Holiday rentals near Keswick Vineyards and Winery
We found 487 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:8 Aug - 15 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$2,571
NZ$2,571
NZ$367 per night
includes taxes & fees
Image gallery for 5 min to Downtown C'ville, 3b/2b Comfortable!
1010 out of 10 rating
Exceptional
(16 reviews)
5 min to Downtown C'ville, 3b/2b Comfortable!
Charlottesville, VA
8% off
Price is NZ$4,426
NZ$4,426
NZ$632 per night
includes taxes & fees
Image gallery for Visit Monticello, Wineries, UVA & More
8.88.8 out of 10 rating
Excellent
(5 reviews)
Visit Monticello, Wineries, UVA & More
Zion Crossroads, VA
22% off
Price is NZ$4,618
NZ$4,618
NZ$660 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$6,429
NZ$6,429
NZ$918 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
17% off
Price is NZ$4,850
NZ$4,850
NZ$693 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 NZ$3,292
NZ$3,292
NZ$470 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$6,811
NZ$6,811
NZ$973 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
(24 reviews)
Boutique Hotel Suite above the Jefferson Theater on the Downtown Mall
Charlottesville, VA
12% off
Price is NZ$1,848
NZ$1,848
NZ$264 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$4,580
NZ$4,580
NZ$654 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$5,906
NZ$5,906
NZ$844 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$10,505
NZ$10,505
NZ$1,501 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$4,618
NZ$4,618
NZ$660 per night
includes taxes & fees
Image gallery for “The Suite”. at Chase Cottage - Private Entrance! Luxury accommodations.
1010 out of 10 rating
Exceptional
(31 reviews)
“The Suite”. at Chase Cottage - Private Entrance! Luxury accommodations.
Gordonsville, VA
8% off
Price is NZ$3,231
NZ$3,231
NZ$462 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$2,798
NZ$2,798
NZ$400 per night
includes taxes & fees
Image gallery for Charlottesville Retreat for Family & Friends
1010 out of 10 rating
Exceptional
(94 reviews)
Charlottesville Retreat for Family & Friends
Charlottesville, VA
16% off
Price is NZ$8,638
NZ$8,638
NZ$1,234 per night
includes taxes & fees
Image gallery for Historic, Quaint Bungalow #157 Pool & Spa
9.69.6 out of 10 rating
Exceptional
(41 reviews)
Historic, Quaint Bungalow #157 Pool & Spa
Gordonsville, VA
8% off
Price is NZ$1,855
NZ$1,855
NZ$265 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
(130 reviews)
Azalea Cottage - adorable cottage within one mile of the University of Virginia
Charlottesville, VA
11% off
Price is NZ$3,308
NZ$3,308
NZ$473 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$1,855
NZ$1,855
NZ$265 per night
includes taxes & fees
Image gallery for Bloomingdale Honeymoon Cabin Vintage Retreat with Mountain Views
9.49.4 out of 10 rating
Exceptional
(13 reviews)
Bloomingdale Honeymoon Cabin Vintage Retreat with Mountain Views
Somerset, VA
6% off
Price is NZ$2,182
NZ$2,182
NZ$312 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$4,451
NZ$4,451
NZ$636 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$2,021
NZ$2,021
NZ$289 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$5,953
NZ$5,953
NZ$850 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$2,854
NZ$2,854
NZ$408 per night
includes taxes & fees
Image gallery for The Natchez - quiet front porch & rockers.
1010 out of 10 rating
Exceptional
(124 reviews)
The Natchez - quiet front porch & rockers.
Ruckersville, VA
8% off
Price is NZ$1,954
NZ$1,954
NZ$279 per night
includes taxes & fees
Find spaces that suit your style
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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)
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)
Charming 3-Bed Cottage on Main Street in Historic Gordonsville
Sleeps 7 · 3 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
Wine Country! Unique 2-bedroom horse farm, close by 5 star dining, 5 wineries
Sleeps 4 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
3 reviews(3 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