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 Jan - 22 Jan
Image gallery for Visit Monticello, Wineries, UVA & More
9.49.4 out of 10, Exceptional, (11 reviews)
Exceptional
(11 reviews)
Visit Monticello, Wineries, UVA & More
Troy
21% off
Price is NZ$5,189
NZ$5,189
for 7 nights, 1 home
NZ$741 per night
includes taxes & fees
Image gallery for Historic 1870's Log Cabin Near Charlottesville
1010 out of 10, Exceptional, (247 reviews)
Exceptional
(247 reviews)
Historic 1870's Log Cabin Near Charlottesville
Afton
7% off
Price is NZ$7,424
NZ$7,424
for 7 nights, 1 cabin
NZ$1,061 per night
includes taxes & fees
Image gallery for Inn at the Woods: Updated Cabin w/Mountain Views
1010 out of 10, Exceptional, (10 reviews)
Exceptional
(10 reviews)
Inn at the Woods: Updated Cabin w/Mountain Views
Afton
7% off
Price is NZ$4,767
NZ$4,767
for 7 nights, 1 cabin
NZ$681 per night
includes taxes & fees
Image gallery for Afton Escape-New Arcade, Winery Brewery EV-Charger
1010 out of 10, Exceptional, (33 reviews)
Exceptional
(33 reviews)
Afton Escape-New Arcade, Winery Brewery EV-Charger
Afton
7% off
Price is NZ$8,918
NZ$8,918
for 7 nights, 1 home
NZ$1,274 per night
includes taxes & fees
Image gallery for Modern Farmhouse in Keswick 5BR/4BA
1010 out of 10, Exceptional, (9 reviews)
Exceptional
(9 reviews)
Modern Farmhouse in Keswick 5BR/4BA
Keswick
8% off
Price is NZ$18,344
NZ$18,344
for 7 nights, 1 home
NZ$2,621 per night
includes taxes & fees
Image gallery for Luxurious Mountian house right in the Heart of Charlottesville!
9.89.8 out of 10, Exceptional, (15 reviews)
Exceptional
(15 reviews)
Luxurious Mountian house right in the Heart of Charlottesville!
Charlottesville
12% off
Price is NZ$14,930
NZ$14,930
for 7 nights, 1 home
NZ$2,133 per night
includes taxes & fees
Image gallery for Charming 6BR, 4.5 BA on Mechums River 15 Min. to Charlottesville
9.89.8 out of 10, Exceptional, (10 reviews)
Exceptional
(10 reviews)
Charming 6BR, 4.5 BA on Mechums River 15 Min. to Charlottesville
Charlottesville
8% off
Price is NZ$11,404
NZ$11,404
for 7 nights, 1 home
NZ$1,629 per night
includes taxes & fees
Image gallery for In the center of Nelson County's wine and beer region, 19 miles to UVA/Cville
1010 out of 10, Exceptional, (88 reviews)
Exceptional
(88 reviews)
In the center of Nelson County's wine and beer region, 19 miles to UVA/Cville
Afton
16% off
Price is NZ$9,066
NZ$9,066
for 7 nights, 1 home
NZ$1,295 per night
includes taxes & fees
Image gallery for UVA Home WALKABLE to Scott Stadium, UVA Grounds, the Corner, & Wineries
1010 out of 10, Exceptional, (58 reviews)
Exceptional
(58 reviews)
UVA Home WALKABLE to Scott Stadium, UVA Grounds, the Corner, & Wineries
Charlottesville
9% off
Price is NZ$8,666
NZ$8,666
for 7 nights, 1 home
NZ$1,238 per night
includes taxes & fees
Image gallery for Private cabin in wine country
9.69.6 out of 10, Exceptional, (11 reviews)
Exceptional
(11 reviews)
Private cabin in wine country
Scottsville
8% off
Price is NZ$2,476
NZ$2,476
for 7 nights, 1 cottage
NZ$354 per night
includes taxes & fees
Image gallery for Newly-renovated 5BR home near UVA, Downtown, i64. Weddings/bachelorette parties!
1010 out of 10, Exceptional, (38 reviews)
Exceptional
(38 reviews)
Newly-renovated 5BR home near UVA, Downtown, i64. Weddings/bachelorette parties!
Charlottesville
18% off
Price is NZ$7,223
NZ$7,223
for 7 nights, 1 home
NZ$1,032 per night
includes taxes & fees
Image gallery for Heated Pool, Hot Tub, panoramic mountain views, near Vineyards + UVA
1010 out of 10, Exceptional, (7 reviews)
Exceptional
(7 reviews)
Heated Pool, Hot Tub, panoramic mountain views, near Vineyards + UVA
Crozet
8% off
Price is NZ$8,962
NZ$8,962
for 7 nights, 1 home
NZ$1,280 per night
includes taxes & fees
Image gallery for Oasis on 151 • Hot Tub • Pool Table • Huge Home
1010 out of 10, Exceptional, (26 reviews)
Exceptional
(26 reviews)
Oasis on 151 • Hot Tub • Pool Table • Huge Home
Faber
16% off
Price is NZ$16,185
NZ$16,185
for 7 nights, 1 home
NZ$2,312 per night
includes taxes & fees
Image gallery for Cozy Home with Walking Distance to Scott Stadium
9.89.8 out of 10, Exceptional, (11 reviews)
Exceptional
(11 reviews)
Cozy Home with Walking Distance to Scott Stadium
Charlottesville
7% off
Price is NZ$6,213
NZ$6,213
for 7 nights, 1 home
NZ$888 per night
includes taxes & fees
Image gallery for Rockfish Farmhouse - Home In the heart of The Rockfish Valley
1010 out of 10, Exceptional, (62 reviews)
Exceptional
(62 reviews)
Rockfish Farmhouse - Home In the heart of The Rockfish Valley
Afton
8% off
Price is NZ$5,083
NZ$5,083
for 7 nights, 1 home
NZ$726 per night
includes taxes & fees
Image gallery for Loveshack, a charming tiny house on a 5 acre farm
8.88.8 out of 10, Excellent, (15 reviews)
Excellent
(15 reviews)
Loveshack, a charming tiny house on a 5 acre farm
Charlottesville
8% off
Price is NZ$3,018
NZ$3,018
for 7 nights, 1 cottage
NZ$431 per night
includes taxes & fees
Image gallery for Afton Escape! NEW Arcade, Wineries, Breweries
1010 out of 10, Exceptional, (28 reviews)
Exceptional
(28 reviews)
Afton Escape! NEW Arcade, Wineries, Breweries
Afton
7% off
Price is NZ$10,930
NZ$10,930
for 7 nights, 1 apartment
NZ$1,561 per night
includes taxes & fees
Image gallery for Relaxing cottage in the woods just minutes from wineries,hiking,restaurants.
1010 out of 10, Exceptional, (11 reviews)
Exceptional
(11 reviews)
Relaxing cottage in the woods just minutes from wineries,hiking,restaurants.
Barboursville
12% off
Price is NZ$3,005
NZ$3,005
for 7 nights, 1 cottage
NZ$429 per night
includes taxes & fees
Image gallery for Pine Grove Cottage - Visit Monticello, Charlottesville & Many Local Wineries
9.29.2 out of 10, Wonderful, (150 reviews)
Wonderful
(150 reviews)
Pine Grove Cottage - Visit Monticello, Charlottesville & Many Local Wineries
Troy
17% off
Price is NZ$2,082
NZ$2,082
for 7 nights, 1 cottage
NZ$297 per night
includes taxes & fees
Image gallery for Bright, Spacious Home Perfect for Groups and Families: 4BR, 5 Beds
1010 out of 10, Exceptional, (72 reviews)
Exceptional
(72 reviews)
Bright, Spacious Home Perfect for Groups and Families: 4BR, 5 Beds
Charlottesville
21% off
Price is NZ$5,805
NZ$5,805
for 7 nights, 1 home
NZ$829 per night
includes taxes & fees
Image gallery for Barn Studio in country setting but close to town
1010 out of 10, Exceptional, (13 reviews)
Exceptional
(13 reviews)
Barn Studio in country setting but close to town
Charlottesville
8% off
Price is NZ$3,649
NZ$3,649
for 7 nights, 1 apartment
NZ$521 per night
includes taxes & fees
Image gallery for Azalea Cottage - adorable cottage within one mile of the University of Virginia
1010 out of 10, Exceptional, (145 reviews)
Exceptional
(145 reviews)
Azalea Cottage - adorable cottage within one mile of the University of Virginia
Charlottesville
12% off
Price is NZ$3,499
NZ$3,499
for 7 nights, 1 cottage
NZ$500 per night
includes taxes & fees
Image gallery for Honey House—beautiful modern loft near UVA, Monticello and downtown
1010 out of 10, Exceptional, (60 reviews)
Exceptional
(60 reviews)
Honey House—beautiful modern loft near UVA, Monticello and downtown
Charlottesville
11% off
Price is NZ$2,534
NZ$2,534
for 7 nights, 1 home
NZ$362 per night
includes taxes & fees
Image gallery for Visit Monticello, Wineries, UVA: Room for a Crowd
9.49.4 out of 10, Exceptional, (25 reviews)
Exceptional
(25 reviews)
Visit Monticello, Wineries, UVA: Room for a Crowd
Troy
22% off
Price is NZ$6,602
NZ$6,602
for 7 nights, 1 home
NZ$943 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find properties near top attractions in Trump Winery
Map Attractions
Loading
Find the best place to stay - Trump Winery
WELCOME TO DEER RIDGE CABIN! YOUR PERFECT, PRIVATE AND COZY GETAWAY!
Sleeps 4 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
322 reviews(322 reviews)
Entire Cottage on Equestrian Farm with Zebras
Sleeps 4 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
18 reviews(18 reviews)
Charming Historic Carriage House Studio Apartment
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
23 reviews(23 reviews)
Loveshack, a charming tiny house on a 5 acre farm
Sleeps 4 · 1 bedroom · 1 bathroom
8.88.8 out of 10
Excellentexcellent
15 reviews(15 reviews)
Cottage at Deer Ridge Farm
Sleeps 4 · 2 bedrooms · 1+ bathroom
1010 out of 10
Exceptionalexceptional
21 reviews(21 reviews)
The Country Retreat – Cozy Comfort Meets Peaceful Countryside
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
6 reviews(6 reviews)
Top rated rentals - Trump Winery
Premier Host
Weekend Getaway
Weekend Getaway
10.0 out of 10, Exceptional, 61 reviews
10
Exceptional
61 reviews
"Wow! Upon pulling up we were amazed with the location but as soon as we entered the front door, it was absolutely stunning! The cabin itself is SO CLEAN!!! We enjoyed sitting out on the large deck enjoying the view. There is a walking path that is cleared that we enjoyed as well! The host John was wonderful and we will definitely be back!! If I could give more STARS I would!"
"Wow! Upon pulling up we were amazed with the location but as soon as we entered the front door, it was absolutely stunning! The cabin itself is SO CLEAN!!! We enjoyed sitting out on the large deck enjoying the view. There is a walking path that is cleared that we enjoyed as well! The host John was wonderful and we will definitely be back!! If I could give more STARS I would!"
Traci D.
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