Holiday rentals near Keswick Vineyards and Winery
We found 506 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:21 Nov - 28 Nov
Image gallery for Family-friendly single home/Walking distance to shopping center and restaurants
9.69.6 out of 10 rating
Exceptional
(29 reviews)
Family-friendly single home/Walking distance to shopping center and restaurants
Charlottesville, VA
26% off
Price is AU$4,695
AU$4,695
AU$671 per night
includes taxes & fees
Image gallery for 1700"s Summer Kitchen Cottage #147 Pool & Spa
9.89.8 out of 10 rating
Exceptional
(51 reviews)
1700"s Summer Kitchen Cottage #147 Pool & Spa
Gordonsville, VA
8% off
Price is AU$1,689
AU$1,689
AU$241 per night
includes taxes & fees
Image gallery for The Franklin Estate - Suite A-Private Apt-King Bed
9.69.6 out of 10 rating
Exceptional
(5 reviews)
The Franklin Estate - Suite A-Private Apt-King Bed
Ruckersville, VA
16% off
Price is AU$2,047
AU$2,047
AU$292 per night
includes taxes & fees
Image gallery for Wine Country! Unique 2-bedroom horse farm, close by 5 star dining, 5 wineries
9.89.8 out of 10 rating
Exceptional
(7 reviews)
Wine Country! Unique 2-bedroom horse farm, close by 5 star dining, 5 wineries
Keswick, VA
8% off
Price is AU$2,297
AU$2,297
AU$328 per night
includes taxes & fees
Image gallery for Historic Farmhouse w/ Chef's Kitchen Near Wineries
9.89.8 out of 10 rating
Exceptional
(37 reviews)
Historic Farmhouse w/ Chef's Kitchen Near Wineries
Gordonsville, Virginia
15% off
Price is AU$5,361
AU$5,361
AU$766 per night
includes taxes & fees
Image gallery for Visit Monticello, Wineries, UVA: Room for a Crowd
9.09.0 out of 10 rating
Wonderful
(15 reviews)
Visit Monticello, Wineries, UVA: Room for a Crowd
Zion Crossroads, VA
21% off
Price is AU$5,684
AU$5,684
AU$812 per night
includes taxes & fees
Image gallery for Whole home on 5 acres. Minutes from vineyards, SNP, and CHO airport. 30 min UVA
1010 out of 10 rating
Exceptional
(29 reviews)
Whole home on 5 acres. Minutes from vineyards, SNP, and CHO airport. 30 min UVA
Ruckersville, VA
8% off
Price is AU$6,043
AU$6,043
AU$863 per night
includes taxes & fees
Image gallery for Loveshack, a charming tiny house on a 5 acre farm
9.69.6 out of 10 rating
Exceptional
(7 reviews)
Loveshack, a charming tiny house on a 5 acre farm
Charlottesville, VA
8% off
Price is AU$2,597
AU$2,597
AU$371 per night
includes taxes & fees
Image gallery for 1802 cottage once part of Monticello and owned by Thomas Jefferson
9.49.4 out of 10 rating
Exceptional
(84 reviews)
1802 cottage once part of Monticello and owned by Thomas Jefferson
Charlottesville, VA
16% off
Price is AU$2,438
AU$2,438
AU$348 per night
includes taxes & fees
Image gallery for Moonfire Farm Shenandoah region cozy getaway
1010 out of 10 rating
Exceptional
(27 reviews)
Moonfire Farm Shenandoah region cozy getaway
Barboursville, VA
8% off
Price is AU$1,766
AU$1,766
AU$252 per night
includes taxes & fees
Image gallery for Enderly - c1859 - English Basement Apartment
1010 out of 10 rating
Exceptional
(30 reviews)
Enderly - c1859 - English Basement Apartment
Charlottesville, VA
8% off
Price is AU$3,739
AU$3,739
AU$534 per night
includes taxes & fees
Image gallery for Cottage and working farm in heart of Virginia wine country near UVA & Woodberry
1010 out of 10 rating
Exceptional
(8 reviews)
Cottage and working farm in heart of Virginia wine country near UVA & Woodberry
Gordonsville, VA
8% off
Price is AU$4,614
AU$4,614
AU$659 per night
includes taxes & fees
Image gallery for Wine Country Cottage
9.89.8 out of 10 rating
Exceptional
(156 reviews)
Wine Country Cottage
Louisa, VA
12% off
Price is AU$2,475
AU$2,475
AU$354 per night
includes taxes & fees
Image gallery for The Natchez - quiet front porch & rockers.
1010 out of 10 rating
Exceptional
(135 reviews)
The Natchez - quiet front porch & rockers.
Ruckersville, VA
8% off
Price is AU$1,781
AU$1,781
AU$254 per night
includes taxes & fees
Image gallery for Perfect vacation home! 100+ REVIEWS AND 5 STARS ON AIRBNB
1010 out of 10 rating
Exceptional
(6 reviews)
Perfect vacation home! 100+ REVIEWS AND 5 STARS ON AIRBNB
Earlysville, VA
12% off
Price is AU$4,191
AU$4,191
AU$599 per night
includes taxes & fees
Image gallery for Farmhouse On 14 Acres. Close to Monticello & Ash Lawn Highland
1010 out of 10 rating
Exceptional
(37 reviews)
Farmhouse On 14 Acres. Close to Monticello & Ash Lawn Highland
Charlottesville, VA
16% off
Price is AU$4,564
AU$4,564
AU$652 per night
includes taxes & fees
Image gallery for Cottage on quiet farm close to town and wineries
9.69.6 out of 10 rating
Exceptional
(57 reviews)
Cottage on quiet farm close to town and wineries
Charlottesville, VA
8% off
Price is AU$2,714
AU$2,714
AU$388 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
(49 reviews)
Honey House—beautiful detached Modern loft near UVA, Downtown and Monticello
Charlottesville, VA
13% off
Price is AU$2,402
AU$2,402
AU$343 per night
includes taxes & fees
Image gallery for Delightful 5-bedroom residence near downtown Charlottesville. Pet-friendly!
9.89.8 out of 10 rating
Exceptional
(7 reviews)
Delightful 5-bedroom residence near downtown Charlottesville. Pet-friendly!
Charlottesville, VA
8% off
Price is AU$7,726
AU$7,726
AU$1,104 per night
includes taxes & fees
Image gallery for Private Hot Tub, Pool, Firepit 3 Bdrm/2 Bth in Wine Region of Year
9.89.8 out of 10 rating
Exceptional
(10 reviews)
Private Hot Tub, Pool, Firepit 3 Bdrm/2 Bth in Wine Region of Year
Charlottesville, VA
8% off
Price is AU$6,387
AU$6,387
AU$912 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
(29 reviews)
Escape the City! Plain Outside; Gorgeous Inside; Huge Horse/Cattle Farm
Gordonsville, VA
18% off
Price is AU$4,350
AU$4,350
AU$621 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
(36 reviews)
Enjoy Horses as your neighbors on our 600 Acre Horse/Cattle Farm.
Gordonsville, VA
17% off
Price is AU$1,810
AU$1,810
AU$259 per night
includes taxes & fees
Image gallery for Walkable to UVA, and Fontaine Research park, Newly Renovated Home.
8.28.2 out of 10 rating
Very good
(27 reviews)
Walkable to UVA, and Fontaine Research park, Newly Renovated Home.
Charlottesville, VA
24% off
Price is AU$2,434
AU$2,434
AU$348 per night
includes taxes & fees
Image gallery for Rugby Road Residential -RRR- near UVa and downtown
1010 out of 10 rating
Exceptional
(32 reviews)
Rugby Road Residential -RRR- near UVa and downtown
Charlottesville, VA
12% off
Price is AU$3,042
AU$3,042
AU$435 per night
includes taxes & fees
Find spaces that suit your style
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Chalet
Find the best place to stay - Keswick Vineyards and Winery
Moonfire Farm Shenandoah region cozy getaway
Sleeps 4 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
27 reviews(27 reviews)
Wine Country! Unique 2-bedroom horse farm, close by 5 star dining, 5 wineries
Sleeps 4 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
7 reviews(7 reviews)
Spacious Modern farmhouse near CHO airport, weddings, wineries, national park!
Sleeps 10 · 5 bedrooms · 3+ bathrooms
1010 out of 10
Exceptionalexceptional
45 reviews(45 reviews)
Spacious Group Stay-Pond Retreat, Fishing & Wineries Near Cville & SNP
Sleeps 12 · 4 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
Long Street Cottage - 5 bdrm/3.5 bath - North Downtown
Sleeps 12 · 5 bedrooms · 3+ bathrooms
1010 out of 10
Exceptionalexceptional
25 reviews(25 reviews)
Modern Farmhouse in Keswick 5BR/4BA
Sleeps 10 · 5 bedrooms · 4 bathrooms
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