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Check prices for these dates

Next weekend
4 Rab. II - 6 Rab. II
In two weeks
11 Rab. II - 13 Rab. II
In one month
25 Rab. II - 27 Rab. II
In two months
23 Jum. I - 25 Jum. I

Compare 180 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 SAR 1,294
SAR 2,661 total
includes taxes & fees
27 Mar - 28 Mar
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, (51)
"This home is just lovely and is in a great location. Neighbors are friendly and I had to call AAA for a flat tire and the local tow truck driver was an earth angel. Can't wait to stay here again!"
The price is SAR 600
SAR 1,211 total
includes taxes & fees
8 Apr - 9 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 SAR 270
SAR 915 total
includes taxes & fees
30 Mar - 31 Mar
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, (34)
"We couldn’t have asked for a more perfect spot for our quick get-a-way. So close to the AT and food and drinks. Will definitely be back!"
The price is SAR 394
SAR 668 total
includes taxes & fees
1 Apr - 2 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, (34)
"Very well stocked, clean, great communication from host, convenient, would definitely recommend "
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 SAR 1,032
SAR 1,477 total
includes taxes & fees
27 Mar - 28 Mar
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 SAR 413
SAR 1,683 total
includes taxes & fees
26 Mar - 27 Mar
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 SAR 1,341
SAR 1,906 total
includes taxes & fees
26 Mar - 27 Mar
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 SAR 375
SAR 1,408 total
includes taxes & fees
31 Mar - 1 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, (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 SAR 792
SAR 1,782 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 SAR 664
SAR 1,575 total
includes taxes & fees
26 Mar - 27 Mar
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 SAR 435
SAR 1,431 total
includes taxes & fees
10 Apr - 11 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 SAR 694
SAR 1,221 total
includes taxes & fees
26 Mar - 27 Mar
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, (307)
"I recently stayed at this cabin over the weekend, and it was an unforgettable experience. The views were absolutely breathtaking — whether it was sunrise over the mountains or relaxing in the evening with a stunning sunset, the scenery was incredible from every angle.The cabin itself was just as impressive. It was beautifully designed, immaculately clean, and had all the comforts of home. From cozy furniture to thoughtful amenities, everything was perfect. The peaceful surroundings made it the...
Star view cabin-Riverfront
Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River
2 bedrooms, WiFi, bed sheets

Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River

9.6 out of 10, Exceptional, (343)
"Amazing view, and very quiet. Exactly what i was looking for. "
Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River
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 SAR 1,084
SAR 1,330 total
includes taxes & fees
24 Apr - 25 Apr
Dreamtime - Modern A-frame Cabin 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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