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Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Our top choices for Middleburg cottages

A stone house with a white picket fence, a front porch, and potted plants.

1. Cottage w/ Furnished Patio & Garden: Dtwn Leesburg

Cottage w/ Furnished Patio & Garden: Dtwn Leesburg
3.0 star property
Leesburg's Old and Historic District
The price is RM1,652
RM2,756 total
includes taxes & fees
22 Nov - 23 Nov
Cottage w/ Furnished Patio & Garden: Dtwn Leesburg
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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Learn more about Middleburg

Nestled in Virginia's horse country, this charming town invites you to explore historic inns and boutique wineries. Saddle up for a guided trail ride or join a polo match, then unwind at a cosy tavern with locally-sourced fare.

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A vineyard with rows of grapevines under a clear sky.
Photo by Stephanie Sutton
Open Photo by Stephanie Sutton

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?

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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.