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 NZ$4,084
NZ$4,084
NZ$583 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 NZ$10,517
NZ$10,517
NZ$1,502 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 NZ$4,913
NZ$4,913
NZ$702 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 NZ$17,384
NZ$17,384
NZ$2,483 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 NZ$8,251
NZ$8,251
NZ$1,179 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 NZ$13,171
NZ$13,171
NZ$1,882 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 NZ$22,975
NZ$22,975
NZ$3,282 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 NZ$10,352
NZ$10,352
NZ$1,479 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 NZ$8,208
NZ$8,208
NZ$1,173 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 NZ$3,100
NZ$3,100
NZ$443 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 NZ$14,837
NZ$14,837
NZ$2,120 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 NZ$14,507
NZ$14,507
NZ$2,072 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 NZ$4,772
NZ$4,772
NZ$682 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 NZ$6,993
NZ$6,993
NZ$999 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 NZ$10,058
NZ$10,058
NZ$1,437 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 NZ$3,474
NZ$3,474
NZ$496 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$2,629
NZ$2,629
NZ$376 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$4,062
NZ$4,062
NZ$580 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$6,998
NZ$6,998
NZ$1,000 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 NZ$2,887
NZ$2,887
NZ$412 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 NZ$7,640
NZ$7,640
NZ$1,091 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 NZ$5,905
NZ$5,905
NZ$844 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 NZ$2,647
NZ$2,647
NZ$378 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 NZ$3,858
NZ$3,858
NZ$551 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Sugarleaf Vineyard
Showing deals for: 10 Oct - 13 Oct
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)
The current price is NZ$953
NZ$953
for 3 nights, 1 cabin
NZ$318 per night
includes taxes & fees
Ivy Retreat | Heated Saltwater Pool & Hot Tub
Sleeps 18 · 5 bedrooms · 6+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
97 reviews(97 reviews)
The current price is NZ$14,695
NZ$14,695
for 3 nights, 1 home
NZ$4,898 per night
includes taxes & fees
Greensview Apt | 2 Bedroom, 2 Bath - Beautiful views!
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
83 reviews(83 reviews)
The current price is NZ$1,960
NZ$1,960
for 3 nights, 1 apartment
NZ$653 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
70 reviews(70 reviews)
The current price is NZ$8,703
NZ$8,703
for 3 nights, 1 apartment
NZ$2,901 per night
includes taxes & fees
Rugby Road Residential -RRR- near UVa and downtown
Sleeps 4 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
30 reviews(30 reviews)
The current price is NZ$2,893
NZ$2,893
for 3 nights, 1 home
NZ$964 per night
includes taxes & fees
Magnolia Hill | 4 Bed, 3.5 Bath
Sleeps 8 · 4 bedrooms · 3+ bathrooms
9.49.4 out of 10
Exceptionalexceptional
13 reviews(13 reviews)
The current price is NZ$10,806
NZ$10,806
for 3 nights, 1 home
NZ$3,602 per night
includes taxes & fees
Top rated rentals - Sugarleaf Vineyard
Weekend Getaway
1010 out of 10
Exceptionalexceptional
45 reviews(45 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