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Check prices for these dates

Next weekend
2 Jum. I - 4 Jum. I
In two weeks
9 Jum. I - 11 Jum. I
In one month
23 Jum. I - 25 Jum. I
In two months
20 Jum. II - 22 Jum. II

Compare 180 Cottages in Winchester with updated reviews, rates, and availability.

Secluded, Cozy Cottage in the Shenandoah Valley
Property grounds

Secluded, Cozy Cottage in the Shenandoah Valley

10.0 out of 10, Exceptional, (170)
"This was the perfect get away. The cottage was clean, comfortable, and had all the amenities we needed. "
Secluded, Cozy Cottage in the Shenandoah Valley
Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi
Outdoor spa tub

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

9.8 out of 10, Exceptional, (26)
"Good location. Large fenced in yard. Plenty of room. Would book again."
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, (55)
"Sweet l, well located property with everything you need for a stay! "
The price is SAR 600
SAR 1,220 total
includes taxes & fees
27 Apr - 28 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 328
SAR 987 total
includes taxes & fees
30 Apr - 1 May
Cozy Retreat - Hot tub + Mountain Views + Pets
The Carriage House at Carrot Top Cottage
1 bedroom, WiFi, bed sheets

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 SAR 394
SAR 668 total
includes taxes & fees
27 Apr - 28 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

10.0 out of 10, Exceptional, (1)
"This was a good place to stay for two guys day hiking in the AT. It is clean, quiet, comfortable, and in a very good location. It had everything we needed."
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, (39)
"Great little cozy cottage near Middleburg with great outdoor space and all necessary amenities. Booking, check-in and communication with owner were excellent. "
The price is SAR 1,032
SAR 1,477 total
includes taxes & fees
27 Apr - 28 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, (40)
"we enjoy our stay everytime"
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.

9.4 out of 10, Exceptional, (8)
"Convenient to where I needed to be. Nice property. Dogs loved the property"
Cozy cottage with a beautiful waterfront view. Pet friendly! 45 min from DC.
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Property grounds

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 574
SAR 1,908 total
includes taxes & fees
8 May - 9 May
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
Outdoor spa tub

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 1,889 total
includes taxes & fees
7 May - 8 May
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 1,419 total
includes taxes & fees
30 Apr - 1 May
Cottage w/ Hot Tub and 100-Mile Valley Views!
Royal Heritage Home @ Historic Leesburg
Fridge, microwave, oven, stovetop

Royal Heritage Home @ Historic Leesburg

9.6 out of 10, Exceptional, (27)
"The place is great! Clean, comfortable, close to downtown. The host was very responsive and friendly. "
The price is SAR 791
SAR 1,782 total
includes taxes & fees
28 Apr - 29 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, (174)
"The Cottage at Ravens Roost was a wonderful venue for us to rest as we explored the Shenandoah Valley. The dogs on the property were so friendly and adorable! We loved watching the horses in the mornings. Not to mention the farm fresh eggs and the raspberry lemon bread that we were surprised with when we arrived! Excellent hosts, excellent stay. Thank you both!!!"
Beautiful 360 views!
Quiet Cottage on Five+ Acres of Woods Close to All That Berkeley Springs Offers
Property grounds

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 1,583 total
includes taxes & fees
28 Apr - 29 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 SAR 375
SAR 1,345 total
includes taxes & fees
27 Apr - 28 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 1,225 total
includes taxes & fees
27 Apr - 28 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, (312)
"This was absolutely just what we needed! The view was so breathtaking and the serenity of this place is to die for! I was very pleased with our stay here and we will definitely be returning de"
Star view cabin-Riverfront
Dreamtime - Modern A-frame Cabin w/ Hot tub
Smart TV, fireplace, books

Dreamtime - Modern A-frame Cabin w/ Hot tub

10.0 out of 10, Exceptional, (37)
"Lovely cabin, very clean and well maintained. A girlfriend weekend and we wanted a great place to hang out and this fit the bill. We never got the TV to work but could be user error. "
The price is SAR 1,084
SAR 1,361 total
includes taxes & fees
30 Apr - 1 May
Dreamtime - Modern A-frame Cabin w/ Hot tub
Riverside cottage, minutes from historic Harpers Ferry! Private river access!
Terrace/patio

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

9.8 out of 10, Exceptional, (96)
"1st time visiting the East Coast and our stay in this beautiful, quaint home was perfect! We felt the warm welcome as soon as we walked in and enjoyed the thoughtful complimentary items. The house was close to Harper’s Ferry & neighboring cities, lots to do in close proximity. Enjoyed the porch on our last night as we sat and listened to the rain and the sound of the river. Host was very attentive & prompt. Definitely recommend as a place to stay for a small family!"
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.