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Our top choices for Winchester cottages

1800s Cozy Kitchen House in Berryville

1800s Cozy Kitchen House in Berryville
2.0 star property
Berryville
10.0 out of 10, Exceptional, (1)
"This unique gem was resurrected and rebirthed. It screams creativity and provides all of the comforts of home with the perfect balance between modern conveniences and days of yore. Great location for Harper’s Ferry goers. Definitely cannot say enough good things because it’s one helluva of a place to rest."
United States
Kelly G.
$164 nightly
The price is $184
Dec 22 - Dec 23
Total with taxes and fees
1800s Cozy Kitchen House in Berryville

The Vue - Mountain top hot tub overlooking the Shenandoah River

The Vue - Mountain top hot tub overlooking the Shenandoah River
2.0 star property
Front Royal
9.8 out of 10, Exceptional, (10)
"Love the view and beautiful appointed decor throughout the home…"
United States
Lynn M.
$308 nightly
The price is $340
Jan 13 - Jan 14, 2026
Total with taxes and fees
The Vue - Mountain top hot tub overlooking the Shenandoah River

"Prima BnB" a Superb 4-bedroom cottage on the mountain near Front Royal

"Prima BnB" a Superb 4-bedroom cottage on the mountain near Front Royal
Front Royal
10.0 out of 10, Exceptional, (3)
"My family and I had a wonderful stay! The property and surrounding views are beautiful. The house was very clean and the host was very responsive when I had a question or two to ask. I highly recommend staying here!"
United States
Jay L.
$370 nightly
The price is $408
Jan 5 - Jan 6, 2026
Total with taxes and fees
"Prima BnB" a Superb 4-bedroom cottage on the mountain near Front Royal

Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi

Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi
Boyce
10.0 out of 10, Exceptional, (31)
"Good location. Large fenced in yard. Plenty of room. Would book again."
United States
Don M.
$606 nightly
The price is $668
Dec 22 - Dec 23
Total with taxes and fees
Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi

Cozy Retreat - Hot tub + Mountain Views + Pets

Cozy Retreat - Hot tub + Mountain Views + Pets
Fort Valley
9.8 out of 10, Exceptional, (54)
"It was a beautiful getaway from all of the busy mess from our normal lives"
United States
Tailor N.
$210 nightly
The price is $232
Dec 22 - Dec 23
Total with taxes and fees
Cozy Retreat - Hot tub + Mountain Views + Pets

'thomson Farm' Classic Home < 10 Mi to Vineyards!

'thomson Farm' Classic Home < 10 Mi to Vineyards!
3.0 star property
Leesburg
$1,603 nightly
The price is $1,827
Dec 21 - Dec 22
Total with taxes and fees
'thomson Farm' Classic Home < 10 Mi to Vineyards!

Wild Hare Cottage

Wild Hare Cottage
Purcellville
10.0 out of 10, Exceptional, (10)
"Perfect spot to relax for a long weekend. Easy drive to Middleburg, VA, wineries, breweries, and hiking. Would stay again. "
United States
Jennifer K.
$209 nightly
The price is $238
Jan 7 - Jan 8, 2026
Total with taxes and fees
Wild Hare Cottage

The Carriage House at Carrot Top Cottage

The Carriage House at Carrot Top Cottage
Harpers Ferry
9.8 out of 10, Exceptional, (43)
"The place was super cute and clean. It was the perfect little getaway spot for my husband and I’s anniversary. "
United States
Holly W.
$153 nightly
The price is $170
Dec 22 - Dec 23
Total with taxes and fees
The Carriage House at Carrot Top Cottage

Amazing dog-friendly cottage. Walk 2 Harpers Ferry

Amazing dog-friendly cottage. Walk 2 Harpers Ferry
2.0 star property
Harpers Ferry
9.8 out of 10, Exceptional, (20)
"Really nice property, and exactly as advertised. There were several local restaurants within easy walking distance (we loved both Bolivar Bread and Snallygaster's) and it was a fairly easy walk to the historic part of Harper's Ferry. We also enjoyed the fire pit in the back yard."
United States
Greg B.
$273 nightly
The price is $304
Jan 4 - Jan 5, 2026
Total with taxes and fees
Amazing dog-friendly cottage. Walk 2 Harpers Ferry

Lake View Retreat - Cottage Near a Peaceful Lake!

Lake View Retreat - Cottage Near a Peaceful Lake!
Harpers Ferry
9.6 out of 10, Exceptional, (21)
"The house was clean, had plenty of rooms and a fantastic location. "
United States
Bryan N.
$323 nightly
The price is $360
Dec 22 - Dec 23
Total with taxes and fees
Lake View Retreat - Cottage Near a Peaceful Lake!

Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*

Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*
Luray
9.8 out of 10, Exceptional, (81)
"Great place. Really enjoyed our mountain getaway!"
United States
Evan C.
$282 nightly
The price is $325
Jan 4 - Jan 5, 2026
Total with taxes and fees
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*

The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!

The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Hamilton
9.6 out of 10, Exceptional, (9)
"It was a great place to starve whole experience was perfect. "
United States
Jaime B.
$346 nightly
The price is $394
Dec 22 - Dec 23
Total with taxes and fees
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!

Quiet Cottage on Five+ Acres of Woods Close to All That Berkeley Springs Offers

Quiet Cottage on Five+ Acres of Woods Close to All That Berkeley Springs Offers
Berkeley Springs
9.4 out of 10, Exceptional, (19)
"Nice place to stay"
United States
Roy C.
$371 nightly
The price is $413
Dec 21 - Dec 22
Total with taxes and fees
Quiet Cottage on Five+ Acres of Woods Close to All That Berkeley Springs Offers

Art Docko - Lakefront Artist Retreat w/ Hot Tub!

Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Harpers Ferry
10.0 out of 10, Exceptional, (23)
"My friends and I absolutely loved this stay on the lake in West Virginia! The artsy vibe of the home, views, and wildlife were amazing. Plenty of places to sit and catch up. The kitchen was well stocked with appliances (thank you for the local coffee!) Each adult having their own bedroom and full bath was a huge perk!"
United States
Matthew P.
$415 nightly
The price is $462
Jan 7 - Jan 8, 2026
Total with taxes and fees
Art Docko - Lakefront Artist Retreat w/ Hot Tub!

Peaceful Waterfall House -- 2 bedroom hidden treasure

Peaceful Waterfall House -- 2 bedroom hidden treasure
Berkeley Springs
9.6 out of 10, Exceptional, (10)
"Loved the privacy of the location & uniqueness of the house which was one reason we chose this place for a get away. We thoroughly enjoyed the stargazing & beauty of the outdoors. Having a soak in the tub was a bonus. We had a very relaxing vacation. "
United States
Annamarie M.
$283 nightly
The price is $315
Dec 21 - Dec 22
Total with taxes and fees
Peaceful Waterfall House -- 2 bedroom hidden treasure

Cottage w/ Hot Tub and 100-Mile Valley Views!

Cottage w/ Hot Tub and 100-Mile Valley Views!
Harpers Ferry
9.8 out of 10, Exceptional, (20)
"Great view, very secluded"
United States
Matt s.
$371 nightly
The price is $413
Jan 7 - Jan 8, 2026
Total with taxes and fees
Cottage w/ Hot Tub and 100-Mile Valley Views!

Peaceful Lakefront Cottage with Mountain Views!

Peaceful Lakefront Cottage with Mountain Views!
Harpers Ferry
10.0 out of 10, Exceptional, (31)
"Great location. Beautiful scenery. House was clean."
United States
Brandon H.
$331 nightly
The price is $369
Dec 22 - Dec 23
Total with taxes and fees
Peaceful Lakefront Cottage with Mountain Views!

Hike, Sip & Explore: Charming Waterford Cottage!

Hike, Sip & Explore: Charming Waterford Cottage!
3.0 star property
Waterford
$425 nightly
The price is $484
Dec 30 - Dec 31
Total with taxes and fees
Hike, Sip & Explore: Charming Waterford Cottage!

Royal Heritage Home @ Historic Leesburg

Royal Heritage Home @ Historic Leesburg
Leesburg's Old and Historic District
9.8 out of 10, Exceptional, (37)
"The property was perfect for our stay. We had everything we needed and the beds were very comfy. We will definitely stay here again!"
United Kingdom
Andrew N.
$415 nightly
The price is $477
Dec 22 - Dec 23
Total with taxes and fees
Royal Heritage Home @ Historic Leesburg

Cozy Mountain Retreat | Hot Tub & Fire Pit & Dogs

Cozy Mountain Retreat | Hot Tub & Fire Pit & Dogs
Harpers Ferry
9.6 out of 10, Exceptional, (7)
"We enjoyed our stay , close to everything we planned for the weekend. Place was very roomy, clean and the beds were very comfortable!!"
United States
Cheryl O.
$547 nightly
The price is $609
Jan 8 - Jan 9, 2026
Total with taxes and fees
Cozy Mountain Retreat | Hot Tub & Fire Pit & Dogs
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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What is there to do in Winchester near my cottage?
Winchester has enough activities and sights to keep you on the hop for weeks, starting with Rock Harbor Golf Course. The Kernstown Battlefield, Museum of the Shenandoah Valley and Apple Blossom Mall are other fantastic attractions. If you're in town a while, Jim Barnett Park and Handley Regional Library are nice final touches to your itinerary.

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