Holiday rentals near Upperville Park
We found 104 holiday rentals — enter your dates for availability
Select the perfect private holiday rental within easy reach of Upperville Park. Holiday homes offer the amenities that you expect for you and your friends, family or even pets, such as air conditioning and Wi-Fi. No matter what you're looking for, you're sure to find a property to rent for everyone's needs, including accessible or non-smoking choices.
Holiday rentals with weekly discounts - Upperville Park
Showing deals for:7 Nov - 14 Nov
Image gallery for Monet HoneymoonSuite Elegant Lrg 2rm w/balcony in villa/Mountn~pasture-pool view
9.89.8 out of 10 rating
Exceptional
(32 reviews)
Monet HoneymoonSuite Elegant Lrg 2rm w/balcony in villa/Mountn~pasture-pool view
Purcellville, VA
30% off
Price is NZ$3,201
NZ$3,201
NZ$457 per night
includes taxes & fees
Image gallery for Peaceful Mountain Retreat Near Appalachian Trail, Wineries, Breweries and More
1010 out of 10 rating
Exceptional
(16 reviews)
Peaceful Mountain Retreat Near Appalachian Trail, Wineries, Breweries and More
Bluemont, VA
8% off
Price is NZ$5,468
NZ$5,468
NZ$781 per night
includes taxes & fees
Image gallery for Stylishly restored 1800's historic home- heart of Virginia hunt & wine country!
1010 out of 10 rating
Exceptional
(65 reviews)
Stylishly restored 1800's historic home- heart of Virginia hunt & wine country!
Marshall, VA
13% off
Price is NZ$4,618
NZ$4,618
NZ$660 per night
includes taxes & fees
Image gallery for The Van Gogh Room in Villa
9.09.0 out of 10 rating
Wonderful
(63 reviews)
The Van Gogh Room in Villa
Purcellville, VA
21% off
Price is NZ$3,044
NZ$3,044
NZ$435 per night
includes taxes & fees
Image gallery for Charming Writer's Cottage in the Heart of Middleburg
9.89.8 out of 10 rating
Exceptional
(139 reviews)
Charming Writer's Cottage in the Heart of Middleburg
Middleburg, VA
21% off
Price is NZ$2,877
NZ$2,877
NZ$411 per night
includes taxes & fees
Image gallery for CEDAR LANE - Private Cottage, Sophisticated Country Charm
1010 out of 10 rating
Exceptional
(150 reviews)
CEDAR LANE - Private Cottage, Sophisticated Country Charm
Middleburg, VA
8% off
Price is NZ$5,389
NZ$5,389
NZ$770 per night
includes taxes & fees
Image gallery for Blue Mountain Log Cabin
1010 out of 10 rating
Exceptional
(78 reviews)
Blue Mountain Log Cabin
Linden, VA
8% off
Price is NZ$3,026
NZ$3,026
NZ$432 per night
includes taxes & fees
Image gallery for Historical Manor 2 bedroom Unit - Minutes from downtown Middleburg
9.49.4 out of 10 rating
Exceptional
(8 reviews)
Historical Manor 2 bedroom Unit - Minutes from downtown Middleburg
Middleburg, VA
17% off
Price is NZ$3,645
NZ$3,645
NZ$521 per night
includes taxes & fees
Image gallery for Charming 3-bedroom cottage located on historic Seaton Place Farm in Delaplane VA
1010 out of 10 rating
Exceptional
(5 reviews)
Charming 3-bedroom cottage located on historic Seaton Place Farm in Delaplane VA
Delaplane, VA
8% off
Price is NZ$4,541
NZ$4,541
NZ$649 per night
includes taxes & fees
Image gallery for Middleburg address - Charming Cottage with super location in country setting
9.89.8 out of 10 rating
Exceptional
(80 reviews)
Middleburg address - Charming Cottage with super location in country setting
Middleburg, VA
8% off
Price is NZ$2,348
NZ$2,348
NZ$335 per night
includes taxes & fees
Image gallery for Hunt Country cottage in Upperville!
1010 out of 10 rating
Exceptional
(18 reviews)
Hunt Country cottage in Upperville!
Upperville, VA
8% off
Price is NZ$2,386
NZ$2,386
NZ$341 per night
includes taxes & fees
Image gallery for #CozyCleanCabin#HotTub#WoodStove#PetsOK#near BMLodge&Skyline D&Wineries
1010 out of 10 rating
Exceptional
(14 reviews)
#CozyCleanCabin#HotTub#WoodStove#PetsOK#near BMLodge&Skyline D&Wineries
Linden, VA
24% off
Price is NZ$2,200
NZ$2,200
NZ$314 per night
includes taxes & fees
Image gallery for Whitetail Summit - Shenandoah/hot tub/wineries
1010 out of 10 rating
Exceptional
(41 reviews)
Whitetail Summit - Shenandoah/hot tub/wineries
Front Royal, VA
8% off
Price is NZ$8,028
NZ$8,028
NZ$1,147 per night
includes taxes & fees
Image gallery for Whiskey Hill Cabin a Mountain escape in Virginia Wine country.
1010 out of 10 rating
Exceptional
(90 reviews)
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.
Front Royal, VA
8% off
Price is NZ$2,689
NZ$2,689
NZ$384 per night
includes taxes & fees
Image gallery for Historical cottage in the town of Paris
9.89.8 out of 10 rating
Exceptional
(45 reviews)
Historical cottage in the town of Paris
Paris, VA
16% off
Price is NZ$2,391
NZ$2,391
NZ$342 per night
includes taxes & fees
Image gallery for Historic home nestled in the heart of horse and wine country. Kids/pet friendly!
1010 out of 10 rating
Exceptional
(7 reviews)
Historic home nestled in the heart of horse and wine country. Kids/pet friendly!
Paris, VA
8% off
Price is NZ$4,082
NZ$4,082
NZ$583 per night
includes taxes & fees
Image gallery for Romantic, family friendly mountain getaway w hot tub near wineries & skyline
1010 out of 10 rating
Exceptional
(16 reviews)
Romantic, family friendly mountain getaway w hot tub near wineries & skyline
Front Royal, VA
12% off
Price is NZ$4,098
NZ$4,098
NZ$585 per night
includes taxes & fees
Image gallery for Historic Bluemont Village Home
1010 out of 10 rating
Exceptional
(36 reviews)
Historic Bluemont Village Home
Bluemont, VA
8% off
Price is NZ$5,053
NZ$5,053
NZ$722 per night
includes taxes & fees
Image gallery for 5-bedroom Farmhouse In Heart Of Virginia Horse Country- Private Trail To Wine
9.89.8 out of 10 rating
Exceptional
(56 reviews)
5-bedroom Farmhouse In Heart Of Virginia Horse Country- Private Trail To Wine
Delaplane, VA
8% off
Price is NZ$8,471
NZ$8,471
NZ$1,210 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Upperville Park
Skyline Yurt: Hot Tub~Wood Stove~WiFi~EVcharger
Sleeps 8 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
5 reviews(5 reviews)
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.
Sleeps 4 · 3 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
90 reviews(90 reviews)
18th Century Stone Cottage minutes from historic Middleburg
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
46 reviews(46 reviews)
Hidden Hollow Farm - Pool; Game Rm; Sleeps 26, 55 min. to DC, Riverwalk & Trails
Sleeps 26 · 6 bedrooms · 3+ bathrooms
1010 out of 10
Exceptionalexceptional
138 reviews(138 reviews)
Historical cottage in the town of Paris
Sleeps 2 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
45 reviews(45 reviews)
Rustic Mountain Log Cabin Perched on a cliff side above the Shenandoah River
Sleeps 4 · 2 bedrooms · 1 bathroom
9.29.2 out of 10
Wonderfulwonderful
232 reviews(232 reviews)
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All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
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