Holiday rentals near Trump Winery
We found 461 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:15 Aug - 22 Aug
Image gallery for Total Privacy - H’Owl at the Moon Farm & Cabin
1010 out of 10 rating
Exceptional
(168 reviews)
Total Privacy - H’Owl at the Moon Farm & Cabin
Schuyler, VA
8% off
Price is NZ$4,252
NZ$4,252
NZ$607 per night
includes taxes & fees
Image gallery for Visit Monticello, Wineries, UVA & More
9.09.0 out of 10 rating
Wonderful
(6 reviews)
Visit Monticello, Wineries, UVA & More
Zion Crossroads, VA
22% off
Price is NZ$4,657
NZ$4,657
NZ$665 per night
includes taxes & fees
Image gallery for 5 min to Downtown C'ville, 3b/2b Comfortable!
1010 out of 10 rating
Exceptional
(17 reviews)
5 min to Downtown C'ville, 3b/2b Comfortable!
Charlottesville, VA
8% off
Price is NZ$4,463
NZ$4,463
NZ$638 per night
includes taxes & fees
Image gallery for Penthouse Apartment Overlooking Downtown Mall
1010 out of 10 rating
Exceptional
(34 reviews)
Penthouse Apartment Overlooking Downtown Mall
Charlottesville, VA
11% off
Price is NZ$6,588
NZ$6,588
NZ$941 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
(82 reviews)
Pop’s Cottage. A private and serene setting in the country 10 minutes from UVa
North Garden, VA
8% off
Price is NZ$3,293
NZ$3,293
NZ$470 per night
includes taxes & fees
Image gallery for Farmhouse On 14 Acres. Close to Monticello & Ash Lawn Highland
1010 out of 10 rating
Exceptional
(32 reviews)
Farmhouse On 14 Acres. Close to Monticello & Ash Lawn Highland
Charlottesville, VA
16% off
Price is NZ$4,932
NZ$4,932
NZ$705 per night
includes taxes & fees
Image gallery for Fulton Belle Vue - Beautiful fully renovated Farmhouse in Afton-great location.
1010 out of 10 rating
Exceptional
(23 reviews)
Fulton Belle Vue - Beautiful fully renovated Farmhouse in Afton-great location.
Afton, VA
8% off
Price is NZ$7,714
NZ$7,714
NZ$1,102 per night
includes taxes & fees
Image gallery for The Recycled House - Walk Downtown
1010 out of 10 rating
Exceptional
(161 reviews)
The Recycled House - Walk Downtown
Charlottesville, VA
24% off
Price is NZ$3,319
NZ$3,319
NZ$474 per night
includes taxes & fees
Image gallery for Rockfish Farmhouse - Home In the heart of The Rockfish Valley
1010 out of 10 rating
Exceptional
(56 reviews)
Rockfish Farmhouse - Home In the heart of The Rockfish Valley
Afton, VA
8% off
Price is NZ$4,257
NZ$4,257
NZ$608 per night
includes taxes & fees
Image gallery for Newly-renovated 5BR home near UVA, Downtown, i64. Weddings/bachelorette parties!
1010 out of 10 rating
Exceptional
(21 reviews)
Newly-renovated 5BR home near UVA, Downtown, i64. Weddings/bachelorette parties!
Charlottesville, VA
18% off
Price is NZ$6,868
NZ$6,868
NZ$981 per night
includes taxes & fees
Image gallery for CritzerShop - route 151- walk to the Brewey!
1010 out of 10 rating
Exceptional
(34 reviews)
CritzerShop - route 151- walk to the Brewey!
Afton, VA
12% off
Price is NZ$3,594
NZ$3,594
NZ$513 per night
includes taxes & fees
Image gallery for Bright, Spacious Home Perfect for Groups and Families: 4BR, 5 Beds
1010 out of 10 rating
Exceptional
(53 reviews)
Bright, Spacious Home Perfect for Groups and Families: 4BR, 5 Beds
Charlottesville, VA
21% off
Price is NZ$5,956
NZ$5,956
NZ$851 per night
includes taxes & fees
Image gallery for Beautiful, Relaxing Getaway for Family and Friends
1010 out of 10 rating
Exceptional
(57 reviews)
Beautiful, Relaxing Getaway for Family and Friends
Charlottesville, VA
8% off
Price is NZ$10,592
NZ$10,592
NZ$1,513 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
(11 reviews)
Gorgeous Tiny Home on Cliff's Edge - 4WD/AWD Access Only
Rockfish, VA
8% off
Price is NZ$2,663
NZ$2,663
NZ$380 per night
includes taxes & fees
Image gallery for Piedmont Place 301| Lux Vineyard & Brewery Getaway in the Heart of Crozet | Pet Friendly
9.89.8 out of 10 rating
Exceptional
(22 reviews)
Piedmont Place 301| Lux Vineyard & Brewery Getaway in the Heart of Crozet | Pet Friendly
Crozet, Virginia
7% off
Price is NZ$3,256
NZ$3,256
NZ$465 per night
includes taxes & fees
Image gallery for Downtown Mall Boutique Hotel Room above The Jefferson Theater
9.49.4 out of 10 rating
Exceptional
(39 reviews)
Downtown Mall Boutique Hotel Room above The Jefferson Theater
Charlottesville, VA
8% off
Price is NZ$2,010
NZ$2,010
NZ$287 per night
includes taxes & fees
Image gallery for Charlottesville Retreat for Family & Friends
1010 out of 10 rating
Exceptional
(95 reviews)
Charlottesville Retreat for Family & Friends
Charlottesville, VA
16% off
Price is NZ$8,710
NZ$8,710
NZ$1,244 per night
includes taxes & fees
Image gallery for Historic, Quaint Bungalow #157 Pool & Spa
9.69.6 out of 10 rating
Exceptional
(42 reviews)
Historic, Quaint Bungalow #157 Pool & Spa
Gordonsville, VA
8% off
Price is NZ$1,870
NZ$1,870
NZ$267 per night
includes taxes & fees
Image gallery for 18th Century Charming Bungalow #127 Pool & Spa.
9.89.8 out of 10 rating
Exceptional
(44 reviews)
18th Century Charming Bungalow #127 Pool & Spa.
Gordonsville, VA
8% off
Price is NZ$1,870
NZ$1,870
NZ$267 per night
includes taxes & fees
Image gallery for Belmont Carriage House
9.29.2 out of 10 rating
Wonderful
(17 reviews)
Belmont Carriage House
Charlottesville, VA
21% off
Price is NZ$4,563
NZ$4,563
NZ$652 per night
includes taxes & fees
Image gallery for Visit Monticello, Wineries, UVA: Room for a Crowd
8.88.8 out of 10 rating
Excellent
(13 reviews)
Visit Monticello, Wineries, UVA: Room for a Crowd
Zion Crossroads, VA
22% off
Price is NZ$6,003
NZ$6,003
NZ$858 per night
includes taxes & fees
Image gallery for Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy
1010 out of 10 rating
Exceptional
(30 reviews)
Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy
Charlottesville, VA
8% off
Price is NZ$2,645
NZ$2,645
NZ$378 per night
includes taxes & fees
Image gallery for Long Street Cottage - 5 bdrm/3.5 bath - North Downtown
1010 out of 10 rating
Exceptional
(22 reviews)
Long Street Cottage - 5 bdrm/3.5 bath - North Downtown
Charlottesville, VA
11% off
Price is NZ$9,082
NZ$9,082
NZ$1,297 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 NZ$2,877
NZ$2,877
NZ$411 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Trump Winery
Showing deals for: 13 Aug - 16 Aug
106 acre Farm with Animals, River & Private Pond, near Wineries and Breweries
Sleeps 6 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
43 reviews(43 reviews)
The current price is NZ$1,381
NZ$1,381
for 3 nights, 1 home
NZ$460 per night
includes taxes & fees
Pine Grove Cottage - Visit Monticello, Charlottesville & Many Local Wineries
Sleeps 7 · 2 bedrooms · 1 bathroom
9.09.0 out of 10
Wonderfulwonderful
105 reviews(105 reviews)
The current price is NZ$1,002
NZ$1,002
for 3 nights, 1 cottage
NZ$334 per night
includes taxes & fees
Private Guest Suite by Wineries/Orchards/Cville
Sleeps 4 · 1 bathroom
1010 out of 10
Exceptionalexceptional
41 reviews(41 reviews)
The current price is NZ$955
NZ$955
for 3 nights, 1 apartment
NZ$318 per night
includes taxes & fees
New Cabin Right on The Rockfish River! Peacefull River Sounds, Stunning views!
Sleeps 4 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
37 reviews(37 reviews)
The current price is NZ$2,520
NZ$2,520
for 3 nights, 1 cabin
NZ$840 per night
includes taxes & fees
Keelona Cottage 2 BR 2 BA near vineyards
Sleeps 4 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
7 reviews(7 reviews)
The current price is NZ$2,429
NZ$2,429
for 3 nights, 1 home
NZ$810 per night
includes taxes & fees
Stay on Working Farm in Central VA Wine Region, 35 Minutes from UVA.
Sleeps 8 · 4 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
39 reviews(39 reviews)
The current price is NZ$2,607
NZ$2,607
for 3 nights, 1 home
NZ$869 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