Search the Best Cabins in Winchester

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Our top choices for Winchester cabin rentals

Exterior
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

Luxury tiny home farm stay on historic property with hot tub in Stephens City
2.0 star property
Stephens City
$151 nightly
The price is $164
Jan 1 - Jan 2, 2026
Total with taxes and fees
Luxury tiny home farm stay on historic property with hot tub in Stephens City
Exterior
Cozy A frame cabin in quaint Front Royal. Dog friendly

Cozy A frame cabin in quaint Front Royal. Dog friendly

Cozy A frame cabin in quaint Front Royal. Dog friendly
2.0 star property
Front Royal
$255 nightly
The price is $281
Dec 21 - Dec 22
Total with taxes and fees
Cozy A frame cabin in quaint Front Royal. Dog friendly
Fridge, microwave, oven, stovetop
Blue Mountain Cabin, secluded, perfect for couples, near main road

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, (25)
"Great place to relax"
United States
Judy
$200 nightly
The price is $221
Dec 21 - Dec 22
Total with taxes and fees
Blue Mountain Cabin, secluded, perfect for couples, near main road
Terrace/patio
Cute cabin retreat near Shenandoah National Park and pet friendly!

Cute cabin retreat near Shenandoah National Park and pet friendly!

Cute cabin retreat near Shenandoah National Park and pet friendly!
Linden
9.4 out of 10, Exceptional, (13)
"Fun location near tons of wineries, bowling, trails, and mountain living. Place is really nice with a grill, solo stove, kfantastic kitchen"
United States
Bret L.
$323 nightly
The price is $356
Jan 7 - Jan 8, 2026
Total with taxes and fees
Cute cabin retreat near Shenandoah National Park and pet friendly!
Outdoor spa tub
The Honeymoon Cabin | Private Retreat w/ hot tub

The Honeymoon Cabin | Private Retreat w/ hot tub

The Honeymoon Cabin | Private Retreat w/ hot tub
Front Royal
10.0 out of 10, Exceptional, (2)
"Absolutely perfect spot for a leaf-peeping getaway. Clean, charming, romantic! Close to antiques, vineyards and Shenandoah!"
United States
Paul B.
$343 nightly
The price is $378
Jan 5 - Jan 6, 2026
Total with taxes and fees
The Honeymoon Cabin | Private Retreat w/ hot tub
Exterior
The Foxwood Cabin: Cozy Retreat w/ Hot Tub, Screened Porch, Firepit & Grill

The Foxwood Cabin: Cozy Retreat w/ Hot Tub, Screened Porch, Firepit & Grill

The Foxwood Cabin: Cozy Retreat w/ Hot Tub, Screened Porch, Firepit & Grill
Front Royal
10.0 out of 10, Exceptional, (5)
"Beautiful, quiet place to stay. Beds are very comfortable. Every room was very clean. "
United States
Alex H.
$360 nightly
The price is $397
Jan 5 - Jan 6, 2026
Total with taxes and fees
The Foxwood Cabin: Cozy Retreat w/ Hot Tub, Screened Porch, Firepit & Grill
Exterior
The Cozy Bear Cabin | Hot Tub, Fenced Yard, Games

The Cozy Bear Cabin | Hot Tub, Fenced Yard, Games

The Cozy Bear Cabin | Hot Tub, Fenced Yard, Games
Front Royal
10.0 out of 10, Exceptional, (4)
"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.
$474 nightly
The price is $523
Jan 6 - Jan 7, 2026
Total with taxes and fees
The Cozy Bear Cabin | Hot Tub, Fenced Yard, Games
Exterior
Wilderness Ridge | Private Cabin w/ Mountain Views

Wilderness Ridge | Private Cabin w/ Mountain Views

Wilderness Ridge | Private Cabin w/ Mountain Views
Linden
9.4 out of 10, Exceptional, (6)
"great get away for a family retreat!!!"
United States
Rex P.
$434 nightly
The price is $479
Jan 4 - Jan 5, 2026
Total with taxes and fees
Wilderness Ridge | Private Cabin w/ Mountain Views
Exterior
Escape to Shenandoah River, Hot Tub after a Hike!

Escape to Shenandoah River, Hot Tub after a Hike!

Escape to Shenandoah River, Hot Tub after a Hike!
Front Royal
10.0 out of 10, Exceptional, (55)
"Its a nice property to stay. Will be back soon "
United States
Faizan A.
$335 nightly
The price is $369
Jan 12 - Jan 13, 2026
Total with taxes and fees
Escape to Shenandoah River, Hot Tub after a Hike!
Exterior
Hidden Gem on Hidden Valley Lane

Hidden Gem on Hidden Valley Lane

Hidden Gem on Hidden Valley Lane
Linden
9.6 out of 10, Exceptional, (27)
"Very clean; beautiful setting; great screened in porch "
United States
Marianne G.
$404 nightly
The price is $433
Dec 22 - Dec 23
Total with taxes and fees
Hidden Gem on Hidden Valley Lane
Exterior
The Pond Cabin: Hot Tub & Stocked Pond

The Pond Cabin: Hot Tub & Stocked Pond

The Pond Cabin: Hot Tub & Stocked Pond
Linden
10.0 out of 10, Exceptional, (33)
"It was the perfect home away from home in a place that allowed our little family to take a breath of nature and just be. Close enough to many fun adventures. The amenities provided on the property also kept us very busy!"
United States
Brena H.
$467 nightly
The price is $515
Jan 6 - Jan 7, 2026
Total with taxes and fees
The Pond Cabin: Hot Tub & Stocked Pond
Outdoor spa tub
Cozy Shenandoah Cabin Mountian Escape w/ Private Hottub, Loft, & Fireplace

Cozy Shenandoah Cabin Mountian Escape w/ Private Hottub, Loft, & Fireplace

Cozy Shenandoah Cabin Mountian Escape w/ Private Hottub, Loft, & Fireplace
Linden
9.2 out of 10, Wonderful, (9)
"Very nice place"
United States
MARTIN D.
$292 nightly
The price is $322
Dec 21 - Dec 22
Total with taxes and fees
Cozy Shenandoah Cabin Mountian Escape w/ Private Hottub, Loft, & Fireplace
Exterior
Your Peaceful Getaway in the Blue Ridge.

Your Peaceful Getaway in the Blue Ridge.

Your Peaceful Getaway in the Blue Ridge.
Bluemont
6.8 out of 10, (3)
"Great experience booking and staying. Would absolutely book again!"
United States
Blake S.
$196 nightly
The price is $216
Dec 21 - Dec 22
Total with taxes and fees
Your Peaceful Getaway in the Blue Ridge.
Exterior
Mountain cabin near national park & wineries

Mountain cabin near national park & wineries

Mountain cabin near national park & wineries
Linden
10.0 out of 10, Exceptional, (28)
"The house and location were perfect for a little getaway with friends. It was very clean, and the location was great! We were very pleased with the entire experience."
United States
Jennifer d.
$509 nightly
The price is $562
Dec 29 - Dec 30
Total with taxes and fees
Mountain cabin near national park & wineries
Exterior
❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.8 out of 10, Exceptional, (66)
"This trip was to celebrate my 64th birthday and wind down from my busy job It was perfect for both .. very relaxing, and very cozy. We'd love to stay again."
United States
Kaleb C
$96 nightly
The price is $107
Jan 1 - Jan 2, 2026
Total with taxes and fees
❤️ Secluded 1940s Romantic Tiny House on the River
Exterior
Primitive Cozy Tiny Cabin with Starlink internet

Primitive Cozy Tiny Cabin with Starlink internet

Primitive Cozy Tiny Cabin with Starlink internet
Great Cacapon
10.0 out of 10, Exceptional, (11)
"Super peaceful and relaxing! We had a great time! Will stay again! Thanks Austin!"
United States
Jason M.
$168 nightly
The price is $187
Dec 23 - Dec 24
Total with taxes and fees
Primitive Cozy Tiny Cabin with Starlink internet
Exterior
Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.

Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.

Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.
Berkeley Springs
9.8 out of 10, Exceptional, (296)
"We especially enjoyed the hot tub and the privacy of the cabin. Was what we expected and was very clean. Had a nice relaxing couple of days that we were there!"
United States
Ann W.
$272 nightly
The price is $303
Dec 22 - Dec 23
Total with taxes and fees
Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.
Exterior
Glamp Shenandoah Valley. Stunning Tiny Home. Farm

Glamp Shenandoah Valley. Stunning Tiny Home. Farm

Glamp Shenandoah Valley. Stunning Tiny Home. Farm
Shenandoah County
10.0 out of 10, Exceptional, (8)
"The cabin was great as well as the host. They thought of everything to make your stay memorable. The place is peaceful and perfect for resting "
United States
cristobal f.
$153 nightly
The price is $155
Jan 1 - Jan 2, 2026
Total with taxes and fees
Glamp Shenandoah Valley. Stunning Tiny Home. Farm
Exterior
Aslan's How - Cabin with Valley Views & Hot Tub!

Aslan's How - Cabin with Valley Views & Hot Tub!

Aslan's How - Cabin with Valley Views & Hot Tub!
2.0 star property
Harpers Ferry
9.8 out of 10, Exceptional, (8)
"We stayed here for our honeymoon and it was very nice and peaceful "
United States
Robert F.
$357 nightly
The price is $398
Jan 4 - Jan 5, 2026
Total with taxes and fees
Aslan's How - Cabin with Valley Views & Hot Tub!
Exterior
Secluded WV Retreat Hot Tub, Fire Pit & Kayaks

Secluded WV Retreat Hot Tub, Fire Pit & Kayaks

Secluded WV Retreat Hot Tub, Fire Pit & Kayaks
Sleepy Hollow
9.8 out of 10, Exceptional, (10)
"Had an amazing stay! The VRBO was cozy, comfortable and clean in an amazing area. We loved the amenities, relaxing on the deck, by the fire pit, and in the hot tub were perfect! The host, Emily, was amazing and gave lots of great info about the area and was very responsive. Would love to stay here again!"
United States
Sarah H.
$278 nightly
The price is $309
Jan 5 - Jan 6, 2026
Total with taxes and fees
Secluded WV Retreat Hot Tub, Fire Pit & Kayaks
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

Hampton Inn Martinsburg

Hampton Inn Martinsburg

10/10 Excellent
"Pleasant stay. Very nice front desk staff on night and day! "
LAURA 1-night trip
Posted 2 days ago
Hampton Inn Martinsburg

Find out more about Winchester

Winchester Cabin Rentals information

Number of reviews
587
Accommodation
538 Cabin Rentals
Lowest Price
$107
Highest Price
$562

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 $107 to $562 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 $107 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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