preparing meals, and every other room had everything we could possibly need. Thank you, Natasha - we’ll definitely be back!"
United States
Indira A.
$428 nightly
The price is $472
Sep 29 - Sep 30
Total with taxes and fees
NEW Zen Cabin in the Clouds . Hot Tub, Wineries, Skyline
An outdoor deck with wooden flooring, two cushioned chairs, a small table, and a ceiling fan.

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

Secluded Couples Retreat Cabin: Hot Tub, Pets Welcome, Beautiful Valley Views
Strasburg
$319 nightly
The price is $351
Sep 29 - Sep 30
Total with taxes and fees
Secluded Couples Retreat Cabin: Hot Tub, Pets Welcome, Beautiful Valley Views
A house with a deck, outdoor hot tub, and a staircase leading to a covered porch.

13. 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.
$377 nightly
The price is $416
Sep 30 - Oct 1
Total with taxes and fees
The Juniper Cabin • Cozy Hideaway w/ Hot Tub
A two-story wooden cabin with a balcony, a staircase, and a driveway.

14. 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
$390 nightly
The price is $430
Sep 29 - Sep 30
Total with taxes and fees
Delicious Cabin • Wine Country Retreat w/ Hot Tub
A rustic log cabin with a covered porch, a stone pathway, and a welcoming 'WELCOME' sign.

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

16. 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.
$400 nightly
The price is $441
Sep 28 - Sep 29
Total with taxes and fees
The Honeymoon Cabin | Private Couple's Retreat w/ hot tub
A cabin with a hot tub, wooden deck, and a staircase leading to the entrance.

17. 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.
$340 nightly
The price is $375
Oct 5 - Oct 6
Total with taxes and fees
Shenandoah Twilight | Hot Tub & Golden Hour Mountain Views
A hot tub with a wooden deck and a cup of coffee, surrounded by trees and a clear sky.

18. 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.
$321 nightly
The price is $354
Sep 29 - Sep 30
Total with taxes and fees
Custom Log Cabin•Hot Tub• Friendly•Close to River,Wineries,Breweries
A two-story house with a balcony, string lights, and a swing.

19. 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.
$262 nightly
The price is $289
Sep 28 - Sep 29
Total with taxes and fees
Cozy A frame cabin in quaint Front Royal. Dog friendly
A house with a covered porch, surrounded by lush greenery and a trampoline.

20. 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.
$514 nightly
The price is $552
Sep 28 - Sep 29
Total with taxes and fees
Hidden Gem on Hidden Valley Lane
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

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent
"Been there at least once a year for past dozen years. Great location. My only complaint was the lightening was dim at the pool during my last visit bur that's a minor issue."
John 1-night trip
Posted 4 hours ago
La Quinta Inn & Suites by Wyndham Winchester

Find out more about Winchester

Winchester Cabin Rentals information

Number of reviews
222
Accommodation
570 Cabin Rentals
Lowest Price
$175
Highest Price
$579

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 $175 to $579 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 $175 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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