Vacation rentals in Middleburg

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Top-rated vacation rentals in Middleburg

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Guest favourite

Home in Middleburg

4.97 out of 5 average rating, 149 reviews

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.

Jan. 13 – 20

$624 CAD per night

Guest favourite

Apartment in The Plains

4.98 out of 5 average rating, 447 reviews

Rose End

Need to social distance? Our quiet country studio is far enough from Washington DC to get away without being gone. Ideal for grabbing some space, a long run, a bike ride, or visiting local wineries. The Appalachian Trail is just a stone's throw away. We respect your privacy. No smoking is allowed and internet access is from your own hot-spot. The studio includes a satellite TV, refrigerator, microwave, and coffee maker. The queen-size bed and skylight make Rose End a cozy escape.

Aug. 2 – 9

$131 CAD per night

Guest favourite

Tiny homes in Purcellville

4.98 out of 5 average rating, 130 reviews

King Bed-Tiny Home-Fire Pit-Historic Farm Stay

Escape to our newly renovated tiny cottage nestled in a charming 25-acre farm dating back to the 1700s! Enjoy a tranquil night in our one bedroom haven, boasting a king bed, speedy wifi, kitchen essentials, blackout shades, and a charming fire pit. Ideal for remote work retreats or romantic getaways! Explore nearby wineries, breweries, and scenic trails, and the quaint town of Purcellville, just 10 minutes away. Say hi to our friendly cows and pigs! Book now for an unforgettable stay!

Aug. 24 – 31

$300 CAD per night

Guest favourite

Barn in Middleburg

4.93 out of 5 average rating, 173 reviews

Middleburg Carriage House

Hunt Country charm with modern design and amenities. The rebuilt carriage house overlooks adjacent vineyard and Blue Ridge Mountains. The interior showcases reclaimed materials and wood from the original dwelling. The large flagstone patio offers rolling mountain views where you can enjoy your morning coffee or glass of local wine after a day of winery visits. A two minute drive to historic downtown Middleburg; next to wineries and polo. Enjoy your next getaway!

Sep. 20 – 27

$525 CAD per night

Guest favourite

Tiny homes in Purcellville

4.96 out of 5 average rating, 313 reviews

Remote Tiny House in Purcellville

Nestled in the heart of Purcellville is a tiny home with a ton of charm. Less than 5 miles from vineyards, LOCO ale trail breweries, cideries, WO&D bike trail & 20 min to historic Leesburg, the Shenandoah river & Appalachian Trail. Our tiny house is a bit larger w/ 2 bedrooms, full kitchen & bath, family room & cozy front porch. Guests enjoy private parking & plenty of privacy. Enjoy a remote work getaway, (our broadband is about 8-10Mbps) relax & enjoy LOCO living!

Feb. 13 – 20

$239 CAD per night

Guest favourite

Cottage in Middleburg

4.92 out of 5 average rating, 106 reviews

English Cottage

MIDDLEBURG ADDRESS. Best country/Middleburg location. Five (+/-) min to town, restaurants, shopping, wedding venues. Centrally located to vineyards, breweries, horse events, more.. Guests 'LOVE' this CLEAN, tasteful, charming/Old English style - private cottage.' Bdrm w/2 twin or together as king bed. (Can separate beds if requested.) Bath with rain shower. Kitchenette appointed with modern appliances. Stainless refrig., microwave, toaster oven & Keurig.

Jul. 20 – 27

$277 CAD per night

Guest favourite

Guesthouse in Warrenton

4.98 out of 5 average rating, 252 reviews

The Alton Cottage -a luxury country retreat

The Alton Cottage is a charming, newly refurbished 1820s guest house- formerly a summer kitchen to the original farm house. Views are of rolling fields and their bovine occupants. We are within 30 minutes of almost 20 wineries and another 20 breweries, 5 min to Airlie, and only 5 mi to Old Town Warrenton. We are also close to several antique stores, farmers markets and Shenandoah National Park. We strive to make every guests stay special.

Jun. 11 – 18

$212 CAD per night

Guest favourite

Loft in Purcellville

4.99 out of 5 average rating, 289 reviews

"When Pigs Fly" Airbnb Most Hospitable Host in VA

Located between Middleburg, VA and Purcellville, VA, our loft is just about 15 minutes away from restaurants, wineries, breweries and many local points of interest. You will have views from every window in addition to all of the amenities you will need for a pleasant stay. We welcome your dogs while you visit. The only thing we ask is that you keep them off the couch, pick up their "business" and crate them if they are left alone.

Dec. 4 – 11

$183 CAD per night

Guest favourite

Home in Middleburg

5.0 out of 5 average rating, 140 reviews

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.

Oct. 20 – 27

$641 CAD per night

Guest favourite

Guesthouse in Round Hill

4.98 out of 5 average rating, 375 reviews

Private Carriage House

A recently renovated carriage house by an interior designer situated on a treed and private property conveniently located for exploring wineries, breweries, horse events or civil war sites in Middleburg, Purcellville, Leesburg, Bluemont or Round HIill. Enjoy the sounds and sights of nature and fresh air. Recharge in a peaceful setting. Adults only. No pets, children or infants.

Jul. 6 – 13

$216 CAD per night

Guest favourite

Place to stay in The Plains

4.94 out of 5 average rating, 162 reviews

The Whistle Stop

Historic, renovated, train station in the heart of Virginia hunt and wine country. This private oasis sits on the second floor above three gorgeous art studios belonging to local artists. Enroll in an art workshop, enjoy twilight polo and horse races at Great Meadows, or find yourself having a romantic dinner in our little village of The Plains.

Aug. 15 – 22

$234 CAD per night

Guest favourite

Guest suite in Bluemont

4.93 out of 5 average rating, 523 reviews

Blueridge Mountain Retreat Apartment

In the middle of VA wine country and only minutes from the Appalachian Trail, enjoy a private apartment in our mountain home with a separate entrance and your own deck with views of the Shenandoah Valley. There is a hot tub on the deck and a fire pit overlooking the valley. Plenty of wildlife. A welcome basket includes breakfast items.

Nov. 23 – 30

$177 CAD per night