Holiday rentals near Lovingston Winery
We found 844 holiday rentals — enter your dates for availability
Choose the right holiday rental that's close to Lovingston Winery. Holiday homes offer the amenities that you expect for your stay with friends, family or just your pet, such as Wi-Fi and a washer and dryer. No matter what you're looking for, you're sure to find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts - Lovingston Winery
Showing deals for:3 Oct - 10 Oct
Image gallery for Secluded 20+ Acre Retreat Near Brew & Wine Trails
9.89.8 out of 10 rating
Exceptional
(7 reviews)
Secluded 20+ Acre Retreat Near Brew & Wine Trails
Afton, VA
7% off
Price is NZ$4,192
NZ$4,192
NZ$599 per night
includes taxes & fees
Image gallery for Luxury Log Cabin Getaway: Near Wintergreen Resort & Shenandoah Valley
1010 out of 10 rating
Exceptional
(12 reviews)
Luxury Log Cabin Getaway: Near Wintergreen Resort & Shenandoah Valley
Shipman, VA
12% off
Price is NZ$3,308
NZ$3,308
NZ$473 per night
includes taxes & fees
Image gallery for Golden Tee 60"TV Fireplace Deck Grill Pool Tennis
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Golden Tee 60"TV Fireplace Deck Grill Pool Tennis
Roseland, VA
7% off
Price is NZ$6,634
NZ$6,634
NZ$948 per night
includes taxes & fees
Image gallery for Sip 'n Dip: Hot Tub Foosball Pool Table Ping Pong
9.29.2 out of 10 rating
Wonderful
(7 reviews)
Sip 'n Dip: Hot Tub Foosball Pool Table Ping Pong
Nellysford, VA
7% off
Price is NZ$5,350
NZ$5,350
NZ$764 per night
includes taxes & fees
Image gallery for 5 BR Wintergreen House w/ Game Room, 75” TV, Ping Pong, Foosball, Wet Bar & Deck
1010 out of 10 rating
Exceptional
(12 reviews)
5 BR Wintergreen House w/ Game Room, 75” TV, Ping Pong, Foosball, Wet Bar & Deck
Nellysford, VA
8% off
Price is NZ$9,624
NZ$9,624
NZ$1,375 per night
includes taxes & fees
Image gallery for Berry Hill Lake - Cabin w/ NEW Infinity Pool - Pet Friendly - Private Lake
1010 out of 10 rating
Exceptional
(105 reviews)
Berry Hill Lake - Cabin w/ NEW Infinity Pool - Pet Friendly - Private Lake
Nellysford, VA
8% off
Price is NZ$13,830
NZ$13,830
NZ$1,976 per night
includes taxes & fees
Image gallery for Upscale Wintergreen Getaway. Golf View Deck, Pool, and Modern Comforts
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Upscale Wintergreen Getaway. Golf View Deck, Pool, and Modern Comforts
Nellysford, VA
7% off
Price is NZ$2,011
NZ$2,011
NZ$287 per night
includes taxes & fees
Image gallery for Apartment on the Knoll with private pool
1010 out of 10 rating
Exceptional
(9 reviews)
Apartment on the Knoll with private pool
Lovingston, VA
8% off
Price is NZ$2,752
NZ$2,752
NZ$393 per night
includes taxes & fees
Image gallery for Gorgeous Tiny Home on Cliff's Edge - 4WD/AWD Access Only
1010 out of 10 rating
Exceptional
(13 reviews)
Gorgeous Tiny Home on Cliff's Edge - 4WD/AWD Access Only
Rockfish, VA
8% off
Price is NZ$3,671
NZ$3,671
NZ$524 per night
includes taxes & fees
Image gallery for Amazing Views! Pool - Hiking - Gazebo - Hot Tub - Pool Table - Multicade - Grill
1010 out of 10 rating
Exceptional
(16 reviews)
Amazing Views! Pool - Hiking - Gazebo - Hot Tub - Pool Table - Multicade - Grill
Nellysford, VA
8% off
Price is NZ$9,458
NZ$9,458
NZ$1,351 per night
includes taxes & fees
Image gallery for Country Farmhouse: Fire Pit, Grill, Updated Amenities, Cows, Stars and Solitude
1010 out of 10 rating
Exceptional
(12 reviews)
Country Farmhouse: Fire Pit, Grill, Updated Amenities, Cows, Stars and Solitude
Monroe, VA
8% off
Price is NZ$2,265
NZ$2,265
NZ$324 per night
includes taxes & fees
Image gallery for Cabin By The Falls
1010 out of 10 rating
Exceptional
(45 reviews)
Cabin By The Falls
Tyro, VA
15% off
Price is NZ$8,608
NZ$8,608
NZ$1,230 per night
includes taxes & fees
Image gallery for Roudy’s Retreat: Secluded Mountain Cabin with Hot Tub and Private Pond
1010 out of 10 rating
Exceptional
(18 reviews)
Roudy’s Retreat: Secluded Mountain Cabin with Hot Tub and Private Pond
Montebello, VA
17% off
Price is NZ$4,563
NZ$4,563
NZ$652 per night
includes taxes & fees
Image gallery for Summer Fun! Game Room+Fire Pit+Hot Tub in spacious family-friendly house
1010 out of 10 rating
Exceptional
(12 reviews)
Summer Fun! Game Room+Fire Pit+Hot Tub in spacious family-friendly house
Nellysford, VA
8% off
Price is NZ$9,003
NZ$9,003
NZ$1,286 per night
includes taxes & fees
Image gallery for The "Small" House
1010 out of 10 rating
Exceptional
(6 reviews)
The "Small" House
Nellysford, VA
8% off
Price is NZ$4,000
NZ$4,000
NZ$571 per night
includes taxes & fees
Image gallery for Luxury mountain home Ski- in-Ski out
1010 out of 10 rating
Exceptional
(19 reviews)
Luxury mountain home Ski- in-Ski out
Wintergreen, VA
12% off
Price is NZ$9,846
NZ$9,846
NZ$1,407 per night
includes taxes & fees
Image gallery for Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14
1010 out of 10 rating
Exceptional
(49 reviews)
Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14
Nellysford, VA
8% off
Price is NZ$8,165
NZ$8,165
NZ$1,166 per night
includes taxes & fees
Image gallery for 4 BR cabin mins to trails & breweries pets welcome
9.89.8 out of 10 rating
Exceptional
(24 reviews)
4 BR cabin mins to trails & breweries pets welcome
Nellysford, VA
22% off
Price is NZ$5,238
NZ$5,238
NZ$748 per night
includes taxes & fees
Image gallery for Three Ridges Haven- Devils Backbone Brewing Company
9.49.4 out of 10 rating
Exceptional
(70 reviews)
Three Ridges Haven- Devils Backbone Brewing Company
Roseland, VA
25% off
Price is NZ$8,186
NZ$8,186
NZ$1,169 per night
includes taxes & fees
Image gallery for Family-favorite rental nestled in the woods at the top of the Wintergreen Resort
1010 out of 10 rating
Exceptional
(5 reviews)
Family-favorite rental nestled in the woods at the top of the Wintergreen Resort
Nellysford, VA
8% off
Price is NZ$5,500
NZ$5,500
NZ$786 per night
includes taxes & fees
Image gallery for Luxe Private Getaway in the Heart of Wintergreen!
8.48.4 out of 10 rating
Very good
(8 reviews)
Luxe Private Getaway in the Heart of Wintergreen!
Nellysford, VA
7% off
Price is NZ$8,487
NZ$8,487
NZ$1,212 per night
includes taxes & fees
Image gallery for Mountain Season Lodge
1010 out of 10 rating
Exceptional
(18 reviews)
Mountain Season Lodge
Nellysford, VA
12% off
Price is NZ$8,878
NZ$8,878
NZ$1,268 per night
includes taxes & fees
Image gallery for Cozy Farmhouse W/Mountain Views
1010 out of 10 rating
Exceptional
(16 reviews)
Cozy Farmhouse W/Mountain Views
Roseland, VA
8% off
Price is NZ$3,280
NZ$3,280
NZ$469 per night
includes taxes & fees
Image gallery for Modern Mountain Retreat: Hot Tub, Chef's Kitchen, Game Room & Ski Access
1010 out of 10 rating
Exceptional
(130 reviews)
Modern Mountain Retreat: Hot Tub, Chef's Kitchen, Game Room & Ski Access
Wintergreen, VA
8% off
Price is NZ$8,934
NZ$8,934
NZ$1,276 per night
includes taxes & fees
Find spaces that suit your style
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Chalet
Find the best place to stay - Lovingston Winery
Showing deals for: 2 Oct - 5 Oct
Bright & Modern 5 BR Wintergreen Home; Minutes from Hiking, Skiing, and Wineries
Sleeps 11 · 5 bedrooms · 3 bathrooms
9.89.8 out of 10
Exceptionalexceptional
8 reviews(8 reviews)
The current price is NZ$3,837
NZ$3,837
for 3 nights, 1 home
NZ$1,279 per night
includes taxes & fees
Mountain Home at Wintergreen Resort...in the heart of Virginia's wine country.
Sleeps 12 · 5 bedrooms · 4+ bathrooms
1010 out of 10
Exceptionalexceptional
90 reviews(90 reviews)
The current price is NZ$3,926
NZ$3,926
for 3 nights, 1 home
NZ$1,309 per night
includes taxes & fees
Spacious Cabin in the Woods near Breweries and Wineries
Sleeps 10 · 4 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
The current price is NZ$3,241
NZ$3,241
for 3 nights, 1 cabin
NZ$1,080 per night
includes taxes & fees
Spectacular Mountain View, Historic House
Sleeps 12 · 6 bedrooms · 6 bathrooms
8.68.6 out of 10
Excellentexcellent
28 reviews(28 reviews)
The current price is NZ$1,993
NZ$1,993
for 3 nights, 1 home
NZ$664 per night
includes taxes & fees
Hickory Hideaway- 5 BR 4 BA with game room and indoor fire place
Sleeps 12 · 5 bedrooms · 4 bathrooms
1010 out of 10
Exceptionalexceptional
7 reviews(7 reviews)
The current price is NZ$3,172
NZ$3,172
for 3 nights, 1 home
NZ$1,057 per night
includes taxes & fees
Panoramic Views by Vineyards 4000 sf new home on 40 acs
Sleeps 12 · 5 bedrooms · 4+ bathrooms
1010 out of 10
Exceptionalexceptional
15 reviews(15 reviews)
The current price is NZ$5,890
NZ$5,890
for 3 nights, 1 home
NZ$1,963 per night
includes taxes & fees
Top rated rentals - Lovingston Winery
Weekend Getaway
1010 out of 10
Exceptionalexceptional
44 reviews(44 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value