Holiday rentals near Keswick Vineyards and Winery
We found 485 holiday rentals — enter your dates for availability
If you'd like to stay close to Keswick Vineyards and Winery, scroll through and discover holiday rentals to find the perfect home base for your trip. Whether you're staying in a holiday rental with family, friends or just your furry companion, you'll find the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a hot tub. You'll be able to choose a property to rent that has what everyone needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Keswick Vineyards and Winery
Showing deals for:1 Aug - 8 Aug
Image gallery for Fairwood Cottage-Exceptional 1BR Cottage Minutes From Charlottesville & Wineries
1010 out of 10 rating
Exceptional
(23 reviews)
Fairwood Cottage-Exceptional 1BR Cottage Minutes From Charlottesville & Wineries
Charlottesville, VA
19% off
Price is NZ$2,565
NZ$2,565
NZ$366 per night
includes taxes & fees
Image gallery for Penthouse Apartment Overlooking Downtown Mall
1010 out of 10 rating
Exceptional
(33 reviews)
Penthouse Apartment Overlooking Downtown Mall
Charlottesville, VA
11% off
Price is NZ$6,509
NZ$6,509
NZ$930 per night
includes taxes & fees
Image gallery for 5 min to Downtown C'ville, 3b/2b Comfortable!
1010 out of 10 rating
Exceptional
(15 reviews)
5 min to Downtown C'ville, 3b/2b Comfortable!
Charlottesville, VA
8% off
Price is NZ$4,415
NZ$4,415
NZ$631 per night
includes taxes & fees
Image gallery for Farmhouse On 14 Acres. Close to Monticello & Ash Lawn Highland
1010 out of 10 rating
Exceptional
(31 reviews)
Farmhouse On 14 Acres. Close to Monticello & Ash Lawn Highland
Charlottesville, VA
16% off
Price is NZ$4,878
NZ$4,878
NZ$697 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
(20 reviews)
Newly-renovated 5BR home near UVA, Downtown, i64. Weddings/bachelorette parties!
Charlottesville, VA
18% off
Price is NZ$6,794
NZ$6,794
NZ$971 per night
includes taxes & fees
Image gallery for Escape the City! Plain Outside; Gorgeous Inside; Huge Horse/Cattle Farm
9.69.6 out of 10 rating
Exceptional
(28 reviews)
Escape the City! Plain Outside; Gorgeous Inside; Huge Horse/Cattle Farm
Gordonsville, VA
18% off
Price is NZ$4,764
NZ$4,764
NZ$681 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$5,891
NZ$5,891
NZ$842 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$10,478
NZ$10,478
NZ$1,497 per night
includes taxes & fees
Image gallery for Luxury Stay on Flower Farm by Wineries Near Charlottesville-Pet-Friendly
1010 out of 10 rating
Exceptional
(19 reviews)
Luxury Stay on Flower Farm by Wineries Near Charlottesville-Pet-Friendly
Somerset, VA
13% off
Price is NZ$4,568
NZ$4,568
NZ$653 per night
includes taxes & fees
Image gallery for Boutique Hotel Suite above the Jefferson Theater on the Downtown Mall
8.68.6 out of 10 rating
Excellent
(23 reviews)
Boutique Hotel Suite above the Jefferson Theater on the Downtown Mall
Charlottesville, VA
12% off
Price is NZ$1,843
NZ$1,843
NZ$263 per night
includes taxes & fees
Image gallery for The Cottage at Still Pond Farm - Horse Farm Stay near the Blue Ridge Mountains
1010 out of 10 rating
Exceptional
(87 reviews)
The Cottage at Still Pond Farm - Horse Farm Stay near the Blue Ridge Mountains
Stanardsville, VA
8% off
Price is NZ$4,606
NZ$4,606
NZ$658 per night
includes taxes & fees
Image gallery for Cozy 2 bedroom on Main St in Gordonsville
1010 out of 10 rating
Exceptional
(14 reviews)
Cozy 2 bedroom on Main St in Gordonsville
Gordonsville, VA
8% off
Price is NZ$2,750
NZ$2,750
NZ$393 per night
includes taxes & fees
Image gallery for Azalea Cottage - adorable cottage within one mile of the University of Virginia
1010 out of 10 rating
Exceptional
(129 reviews)
Azalea Cottage - adorable cottage within one mile of the University of Virginia
Charlottesville, VA
11% off
Price is NZ$3,300
NZ$3,300
NZ$471 per night
includes taxes & fees
Image gallery for 18th Century Charming Bungalow #127 Pool & Spa.
9.89.8 out of 10 rating
Exceptional
(43 reviews)
18th Century Charming Bungalow #127 Pool & Spa.
Gordonsville, VA
8% off
Price is NZ$1,850
NZ$1,850
NZ$264 per night
includes taxes & fees
Image gallery for Enjoy Horses as your neighbors on our 600 Acre Horse/Cattle Farm.
9.69.6 out of 10 rating
Exceptional
(35 reviews)
Enjoy Horses as your neighbors on our 600 Acre Horse/Cattle Farm.
Gordonsville, VA
17% off
Price is NZ$1,981
NZ$1,981
NZ$283 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 NZ$4,440
NZ$4,440
NZ$634 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$2,846
NZ$2,846
NZ$407 per night
includes taxes & fees
Image gallery for Long Street Cottage - 5 bdrm/3.5 bath - North Downtown
1010 out of 10 rating
Exceptional
(21 reviews)
Long Street Cottage - 5 bdrm/3.5 bath - North Downtown
Charlottesville, VA
11% off
Price is NZ$9,491
NZ$9,491
NZ$1,356 per night
includes taxes & fees
Image gallery for The Natchez - quiet front porch & rockers.
1010 out of 10 rating
Exceptional
(123 reviews)
The Natchez - quiet front porch & rockers.
Ruckersville, VA
8% off
Price is NZ$1,949
NZ$1,949
NZ$278 per night
includes taxes & fees
Image gallery for 1700"s Summer Kitchen Cottage #147 Pool & Spa
9.89.8 out of 10 rating
Exceptional
(45 reviews)
1700"s Summer Kitchen Cottage #147 Pool & Spa
Gordonsville, VA
8% off
Price is NZ$1,850
NZ$1,850
NZ$264 per night
includes taxes & fees
Image gallery for The Franklin Estate - Suite D-Private Apt-King Bed
1010 out of 10 rating
Exceptional
(12 reviews)
The Franklin Estate - Suite D-Private Apt-King Bed
Ruckersville, VA
15% off
Price is NZ$1,271
NZ$1,271
NZ$182 per night
includes taxes & fees
Image gallery for Rugby Hills-Walk to University Rotunda/Downtown
9.89.8 out of 10 rating
Exceptional
(93 reviews)
Rugby Hills-Walk to University Rotunda/Downtown
Charlottesville, VA
8% off
Price is NZ$3,547
NZ$3,547
NZ$507 per night
includes taxes & fees
Image gallery for Rugby Road Residential -RRR- near UVa and downtown
1010 out of 10 rating
Exceptional
(26 reviews)
Rugby Road Residential -RRR- near UVa and downtown
Charlottesville, VA
12% off
Price is NZ$2,461
NZ$2,461
NZ$352 per night
includes taxes & fees
Image gallery for Honey House—beautiful detached Modern loft near UVA, Downtown and Monticello
1010 out of 10 rating
Exceptional
(47 reviews)
Honey House—beautiful detached Modern loft near UVA, Downtown and Monticello
Charlottesville, VA
12% off
Price is NZ$2,627
NZ$2,627
NZ$375 per night
includes taxes & fees
Find spaces that suit your style
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Cottage
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Chalet
Find the best place to stay - Keswick Vineyards and Winery
Charlottesville Retreat for Family & Friends
Sleeps 20 · 5 bedrooms · 4 bathrooms
1010 out of 10
Exceptionalexceptional
94 reviews(94 reviews)
Cottage and working farm in heart of Virginia wine country near UVA & Woodberry
Sleeps 5 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
8 reviews(8 reviews)
Broadhead Mountain Retreat | 2 Bedroom, 2 Bath
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
47 reviews(47 reviews)
Cozy 2 bedroom on Main St in Gordonsville
Sleeps 4 · 2 bedrooms · 1+ bathroom
1010 out of 10
Exceptionalexceptional
14 reviews(14 reviews)
Shire Suite at White Lotus Eco Spa Retreat
Sleeps 2 · 1 bedroom · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
11 reviews(11 reviews)
The Ranch at Wine Country - Complimentary Bottle!
Sleeps 6 · 3 bedrooms · 1+ bathroom
1010 out of 10
Exceptionalexceptional
42 reviews(42 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