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

The Carriage House at Carrot Top Cottage

9.8 out of 10, Exceptional, (36)
"We enjoyed the stay and it was an easy walk to the places we wanted to go!"
The price is AED 386
AED 655 total
includes taxes & fees
9 Jun - 10 Jun
The Carriage House at Carrot Top Cottage

Cozy Retreat - Hot tub + Mountain Views + Pets

9.6 out of 10, Exceptional, (35)
"Great time at a great place"
The price is AED 340
AED 979 total
includes taxes & fees
15 Jun - 16 Jun
Cozy Retreat - Hot tub + Mountain Views + Pets

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

10.0 out of 10, Exceptional, (61)
"We had a long weekend visit to Luray and the central Shenandoah Valley and this was the perfect spot to stay. Beautiful, well maintained accommodations. We loved it."
The price is AED 529
AED 1,135 total
includes taxes & fees
5 Jun - 6 Jun
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*

18th Century Stone Cottage minutes from historic Middleburg

10.0 out of 10, Exceptional, (41)
"Nice place! Clean, beautiful, and located just two miles from town. "
The price is AED 1,010
AED 1,431 total
includes taxes & fees
23 Jun - 24 Jun
18th Century Stone Cottage minutes from historic Middleburg

Amazing dog-friendly cottage. Walk 2 Harpers Ferry

2.0 star property
10.0 out of 10, Exceptional, (13)
"We loved our stay. The location was central to everything we did; the car stayed in the driveway for almost our entire trip, and the yard is perfect for dogs. The house itself is exactly as shown in the pcs. Highly recommended "
The price is AED 679
AED 1,184 total
includes taxes & fees
15 Jun - 16 Jun
Amazing dog-friendly cottage. Walk 2 Harpers Ferry

Firehouse Cottage | Walk to all of downtown HF

9.0 out of 10, Wonderful, (2)
"Walking is easy to downtown. Property is quiet location. Enjoyed our stay without ouo"
The price is AED 514
AED 870 total
includes taxes & fees
5 Jun - 6 Jun
Firehouse Cottage | Walk to all of downtown HF

Charming Cottage, Fresh Eggs, Friendly Pets AND Pet Friendly!

10.0 out of 10, Exceptional, (177)
"I loved my stay! The cottage was clean and cozy, and being able to use the hot tub was amazing. Ed and Betsy and all the animals were welcoming. The cottage was especially beautiful during sunrise. A very peaceful environment to stay in. "
Charming Cottage, Fresh Eggs, Friendly Pets AND Pet Friendly!

Peaceful Lakefront Cottage with Mountain Views!

9.8 out of 10, Exceptional, (26)
"Wintertime visit. Very peaceful. "
Peaceful Lakefront Cottage with Mountain Views!

Wild & Cozy | Harpers Ferry Mountain Escape

10.0 out of 10, Exceptional, (1)
"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!"
The price is AED 458
AED 1,508 total
includes taxes & fees
10 Jun - 11 Jun
Wild & Cozy | Harpers Ferry Mountain Escape

Cozy Stone Cottage in Round Hill, VA

10.0 out of 10, Exceptional, (3)
"We had an excellent stay at cottage! It was perfect for a short weekend away with girlfriends. It was quaint and historic but didn't lack modern day comforts. Highly recommend for anyone looking for a few days away, with easy access to all Round Hill & Purcellville has to offer. "
Cozy Stone Cottage in Round Hill, VA

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

9.8 out of 10, Exceptional, (26)
"We enjoyed our stay. Communications were great and the house was as described. No issues."
Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi

Carrot Top Cottage surrounded by National Park

10.0 out of 10, Exceptional, (35)
"This cottage was like a home away from home! It was the perfect location and spotless. We would definitely stay again and recommend to anyone "
Carrot Top Cottage surrounded by National Park

Royal Heritage Home @ Historic Leesburg

9.6 out of 10, Exceptional, (28)
"Cute place, well cared for and a great location. Walking distance to good restaurants."
The price is AED 896
AED 1,858 total
includes taxes & fees
19 Jun - 20 Jun
Royal Heritage Home @ Historic Leesburg

Brookside Cottage is a beautiful open concept doll house stay for two.

10.0 out of 10, Exceptional, (12)
"Close to town, great location, nice selection of restaurants but the town shuts down early. Bath house and Atasia spa both very nice. Recommend a visit for a day or one night visit."
Brookside Cottage is a beautiful open concept doll house stay for two.

Historical cottage in the town of Paris

9.8 out of 10, Exceptional, (41)
"Had a wonderful stay - - beautiful country and delightful cottage."
Historical cottage in the town of Paris

Lake View Retreat - Cottage Near a Peaceful Lake!

9.6 out of 10, Exceptional, (17)
"Was really able to relax and enjoy during our brief stay. Would come again."
The price is AED 367
AED 1,324 total
includes taxes & fees
11 Jun - 12 Jun
Lake View Retreat - Cottage Near a Peaceful Lake!

Coolfont 4 BDRM, lots of beds! Cozy Wooded Cottage.

9.2 out of 10, Wonderful, (119)
"Perfect house and setting for a friend group. Lots of comfortable spaces and great setting!"
Coolfont 4 BDRM, lots of beds! Cozy Wooded Cottage.

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

9.4 out of 10, Exceptional, (9)
"What a stay. Beautiful property, excellent communication with the host, very nice accommodations. "
Cozy cottage with a beautiful waterfront view. Pet friendly! 45 min from DC.

Waterfront Cabin on 32 Acres in Leesburg!

10.0 out of 10, Exceptional, (1)
"Caught lots of fish; woodland walks and fun games; cooked on the outside fire place; family time around the fire pit. Every one had a great time!! "
Waterfront Cabin on 32 Acres in Leesburg!

Charming 1-bedroom cottage in Shepherdstown walking distance

10.0 out of 10, Exceptional, (2)
"Great, easy to find location. Nancy was a great communicator A wonderful option for us, as we were in the area for a wedding in Sharpsburg where overnight accommodations were a bit slim. Shepherdstown was a cute town with lots of cute local shops and places to eat. Would stay here again! "
Charming 1-bedroom cottage in Shepherdstown walking distance
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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