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 AU$3,857
AU$3,857
AU$551 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 AU$3,045
AU$3,045
AU$435 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 AU$6,049
AU$6,049
AU$864 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 AU$8,938
AU$8,938
AU$1,277 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 AU$4,932
AU$4,932
AU$705 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 AU$12,415
AU$12,415
AU$1,774 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 AU$1,888
AU$1,888
AU$270 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 AU$2,530
AU$2,530
AU$361 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 AU$3,371
AU$3,371
AU$482 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 AU$8,534
AU$8,534
AU$1,219 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 AU$2,112
AU$2,112
AU$302 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 AU$4,200
AU$4,200
AU$600 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 AU$7,770
AU$7,770
AU$1,110 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 AU$8,326
AU$8,326
AU$1,189 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 AU$3,676
AU$3,676
AU$525 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 AU$9,149
AU$9,149
AU$1,307 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 AU$7,370
AU$7,370
AU$1,053 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 AU$4,825
AU$4,825
AU$689 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 AU$7,389
AU$7,389
AU$1,056 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 AU$5,097
AU$5,097
AU$728 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 AU$8,234
AU$8,234
AU$1,176 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 AU$7,661
AU$7,661
AU$1,094 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 AU$3,017
AU$3,017
AU$431 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 AU$8,284
AU$8,284
AU$1,183 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 AU$3,525
AU$3,525
for 3 nights, 1 home
AU$1,175 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 AU$3,609
AU$3,609
for 3 nights, 1 home
AU$1,203 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 AU$2,994
AU$2,994
for 3 nights, 1 cabin
AU$998 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 AU$1,830
AU$1,830
for 3 nights, 1 home
AU$610 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 AU$2,863
AU$2,863
for 3 nights, 1 home
AU$954 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 AU$5,253
AU$5,253
for 3 nights, 1 home
AU$1,751 per night
includes taxes & fees
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