Holiday rentals near Trump Winery
We found 463 holiday rentals — enter your dates for availability
Choose the right private holiday rental within close proximity to Trump Winery. Holiday homes provide the amenities that you need and want for your stay with friends, family or just your pet, such as a garden and pool. At the end of the day, you'll be able to choose a property to rent to meet everyone's needs, including accessible or non-smoking choices.
Holiday rentals with weekly discounts - Trump Winery
Showing deals for:7 Nov - 14 Nov
Image gallery for Estate in Blue Ridge Foothills - 20 min to Charlottesville
1010 out of 10 rating
Exceptional
(23 reviews)
Estate in Blue Ridge Foothills - 20 min to Charlottesville
Afton, VA
24% off
Price is AU$16,936
AU$16,936
AU$2,419 per night
includes taxes & fees
Image gallery for 1700"s Summer Kitchen Cottage #147 Pool & Spa
9.89.8 out of 10 rating
Exceptional
(51 reviews)
1700"s Summer Kitchen Cottage #147 Pool & Spa
Gordonsville, VA
8% off
Price is AU$1,698
AU$1,698
AU$243 per night
includes taxes & fees
Image gallery for Total Privacy - H’Owl at the Moon Farm & Cabin
1010 out of 10 rating
Exceptional
(171 reviews)
Total Privacy - H’Owl at the Moon Farm & Cabin
Schuyler, VA
8% off
Price is AU$5,432
AU$5,432
AU$776 per night
includes taxes & fees
Image gallery for Afton Cottage w/ Hot Tub, Firepit, Mountain Views
9.89.8 out of 10 rating
Exceptional
(8 reviews)
Afton Cottage w/ Hot Tub, Firepit, Mountain Views
Afton, VA
8% off
Price is AU$3,664
AU$3,664
AU$523 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
(14 reviews)
Gorgeous Tiny Home on Cliff's Edge - 4WD/AWD Access Only
Rockfish, VA
8% off
Price is AU$2,957
AU$2,957
AU$422 per night
includes taxes & fees
Image gallery for 1802 cottage once part of Monticello and owned by Thomas Jefferson
9.49.4 out of 10 rating
Exceptional
(81 reviews)
1802 cottage once part of Monticello and owned by Thomas Jefferson
Charlottesville, VA
16% off
Price is AU$2,451
AU$2,451
AU$350 per night
includes taxes & fees
Image gallery for Perfect vacation home! 100+ REVIEWS AND 5 STARS ON AIRBNB
1010 out of 10 rating
Exceptional
(6 reviews)
Perfect vacation home! 100+ REVIEWS AND 5 STARS ON AIRBNB
Earlysville, VA
12% off
Price is AU$7,131
AU$7,131
AU$1,019 per night
includes taxes & fees
Image gallery for Loveshack, a charming tiny house on a 5 acre farm
9.49.4 out of 10 rating
Exceptional
(6 reviews)
Loveshack, a charming tiny house on a 5 acre farm
Charlottesville, VA
8% off
Price is AU$2,612
AU$2,612
AU$373 per night
includes taxes & fees
Image gallery for Cottage and working farm in heart of Virginia wine country near UVA & Woodberry
1010 out of 10 rating
Exceptional
(8 reviews)
Cottage and working farm in heart of Virginia wine country near UVA & Woodberry
Gordonsville, VA
8% off
Price is AU$4,639
AU$4,639
AU$663 per night
includes taxes & fees
Image gallery for Cottage on quiet farm close to town and wineries
9.69.6 out of 10 rating
Exceptional
(57 reviews)
Cottage on quiet farm close to town and wineries
Charlottesville, VA
8% off
Price is AU$2,729
AU$2,729
AU$390 per night
includes taxes & fees
Image gallery for The Lodge in Sugar Hollow -Charlottesville near Crozet
1010 out of 10 rating
Exceptional
(59 reviews)
The Lodge in Sugar Hollow -Charlottesville near Crozet
Crozet, VA
28% off
Price is AU$4,616
AU$4,616
AU$659 per night
includes taxes & fees
Image gallery for Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy
1010 out of 10 rating
Exceptional
(36 reviews)
Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy
Charlottesville, VA
8% off
Price is AU$4,999
AU$4,999
AU$714 per night
includes taxes & fees
Image gallery for 106 acre Farm with Animals, River & Private Pond, near Wineries and Breweries
1010 out of 10 rating
Exceptional
(46 reviews)
106 acre Farm with Animals, River & Private Pond, near Wineries and Breweries
Scottsville, VA
10% off
Price is AU$2,481
AU$2,481
AU$354 per night
includes taxes & fees
Image gallery for Afton Farmhouse - Mountain Views off Route 151
1010 out of 10 rating
Exceptional
(22 reviews)
Afton Farmhouse - Mountain Views off Route 151
Afton, VA
8% off
Price is AU$5,030
AU$5,030
AU$719 per night
includes taxes & fees
Image gallery for Charming 2-bedroom tiny house close to hiking trails and Nelson 151
1010 out of 10 rating
Exceptional
(6 reviews)
Charming 2-bedroom tiny house close to hiking trails and Nelson 151
Schuyler, VA
7% off
Price is AU$2,959
AU$2,959
AU$423 per night
includes taxes & fees
Image gallery for Peaceful Retreat w/ Hot Tub, Fire Pit, Mountain Views
1010 out of 10 rating
Exceptional
(17 reviews)
Peaceful Retreat w/ Hot Tub, Fire Pit, Mountain Views
Afton, VA
8% off
Price is AU$5,258
AU$5,258
AU$751 per night
includes taxes & fees
Image gallery for Fairwood Cottage-Exceptional 1BR Cottage Minutes From Charlottesville & Wineries
1010 out of 10 rating
Exceptional
(25 reviews)
Fairwood Cottage-Exceptional 1BR Cottage Minutes From Charlottesville & Wineries
Charlottesville, VA
19% off
Price is AU$2,353
AU$2,353
AU$336 per night
includes taxes & fees
Image gallery for One Bedroom One Bath Cottage On 250 Acre Cattle Farm.
1010 out of 10 rating
Exceptional
(47 reviews)
One Bedroom One Bath Cottage On 250 Acre Cattle Farm.
Scottsville, VA
22% off
Price is AU$1,681
AU$1,681
AU$240 per night
includes taxes & fees
Image gallery for Isolated cottage with good view close to many winery and Brewers.
9.09.0 out of 10 rating
Wonderful
(22 reviews)
Isolated cottage with good view close to many winery and Brewers.
Greenwood, VA
8% off
Price is AU$2,476
AU$2,476
AU$354 per night
includes taxes & fees
Image gallery for Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious
1010 out of 10 rating
Exceptional
(243 reviews)
Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious
Charlottesville, VA
16% off
Price is AU$4,133
AU$4,133
AU$590 per night
includes taxes & fees
Image gallery for Studio with close proximity to the wineries and hiking
1010 out of 10 rating
Exceptional
(10 reviews)
Studio with close proximity to the wineries and hiking
Afton, VA
8% off
Price is AU$2,053
AU$2,053
AU$293 per night
includes taxes & fees
Image gallery for Moonfire Farm Shenandoah region cozy getaway
1010 out of 10 rating
Exceptional
(25 reviews)
Moonfire Farm Shenandoah region cozy getaway
Barboursville, VA
8% off
Price is AU$1,776
AU$1,776
AU$254 per night
includes taxes & fees
Image gallery for Pop’s Cottage. A private and serene setting in the country 10 minutes from UVa
1010 out of 10 rating
Exceptional
(85 reviews)
Pop’s Cottage. A private and serene setting in the country 10 minutes from UVa
North Garden, VA
8% off
Price is AU$2,639
AU$2,639
AU$377 per night
includes taxes & fees
Image gallery for Rugby Road Residential -RRR- near UVa and downtown
1010 out of 10 rating
Exceptional
(32 reviews)
Rugby Road Residential -RRR- near UVa and downtown
Charlottesville, VA
12% off
Price is AU$4,965
AU$4,965
AU$709 per night
includes taxes & fees
Find spaces that suit your style
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Chalet
Find the best place to stay - Trump Winery
Charming 3-bedroom house with AC and WiFi in delightful Charlottesville
Sleeps 6 · 3 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
11 reviews(11 reviews)
DEER RIDGE CABIN IS YOUR PERFECT, PRIVATE AND COZY GETAWAY!
Sleeps 4 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
300 reviews(300 reviews)
Wine Country! Unique 2-bedroom horse farm, close by 5 star dining, 5 wineries
Sleeps 4 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
7 reviews(7 reviews)
Keelona Cottage 2 BR 2 BA near vineyards
Sleeps 4 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
10 reviews(10 reviews)
Cowboy hide-a-way cottage with hot tub on historic farm close to everything
Sleeps 4 · 2 bedrooms · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
25 reviews(25 reviews)
Aftonshire Cottage - Heart of Afton's Wine Region
Sleeps 4 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
4 reviews(4 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