Holiday rentals near Keswick Vineyards and Winery
We found 495 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:3 Oct - 10 Oct
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$3,107
NZ$3,107
NZ$444 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
(26 reviews)
Whole home on 5 acres. Minutes from vineyards, SNP, and CHO airport. 30 min UVA
Ruckersville, VA
8% off
Price is NZ$4,289
NZ$4,289
NZ$613 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
(6 reviews)
Wine Country! Unique 2-bedroom horse farm, close by 5 star dining, 5 wineries
Keswick, VA
8% off
Price is NZ$2,531
NZ$2,531
NZ$362 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$2,129
NZ$2,129
NZ$304 per night
includes taxes & fees
Image gallery for Charming Farmhouse Cottage with Mountain Views
8.68.6 out of 10 rating
Excellent
(15 reviews)
Charming Farmhouse Cottage with Mountain Views
Somerset, VA
8% off
Price is NZ$2,105
NZ$2,105
NZ$301 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$2,784
NZ$2,784
NZ$398 per night
includes taxes & fees
Image gallery for Farmhouse close to Wedding venues, Wineries, breweries, shops. Dogs welcome!
1010 out of 10 rating
Exceptional
(9 reviews)
Farmhouse close to Wedding venues, Wineries, breweries, shops. Dogs welcome!
Madison, VA
8% off
Price is NZ$4,041
NZ$4,041
NZ$577 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
15% off
Price is NZ$2,195
NZ$2,195
NZ$314 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 NZ$6,657
NZ$6,657
NZ$951 per night
includes taxes & fees
Image gallery for Enderly - c1859 - English Basement Apartment
1010 out of 10 rating
Exceptional
(28 reviews)
Enderly - c1859 - English Basement Apartment
Charlottesville, VA
8% off
Price is NZ$4,013
NZ$4,013
NZ$573 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
14% off
Price is NZ$2,571
NZ$2,571
NZ$367 per night
includes taxes & fees
Image gallery for Spacious Modern farmhouse near CHO airport, weddings, wineries, national park!
1010 out of 10 rating
Exceptional
(45 reviews)
Spacious Modern farmhouse near CHO airport, weddings, wineries, national park!
Barboursville, VA
46% off
Price is NZ$3,498
NZ$3,498
NZ$500 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$10,250
NZ$10,250
NZ$1,464 per night
includes taxes & fees
Image gallery for Charming 2-bedroom Downtown Retreat in Charlottesville with parking & wifi
8.88.8 out of 10 rating
Excellent
(6 reviews)
Charming 2-bedroom Downtown Retreat in Charlottesville with parking & wifi
Charlottesville, VA
8% off
Price is NZ$2,859
NZ$2,859
NZ$408 per night
includes taxes & fees
Image gallery for 5 BDRM Dog Friendly, Lake Access Getaway w/Playground, Fire Pit & more
1010 out of 10 rating
Exceptional
(6 reviews)
5 BDRM Dog Friendly, Lake Access Getaway w/Playground, Fire Pit & more
Louisa, VA
8% off
Price is NZ$4,089
NZ$4,089
NZ$584 per night
includes taxes & fees
Image gallery for Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy
1010 out of 10 rating
Exceptional
(33 reviews)
Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy
Charlottesville, VA
8% off
Price is NZ$3,086
NZ$3,086
NZ$441 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
(26 reviews)
Walkable to UVA, and Fontaine Research park, Newly Renovated Home.
Charlottesville, VA
24% off
Price is NZ$2,610
NZ$2,610
NZ$373 per night
includes taxes & fees
Image gallery for Newly renovated entire guest suite in Orange County.
9.89.8 out of 10 rating
Exceptional
(40 reviews)
Newly renovated entire guest suite in Orange County.
Orange, VA
17% off
Price is NZ$1,318
NZ$1,318
NZ$188 per night
includes taxes & fees
Image gallery for Visit Monticello, Wineries, UVA & More
9.09.0 out of 10 rating
Wonderful
(8 reviews)
Visit Monticello, Wineries, UVA & More
Zion Crossroads, VA
22% off
Price is NZ$4,506
NZ$4,506
NZ$644 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 NZ$1,938
NZ$1,938
NZ$277 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 NZ$4,660
NZ$4,660
NZ$666 per night
includes taxes & fees
Image gallery for Lovers Lane FarmStay on a working family farm. Horses, cows, sheep, bees & more
9.69.6 out of 10 rating
Exceptional
(7 reviews)
Lovers Lane FarmStay on a working family farm. Horses, cows, sheep, bees & more
Gordonsville, VA
17% off
Price is NZ$1,288
NZ$1,288
NZ$184 per night
includes taxes & fees
Image gallery for Historic Manor House with Saltwater pool and Mountain Views
9.89.8 out of 10 rating
Exceptional
(8 reviews)
Historic Manor House with Saltwater pool and Mountain Views
Somerset, VA
8% off
Price is NZ$10,275
NZ$10,275
NZ$1,468 per night
includes taxes & fees
Image gallery for One of Central Virginia's most historic Private Guest Residences
1010 out of 10 rating
Exceptional
(95 reviews)
One of Central Virginia's most historic Private Guest Residences
Orange, VA
6% off
Price is NZ$2,852
NZ$2,852
NZ$407 per night
includes taxes & fees
Find spaces that suit your style
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Condo/Apartment
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Cottage
Villa
Chalet
Find the best place to stay - Keswick Vineyards and Winery
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
6 reviews(6 reviews)
Charlottesville Retreat for Family & Friends
Sleeps 20 · 5 bedrooms · 4 bathrooms
1010 out of 10
Exceptionalexceptional
98 reviews(98 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)
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)
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)
Broadhead Mountain Retreat | 2 Bedroom, 2 Bath
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
50 reviews(50 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