Photo by Stephanie Sutton

Book a Middleburg Cottage

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Featured Cottages in Middleburg

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
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
18th Century Stone Cottage minutes from historic Middleburg
10.0 out of 10, Exceptional, (26)
"My husband and I had a wonderful stay in this charming, well equipped house located in an ideal spot for local hiking and fine dining. The upstairs bedroom is spacious, but cozy, and has a nice area for reading and doing work. Downstairs is a small kitchen, comfy couch and large TV. We sat outside for our morning coffee overlooking the Blue Ridge Mountain-- and our host couldn't be more accommodating and friendly! Highly recommend."
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 NZ$480
includes taxes & fees
20 Oct - 21 Oct
Historical cottage in the town of Paris
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. "
Peaceful Lakefront Cottage with Mountain Views!
Bluemont Escape: Hot tub, Walk to Bears Den, AT Trail and Bear Chase Brewery
10.0 out of 10, Exceptional, (12)
"Bed in main room seemed to be broken on left side. Sloping down. Otherwise everything was great "
The price is NZ$676
includes taxes & fees
28 Oct - 29 Oct
Bluemont Escape: Hot tub, Walk to Bears Den, AT Trail and Bear Chase Brewery
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!
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
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.
Cozy Virginia Vacation Rental w/ Seasonal Pool!
10.0 out of 10, Exceptional, (13)
"This is a wonderful property! Private, secluded area yet not to far from all the amenities that you need! The owners are great and you feel very welcomed at the start of your stay! Highly recommended for a couples retreat!!!"
Cozy Virginia Vacation Rental w/ Seasonal Pool!
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!
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”
Cozy Mountain Cottage - Perfect for Friends, Family
10.0 out of 10, Exceptional, (8)
"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
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
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 NZ$1,267
includes taxes & fees
24 Oct - 25 Oct
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Alpacas & The Stars at night. Private Retreat. Fun & Peace
10.0 out of 10, Exceptional, (43)
"We had a fantastic girls weekend in Alpaca Country. The cottage is decked out in African decor and surrounded by alpaca and horses. It’s very quiet and comfortable. Our host Mary met us and toured the unit and was always willing to help out. The grounds are gorgeous and there is a little store where you can purchase alpaca wool productsThere are several wineries nearby and we made meals in week equipped kitchen. . "
Alpacas & The Stars at night. Private Retreat. Fun & Peace
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 NZ$834
includes taxes & fees
2 Oct - 3 Oct
Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi
Cottage at Gray Fox- Many Attraction- Pet Friendly
10.0 out of 10, Exceptional, (18)
"House was very clean with had everything we needed for our stay. Property located close to HarpersFerry, Bluemont, Hillsboro and Charles Town. "
Cottage at Gray Fox- Many Attraction- Pet Friendly
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Other property types in Middleburg

18th Century Stone Cottage minutes from historic Middleburg
10.0 out of 10, Exceptional, (26)
"My husband and I had a wonderful stay in this charming, well equipped house located in an ideal spot for local hiking and fine dining. The upstairs bedroom is spacious, but cozy, and has a nice area for reading and doing work. Downstairs is a small kitchen, comfy couch and large TV. We sat outside for our morning coffee overlooking the Blue Ridge Mountain-- and our host couldn't be more accommodating and friendly! Highly recommend."
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 NZ$227
includes taxes & fees
4 Oct - 5 Oct
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 NZ$529
includes taxes & fees
29 Sept - 30 Sept
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

What is there to do in Middleburg near my cottage?
No matter your interests, Middleburg has lots of things to keep you occupied. Greenhill Winery & Vineyards, Cana Vineyards and Winery and Chrysalis Vineyards are on most travellers’ schedules. Don’t forget to check out National Sporting Library & Museum, Red Fox Fine Art and The Sporting Gallery either. With Expedia’s Middleburg hotel deals, you can discover even more fantastic attractions like these with the money you save.