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Nov 14 - Nov 16
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Nov 21 - Nov 23
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Dec 5 - Dec 7
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Cottages in Winchester

Property grounds
The Vue - Mountain top hot tub overlooking the Shenandoah River
The Vue - Mountain top hot tub overlooking the Shenandoah River
2.0 star property
9.8 out of 10, Exceptional, (8)
"Love the view and beautiful appointed decor throughout the home…"
United States
Lynn M.
$369 nightly
The price is $407
Nov 24 - Nov 25
Total with taxes and fees
The Vue - Mountain top hot tub overlooking the Shenandoah River
Property grounds
"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
10.0 out of 10, Exceptional, (1)
$366 nightly
The price is $404
Nov 17 - Nov 18
Total with taxes and fees
"Prima BnB" a Superb 4-bedroom cottage on the mountain near Front Royal
Outdoor spa tub
Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi
Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi
9.8 out of 10, Exceptional, (29)
"Came for my daughters wedding and this place was amazing. Awesome place to relax, firepit to chat around, outside table to enjoy a meal was amazing, comfy beds. Just awesome and amazing stay!!"
United States
Deborah D.
$538 nightly
The price is $594
Nov 6 - Nov 7
Total with taxes and fees
Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi
House (Multiple Bedrooms) | Interior
'thomson Farm' Classic Home < 10 Mi to Vineyards!
'thomson Farm' Classic Home < 10 Mi to Vineyards!
3.0 star property
$1,623 nightly
The price is $1,850
Nov 5 - Nov 6
Total with taxes and fees
'thomson Farm' Classic Home < 10 Mi to Vineyards!
Outdoor spa tub
Cozy Retreat - Hot tub + Mountain Views + Pets
Cozy Retreat - Hot tub + Mountain Views + Pets
9.8 out of 10, Exceptional, (51)
"We loved our stay! The house was perfect and my girls just loved all the charm and little touches. The views on the property were gorgeous and it was a perfect location."
United States
Danielle M.
$232 nightly
The price is $256
Nov 11 - Nov 12
Total with taxes and fees
Cozy Retreat - Hot tub + Mountain Views + Pets
Property grounds
Peaceful Lakefront Cottage with Mountain Views!
Peaceful Lakefront Cottage with Mountain Views!
9.8 out of 10, Exceptional, (29)
"Really enjoyed stay home was great "
United States
zachary b.
$327 nightly
The price is $364
Nov 5 - Nov 6
Total with taxes and fees
Peaceful Lakefront Cottage with Mountain Views!
Exterior
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*
9.8 out of 10, Exceptional, (79)
"We had a great experience for a family wedding! The place was very clean and was in a great local spot that was easy to get to our wedding venue. "
United States
Rebecca W.
$267 nightly
The price is $308
Nov 5 - Nov 6
Total with taxes and fees
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*
Exterior
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
10.0 out of 10, Exceptional, (15)
"This is a very comfortable, quiet, and clean home, easily accessible by GPS. Great for our family of 6 with plenty of room and the home is stocked with essentials and conveniences (books, games, extra air mattress, crib, booster seat, etc.) Would definitely stay again for a get away to Berkeley Springs."
United States
Margaret Z.
$371 nightly
The price is $413
Nov 6 - Nov 7
Total with taxes and fees
Quiet Cottage on Five+ Acres of Woods Close to All That Berkeley Springs Offers
Exterior
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
2.0 star property
9.8 out of 10, Exceptional, (19)
"The house was beautiful and clean. All the beds were so comfortable! Kids had a lot of fun running around the huge backyard and playing croquet. We're already wanting to go back!"
United States
Abigail R.
$275 nightly
The price is $306
Nov 12 - Nov 13
Total with taxes and fees
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Exterior
Peaceful Waterfall House -- 2 bedroom hidden treasure
Peaceful Waterfall House -- 2 bedroom hidden treasure
9.6 out of 10, Exceptional, (9)
"The setting is peaceful and beautiful. The property has a rich history. The house has a lot of quirky character and exploring it is a trip within itself. We have stayed in several places in WV but this one is currently our favorite."
United States
Gregory S.
$283 nightly
The price is $315
Nov 5 - Nov 6
Total with taxes and fees
Peaceful Waterfall House -- 2 bedroom hidden treasure
Property grounds
Lake View Retreat - Cottage Near a Peaceful Lake!
Lake View Retreat - Cottage Near a Peaceful Lake!
9.6 out of 10, Exceptional, (21)
"Was really able to relax and enjoy during our brief stay. Would come again."
United States
Emily B.
$323 nightly
The price is $360
Nov 6 - Nov 7
Total with taxes and fees
Lake View Retreat - Cottage Near a Peaceful Lake!
Property grounds
Cottage w/ Hot Tub and 100-Mile Valley Views!
Cottage w/ Hot Tub and 100-Mile Valley Views!
9.8 out of 10, Exceptional, (20)
"Pretty cabin with a wonderful view, especially from the hot tub. We will return!"
United States
Holly C.
$339 nightly
The price is $377
Nov 5 - Nov 6
Total with taxes and fees
Cottage w/ Hot Tub and 100-Mile Valley Views!
Outdoor dining
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
10.0 out of 10, Exceptional, (23)
"Loved this house for relaxing, enjoying nature and reconnecting with friends!"
United States
Ellen P.
$408 nightly
The price is $454
Nov 20 - Nov 21
Total with taxes and fees
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Exterior
Modern Mountain Cottage with Hot Tub, Fire Pit Nestled in the Woods of Gerrardstown, WV
Modern Mountain Cottage with Hot Tub, Fire Pit Nestled in the Woods of Gerrardstown, WV
2.0 star property
$237 nightly
The price is $239
Nov 9 - Nov 10
Total with taxes and fees
Modern Mountain Cottage with Hot Tub, Fire Pit Nestled in the Woods of Gerrardstown, WV
Exterior
Spectacular Cottage Perfect for Groups and Water Activities in Luray, Virginia
Spectacular Cottage Perfect for Groups and Water Activities in Luray, Virginia
2.0 star property
$240 nightly
The price is $245
Nov 5 - Nov 6
Total with taxes and fees
Spectacular Cottage Perfect for Groups and Water Activities in Luray, Virginia
Terrace/patio
Wild Hare Cottage
Wild Hare Cottage
10.0 out of 10, Exceptional, (9)
"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
Dec 3 - Dec 4
Total with taxes and fees
Wild Hare Cottage
Terrace/patio
Woodsy Retreat with a Hot Tub and Seasonal Views!
Woodsy Retreat with a Hot Tub and Seasonal Views!
9.8 out of 10, Exceptional, (23)
"This property was everything we hoped for in a weekend getaway home! So clean, beautifully decorated, and decked out with everything we wanted and more. We will definitely be booking with Mountain Mama again. "
United States
Carly H.
$305 nightly
The price is $340
Nov 5 - Nov 6
Total with taxes and fees
Woodsy Retreat with a Hot Tub and Seasonal Views!
1 bedroom, WiFi, bed sheets
The Carriage House at Carrot Top Cottage
The Carriage House at Carrot Top Cottage
9.8 out of 10, Exceptional, (42)
"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
Nov 11 - Nov 12
Total with taxes and fees
The Carriage House at Carrot Top Cottage
Exterior
Peaceful Hedgesville Cottage with Hot Tub, Fireplace & Resort Amenities in West Virginia
Peaceful Hedgesville Cottage with Hot Tub, Fireplace & Resort Amenities in West Virginia
2.0 star property
$325 nightly
The price is $362
Nov 5 - Nov 6
Total with taxes and fees
Peaceful Hedgesville Cottage with Hot Tub, Fireplace & Resort Amenities in West Virginia
Property grounds
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
9.6 out of 10, Exceptional, (7)
"It was a great place to starve whole experience was perfect. "
United States
Jaime B.
$344 nightly
The price is $392
Nov 6 - Nov 7
Total with taxes and fees
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
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

Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

10/10 Excellent
"Clean room, great location. "
Evan 2-night trip
Posted 1 day ago
Travelodge by Wyndham Winchester

Find out more about Winchester

Winchester Cottages information

Number of reviews
375
Accommodation
192 Cottages
Lowest Price
$170
Highest Price
$1,850

Frequently asked questions

Why book your cottage in Winchester with Expedia?
We think that vacations should be simple, so if you're in search of cottages in Winchester at a competitive price, Expedia has got your back. Keep costs down and check in to a cheap option far away from the city rush, or splurge on an upmarket cottage to spoil your favorite people.
How can I find cheap cottages in Winchester?
The easiest way to locate cheap cottages in Winchester is with Expedia's useful filter tool. Narrow your search results by star rating, amenities and budget to snag awesome prices in just a few keystrokes.
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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