Middleburg vacation rentals

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Top-rated vacation rentals in Middleburg

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Cottage in The Plains

4.98 out of 5 average rating, 174 reviews

The Cottage on Main -Virginia Wine & Horse Country

The Cottage on Main, originally built around 1840 recently underwent a full renovation! Walk to the restaurants and shops of The Plains or explore the quaint towns of Marshall, Middleburg, Warrenton, Upperville with just a few minutes drive. This one bedroom, 1 bath cottage with full kitchen, living & dining area has everything you need for a weekend getaway or extended stay. The Plains is home to Gold Cup & many other equestrian events, amazing dining & shopping and the Virginia wine country!

Jul 28 – Aug 4

G$40,413 GYD per night

Guest favorite

Home in Middleburg

4.97 out of 5 average rating, 148 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 24 – 31

G$78,069 GYD per night

Guest favorite

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 13 – 20

G$18,457 GYD per night

Guest favorite

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!

Dec 18 – 25

G$57,478 GYD per night

Guest favorite

Tiny home 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!

Mar 28 – Apr 4

G$31,368 GYD per night

Guest favorite

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 6 – 13

G$35,560 GYD per night

Guest favorite

Farm stay in Purcellville

4.99 out of 5 average rating, 313 reviews

Cozy Cuddle up on 1700’s Clydesdale Farm

The Hunt Box at Sylvanside Farm is a couples favorite! Cozy bedroom with bay window overlooks the stone barn, Clydesdales field and pond. Full kitchen, full bath and small living room. Enjoy a glass of wine on dock, hike the fields and streams, enjoy the animals, roam the our beautiful 25 acres. Escape the city and relax. Our visitors to date have proclaimed it magical and we hope you agree. In accordance with Airbnb’s policies parties are not permitted.

G$34,793 GYD per night

Guest favorite

Guesthouse in Warrenton

4.98 out of 5 average rating, 251 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 14 – 21

G$29,062 GYD per night

Guest favorite

Loft in Purcellville

4.99 out of 5 average rating, 286 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.

Nov 24 – Dec 1

G$24,083 GYD per night

Guest favorite

Guest suite in The Plains

5.0 out of 5 average rating, 116 reviews

Luxury hunt country getaway!

Charming 1100 sq. ft space in the heart of Hunt Country. Lower level private entrance and parking. Fully outfitted kitchen, Nespresso coffee maker, french press and all the kitchen necessities. Walking distance to coffee shops, restaurants and antique stores. Close to wineries, Great Meadows and popular cycling routes. Convenient location 40 miles just outside of DC, right off route 66 but nestled away in the countryside.

Sep 22 – 29

G$42,413 GYD per night

Guest favorite

Home in Middleburg

5.0 out of 5 average rating, 138 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.

Dec 30 – Jan 6

G$79,337 GYD per night

Guest favorite

Guesthouse in Round Hill

4.98 out of 5 average rating, 372 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 7 – 14

G$26,851 GYD per night