Holiday rentals near Sugarleaf Vineyard
We found 1,158 holiday rentals — enter your dates for availability
Choose the perfect holiday home that's close to Sugarleaf Vineyard. Holiday homes offer the best amenities for you and your friends, family or even pets, such as parking and a washer and dryer. No matter what you're looking for, you'll be sure to find a property to rent for everyone's needs, including a place that is accessible or non-smoking.
Holiday rentals with weekly discounts - Sugarleaf Vineyard
Showing deals for:10 Oct - 17 Oct
Image gallery for Family-friendly single home/Walking distance to shopping center and restaurants
9.69.6 out of 10 rating
Exceptional
(28 reviews)
Family-friendly single home/Walking distance to shopping center and restaurants
Charlottesville, VA
26% off
Price is AU$3,717
AU$3,717
AU$531 per night
includes taxes & fees
Image gallery for Golden Tee 60"TV Fireplace Deck Grill Pool Tennis
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Golden Tee 60"TV Fireplace Deck Grill Pool Tennis
Roseland, VA
8% off
Price is AU$9,612
AU$9,612
AU$1,373 per night
includes taxes & fees
Image gallery for The Cottage @ Afton Mountain- Close to Wineries!
1010 out of 10 rating
Exceptional
(13 reviews)
The Cottage @ Afton Mountain- Close to Wineries!
Afton, VA
12% off
Price is AU$4,472
AU$4,472
AU$639 per night
includes taxes & fees
Image gallery for Charming 5 Bedroom Historic brick home w/ sprawling river views, pool & hot tub!
1010 out of 10 rating
Exceptional
(6 reviews)
Charming 5 Bedroom Historic brick home w/ sprawling river views, pool & hot tub!
Waynesboro, VA
8% off
Price is AU$15,474
AU$15,474
AU$2,211 per night
includes taxes & fees
Image gallery for Sip 'n Dip: Hot Tub Foosball Pool Table Ping Pong
8.88.8 out of 10 rating
Excellent
(8 reviews)
Sip 'n Dip: Hot Tub Foosball Pool Table Ping Pong
Nellysford, VA
8% off
Price is AU$7,576
AU$7,576
AU$1,082 per night
includes taxes & fees
Image gallery for Luxury Designer Home, Dome and Top amenities
1010 out of 10 rating
Exceptional
(9 reviews)
Luxury Designer Home, Dome and Top amenities
Nellysford, VA
8% off
Price is AU$11,764
AU$11,764
AU$1,681 per night
includes taxes & fees
Image gallery for Berry Hill Lake - Cabin w/ NEW Infinity Pool - Pet Friendly - Private Lake
1010 out of 10 rating
Exceptional
(105 reviews)
Berry Hill Lake - Cabin w/ NEW Infinity Pool - Pet Friendly - Private Lake
Nellysford, VA
8% off
Price is AU$20,741
AU$20,741
AU$2,963 per night
includes taxes & fees
Image gallery for Extreme privacy/Acreage/Hot Tub/Mountain Views/Central!!
1010 out of 10 rating
Exceptional
(5 reviews)
Extreme privacy/Acreage/Hot Tub/Mountain Views/Central!!
Afton, VA
8% off
Price is AU$9,466
AU$9,466
AU$1,352 per night
includes taxes & fees
Image gallery for Total Privacy - H’Owl at the Moon Farm & Cabin
1010 out of 10 rating
Exceptional
(168 reviews)
Total Privacy - H’Owl at the Moon Farm & Cabin
Schuyler, VA
8% off
Price is AU$7,533
AU$7,533
AU$1,076 per night
includes taxes & fees
Image gallery for Apartment on the Knoll with private pool
1010 out of 10 rating
Exceptional
(9 reviews)
Apartment on the Knoll with private pool
Lovingston, VA
8% off
Price is AU$2,820
AU$2,820
AU$403 per night
includes taxes & fees
Image gallery for Amazing Views! Pool - Hiking - Gazebo - Hot Tub - Pool Table - Multicade - Grill
1010 out of 10 rating
Exceptional
(16 reviews)
Amazing Views! Pool - Hiking - Gazebo - Hot Tub - Pool Table - Multicade - Grill
Nellysford, VA
8% off
Price is AU$13,276
AU$13,276
AU$1,897 per night
includes taxes & fees
Image gallery for Summer Fun! Game Room+Fire Pit+Hot Tub in spacious family-friendly house
1010 out of 10 rating
Exceptional
(12 reviews)
Summer Fun! Game Room+Fire Pit+Hot Tub in spacious family-friendly house
Nellysford, VA
8% off
Price is AU$12,991
AU$12,991
AU$1,856 per night
includes taxes & fees
Image gallery for Rosé All Day: Wine Country Getaway! Walk to Dining
1010 out of 10 rating
Exceptional
(13 reviews)
Rosé All Day: Wine Country Getaway! Walk to Dining
Crozet, VA
8% off
Price is AU$4,344
AU$4,344
AU$621 per night
includes taxes & fees
Image gallery for Modern Wintergreen Cabin with Hot Tub, Sauna
1010 out of 10 rating
Exceptional
(25 reviews)
Modern Wintergreen Cabin with Hot Tub, Sauna
Roseland, VA
8% off
Price is AU$6,415
AU$6,415
AU$916 per night
includes taxes & fees
Image gallery for Luxury mountain home Ski- in-Ski out
1010 out of 10 rating
Exceptional
(19 reviews)
Luxury mountain home Ski- in-Ski out
Wintergreen, VA
12% off
Price is AU$9,179
AU$9,179
AU$1,311 per night
includes taxes & fees
Image gallery for Piedmont Place 301| Lux Vineyard & Brewery Getaway in the Heart of Crozet | Pet Friendly
9.89.8 out of 10 rating
Exceptional
(25 reviews)
Piedmont Place 301| Lux Vineyard & Brewery Getaway in the Heart of Crozet | Pet Friendly
Crozet, Virginia
7% off
Price is AU$3,162
AU$3,162
AU$452 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$2,391
AU$2,391
AU$342 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$3,698
AU$3,698
AU$528 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$6,421
AU$6,421
AU$917 per night
includes taxes & fees
Image gallery for 106 acre Farm with Animals, River & Private Pond, near Wineries and Breweries
1010 out of 10 rating
Exceptional
(45 reviews)
106 acre Farm with Animals, River & Private Pond, near Wineries and Breweries
Scottsville, VA
10% off
Price is AU$2,625
AU$2,625
AU$375 per night
includes taxes & fees
Image gallery for 4 BR cabin mins to trails & breweries pets welcome
9.89.8 out of 10 rating
Exceptional
(24 reviews)
4 BR cabin mins to trails & breweries pets welcome
Nellysford, VA
23% off
Price is AU$7,007
AU$7,007
AU$1,001 per night
includes taxes & fees
Image gallery for Family-favorite rental nestled in the woods at the top of the Wintergreen Resort
1010 out of 10 rating
Exceptional
(5 reviews)
Family-favorite rental nestled in the woods at the top of the Wintergreen Resort
Nellysford, VA
8% off
Price is AU$5,402
AU$5,402
AU$772 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$2,408
AU$2,408
AU$344 per night
includes taxes & fees
Image gallery for Lux 2 Bed 2 Bath Apt | Dwtn Crozet (30 Nt Min)
9.69.6 out of 10 rating
Exceptional
(20 reviews)
Lux 2 Bed 2 Bath Apt | Dwtn Crozet (30 Nt Min)
Crozet, VA
7% off
Price is AU$3,510
AU$3,510
AU$501 per night
includes taxes & fees
Find spaces that suit your style
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Chalet
Find the best place to stay - Sugarleaf Vineyard
DEER RIDGE CABIN IS YOUR PERFECT, PRIVATE AND COZY GETAWAY!
Sleeps 4 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
299 reviews(299 reviews)
Ivy Retreat | Heated Saltwater Pool & Hot Tub
Sleeps 18 · 5 bedrooms · 6+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
97 reviews(97 reviews)
Private Retreat on 10 Acres Minutes from Monticello, Wineries & Charlottesville!
Sleeps 8 · 3 bedrooms · 3+ bathrooms
1010 out of 10
Exceptionalexceptional
354 reviews(354 reviews)
1802 cottage once part of Monticello and owned by Thomas Jefferson
Sleeps 2 · 1 bedroom · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
78 reviews(78 reviews)
The Recycled House - Walk Downtown
Sleeps 6 · 1 bedroom · 1+ bathroom
1010 out of 10
Exceptionalexceptional
166 reviews(166 reviews)
Newly-renovated 5BR home near UVA, Downtown, i64. Weddings/bachelorette parties!
Sleeps 12 · 5 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
21 reviews(21 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