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Check prices for these dates

Next weekend
11 Apr - 13 Apr
In two weeks
18 Apr - 20 Apr
In one month
2 May - 4 May
In two months
30 May - 1 Jun

Compare 184 Cottages in Winchester with updated reviews, rates, and availability.

Secluded, Cozy Cottage in the Shenandoah Valley

Secluded, Cozy Cottage in the Shenandoah Valley

10.0 out of 10, Exceptional, (168)
"Private and cute cottage in the woods. Shenandoah valley is beautiful!"
Secluded, Cozy Cottage in the Shenandoah Valley
Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi
Bar (on property)

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

9.8 out of 10, Exceptional, (25)
"This was a good little cozy cottage for a weekend away with friends. Convienient to wineries and breweries. Comfy and Cozy for a 2 day getaway!"
The price is AED 1,192
AED 2,510 total
includes taxes & fees
16 Apr - 17 Apr
Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi
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, (53)
"Second time here and I just love it. Such a cute place and location. I'll be back for sure."
The price is AED 588
AED 1,186 total
includes taxes & fees
6 Apr - 7 Apr
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*
Cozy Retreat - Hot tub + Mountain Views + Pets
Smart TV, stereo

Cozy Retreat - Hot tub + Mountain Views + Pets

10.0 out of 10, Exceptional, (25)
"Great stay! Attentive and caring host! We will definitely be coming back. "
The price is AED 265
AED 892 total
includes taxes & fees
4 Apr - 5 Apr
Cozy Retreat - Hot tub + Mountain Views + Pets
The Carriage House at Carrot Top Cottage
Aerial view

The Carriage House at Carrot Top Cottage

9.8 out of 10, Exceptional, (35)
"My girlfriend and I will definitely be coming back to this spot when we visit Harpers Ferry again. Frederick MD is also just 20 mins away for more food options. "
The price is AED 386
AED 655 total
includes taxes & fees
15 Apr - 16 Apr
The Carriage House at Carrot Top Cottage
Carrot Top Cottage surrounded by National Park
Exterior

Carrot Top Cottage surrounded by National Park

10.0 out of 10, Exceptional, (35)
"The house is adorable inside and out! Pulling up to the house you just know that you are in for a treat! The decor is absolutely perfect. The home is very comfortable and has all that you need for a exceptional stay...and then some. Walking the streets and admiring the beautiful old homes is so relaxing! This Is Our New " Happy Place!""
Carrot Top Cottage surrounded by National Park
Charming 2-Bedroom Cottage in Loudoun Co, VA on 12 Gorgeous Acres w/ 2-Acre Pond
Fridge, microwave, oven, stovetop

Charming 2-Bedroom Cottage in Loudoun Co, VA on 12 Gorgeous Acres w/ 2-Acre Pond

Charming 2-Bedroom Cottage in Loudoun Co, VA on 12 Gorgeous Acres w/ 2-Acre Pond
18th Century Stone Cottage minutes from historic Middleburg
Exterior

18th Century Stone Cottage minutes from historic Middleburg

10.0 out of 10, Exceptional, (38)
"Very clean, Beautiful Property. Super peaceful. Will come back in the summer to enjoy town summer time activities. "
The price is AED 1,010
AED 1,446 total
includes taxes & fees
6 Apr - 7 Apr
18th Century Stone Cottage minutes from historic Middleburg
Historical cottage in the town of Paris
Exterior

Historical cottage in the town of Paris

9.8 out of 10, Exceptional, (39)
"We loved our stay at the cottage! Will is a wonderful host!"
Historical cottage in the town of Paris
Cozy cottage with a beautiful waterfront view. Pet friendly! 45 min from DC.
Terrace/patio

Cozy cottage with a beautiful waterfront view. Pet friendly! 45 min from DC.

9.2 out of 10, Wonderful, (7)
"Overall we loved the place. The beds slept great even the sofa bed. They had a nice thick memory foam for it. The grounds were beautiful and we had a garage to pull into to get out of the weather. The only complaint one of the girls had was the shower was not for big girls. It was a tight squeeze but we totally enjoyed it and will rebook in warmer weather. "
Cozy cottage with a beautiful waterfront view. Pet friendly! 45 min from DC.
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 AED 782
AED 2,173 total
includes taxes & fees
6 Apr - 7 Apr
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
Dining

Riverfront! Shenandoah River! Sleeps 4! New Hot Tub

9.6 out of 10, Exceptional, (10)
"Excellent place to stay. Shelly is an excellent host. Nice location "
The price is AED 1,313
AED 1,878 total
includes taxes & fees
4 Apr - 5 Apr
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
Cottage w/ Hot Tub and 100-Mile Valley Views!
Outdoor spa tub

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

10.0 out of 10, Exceptional, (15)
"The view of this house is amazing! Absolutely beautiful!"
The price is AED 382
AED 1,404 total
includes taxes & fees
6 Apr - 7 Apr
Cottage w/ Hot Tub and 100-Mile Valley Views!
Royal Heritage Home @ Historic Leesburg
Fridge, microwave, oven, stovetop

Royal Heritage Home @ Historic Leesburg

9.8 out of 10, Exceptional, (25)
"The house was simply perfect for our stay. All you can ask for. Our daughter’s wedding was near by and wanted to explore downtown Leesburg as well. Everything was walkable and so many places to explore. Michael the host was amazing and hospitality 5 stars!!! We will definitely book again when in the area. "
The price is AED 775
AED 1,719 total
includes taxes & fees
7 Apr - 8 Apr
Royal Heritage Home @ Historic Leesburg
Secluded Cottage on 10 Acres. Close to Shen. Natl. Park and Luray Caverns
Property grounds

Secluded Cottage on 10 Acres. Close to Shen. Natl. Park and Luray Caverns

9.6 out of 10, Exceptional, (207)
"Always a wonderful experience! A perfect retreat to relax and unwind. Hosts are always so gracious and accommodating. Will be back again!"
Secluded Cottage on 10 Acres. Close to Shen. Natl. Park and Luray Caverns
4 BDRM, lots of beds! Cozy Wooded Cottage.
Outdoor pool

4 BDRM, lots of beds! Cozy Wooded Cottage.

9.2 out of 10, Wonderful, (118)
"From the moment we booked, Carolyn was very communicative and helpful throughout our entire stay - providing updates of checking in/out, local entertainment & activities, touching base throughout our visit to ensure all was well. Treetops was spacious for our family of 9 - plenty of sleeping accommodations, towels, quiet nooks for reading and conversing, firewood for evening fires…There’s an additional sunroom and large deck which would be fun if we’d been there in the summer months. The large...
4 BDRM, lots of beds! Cozy Wooded Cottage.
Beautiful 360 views!
Exterior

Beautiful 360 views!

10.0 out of 10, Exceptional, (173)
"We had a wonderful time staying here. Every morning was amazing with the sun rises, the space was cozy and comfy. We fully enjoyed ourselves."
Beautiful 360 views!
Quiet Cottage on Five+ Acres of Woods Close to All That Berkeley Springs Offers
Exterior detail

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

9.8 out of 10, Exceptional, (7)
"Good place for a nice quite weekend."
The price is AED 650
AED 1,550 total
includes taxes & fees
4 Apr - 5 Apr
Quiet Cottage on Five+ Acres of Woods Close to All That Berkeley Springs Offers
Lake View Retreat - Cottage Near a Peaceful Lake!
Property grounds

Lake View Retreat - Cottage Near a Peaceful Lake!

9.6 out of 10, Exceptional, (17)
"Beautiful location to relax and enjoy friends. This house was huge. Plenty of room for the 3 of us...could have been 8, lol. "
The price is AED 367
AED 1,321 total
includes taxes & fees
8 Apr - 9 Apr
Lake View Retreat - Cottage Near a Peaceful Lake!
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!!"
The price is AED 680
AED 1,191 total
includes taxes & fees
6 Apr - 7 Apr
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
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

Star view cabin-Riverfront
Property grounds

Star view cabin-Riverfront

9.8 out of 10, Exceptional, (308)
"We thoroughly enjoyed our stay here. From the moment you walk into the cabin, the views are spectacular and the surroundings are relaxing. We had a wonderful time and can’t wait to come back in the warmer weather to enjoy the outdoors more within a quick drive of lots of parks and scenic views Very clean and well appointed top-notch. "
Star view cabin-Riverfront
Dreamtime - Modern A-frame Cabin w/ Hot tub
Outdoor dining

Dreamtime - Modern A-frame Cabin w/ Hot tub

10.0 out of 10, Exceptional, (36)
"We stayed here for our anniversary and had a great time. Hosts were very responsive when we had a question about the hot tub, "
The price is AED 1,062
AED 1,329 total
includes taxes & fees
24 Apr - 25 Apr
Dreamtime - Modern A-frame Cabin w/ Hot tub
Riverside cottage, minutes from historic Harpers Ferry! Private river access!
Miscellaneous

Riverside cottage, minutes from historic Harpers Ferry! Private river access!

9.8 out of 10, Exceptional, (92)
"We enjoyed a very comfortable stay. House was very clean and cozy. We were a little surprised by the close proximity to other homes, but other than that it was as described. Hosts were easy to communicate with and created a very welcoming space for us. Thank you! "
Riverside cottage, minutes from historic Harpers Ferry! Private river access!
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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