Photo by Stephanie Sutton

Search Middleburg Cottage Rentals from CA $229

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Browse Select Middleburg Cottages

18th Century Stone Cottage minutes from historic Middleburg
10.0 out of 10, Exceptional, (26)
"Fantastic experience. Would book again."
18th Century Stone Cottage minutes from historic Middleburg
Historical cottage in the town of Paris
9.8 out of 10, Exceptional, (33)
"What a quaint getaway! Charming little borough in a clean, comfortable cottage! Loved every minute spent there!"
The price is CA $229
CA $414 total
includes taxes & fees
Sep 26 - Sep 27
Historical cottage in the town of Paris
Bear Mountain Cottage
10.0 out of 10, Exceptional, (5)
"The cottage is immaculate and nicely decorated. While it's located in the woods, it's just minutes away from town and close to many wineries. Would definitely consider staying here in the future and recommend to our friends."
Bear Mountain Cottage
Cozy cottage with a beautiful waterfront view. Pet friendly! 45 min from DC.
8.6 out of 10, Excellent, (4)
"The inside of the cottage was very clean. The bathroom towels are like blankets! SO nice! The kitchen is decent (with a little coffee/tea bar and fresh eggs in the refrigerator!!), the living room is spacious and the beds are very comfortable. My only issue with the interior was there was no place to put the luggage in the bedrooms. I had to put my suitcase on the floor and kept having to bend down to get things out of it. It would be nice to have a luggage rack or a small dresser in each room....
Cozy cottage with a beautiful waterfront view. Pet friendly! 45 min from DC.
Peaceful Lakefront Cottage with Mountain Views!
10.0 out of 10, Exceptional, (20)
"Stayed here for a girls getaway. House was beautiful and the view was so tranquil and beautiful overlooking the lake. The decor was fresh and modern as were the appliances. Well stocked and beautiful kitchen. We enjoyed a very relaxing time. The communication from Mountain Mama was exceptional. "
The price is CA $415
CA $889 total
includes taxes & fees
Oct 6 - Oct 7
Peaceful Lakefront Cottage with Mountain Views!
Lake View Retreat - Cottage Near a Peaceful Lake!
9.6 out of 10, Exceptional, (14)
"This property was a perfect place to stay for our group. While it was a little out of the way, it suited our needs, was clean, and very comfortable. The owners made quick communication with them easy. Definitely recommend!"
Lake View Retreat - Cottage Near a Peaceful Lake!
Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi
9.8 out of 10, Exceptional, (20)
"We enjoyed our stay at the cottage. We were 15-20 minutes away from lots of breweries and outdoor dining places yet felt like we were staying in the country. Enjoyed the hot tub and basketball hoop and the fire pit was ready for us when we arrived. Our little dog was welcomed and enjoyed the yard too. Great communication with the owner. There is some noise from the train and road nearby but it did not bother us."
The price is CA $294
CA $743 total
includes taxes & fees
Oct 2 - Oct 3
Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi
Lovettsville Cottage in Heart of Wine Country
10.0 out of 10, Exceptional, (27)
"This was such a nice place to stay while in Virginia visiting family! The area is full of antiques, wineries, breweries and gorgeous scenery. The cabin itself is on a pretty piece of property with a well-kept large lawn and attached to the main house, though it felt very private and we never heard the occupants. It was very comfortable and clean. Keep in mind most places in the this rural area are on some kind of gravel road. Expect to wash your car:) I will definitely book this one again! "
Lovettsville Cottage in Heart of Wine Country
Historic Schoolhouse on Winery Row
10.0 out of 10, Exceptional, (10)
"We had a wonderful 4 night stay at this charming property. This converted schoolhouse was very well appointed, and provided all that we needed for a pleasant experience. We also had the opportunity to enjoy the fire pit by the stream one evening, and would highly recommend it . "
Historic Schoolhouse on Winery Row
Welcome to the “old town cottage”
10.0 out of 10, Exceptional, (57)
"SO much bigger than pictures show- lots of nooks!"
Welcome to the “old town cottage”
Woodsy Retreat with a Hot Tub and Seasonal Views!
10.0 out of 10, Exceptional, (14)
"I thought your place was fabulous. The check-in and online access was great. The house was adorable. I loved the outdoor screened in porch and felt the rooms were very cozy."
The price is CA $255
CA $628 total
includes taxes & fees
Oct 24 - Oct 25
Woodsy Retreat with a Hot Tub and Seasonal Views!
Magical Treehouse in Woods, Close many Wineries & Breweries, Pet Friendly!
Magical Treehouse in Woods, Close many Wineries & Breweries, Pet Friendly!
Hunt Country cottage in Upperville!
9.8 out of 10, Exceptional, (7)
"The owner Constance is wonderful and very responsive. Beautiful home."
Hunt Country cottage in Upperville!
Cozy Mountain Cottage - Perfect for Friends, Family
10.0 out of 10, Exceptional, (7)
"The home was welcoming, comfortable, clean, well supplied, and laid out perfectly. We gathered with our adult children and their spouses and it was perfect for what we wanted to do: enjoy meals, play cards, grill, play cornhole, sit on the porch, sit around the firepit, and hike in Harper’s Ferry. "
Cozy Mountain Cottage - Perfect for Friends, Family
Romantic Shabby Chic Cottage on 5 acre property near wineries and Blue Ridge MTS
10.0 out of 10, Exceptional, (43)
"This property and its amazing owners went way above our expectations! The cottage was perfect, food was delicious and the owners were lovely! Local wineries, hikes and restaurants were great. We highly recommend staying here!"
Romantic Shabby Chic Cottage on 5 acre property near wineries and Blue Ridge MTS
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
Littlefield Cottage
10.0 out of 10, Exceptional, (5)
"Just a pleasure."
Littlefield Cottage
Country Elegance overlooking the Shenandoah River
10.0 out of 10, Exceptional, (97)
"What a treat to enjoy such a peaceful place in nature with deer and turkeys running around each day. The birds were also amazing. Then to enjoy such a great spot along the river with an open area, dock and places to sit was very special. The fire pit was great for the family and for our grandson to experience his first marshmallow roast. The cabin was well done -with nice furniture, comfy beds, and just very quaint. Everything was stocked well in the kitchen. The outside deck sitting area was...
Country Elegance overlooking the Shenandoah River
Bear Chase Cottage
10.0 out of 10, Exceptional, (28)
"The Bear Chase Cottage is an ideal spot to stay! The area is beautiful and it's perfect if you want to spend the day at the Bear Chase Brewery and walk 30 seconds home. The house is cute, comfortable and completely updated. We'll definitely be back!"
Bear Chase Cottage
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
10.0 out of 10, Exceptional, (15)
"Beautiful setting if you love the outdoors. This property was designed to be everything to anyone. It was very well furnished; it had a layout that was optimized for multi-family / multi-guest. It had all the amenities that I could think of and we entertained guests while there. This property is definitely managed by people who have a solid professional background in the business of property rentals. "
The price is CA $468
CA $1,059 total
includes taxes & fees
Oct 24 - Oct 25
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
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Other property types in Middleburg

18th Century Stone Cottage minutes from historic Middleburg
10.0 out of 10, Exceptional, (26)
"Fantastic experience. Would book again."
18th Century Stone Cottage minutes from historic Middleburg
Hyatt House Herndon/Reston
3.0 star property
9.0 out of 10, Wonderful, (1174)
"Short drive from airport and clean room. Great gym for size of hotel. "
The price is CA $166
CA $195 total
includes taxes & fees
Sep 28 - Sep 29
Hyatt House Herndon/Reston
Global Luxury Suites at Reston Town Center
3.5 star property
8.2 out of 10, Very good, (111)
"Great place. I would stay here again."
The price is CA $255
CA $442 total
includes taxes & fees
Sep 29 - Sep 30
Global Luxury Suites at Reston Town Center
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.

Frequently asked questions

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How can I find cheap cottages in Middleburg?
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What is there to do in Middleburg near my cottage?
There are plenty of fantastic things to do and see in Middleburg. Check out leading attractions like Greenhill Winery & Vineyards, Cana Vineyards and Winery and Chrysalis Vineyards. National Sporting Library & Museum, Red Fox Fine Art and The Sporting Gallery are other must-do’s.