Photo by Stephanie Sutton

Search Cottages in Middleburg

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Cottages in Middleburg and around

Historical cottage in the town of Paris
Exterior

Historical cottage in the town of Paris

9.8 out of 10, Exceptional, (45)
"This is a nice home near sky meadow park. A great place to see the stars... Very close to DC. "
Historical cottage in the town of Paris
18th Century Stone Cottage minutes from historic Middleburg
Exterior

18th Century Stone Cottage minutes from historic Middleburg

10.0 out of 10, Exceptional, (46)
"Very clean, Beautiful Property. Super peaceful. Will come back in the summer to enjoy town summer time activities. "
The price is €345
includes taxes & fees
17 Aug - 18 Aug
18th Century Stone Cottage minutes from historic Middleburg
Wild Hare Cottage
2 bedrooms, WiFi

Wild Hare Cottage

10.0 out of 10, Exceptional, (7)
"We had just a quick overnight stay, the cottage is cozy, clean, and charming. Communication was easy and clear, we'd love to stay again!"
The price is €209
includes taxes & fees
20 Aug - 21 Aug
Wild Hare Cottage
Raspberry Retreat Cottage
Outdoor dining

Raspberry Retreat Cottage

10.0 out of 10, Exceptional, (1)
"The cutest cottage ever!! Totally loved this place. Clean, quiet, well decorated and cozy. Just what we were looking for. Don’t sleep on this home! Hosts are very responsive, too. "
Raspberry Retreat Cottage
Cozy cottage with a beautiful waterfront view. Pet friendly! 45 min from DC.
Terrace/patio

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

9.4 out of 10, Exceptional, (11)
"Convenient to where I needed to be. Nice property. Dogs loved the property"
Cozy cottage with a beautiful waterfront view. Pet friendly! 45 min from DC.
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Dining

Art Docko - Lakefront Artist Retreat w/ Hot Tub!

10.0 out of 10, Exceptional, (21)
"Loved this house for relaxing, enjoying nature and reconnecting with friends!"
The price is €497
includes taxes & fees
28 Aug - 29 Aug
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Cozy Mountain Cottage - Perfect for Friends, Family
Exterior

Cozy Mountain Cottage - Perfect for Friends, Family

10.0 out of 10, Exceptional, (14)
"We had a great time over Thanksgiving. The house , yard and host were all great. I woood definitely stay here again. "
Cozy Mountain Cottage - Perfect for Friends, Family
Lovettsville Cottage in Heart of Wine Country
TV, Netflix, streaming services

Lovettsville Cottage in Heart of Wine Country

9.8 out of 10, Exceptional, (34)
"We stayed here for a few days over the Thanksgiving holiday. It was cozy, comfortable, and had all the great comforts of a home away from home. "
Lovettsville Cottage in Heart of Wine Country
Lake View Retreat - Cottage Near a Peaceful Lake!
Property grounds

Lake View Retreat - Cottage Near a Peaceful Lake!

9.6 out of 10, Exceptional, (18)
"Was really able to relax and enjoy during our brief stay. Would come again."
Lake View Retreat - Cottage Near a Peaceful Lake!
Charming 2-Bedroom Cottage in Loudoun Co, VA on 12 Gorgeous Acres w/ 2-Acre Pond
Fridge, microwave, oven, stovetop

Charming 2-Bedroom Cottage in Loudoun Co, VA on 12 Gorgeous Acres w/ 2-Acre Pond

9.8 out of 10, Exceptional, (7)
"This was a good place to stay for two guys day hiking in the AT. It is clean, quiet, comfortable, and in a very good location. It had everything we needed."
Charming 2-Bedroom Cottage in Loudoun Co, VA on 12 Gorgeous Acres w/ 2-Acre Pond
Cozy Stone Cottage in Round Hill, VA
Fridge, microwave, oven, stovetop

Cozy Stone Cottage in Round Hill, VA

9.8 out of 10, Exceptional, (6)
"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
Historic Schoolhouse on Winery Row
Outdoor dining

Historic Schoolhouse on Winery Row

10.0 out of 10, Exceptional, (13)
"House and property are great. Just what we needed and had everything easily accessible. We enjoyed our stay."
Historic Schoolhouse on Winery Row
Hilltop Cottage @ Shiloh
Property grounds

Hilltop Cottage @ Shiloh

10.0 out of 10, Exceptional, (1)
"Wonderful accommodations!! Everything you could hope hope and then some!! Highly recommend!!! A"
Hilltop Cottage @ Shiloh
Weekend getaway short distance from DC/Northern Virginia
Exterior

Weekend getaway short distance from DC/Northern Virginia

10.0 out of 10, Exceptional, (86)
"This place was cozy and welcoming, exactly what we were looking for on a weekend away."
Weekend getaway short distance from DC/Northern Virginia
Modern Country Cottage in Wine Country
Fridge, microwave, oven, stovetop

Modern Country Cottage in Wine Country

8.8 out of 10, Excellent, (3)
"Description of property was accurate. It worked well for our purpose. Location was.close to Leesburg and easy to get to. Mice"
Modern Country Cottage in Wine Country
Waterfront Cabin on 32 Acres in Leesburg!
TV, DVD player, books, video library

Waterfront Cabin on 32 Acres in Leesburg!

10.0 out of 10, Exceptional, (3)
"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!
Guest House in Private Villa ~ 23 Mi to Washington
House (4 Bedrooms) | Interior

Guest House in Private Villa ~ 23 Mi to Washington

3.0 star property
Guest House in Private Villa ~ 23 Mi to Washington
Peaceful Lakefront Cottage with Mountain Views!
Fridge, microwave, oven, stovetop

Peaceful Lakefront Cottage with Mountain Views!

9.8 out of 10, Exceptional, (27)
"Really enjoyed stay home was great "
The price is €543
includes taxes & fees
17 Aug - 18 Aug
Peaceful Lakefront Cottage with Mountain Views!
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, (18)
"Great tucked away location for a friends weekend. Some cute towns with good restaurants not too far. Beautiful views from the hot tub. House was very cute and beds were comfortable. Showers worked well and plenty of towels. Working fireplace was also nice."
The price is €335
includes taxes & fees
19 Aug - 20 Aug
Cottage w/ Hot Tub and 100-Mile Valley Views!
Cottage at Gray Fox- Many Attraction- Pet Friendly
Fridge, microwave, oven, stovetop

Cottage at Gray Fox- Many Attraction- Pet Friendly

10.0 out of 10, Exceptional, (21)
"We had a great stay. The little added touches made the stay very enjoyable and we loved the hot tub time!"
Cottage at Gray Fox- Many Attraction- Pet Friendly
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middleburg Hotel Reviews

Holiday Inn Washington-Dulles International Airport by IHG

Holiday Inn Washington-Dulles International Airport by IHG

10/10 Excellent
"I was stay there for just 4 hours but the service desk is so friendly I can’t expect more! Great experience "
kun 1-night trip
Posted 22 hours ago
Holiday Inn Washington-Dulles International Airport by IHG

Frequently asked questions

Why book your cottage in Middleburg with Expedia?
We think that a holiday should be simple, so if you're seeking cottages in Middleburg at a competitive rate, Expedia has you covered. Save cash and go for an inexpensive option surrounded by nature, or book an upscale cottage to pamper your loved ones.
How can I find cheap cottages in Middleburg?
The quickest way to find cheap cottages in Middleburg is with Expedia's handy filter tool. Narrow your search by amenities, budget and star rating to access awesome bargains in a few clicks.
What is there to do in Middleburg near my cottage?
You'll find loads of fun things to fill your itinerary with in Middleburg. Explore popular attractions like Greenhill Winery & Vineyards, Cana Vineyards and Winery and Chrysalis Vineyards. Glenwood Park, Red Fox Fine Art and The Sporting Gallery also appeal to many visitors.