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Our top choices for Winchester cottages
Cottage in Berryville
1800s Cozy Kitchen House in Berryville10.0 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."
Kelly G.
$164 nightly
The price is $184
Dec 22 - Dec 23
Total with taxes and fees
Cottage in Front Royal
The Vue - Mountain top hot tub overlooking the Shenandoah River9.8 out of 10, Exceptional, (10)
"Love the view and beautiful appointed decor throughout the home…"
Lynn M.
$328 nightly
The price is $361
Jan 11 - Jan 12, 2026
Total with taxes and fees
Cottage in Front Royal
"Prima BnB" a Superb 4-bedroom cottage on the mountain near Front Royal10.0 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!"
Jay L.
$370 nightly
The price is $408
Jan 5 - Jan 6, 2026
Total with taxes and fees
Cottage in Boyce
Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi10.0 out of 10, Exceptional, (31)
"Good location. Large fenced in yard. Plenty of room. Would book again."
Don M.
$606 nightly
The price is $668
Dec 22 - Dec 23
Total with taxes and fees
Cottage in Fort Valley
Cozy Retreat - Hot tub + Mountain Views + Pets9.8 out of 10, Exceptional, (54)
"It was a beautiful getaway from all of the busy mess from our normal lives"
Tailor N.
$210 nightly
The price is $232
Dec 22 - Dec 23
Total with taxes and fees
Cottage in Leesburg
'thomson Farm' Classic Home < 10 Mi to Vineyards!$1,603 nightly
The price is $1,827
Dec 21 - Dec 22
Total with taxes and fees
Cottage in Purcellville
Wild Hare Cottage10.0 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. "
Jennifer K.
$209 nightly
The price is $238
Jan 7 - Jan 8, 2026
Total with taxes and fees
Cottage in Harpers Ferry
The Carriage House at Carrot Top Cottage9.8 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. "
Holly W.
$153 nightly
The price is $170
Dec 22 - Dec 23
Total with taxes and fees
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
Quality Inn Winchester
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Winchester Cottages information
Number of reviews | 422 |
|---|---|
Accommodation | 191 Cottages |
Lowest Price | $170 |
Highest Price | $1,827 |
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