Photo by Stephanie Sutton

Search Cottages in Middleburg

  • Plan, book, stay with confidence
    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 66 Cottages in Middleburg 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
Hunt Country cottage in Upperville!
Living area
Hunt Country cottage in Upperville!
10.0 out of 10, Exceptional, (11)
"Met daughter in middle for fun filled weekend"
Hunt Country cottage in Upperville!
Welcome to the “old town cottage”
Exterior
Welcome to the “old town cottage”
10.0 out of 10, Exceptional, (61)
"The cottage was perfect for our Anniversary get away! Location was so close to town with all the shops, restaurants & entertainment. We had a wonderful time. The property owner was just as great!"
Welcome to the “old town cottage”
Historical cottage in the town of Paris
Exterior
Historical cottage in the town of Paris
9.8 out of 10, Exceptional, (36)
"If I could give 10 stars, I would! This cabin in Paris, VA was everything I was looking for and more. Clean, spacious, quiet, and comfortable. The arboretum up the road was also a nice treat to enjoy. I can't wait to come back for another stay. "
The price is AED 621
AED 1,107 total
includes taxes & fees
3 Dec - 4 Dec
Historical cottage in the town of Paris
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. "
The price is AED 433
AED 1,396 total
includes taxes & fees
24 Nov - 25 Nov
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
Cozy Virginia Vacation Rental w/ Seasonal Pool!
Nokesville Vacation Rental | 1BR | 2.5BA | Stairs Required | 800 Sq Ft
Cozy Virginia Vacation Rental w/ Seasonal Pool!
10.0 out of 10, Exceptional, (15)
"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!
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 AED 779
AED 1,910 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 AED 1,098
AED 1,419 total
includes taxes & fees
24 Nov - 25 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, (7)
"A friend and I stayed in this modern cottage, tucked away in the woods about 10 minutes outside Leesburg's historic downtown. It has 1 bedroom (King) and a sitting room with a daybed, which would be a very cozy sleep for two (and I don't believe there was a door to close off the room). We shared the king and was glad another couple didn't join us, as it would have been quite tight sleeping. Also the one bathroom is shared so that creates some noise between the rooms. For two people, however,...
Bear Mountain Cottage
Royal Heritage Home @ Historic Leesburg
Living area
Royal Heritage Home @ Historic Leesburg
9.8 out of 10, Exceptional, (24)
"Great location"
The price is AED 871
AED 1,867 total
includes taxes & fees
25 Nov - 26 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
Weekend getaway short distance from DC/Northern Virginia
Weekend getaway short distance from DC/Northern Virginia
10.0 out of 10, Exceptional, (82)
"We just love this place! Heaven on Earth! Great location, great property, gracious hosts, a perhaps rental home for our needs!"
Weekend getaway short distance from DC/Northern Virginia
Country Elegance overlooking the Shenandoah River
Rear View of the River Snug
Country Elegance overlooking the Shenandoah River
10.0 out of 10, Exceptional, (102)
"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
Charming 3-bedroom cottage in farm & wine country
Room
Charming 3-bedroom cottage in farm & wine country
2.0 star property
Charming 3-bedroom cottage in farm & 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 AED 1,010
AED 1,458 total
includes taxes & fees
24 Nov - 25 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.
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.
Don't see what you're looking for?
See all available properties in Middleburg
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Middleburg

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 AED 1,010
AED 1,458 total
includes taxes & fees
24 Nov - 25 Nov
18th Century Stone Cottage minutes from historic Middleburg
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, (118)
"Great stay! Property manager was easy to communicate with and allowed a late checkout and the unit was clean. Highly recommend "
The price is AED 508
AED 989 total
includes taxes & fees
24 Nov - 25 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.

Frequently asked questions

Why book your cottage in Middleburg with Expedia?
We think that a vacay should be simple, so if you’re searching for cottages in Middleburg at an affordable rate, Expedia is here to help. Stick to the budget and choose an economical option surrounded by nature, or book a luxury cottage to pamper your favorite people.
How can I find cheap cottages in Middleburg?
With Expedia’s convenient filter tool, scoring cheap cottages in Middleburg has never been simpler. To discover stays that’ll make your wallet smile, narrow your search results by star rating, amenities and budget.