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Check prices for these dates

Next weekend
31 Jan - 2 Feb
In two weeks
7 Feb - 9 Feb
In one month
21 Feb - 23 Feb
In two months
21 Mar - 23 Mar
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*
Smart TV, books

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

9.8 out of 10, Exceptional, (46)
"This is close to the thornton gap entrance. With the shades open, it's a very sunny house. The house is right in the town of Luray, so you're close to your neighbors, but they're quiet. If possible, the owners should put a curtain in front of the front glass door."
The price is HK$1,245
HK$2,530 total
includes taxes & fees
12 Feb - 13 Feb
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*
Carrot Top Cottage surrounded by National Park
Exterior

Carrot Top Cottage surrounded by National Park

10.0 out of 10, Exceptional, (31)
"Unique little cottage in a historic neighborhood within walking distance to Harpers Ferry!"
Carrot Top Cottage surrounded by National Park
Cozy Retreat - Hot tub + Mountain Views + Pets
Smart TV, stereo

Cozy Retreat - Hot tub + Mountain Views + Pets

10.0 out of 10, Exceptional, (24)
"Lovely spot. Definitely Recommend it! "
The price is HK$641
HK$2,037 total
includes taxes & fees
30 Jan - 31 Jan
Cozy Retreat - Hot tub + Mountain Views + Pets
18th Century Stone Cottage minutes from historic Middleburg
Exterior

18th Century Stone Cottage minutes from historic Middleburg

10.0 out of 10, Exceptional, (35)
"Lovely cottage in ideal local. Host was super accommodating and generous with provisions and answers to multiple questions. "
The price is HK$2,140
HK$3,064 total
includes taxes & fees
26 Jan - 27 Jan
18th Century Stone Cottage minutes from historic Middleburg
Beautiful 360 views!
Exterior

Beautiful 360 views!

10.0 out of 10, Exceptional, (172)
"This is our third stay at this cottage. We wouldn't stay anywhere else."
Beautiful 360 views!
Bear Chase Cottage
Property grounds

Bear Chase Cottage

10.0 out of 10, Exceptional, (33)
"The staff and property were wonderful. Everyone was so helpful; it was nice to be able to walk up to the restaurant and see the amazing mountain views with fire pits and lookouts. It was an added surprise to see the home decorated for the holidays! "
Bear Chase Cottage
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Interior

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

10.0 out of 10, Exceptional, (1)
"We had a a great experience at this cabin getaway. The property was immaculate, cozy and well-equipped. The host was incredibly responsive and thoughtful. We can't wait to come back!"
The price is HK$1,945
HK$3,300 total
includes taxes & fees
29 Jan - 30 Jan
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Charming Cottage in Purcellville on 12 Gorgeous Acres with 2 Acre Stocked Pond
Exterior

Charming Cottage in Purcellville on 12 Gorgeous Acres with 2 Acre Stocked Pond

Charming Cottage in Purcellville on 12 Gorgeous Acres with 2 Acre Stocked Pond
Lovettsville Cottage in Heart of Wine Country
TV, Netflix, streaming services

Lovettsville Cottage in Heart of Wine Country

9.8 out of 10, Exceptional, (31)
"We stayed here for a few days over the Thanksgiving holiday. It was cozy, comfortable, and had all the great comforts of a home away from home. "
Lovettsville Cottage in Heart of Wine Country
The Carriage House at Carrot Top Cottage
Aerial view

The Carriage House at Carrot Top Cottage

9.8 out of 10, Exceptional, (30)
"We had a wonderful stay at the Carriage House. It was very comfortable. The location is perfectfor exploring historic Harper’s Ferry and the hiking trails. "
The Carriage House at Carrot Top Cottage
Royal Heritage Home @ Historic Leesburg
Fridge, microwave, oven, stovetop

Royal Heritage Home @ Historic Leesburg

9.8 out of 10, Exceptional, (24)
"We stayed at this property during our annual visit to Leesburg. We enjoy the downtown area (easy to walk) and catching an Uber to the local vineyards! House was perfect for our group of 5. Majority of our time at the house was spent sleeping, but we all felt comfortable and had enough space. Three bathrooms were great! "
The price is HK$1,642
HK$3,642 total
includes taxes & fees
3 Feb - 4 Feb
Royal Heritage Home @ Historic Leesburg
Chic Hedgesville Cabin w/ Golf Course Views!
Interior

Chic Hedgesville Cabin w/ Golf Course Views!

3.0 star property
8.0 out of 10, Very good, (1)
"My daughter lives close to this property. We picked up our 3 grandchildren and took our 2 dogs with us. We has a great time and the place was really fun. The kids especially enjoyed the garage with all the fun games !"
Chic Hedgesville Cabin w/ Golf Course Views!
Riversong Luxe Cabin w/ Fire Pit on North River
Interior

Riversong Luxe Cabin w/ Fire Pit on North River

3.0 star property
Riversong Luxe Cabin w/ Fire Pit on North River
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Exterior

Amazing dog-friendly cottage. Walk 2 Harpers Ferry

2.0 star property
9.8 out of 10, Exceptional, (9)
"What a lovely, cozy, clean property! The location was in the heart of Harper’s Ferry. Everything advertised was exactly as described, even nicer, inside and out! Cathy, our property manager was communicative and helpful. We will be back!!"
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
COZY CABIN. One room cottage with loft.
Outdoor dining

COZY CABIN. One room cottage with loft.

10.0 out of 10, Exceptional, (3)
"My friend and I came up to do some biking on the C&O and western Maryland rail trail, and to also do some hiking! Weather was perfect and the cozy cabin fit all our needs perfectly!. Very cutely decorated…Clean…Beautiful views. The host even invited us for dinner one night if we wanted to join them! Check in was easy and there was even a few snacks and waters provided. All very thoughtful gestures. We were warned that there was a two mile stretch of rougher road leading up to the cabin but...
COZY CABIN. One room cottage with loft.
Close to Hiking | Hot Tub | Fire Pit | Pets OK
Outdoor spa tub

Close to Hiking | Hot Tub | Fire Pit | Pets OK

8.0 out of 10, Very good, (1)
"We enjoyed a post-holiday family gathering staying at the house. The house was close to hiking and historic Harpers Ferry. "
Close to Hiking | Hot Tub | Fire Pit | Pets OK
Spectacular Cottage with Shenandoah River Views
Outdoor spa tub

Spectacular Cottage with Shenandoah River Views

10.0 out of 10, Exceptional, (206)
"Overall this was a great place for a getaway with my husband! The cottage is very well done. It's incredibly clean, well stocked, and the furnishings and supplies are quite nice. The view is absolutely gorgeous and very peaceful. The "downsides" were that a bridge is under construction until late 2025 in the area so it takes longer to get to any stores. The last 5 minutes to the property are complete gravel roads and the very last part is a little steep. It's secluded but there is a house next...
Spectacular Cottage with Shenandoah River Views
Pet-friendly Virginia Cabin: 3 Mi to Luray Caverns
Interior

Pet-friendly Virginia Cabin: 3 Mi to Luray Caverns

3.0 star property
10.0 out of 10, Exceptional, (1)
Pet-friendly Virginia Cabin: 3 Mi to Luray Caverns
RIVERKEEPER INN, Waterfront Property on the Potomac River
View from property

RIVERKEEPER INN, Waterfront Property on the Potomac River

9.2 out of 10, Wonderful, (116)
"The hosts are wonderful. I had a great time in their cozy, clean and beautiful place. Highly recommend for a visit to beautiful and historic WV.I particularly appreciated their fondness for dogs. Mine had a great time too!"
RIVERKEEPER INN, Waterfront Property on the Potomac River
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Outdoor dining

Art Docko - Lakefront Artist Retreat w/ Hot Tub!

10.0 out of 10, Exceptional, (16)
"Check in was seamless. The place was perfect for three couples with all the master suites. "
The price is HK$1,067
HK$3,803 total
includes taxes & fees
30 Jan - 31 Jan
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
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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Other property types in Winchester

Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails

Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails

9.8 out of 10, Exceptional, (174)
"The location was exactly what we needed and wanted. If you want to totally relax, get semi off the grid, this is your place. Take a hike and take it all in. Thank you to our hosts for making such a great property available."
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
Dreamtime - Modern A-frame Cabin w/ Hot tub
Outdoor dining

Dreamtime - Modern A-frame Cabin w/ Hot tub

10.0 out of 10, Exceptional, (34)
"The cabin was in a beautiful community and setting with a fabulous outdoor area facing the woods. Many amenities in the home that made our stay easy with nicely renovated interior. Owner was very willing and able to offer help with anything and was receptive to feedback. Thank you!"
The price is HK$2,326
HK$2,919 total
includes taxes & fees
6 Feb - 7 Feb
Dreamtime - Modern A-frame Cabin w/ Hot tub
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
Outdoor dining

Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails

9.8 out of 10, Exceptional, (211)
"Highly recommend staying here. We even had a little snow! Family friendly and cozy. "
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
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.

Frequently asked questions

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How can I find cheap cottages in Winchester?
Expedia can help you locate cheap cottages in Winchester. To reserve a fantastic stay in a matter of clicks, try out our handy filter tool to tailor your search results by budget, amenities and star rating.
What is there to do in Winchester near my cottage?
You’ll find tons of fantastic things to sink your teeth into in Winchester. You won’t want to miss attractions like Museum of the Shenandoah Valley, Shenandoah Valley Discovery Museum and Bright Box Theatre. Winchester Little Theatre, Shenandoah University and Jim Barnett Park are other must-see’s.