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 AU$2,865
AU$2,865
AU$409 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 AU$3,959
AU$3,959
AU$566 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 AU$2,364
AU$2,364
AU$338 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 AU$1,989
AU$1,989
AU$284 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 AU$1,967
AU$1,967
AU$281 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$2,600
AU$2,600
AU$371 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 AU$3,722
AU$3,722
AU$532 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 AU$2,052
AU$2,052
AU$293 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$6,162
AU$6,162
AU$880 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 AU$3,696
AU$3,696
AU$528 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 AU$2,403
AU$2,403
AU$343 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 AU$3,221
AU$3,221
AU$460 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$9,553
AU$9,553
AU$1,365 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 AU$2,669
AU$2,669
AU$381 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 AU$3,767
AU$3,767
AU$538 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 AU$2,844
AU$2,844
AU$406 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 AU$2,437
AU$2,437
AU$348 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 AU$1,205
AU$1,205
AU$172 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 AU$4,158
AU$4,158
AU$594 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$1,823
AU$1,823
AU$260 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$4,300
AU$4,300
AU$614 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 AU$1,177
AU$1,177
AU$168 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 AU$9,586
AU$9,586
AU$1,369 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 AU$2,630
AU$2,630
AU$376 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Keswick Vineyards and Winery
Showing deals for: 29 Sept - 2 Oct
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)
The current price is AU$1,181
AU$1,181
for 3 nights, 1 room
AU$394 per night
includes taxes & fees
Charlottesville Retreat for Family & Friends
Sleeps 20 · 5 bedrooms · 4 bathrooms
1010 out of 10
Exceptionalexceptional
98 reviews(98 reviews)
The current price is AU$4,274
AU$4,274
for 3 nights, 1 home
AU$1,425 per night
includes taxes & fees
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)
The current price is AU$2,162
AU$2,162
for 3 nights, 1 room
AU$721 per night
includes taxes & fees
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)
The current price is AU$1,359
AU$1,359
for 3 nights, 1 home
AU$453 per night
includes taxes & fees
Broadhead Mountain Retreat | 2 Bedroom, 2 Bath
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
50 reviews(50 reviews)
The current price is AU$1,399
AU$1,399
for 3 nights, 1 home
AU$466 per night
includes taxes & fees
The White Elephant Inn Getaway w/ Pool & Hot Tub!
Sleeps 12 · 5 bedrooms · 5 bathrooms
9.89.8 out of 10
Exceptionalexceptional
68 reviews(68 reviews)
The current price is AU$5,070
AU$5,070
for 3 nights, 1 apartment
AU$1,690 per night
includes taxes & fees
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