
House vacation rentals in Middleburg
Find and book unique houses on Airbnb
Top-rated house rentals in Middleburg
Guests agree: these houses are highly rated for location, cleanliness, and more.

Middleburg/Upperville-Stunning,renovated cottage
The Atoka House,a stunning 1801 log home on the historic register in Virginia hunt country.This 2-bedroom, 2.5 bath home with both upstairs and downstairs living rooms,is only 4 miles from Middleburg.Relax in the coziness of the log cabin, catch the spectacular sunsets from the deck and large fenced yard. Gas grill and outdoor firepit. Fireplace may only be used with a duraflame log(provided) for the safety of this historic home. Minutes from wineries, great meadow, polo and Upperville (UCHS)

Spectacular View, PET FREE, Skylight and Hot Tub
Enjoy majestic views of the Shenandoah River in our tiny home centrally located just 5 mins from AppalachianTrail, 6 mins from the rivers, 12 mins from Old Town Harpers Ferry, quiet peace no train noise unlike old town. Large patio, courtyard, firepit, hammock, "Mind Blowing" 2 person soaking tub. The outdoor space provides private vistas of Shenandoah, moonlit nights, star gazing, or taking in beautiful scenery while enjoying a relaxing shower in our cedar outdoor shower under the sun or stars

Modern Home on Middleburg Equestrian Farm
Surprise and delight abound around every corner in this newly renovated, open floor-plan 3 bedroom, 2 bath getaway. Furnished by BoConcept and outfitted with the latest appliances, Gibson House is the ideal getaway for couples or small families looking for a weekend escape with all the comforts of home. Visit with the horses in the adjacent paddocks. Come enjoy wineries, shopping, history, steeplechase racing and polo in Middleburg and the nearby towns of Upperville, The Plains, and Marshall.

Cozy Reliance Retreat with Beautiful Views
Welcome to the Reliance Retreat in the heart of the Shenandoah Valley! Our luxurious space is inviting and tranquil. Whether you're just passing through or need some peace and quiet away from the city, this cozy house has an amazing mountain view we know you'll enjoy. The house sleeps four and includes all the amenities you'll need in every area of the home. We hope you'll grab a book, your favorite snacks and find yourself a cozy spot whether it's inside, on the patio, or out by the fire pit

Leesburg Hideaway w/ King Bed + Private Backyard
Escape to this light-filled two bedroom, one bathroom bungalow located minutes from the heart of Leesburg's historic district. Just a short drive from unique shops, restaurants, and outdoor activities. This is the perfect home base whether you're in town for a weekend getaway or an extended stay. Located near the W&OD Bike Trail, Birkby House, Morven Park, breweries, wineries,and Rust Manor. We're excited to host you in our little slice of Leesburg charm! Bikes included: 1 mtn. & 1 cruiser

Hot tub, prime leaf peeping and more! Gorgeous 4BR
This gorgeous chalet perched on a high hill is surrounded with trees and features an enormous wrap-around deck, HOT TUB, wood-burning fireplace, huge smart TVs and a GAME ROOM for adults and kids with every fun game you can imagine- pool, ping pong, PacMan video arcades, darts and more. Each bed is new and there are king beds and trundle beds to accommodate visitors of all ages. Please note there is an extra charge of $75 for first dog, $25/ea for 2nd/3rd (2nd/3rd dog fees charged later).

WILD HARE COTTAGE king bed
Perfect for exploring wine country we are 10 minutes from Bluemont Station and Dirt Farm Brewing This property has two bedrooms King and Queen beautiful bathroom in the middle. The kitchen perfectly sized to gather four people. large sitting room out front. Sit on the front porch and watch the travelers pass by on the gravel road. Walk up to the historic Philomont store. Please note this cottage is attached to the front of the main house it’s completely separate utilites and all

Whole House -Seven Elms Farm B&B
Come and enjoy peaceful setting of our 1870 farmhouse situated close to historical Town of Purcellville, great for shopping and enjoying a good meal, W&OD trail is nearby for a walk or a jog. Or you can just sit on either one of the two covered porches with a good book and take in natural open spaces and a view of a serene pond. And of course we are located in heart of Loudoun County's wine country, great spots for picnic and tasting of great selection of wines.

Restored 1820 Waterford Village Farmhouse
We restored this 1820 village farmhouse in 2016. It is situated in the heart of the historic village of Waterford. It has 2 1/2 acres behind, with two barns, a herd of very friendly goats, chickens, and vegetable, herb and flower gardens. The house backs up to The Phillips Farm, 150 acres of preserved land and public walking trails. Beautiful sunset views from the back porch. The house, a work in progress, was featured in both Country Living and Preservation Magazines.

Downtown Leesburg Cottage. Walk to everything!
Beautiful cottage in Downtown Leesburg! Walkable to all that Downtown has to offer! Across the street from the iconic Mom's Apple Pie and a short walk to restaurants, shopping, breweries and W&OD trail. Just a short drive to many local wineries, wedding venues, hiking and only 20 minutes from the Dulles Airport. Escape for the weekend or week and enjoy this beautiful 2 bedroom/1 bath home. Equipped with the essentials you need for a more than enjoyable stay!

Littlefield Cottage
If you are looking for a super sweet and charming cottage to escape to, you've come to the right place. Live like a local in our little cottage and find out for yourself all the beauty that can be found in the country sides of Virginia. Comfortably blending modern conveniences with historic charm, the cottage sits just 1 mile outside of the quaint town of Middelburg and next door to Greenhill Winery.

Historic Tip of the Hill, Purcellville, Virginia
Historic Tip of the Hill, ca 1762, is located just a 1/2 mile outside of the town of Purcellville, VA. Close to all the major wedding venues. Restaurants, wine tasting, breweries, live music, the AT, Shenandoah River, W,O&D bike trail & more are just minutes away. This 18th century home has been completely updated but with its charm and character intact. 3 BR, 1.5 BA, sleeps up to 6.
Popular amenities for Middleburg house rentals
House rentals with a pool

Peacefield - Blue Ridge views near Culpeper

The Historic Booth House at the Harpers Ferry KOA

Historic Farmhouse w/ Heated Pool, Harpers Ferry

Clean 5BR w Heated Pool/Spa - Horse & Wine Country

Cedar Creek Wayside Castle

Nature Zen *Metro Walk *Visit DC *Relaxing Lakes

Walnut Lane

Potomac Overlook Farms: 6 BR, 10 Acre River Estate
Weekly house rentals

Historic Farmhouse, Fully Renovated in Fall 2023

The Dutchmans Creek Farmhouse

Gorgeous cabin on Blue Ridge

The Upperville Academy

Peaceful Country Retreat

Peaceful, Authentic Stone Cottage with Cozy Charm

Mountaintop Home in Harpers Ferry

Countryside cottage quiet setting in Middleburg
Private house rentals

Reynard's Retreat in Upperville

The Fort At Workhorse

Historic 1793 Stone House

The Cabin at Blue Valley Farm

The Cottage at Oakland Green Farm

Luxury 5BR Getaway |Hot Tub, Game Room & Fire Pit

Delightful home, ideal location in VA Wine Country

Atoka Cottage
Quick stats about house rentals in Middleburg
Nightly prices starting at
Middleburg vacation rentals start at ﺩ.ﺇ2,828 per night before taxes and fees
Verified guest reviews
Over 30 verified reviews to help you choose
Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Middleburg rentals
5 Average rating
Middleburg stays are highly rated by guests—averaging 5 out of 5!
Destinations to explore
- Plainview Vacation rentals
- New York Vacation rentals
- Long Island Vacation rentals
- Washington Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- Jersey Shore Vacation rentals
- Philadelphia Vacation rentals
- South Jersey Vacation rentals
- Mount Pocono Vacation rentals
- Outer Banks Vacation rentals
- Ocean City Vacation rentals
- Nationals Park
- Georgetown University
- The White House
- National Mall
- District Wharf
- Smithsonian National Museum of Natural History
- Luray Caverns
- National Museum of African American History and Culture
- Stone Tower Winery
- Arlington National Cemetery
- Georgetown Waterfront Park
- National Harbor
- Cunningham Falls State Park
- Washington Monument
- Great Falls Park
- The Pentagon
- Smithsonian American Art Museum
- Library of Congress
- Lincoln Park
- Shenandoah Valley Golf Club
- Cacapon Resort State Park
- Gambrill State Park
- Creighton Farms
- American African Museum