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: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 AU$4,004
AU$4,004
AU$572 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 AU$4,295
AU$4,295
AU$614 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 AU$4,118
AU$4,118
AU$588 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 AU$3,036
AU$3,036
AU$434 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 AU$6,091
AU$6,091
AU$870 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 AU$4,550
AU$4,550
AU$650 per night
includes taxes & fees
Image gallery for The Recycled House - Walk Downtown
1010 out of 10 rating
Exceptional
(160 reviews)
The Recycled House - Walk Downtown
Charlottesville, VA
24% off
Price is AU$3,061
AU$3,061
AU$437 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 AU$6,974
AU$6,974
AU$996 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 AU$3,919
AU$3,919
AU$560 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 AU$6,353
AU$6,353
AU$908 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 AU$3,314
AU$3,314
AU$473 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 AU$5,495
AU$5,495
AU$785 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 AU$9,869
AU$9,869
AU$1,410 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 AU$2,488
AU$2,488
AU$355 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 AU$3,002
AU$3,002
AU$429 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 AU$1,891
AU$1,891
AU$270 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 AU$7,882
AU$7,882
AU$1,126 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 AU$1,757
AU$1,757
AU$251 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 AU$1,757
AU$1,757
AU$251 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
19% off
Price is AU$4,141
AU$4,141
AU$592 per night
includes taxes & fees
Image gallery for Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy
1010 out of 10 rating
Exceptional
(29 reviews)
Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy
Charlottesville, VA
8% off
Price is AU$2,476
AU$2,476
AU$354 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 AU$5,545
AU$5,545
AU$792 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$2,686
AU$2,686
AU$384 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 AU$8,437
AU$8,437
AU$1,205 per night
includes taxes & fees
Find spaces that suit your style
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Cabin
Cottage
Villa
Chalet
Find the best place to stay - Trump Winery
DEER RIDGE CABIN IS YOUR PERFECT, PRIVATE AND COZY GETAWAY!
Sleeps 4 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
295 reviews(295 reviews)
Bluebird Cottage B: Firepit, Patio, Games; Near Charlottesville, Wineries
Sleeps 4 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
32 reviews(32 reviews)
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)
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)
Private Guest Suite by Wineries/Orchards/Cville
Sleeps 4 · 1 bathroom
1010 out of 10
Exceptionalexceptional
41 reviews(41 reviews)
New Cabin Right on The Rockfish River! Peacefull River Sounds, Stunning views!
Sleeps 4 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
36 reviews(36 reviews)
Top rated rentals - Trump Winery
Animal Lovers Trip
1010 out of 10
Exceptionalexceptional
22 reviews(22 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