Vacation rentals in Upperville

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Top-rated vacation rentals in Upperville

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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.

Nov 10 – 17

ﺩ.ﺇ1,450 per night

Superhost

Cottage in Upperville

4.88 out of 5 average rating, 114 reviews

Cottage on Pantherskin Creek - Upperville

Newly restored Historic Charity Cottage is nestled on the edge of Upperville, overlooking the Pantherskin Creek. Cottage is private, beautifully decorated, cozy, restored with top craftmanship, and equipped with modern amenities. Surrounded by areas top attractions, including a 5 min. drive to popular Hunters Head Tavern, and 8 miles west of Downtown Middleburg, just to name a few. Whether you are hear for a couples getaway, history buff, or weekend away this cottage is sure to impress.

Aug 14 – 21

ﺩ.ﺇ834 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.

Sep 10 – 17

ﺩ.ﺇ324 per night

Guest favorite

Home in Bluemont

4.93 out of 5 average rating, 202 reviews

The Country French Cottage at High Meadows Estate

Come visit the alluring wine country of Bluemont Virginia, and stay in a beautifully appointed country French cottage on the 50 acre circa 1896 High Meadows Estate atop the Blueridge Mountains. Just 50 minutes west of Washington DC, this stunning country retreat is just 5 minute from the vineyards of Bluemont, the Shenandoah River, the Appalachian Trail, Hiking, Canoeing, Kayaking, Farmers Markets, the the cute villages or Berryville, Harpers Ferry, Luckettes, Middleburg and many more.

Jul 13 – 20

ﺩ.ﺇ555 per night

Guest favorite

Home in Upperville

4.91 out of 5 average rating, 161 reviews

Upperville Hunt Country Cottage

The home has a standing seam metal roof, clapboard-style siding, a stone foundation, a cozy front porch, and second-floor dormer windows. The interior is painted with warm colors and accented by antique oak barn wood paneling and trim in the family room. The flooring is the original antique heart pine. The cottage is decorated as a traditional English Hunt Box, with equine art and memorabilia, lovely antiques, warm carpets on the heart pine floors, and high-end bed linens.

Nov 23 – 30

ﺩ.ﺇ1,204 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!

Sep 10 – 17

ﺩ.ﺇ1,171 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 23 – 30

ﺩ.ﺇ625 per night

Guest favorite

Cabin in Upperville

4.93 out of 5 average rating, 124 reviews

Island cabin

Getaway from the city and escape to the countryside in this beautiful cabin recently renovated. Situated on a beautiful private lake, enjoy your morning coffee on the porch over looking the water, or enjoy the fire pit with the sunset. The cabin features a queen size bed, a full bathroom, a kitchenette, and a cozy living room area. There is also an outside grill and fire pit. We recently updated the kitchen and added a full size fridge/freezer.

Nov 9 – 16

ﺩ.ﺇ977 per night

Guest favorite

Loft in Purcellville

4.99 out of 5 average rating, 287 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 19 – 26

ﺩ.ﺇ399 per night

Guest favorite

Home in Middleburg

5.0 out of 5 average rating, 139 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.

Jul 13 – 20

ﺩ.ﺇ1,385 per night

Guest favorite

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 10 – 17

ﺩ.ﺇ467 per night

Superhost

Cottage in Bluemont

4.83 out of 5 average rating, 189 reviews

Wine Country Cottage

Cottage in the heart of wine country! Access 4 wineries within a 5-mile radius as well as the AppalacionTrail, breweries, hikes, and historic battlefields. 1 min drive/5 minute walk to Shenandoah River. Check-in and check-out can be somewhat flexible with advance notice. If you need a different time feel free to ask. Pet friendly with a non-refundable fee.

ﺩ.ﺇ364 per night