Middleburg Vacation Rentals

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Our top choices for Middleburg vacation rentals

Spacious Modern Home on Middleburg Horse Farm

Spacious Modern Home on Middleburg Horse Farm
Middleburg
10.0 out of 10, Exceptional, (17 reviews)
"We loved the huge kitchen and family room, and the location in Virginia horse country was amazing!"
United States
STAN P.
The price is CA $313
CA $722 total
includes taxes & fees
Apr 5 - Apr 6
Spacious Modern Home on Middleburg Horse Farm

18th Century Stone Cottage minutes from historic Middleburg

18th Century Stone Cottage minutes from historic Middleburg
Middleburg
10.0 out of 10, Exceptional, (57 reviews)
"Loved out stay! "
United States
Emilee
The price is CA $383
CA $552 total
includes taxes & fees
Apr 5 - Apr 6
18th Century Stone Cottage minutes from historic Middleburg

Hunters Retreat with High Speed Internet

Hunters Retreat with High Speed Internet
Middleburg
10.0 out of 10, Exceptional, (6 reviews)
"We had the best fall weekend and the property is amazing "
United States
Kelly T.
The price is CA $487
CA $1,178 total
includes taxes & fees
Apr 19 - Apr 20
Hunters Retreat with High Speed Internet

Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.

Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.
Middleburg
9.8 out of 10, Exceptional, (24 reviews)
"Lovely clean room."
United States
Rory O.
The price is CA $209
CA $379 total
includes taxes & fees
Apr 2 - Apr 3
Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.

'thomson Farm' Classic Home < 10 Mi to Vineyards!

'thomson Farm' Classic Home < 10 Mi to Vineyards!
3.0 star property
Leesburg
The price is CA $1,511
CA $2,542 total
includes taxes & fees
Apr 2 - Apr 3
'thomson Farm' Classic Home < 10 Mi to Vineyards!

Blue Mountain Cabin, secluded, perfect for couples, near main road

Blue Mountain Cabin, secluded, perfect for couples, near main road
Front Royal
10.0 out of 10, Exceptional, (31 reviews)
"Great stay! The place was clean, comfortable, and exactly as described. Host was responsive and helpful. Would definitely stay again."
United States
Wafaa L.
The price is CA $264
CA $330 total
includes taxes & fees
Apr 2 - Apr 3
Blue Mountain Cabin, secluded, perfect for couples, near main road

Mountain Retreat w/2 Living Spaces, Hot Tub & Deck

Mountain Retreat w/2 Living Spaces, Hot Tub & Deck
Harpers Ferry
The price is CA $224
CA $461 total
includes taxes & fees
Apr 5 - Apr 6
Mountain Retreat w/2 Living Spaces, Hot Tub & Deck

The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!

The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Hamilton
9.8 out of 10, Exceptional, (16 reviews)
"Absolutely amazing place and stay! I could not possibly be more impressed and I look forward to coming back."
United States
Jasmine M.
The price is CA $313
CA $550 total
includes taxes & fees
Apr 3 - Apr 4
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!

Skyland Hideaway | Mountain Cabin w/ Hot Tub

Skyland Hideaway | Mountain Cabin w/ Hot Tub
Linden
10.0 out of 10, Exceptional, (15 reviews)
"Quiet with amenities to support R&R, enjoying nature, and togetherness."
United States
Patricia B.
Skyland Hideaway | Mountain Cabin w/ Hot Tub

Front royal majestic paradise

Front royal majestic paradise
Front Royal
The price is CA $1,669
CA $2,174 total
includes taxes & fees
Apr 6 - Apr 7
Front royal majestic paradise

Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI

Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI
Harpers Ferry
9.2 out of 10, Wonderful, (32 reviews)
"Enjoyed the levels, hot tub, porch to get outside with my coffee, pet strolling area marvelous and washer/dryer."
United States
tracey b.
The price is CA $276
CA $476 total
includes taxes & fees
Apr 21 - Apr 22
Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI

Cottage on King | Charming Historic Leesburg Home

Cottage on King | Charming Historic Leesburg Home
Leesburg's Old and Historic District
9.6 out of 10, Exceptional, (69 reviews)
"the cottage had everything we needed. "
United States
christa S.
The price is CA $396
CA $704 total
includes taxes & fees
Apr 8 - Apr 9
Cottage on King | Charming Historic Leesburg Home

Global Luxury Suites at Reston

Global Luxury Suites at Reston
4.0 star property
Reston
7.8 out of 10, Good, (38 reviews)
"Great location and facilities. I would stay there again."
United States
Kim
The price is CA $211
CA $289 total
includes taxes & fees
Apr 2 - Apr 3
Global Luxury Suites at Reston

A Luxurious Home for Rest and Work.

A Luxurious Home for Rest and Work.
Ashburn
10.0 out of 10, Exceptional, (18 reviews)
"We had a lovely stay at this home! "
United States
Kristina P.
A Luxurious Home for Rest and Work.

A peaceful, forest retreat with stunning views near historic Harpers Ferry.

A peaceful, forest retreat with stunning views near historic Harpers Ferry.
Harpers Ferry
9.8 out of 10, Exceptional, (6 reviews)
"Great place to stay!! Very happy with the accommodations "
United States
Amanda E.
The price is CA $250
CA $540 total
includes taxes & fees
Apr 6 - Apr 7
A peaceful, forest retreat with stunning views near historic Harpers Ferry.

The Black Aframe ⛺️ - HOT TUB & ⛰Mountain Views

The Black Aframe ⛺️ - HOT TUB & ⛰Mountain Views
Haymarket
8.6 out of 10, Excellent, (15 reviews)
"Absolutely amazing place!Very clean and great viewThe hot tub was stellar and sparkling clean!A lot of stairs up to it and switchbacks driving but totally worth it!Bed was sooo comfortable!Definitely take Logmill Road untilit meets Gore Road and ignore GPS….A fabulous place with a lot ofhistory!Great sunrises but close the downstairs bedroomdoor if you don’t want to wake up that earlyLoved our stay and would definitely return!Spent the week over Thanksgiving visiting family"
United States
Kathleen G.
The price is CA $364
CA $686 total
includes taxes & fees
Apr 14 - Apr 15
The Black Aframe ⛺️ - HOT TUB & ⛰Mountain Views

Luxurious 2BR Movie Theater Game Room Kitchen Gym

Luxurious 2BR Movie Theater Game Room Kitchen Gym
Clifton
9.8 out of 10, Exceptional, (7 reviews)
"Everything was welcoming and clean. It was comfy and had everything we needed. Would stay there again!"
United States
Matt N.
The price is CA $184
CA $400 total
includes taxes & fees
Apr 2 - Apr 3
Luxurious 2BR Movie Theater Game Room Kitchen Gym

Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi

Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi
Boyce
10.0 out of 10, Exceptional, (32 reviews)
"A very spacious and well equipped home to get away from it all; but, also convenient to Winchester for a night out. The fenced in areas for dogs were lovely."
United States
David A.
The price is CA $279
CA $744 total
includes taxes & fees
Apr 2 - Apr 3
Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi

Mountain cabin near national park & wineries

Mountain cabin near national park & wineries
Linden
10.0 out of 10, Exceptional, (30 reviews)
"The house and location were perfect for a little getaway with friends. It was very clean, and the location was great! We were very pleased with the entire experience."
United States
Jennifer d.
The price is CA $313
CA $655 total
includes taxes & fees
Apr 5 - Apr 6
Mountain cabin near national park & wineries

A unique mountaintop getaway overlooking Willow Croft Winery.

A unique mountaintop getaway overlooking Willow Croft Winery.
Leesburg
10.0 out of 10, Exceptional, (116 reviews)
"Wonderful home with outstanding hosts! Will hope to stay here every time we visit Leesburg!"
United States
Ethan R.
The price is CA $438
CA $844 total
includes taxes & fees
Apr 14 - Apr 15
A unique mountaintop getaway overlooking Willow Croft Winery.
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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Top Middleburg Hotel Reviews

Find out more about Middleburg

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Middleburg. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find vacation rentals in Middleburg?

Yes, we offer vacation rentals in Middleburg near National Sporting Library & Museum, or you can go with a more secluded option if you want a relaxing stay. The spas and restaurants are several reasons why visitors like Middleburg. Make sure you have time to check out the wineries while you're in the area.

What are some of the best vacation rentals in Middleburg?

Grand 9BR Provenance Manor Ideal for Weddings & Gatherings: This Middleburg vacation home rental has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

How many vacation rentals will I find in Middleburg?

Expedia has 13 vacation rentals for your stay in Middleburg.

What’s there to see and do in Middleburg?

Cultural attractions include Red Fox Fine Art and The Byrne Gallery, whereas National Sporting Library & Museum is just one of the family-friendly sights. Other places in town to visit include Middleburg Historic District and Greenhill Winery & Vineyards.

What’s a vacation rental in Middleburg like?

Vacation rentals are privately owned properties where you can stay for several days or longer in Middleburg. Vacation rentals offer extras like kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about cleanliness, vacation rentals can offer a sense of privacy away from shared hotel elevators and busy concierge desks while still allowing you to travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for a family trip or a small group gathering.