Uppervilleholiday rentals

From simple studios to luxe lofts, find holiday rentals that are right for you on Airbnb.

Holiday rentals in Upperville

$369 AUD Ashby's Perch -- A Very Special Retreat
16 reviews

Sweeping views of Ashby's Gap just minutes away from Upperville and Middleburg, 1 hour outside of DC. Newly renovated with a vintage flair, private and secluded. Ideal weekend ... read more
$267 AUD The Stone Cottage at Bluemont Vineyard
21 reviews

The Stone Cottage is located in the middle of Bluemont Vineyard with over 40 other vineyards to visit within an hour's drive. Great hiking abounds in the area with the Appalach... read more
$181 AUD Gaelhurst: Spacious & Scenic Bluemont Retreat
8 reviews

Surrounded by spectacular scenery in the foothills of the Blue Ridge Mtns, one hour to DC. There’s so much to do--wineries, craft brewers, horse rides, AT hiking, Shenandoah tub... read more
$107 AUD Pvt Apt in Blueridge Mtn Retreat
2 reviews

Private apartment in our mountain home with separate entrance. You will walk out onto your own deck with spectacular views of the Shenandoah Valley. You will have access to an ... read more
$201 AUD Charming private apartment
13 reviews

"Magical." This second story apartment, surrounded by giant spruces, is sited at the top of the Blue Ridge mountains, with a long sweep of lawn guiding the eye to the Shenandoah... read more
$269 AUD Hunt Country Retreat near Middleburg, VA
6 reviews

We sit in the little village of Unison, site of a Civil War battle, in the Middleburg hunt country, an area of wineries, a home to artist and writers, surrounded by open farmlan... read more

Favourite Upperville holiday rentals

$134 AUD Historic, private, unique, location
11 reviews

Cozy, country 2nd floor suite with full bath and private staircase with additional half bath on first floor and fully equipped kitchen. Mattresses and linens are the best you wi... read more
$302 AUD The Abbey in Virginia Wine and Orchard Country
1 review

Historic, and conveniently placed. Our 1830 school house cabin sits a few miles off of Rt. 66 - right on Peach Way; attractions within a 10-mile radius include - 15 wineries, 5... read more
$223 AUD Rainbow View Cabin - ShenandoahValleyview & hottub
4 reviews

Escape to the Blue Ridge Mountains. View over Shenandoah Valley above village of Linden, 5 miles from Front Royal, northern gateway to Skyline Drive/Shenandoah National Park. Ne... read more
$536 AUD One Nest Home in Hunt Country
60 reviews

This home and setting will blow you away. Featured in the Washington Post, Virginia Living and Home and Design - its a place that will both inspire and calm you. It has a soul a... read more
$120 AUD Private detached garage suite
41 reviews

a large bedroom of 700 sq feet, a kitchenette, private parking, full bath with shower, coffee maker and refrigerator, and cable television Kitchenette is included and a full si... read more
$93 AUD Entire basement suite and private entrance
1 review

Our B&B is perfectly located in the wine country and situated in the Blue Ridge Mountain. Only about 30 minutes from Washington Dulles International Airport and approximately a ... read more

More holiday rentals in Upperville

$201 AUD Monet Suite, elegnt lrg 2rm suite/blcny in villa
34 reviews

"Monet Suite", elegant furnished 2 room spacious master suite with original oil paintings; private balcony. Magnificent Blue Ridge Mountain views in artist villa located in the... read more
$207 AUD Trillium Treehouse
37 reviews

The farm is 10 miles east of Front Royal where you can explore wineries, Shenandoah Park, the river, the Appalachian Trail. Staying in a tree house is the most unique experience... read more
$181 AUD Virginia Wine Country Retreat
29 reviews

Tucked away in the foot hills of the Virginia Blue Ridge, surrounded by nature forests and bucolic pastures this retreat offers serenity away from the maddening urban crowds. V... read more

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