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Compare 50 Cottages in Leesburg's Old and Historic District with updated reviews, rates, and availability.

Lovettsville Cottage in Heart of Wine Country
Lovettville Vacation Rental | 1BR | 2BA | 2 Stories | 3 Steps Required
Lovettsville Cottage in Heart of Wine Country
10.0 out of 10, Exceptional, (29)
"Family reunion to get 3 sisters together. My Mother-in-Law is 90 and we drove to VA so she can visit with her 88 and 80 year old sisters. We did have an issue wtih the 2 statements below provided in an email on 9Sept2024, which is after the window for cancelation. The homeowner isn't just next door, they are adjoining, which isn't clear in the description. It is also not shown in the pictures. We expected quiet time for morning coffee outdoors, instead we were able to hear the homeowner on...
Lovettsville Cottage in Heart of Wine Country
The Carriage House at Carrot Top Cottage
Terrace/patio
The Carriage House at Carrot Top Cottage
9.8 out of 10, Exceptional, (28)
"My wife and I had a fantastic time. Very warm and cozy cottage. Walking distance to everything, but tucked away enough to enjoy your privacy. Would definitely stay with them again."
The price is SAR 368
SAR 634 total
includes taxes & fees
18 Nov - 19 Nov
The Carriage House at Carrot Top Cottage
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, (8)
"Place was clean ..had all the necessary bath and kitchen items. Very convenient to historic part of Harpers Ferry.. Large fenced backyard for our dog… Would give it 5 stars but winding , circular metal stairway was very tight.Fortunately both of us are slim so was manageable. Plan on staying here again if visiting Harper’s Ferry/Charles Town area.."
The price is SAR 619
SAR 1,141 total
includes taxes & fees
18 Nov - 19 Nov
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Lake View Retreat - Cottage Near a Peaceful Lake!
This home is just a short walk to Lake Shannondale, and has wintertime views of the lake! Spend your mornings on the front porch, or take a leisurely stroll around the lake.
Lake View Retreat - Cottage Near a Peaceful Lake!
9.4 out of 10, Exceptional, (16)
"Beautiful location to relax and enjoy friends. This house was huge. Plenty of room for the 3 of us...could have been 8, lol. "
Lake View Retreat - Cottage Near a Peaceful Lake!
Bear Chase Cottage
Living area
Bear Chase Cottage
10.0 out of 10, Exceptional, (30)
"Everything about the Cottage was amazing. Not sure when it was built/remodeled, but it seemed brand new! The size was perfect for a small friend group bday getaway. The location is ideal. Can’t wait to go back. "
Bear Chase Cottage
Peaceful Lakefront Cottage with Mountain Views!
Enjoy a soak in the hot tub!
Peaceful Lakefront Cottage with Mountain Views!
10.0 out of 10, Exceptional, (22)
"Although short, we had a wonderful stay. Beautiful house with amazing views. Great communication with property host. Cant wait to come back! Thank you for hosting us last minute! "
The price is SAR 878
SAR 2,070 total
includes taxes & fees
5 Dec - 6 Dec
Peaceful Lakefront Cottage with Mountain Views!
Bluemont Escape: Hot tub, Walk to Bears Den, AT Trail and Bear Chase Brewery
Exterior
Bluemont Escape: Hot tub, Walk to Bears Den, AT Trail and Bear Chase Brewery
10.0 out of 10, Exceptional, (13)
"The house was super cute and the location was perfect!"
The price is SAR 1,123
SAR 1,455 total
includes taxes & fees
18 Nov - 19 Nov
Bluemont Escape: Hot tub, Walk to Bears Den, AT Trail and Bear Chase Brewery
Bear Mountain Cottage
Exterior
Bear Mountain Cottage
10.0 out of 10, Exceptional, (6)
"We were in town for a wedding, Bear Mountain Cottage felt like home! Everyone was super helpful to booking/recommendations of things to do! Bonus points for the cottage being super clean/updated and even better pet friendly! We hope to be back! "
Bear Mountain Cottage
Royal Heritage Home @ Historic Leesburg
Living area
Royal Heritage Home @ Historic Leesburg
9.8 out of 10, Exceptional, (23)
"Great location"
The price is SAR 890
SAR 1,895 total
includes taxes & fees
18 Nov - 19 Nov
Royal Heritage Home @ Historic Leesburg
Magical Treehouse in Woods, Close many Wineries & Breweries, Pet Friendly!
Exterior
Magical Treehouse in Woods, Close many Wineries & Breweries, Pet Friendly!
Magical Treehouse in Woods, Close many Wineries & Breweries, Pet Friendly!
Historic Artist's Cottage on 5 Acre Property Near Blue Ridge Mts. and Wineries
Powell's Studio
Historic Artist's Cottage on 5 Acre Property Near Blue Ridge Mts. and Wineries
10.0 out of 10, Exceptional, (55)
"Lisa and Todd were very friendly and made staying at their cottage super easy. They have options for breakfast to be brought to your cottage, as well as chocolate fondue at night! We were able to bring our dog as well, that was a bonus. Many wineries and breweries around the location."
Historic Artist's Cottage on 5 Acre Property Near Blue Ridge Mts. and Wineries
Modern Country Cottage in Wine Country
Living area
Modern Country Cottage in Wine Country
8.8 out of 10, Excellent, (3)
"Our family was in the area for a wedding and chose this property because it had 3 bedrooms and bathrooms. It was quiet and comfortable. Basement area seems like it is a work in progress."
Modern Country Cottage in Wine Country
18th Century Stone Cottage minutes from historic Middleburg
Exterior
18th Century Stone Cottage minutes from historic Middleburg
10.0 out of 10, Exceptional, (32)
"Nice place! Clean, beautiful, and located just two miles from town. "
The price is SAR 1,032
SAR 1,478 total
includes taxes & fees
18 Nov - 19 Nov
18th Century Stone Cottage minutes from historic Middleburg
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. "
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Cozy cottage with a beautiful waterfront view. Pet friendly! 45 min from DC.
Cozy cottage with a beautiful waterfront view. Pet friendly! 45 min from DC.
8.8 out of 10, Excellent, (5)
"the place is so cozy, has all the amenities that one would need, out in the country yet near the big city, quiet, and a lovely home. they thought of everything!"
Cozy cottage with a beautiful waterfront view. Pet friendly! 45 min from DC.
Cottage at Gray Fox- Many Attraction- Pet Friendly
Private kitchen
Cottage at Gray Fox- Many Attraction- Pet Friendly
10.0 out of 10, Exceptional, (20)
"Our family of four enjoyed the weekend away"
Cottage at Gray Fox- Many Attraction- Pet Friendly
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, (14)
"The view of this house is amazing! Absolutely beautiful!"
Cottage w/ Hot Tub and 100-Mile Valley Views!
Carrot Top Cottage surrounded by National Park
Exterior
Carrot Top Cottage surrounded by National Park
10.0 out of 10, Exceptional, (26)
"We thoroughly enjoyed our stay here. The home was full of amenities and super clean. We were able to park our car at the cottage and walk to the Appalachian Trail, and on down to the town. We would definitely stay here again."
Carrot Top Cottage surrounded by National Park
Historic Schoolhouse on Winery Row
Quaint, historic village schoolhouse built 1885.
Historic Schoolhouse on Winery Row
10.0 out of 10, Exceptional, (12)
"This VRBO home could not have been any better! It was clean, cozy, comfortable, and well stocked with everything you can possibly need. The owner, Lynn, answered all of our questions and responded to our text messages quickly. She could not have been more helpful. Location is ideal close to wineries and great restaurants. we enjoyed the grill on the back deck as well as the relaxing creek and chairs around the fire pit We enjoyed our stay here so much. We are looking forward to going back...
Historic Schoolhouse on Winery Row
Charming Home With Yard Near Shenandoah River!
Exterior
Charming Home With Yard Near Shenandoah River!
3.0 star property
10.0 out of 10, Exceptional, (3)
"Cozy house nestled in the mountains of West Virginia. Well-maintained, clean, great yard for pets and/or kids! Lovely grilling and fire pit area. We throughly enjoyed our stay!"
Charming Home With Yard Near Shenandoah River!
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 Leesburg's Old and Historic District

Cottage on King | Charming Historic Leesburg Home
Exterior detail
Cottage on King | Charming Historic Leesburg Home
9.6 out of 10, Exceptional, (44)
"Perfect. No complaints at all. Thank you again. "
The price is SAR 668
SAR 1,239 total
includes taxes & fees
18 Nov - 19 Nov
Cottage on King | Charming Historic Leesburg Home
Global Luxury Suites at Reston Town Center
Fireplace
Global Luxury Suites at Reston Town Center
3.5 star property
8.2 out of 10, Very Good, (116)
"Great stay! Property manager was easy to communicate with and allowed a late checkout and the unit was clean. Highly recommend "
The price is SAR 544
SAR 1,039 total
includes taxes & fees
25 Nov - 26 Nov
Global Luxury Suites at Reston Town Center
Breathtaking views with an indoor private pool, come escape with us
Exterior
Breathtaking views with an indoor private pool, come escape with us
9.8 out of 10, Exceptional, (240)
"Great place to relax & enjoy! We loved the pool & hot tub as well abundant indoor/outdoor space. There was a musty smell that lingered on all my clothes and I stayed in the very top floor master & put my clothes in dresser and closet. You may need a dehumidifier in that closet…."
Breathtaking views with an indoor private pool, come escape with us
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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