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Check prices for these dates

Next weekend
21 Nov - 23 Nov
In two weeks
28 Nov - 30 Nov
In one month
12 Dec - 14 Dec
In two months
9 Jan - 11 Jan

Featured Cottages in Winchester

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

Front Royal
10.0 out of 10, Exceptional, (2)
"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.
The price is NZ$699
includes taxes & fees
19 Nov - 20 Nov
"Prima BnB" a Superb 4-bedroom cottage on the mountain near Front Royal
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
Front Royal
9.8 out of 10, Exceptional, (8)
"Love the view and beautiful appointed decor throughout the home…"
United States
Lynn M.
The price is NZ$748
includes taxes & fees
23 Nov - 24 Nov
The Vue - Mountain top hot tub overlooking the Shenandoah River
Outdoor spa tub
Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi

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

Boyce
9.8 out of 10, Exceptional, (29)
"My husband and I stayed here the week before Christmas. Once we arrived, the first thing I noticed was the Christmas tree in the living room. I was very pleased the house was decorated. We had a wonderful stay and would definitely come back. The train didn’t bother us at all. Very quiet. Thank you for making our stay magical!"
United States
Andrea M.
The price is NZ$1,000
includes taxes & fees
24 Nov - 25 Nov
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
Leesburg
The price is NZ$3,290
includes taxes & fees
11 Nov - 12 Nov
'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

Fort Valley
9.8 out of 10, Exceptional, (52)
"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.
The price is NZ$424
includes taxes & fees
11 Nov - 12 Nov
Cozy Retreat - Hot tub + Mountain Views + Pets
Exterior
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, (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.
The price is NZ$537
includes taxes & fees
12 Nov - 13 Nov
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Terrace/patio
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.
The price is NZ$424
includes taxes & fees
3 Dec - 4 Dec
Wild Hare Cottage
1 bedroom, WiFi, bed sheets
The Carriage House at Carrot Top Cottage

The Carriage House at Carrot Top Cottage

Harpers Ferry
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.
The price is NZ$303
includes taxes & fees
11 Nov - 12 Nov
The Carriage House at Carrot Top Cottage
Outdoor dining
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)
"Loved this house for relaxing, enjoying nature and reconnecting with friends!"
United States
Ellen P.
The price is NZ$808
includes taxes & fees
13 Nov - 14 Nov
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
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

Berkeley Springs
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.
The price is NZ$744
includes taxes & fees
11 Nov - 12 Nov
Quiet Cottage on Five+ Acres of Woods Close to All That Berkeley Springs Offers
Property grounds
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)
"Was really able to relax and enjoy during our brief stay. Would come again."
United States
Emily B.
The price is NZ$647
includes taxes & fees
12 Nov - 13 Nov
Lake View Retreat - Cottage Near a Peaceful Lake!
Property grounds
Peaceful Lakefront Cottage with Mountain Views!

Peaceful Lakefront Cottage with Mountain Views!

Harpers Ferry
9.8 out of 10, Exceptional, (29)
"Really enjoyed stay home was great "
United States
zachary b.
The price is NZ$657
includes taxes & fees
20 Nov - 21 Nov
Peaceful Lakefront Cottage with Mountain Views!
Exterior
Peaceful Waterfall House -- 2 bedroom hidden treasure

Peaceful Waterfall House -- 2 bedroom hidden treasure

Berkeley Springs
9.6 out of 10, Exceptional, (10)
"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.
The price is NZ$560
includes taxes & fees
11 Nov - 12 Nov
Peaceful Waterfall House -- 2 bedroom hidden treasure
Property grounds
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, (7)
"It was a great place to starve whole experience was perfect. "
United States
Jaime B.
The price is NZ$698
includes taxes & fees
16 Nov - 17 Nov
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Terrace/patio
Woodsy Retreat with a Hot Tub and Seasonal Views!

Woodsy Retreat with a Hot Tub and Seasonal Views!

Harpers Ferry
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.
The price is NZ$611
includes taxes & fees
13 Nov - 14 Nov
Woodsy Retreat with a Hot Tub and Seasonal Views!
Property grounds
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 place to stay with our family of 4. The house was clean and had everything we needed. The view is beautiful and the neighborhood is nice and quiet."
United States
James D.
The price is NZ$679
includes taxes & fees
20 Nov - 21 Nov
Cottage w/ Hot Tub and 100-Mile Valley Views!
Outdoor dining
Cozy Mountain Retreat | Hot Tub & Fire Pit & Dogs

Cozy Mountain Retreat | Hot Tub & Fire Pit & Dogs

Harpers Ferry
9.4 out of 10, Exceptional, (6)
"We really enjoyed our stay, the four bedrooms gave us lots of space. The hot tub was great and we enjoyed the balcony, too. Very close to lots of fun wineries and Harper’s Ferry. Quiet location on a road with other houses. I’d recommend bringing extra towels and a few wine glasses if you’re drinking nice wine. Lots of thoughtful touches — games, fireplace, spacious kitchen. It was great!"
United States
Renee P.
The price is NZ$1,120
includes taxes & fees
11 Nov - 12 Nov
Cozy Mountain Retreat | Hot Tub & Fire Pit & Dogs
Fridge, microwave, oven, stovetop
Royal Heritage Home @ Historic Leesburg

Royal Heritage Home @ Historic Leesburg

Leesburg's Old and Historic District
9.8 out of 10, Exceptional, (37)
"Beautiful home, three full bathrooms were all updated and large. Very clean. Walking distance to great restaurants and shops. We had a great weekend!"
United States
Alexa F.
The price is NZ$848
includes taxes & fees
11 Nov - 12 Nov
Royal Heritage Home @ Historic Leesburg
Exterior
18th Century Stone Cottage minutes from historic Middleburg

18th Century Stone Cottage minutes from historic Middleburg

Middleburg
10.0 out of 10, Exceptional, (51)
"What a peaceful place and wonderful views."
United States
Debbie M.
The price is NZ$706
includes taxes & fees
17 Nov - 18 Nov
18th Century Stone Cottage minutes from historic Middleburg
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

SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester

10/10 Excellent
"Clean room, nice area, friendly staff "
chad 1-night trip
Posted 1 day ago
SpringHill Suites by Marriott Winchester

Find out more about Winchester

Winchester Cottages information

Number of reviews
395
Accommodation
192 Cottages
Lowest Price
NZ$303
Highest Price
NZ$3,290

Frequently asked questions

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 Harbour 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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