Holiday rentals near Monticello
We found 1,513 holiday rentals — enter your dates for availability
Choose the right holiday home that's near Monticello. Holiday homes offer the amenities that you expect for you and your friends, family or even pets, such as a hot tub and a washer and dryer. At the end of the day, you're 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 - Monticello
Showing deals for:1 Aug - 8 Aug
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$19,839
NZ$19,839
NZ$2,834 per night
includes taxes & fees
Image gallery for Hot tub+Game Room+Fire Pit+Views+King beds in spacious family-friendly house
1010 out of 10 rating
Exceptional
(11 reviews)
Hot tub+Game Room+Fire Pit+Views+King beds in spacious family-friendly house
Nellysford, VA
8% off
Price is NZ$7,393
NZ$7,393
NZ$1,056 per night
includes taxes & fees
Image gallery for 180 Degree Breathtaking Views
1010 out of 10 rating
Exceptional
(14 reviews)
180 Degree Breathtaking Views
Nellysford, VA
24% off
Price is NZ$4,270
NZ$4,270
NZ$610 per night
includes taxes & fees
Image gallery for *Having cabin fever at home?* Come stay at our cabin!
9.89.8 out of 10 rating
Exceptional
(18 reviews)
*Having cabin fever at home?* Come stay at our cabin!
Roseland, VA
15% off
Price is NZ$2,671
NZ$2,671
NZ$382 per night
includes taxes & fees
Image gallery for Hawks Nest · Mountain Top Cabin w/ Amazing Views, Coffee, Games
9.89.8 out of 10 rating
Exceptional
(24 reviews)
Hawks Nest · Mountain Top Cabin w/ Amazing Views, Coffee, Games
Free Union, VA
13% off
Price is NZ$6,120
NZ$6,120
NZ$874 per night
includes taxes & fees
Image gallery for Modern Wintergreen Cabin with Hot Tub, Sauna
1010 out of 10 rating
Exceptional
(24 reviews)
Modern Wintergreen Cabin with Hot Tub, Sauna
Roseland, VA
7% off
Price is NZ$7,745
NZ$7,745
NZ$1,106 per night
includes taxes & fees
Image gallery for Fairwood Cottage-Exceptional 1BR Cottage Minutes From Charlottesville & Wineries
1010 out of 10 rating
Exceptional
(23 reviews)
Fairwood Cottage-Exceptional 1BR Cottage Minutes From Charlottesville & Wineries
Charlottesville, VA
19% off
Price is NZ$2,571
NZ$2,571
NZ$367 per night
includes taxes & fees
Image gallery for Luxury Chalet, Best Views in Virginia
9.89.8 out of 10 rating
Exceptional
(28 reviews)
Luxury Chalet, Best Views in Virginia
Wintergreen, VA
8% off
Price is NZ$18,433
NZ$18,433
NZ$2,633 per night
includes taxes & fees
Image gallery for Pop’s Cottage. A private and serene setting in the country 10 minutes from UVa
1010 out of 10 rating
Exceptional
(80 reviews)
Pop’s Cottage. A private and serene setting in the country 10 minutes from UVa
North Garden, VA
8% off
Price is NZ$3,266
NZ$3,266
NZ$467 per night
includes taxes & fees
Image gallery for Total Privacy - H’Owl at the Moon Farm & Cabin
1010 out of 10 rating
Exceptional
(167 reviews)
Total Privacy - H’Owl at the Moon Farm & Cabin
Schuyler, VA
8% off
Price is NZ$4,531
NZ$4,531
NZ$647 per night
includes taxes & fees
Image gallery for 5 min to Downtown C'ville, 3b/2b Comfortable!
1010 out of 10 rating
Exceptional
(16 reviews)
5 min to Downtown C'ville, 3b/2b Comfortable!
Charlottesville, VA
8% off
Price is NZ$4,426
NZ$4,426
NZ$632 per night
includes taxes & fees
Image gallery for 5 Bedroom Hilltop Villa with Magnificent Views
1010 out of 10 rating
Exceptional
(24 reviews)
5 Bedroom Hilltop Villa with Magnificent Views
Buckingham, VA
8% off
Price is NZ$5,937
NZ$5,937
NZ$848 per night
includes taxes & fees
Image gallery for Luxurious Family Friendly Mountain Home! Great Location on Devils Knob
1010 out of 10 rating
Exceptional
(94 reviews)
Luxurious Family Friendly Mountain Home! Great Location on Devils Knob
Nellysford, VA
8% off
Price is NZ$4,170
NZ$4,170
NZ$596 per night
includes taxes & fees
Image gallery for Beautiful, Remodeled Cottage in the Heart of Afton
1010 out of 10 rating
Exceptional
(61 reviews)
Beautiful, Remodeled Cottage in the Heart of Afton
Afton, VA
11% off
Price is NZ$2,062
NZ$2,062
NZ$295 per night
includes taxes & fees
Image gallery for Luxe Private Getaway in the Heart of Wintergreen!
8.48.4 out of 10 rating
Very good
(8 reviews)
Luxe Private Getaway in the Heart of Wintergreen!
Nellysford, VA
7% off
Price is NZ$7,666
NZ$7,666
NZ$1,095 per night
includes taxes & fees
Image gallery for Penthouse Apartment Overlooking Downtown Mall
1010 out of 10 rating
Exceptional
(33 reviews)
Penthouse Apartment Overlooking Downtown Mall
Charlottesville, VA
11% off
Price is NZ$6,525
NZ$6,525
NZ$932 per night
includes taxes & fees
Image gallery for Farmhouse On 14 Acres. Close to Monticello & Ash Lawn Highland
1010 out of 10 rating
Exceptional
(31 reviews)
Farmhouse On 14 Acres. Close to Monticello & Ash Lawn Highland
Charlottesville, VA
16% off
Price is NZ$4,891
NZ$4,891
NZ$699 per night
includes taxes & fees
Image gallery for Spectacular mountain home perfect for multiple families! Just added '80s arcade!
9.69.6 out of 10 rating
Exceptional
(57 reviews)
Spectacular mountain home perfect for multiple families! Just added '80s arcade!
Nellysford, VA
7% off
Price is NZ$3,892
NZ$3,892
NZ$556 per night
includes taxes & fees
Image gallery for Blue Ridge Retreat: Your Cozy Mountain Getaway
1010 out of 10 rating
Exceptional
(22 reviews)
Blue Ridge Retreat: Your Cozy Mountain Getaway
Nellysford, VA
11% off
Price is NZ$1,884
NZ$1,884
NZ$269 per night
includes taxes & fees
Image gallery for Beautiful Mountain House Close to the Slopes
1010 out of 10 rating
Exceptional
(22 reviews)
Beautiful Mountain House Close to the Slopes
Nellysford, VA
8% off
Price is NZ$6,270
NZ$6,270
NZ$896 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
(28 reviews)
Escape the City! Plain Outside; Gorgeous Inside; Huge Horse/Cattle Farm
Gordonsville, VA
18% off
Price is NZ$4,776
NZ$4,776
NZ$682 per night
includes taxes & fees
Image gallery for Wintergreen Resort Home, @ top of mountain with shuttle acces to Ski Lifts
9.89.8 out of 10 rating
Exceptional
(58 reviews)
Wintergreen Resort Home, @ top of mountain with shuttle acces to Ski Lifts
Nellysford, VA
11% off
Price is NZ$3,223
NZ$3,223
NZ$460 per night
includes taxes & fees
Image gallery for Hot Tub Pool Table Dog OK Tennis Golf Shuffleboard
9.49.4 out of 10 rating
Exceptional
(25 reviews)
Hot Tub Pool Table Dog OK Tennis Golf Shuffleboard
Wintergreen, VA
7% off
Price is NZ$7,125
NZ$7,125
NZ$1,018 per night
includes taxes & fees
Image gallery for 2-Level Modern Home on 25 Wooded Acres with Amazing Mountain Views
1010 out of 10 rating
Exceptional
(48 reviews)
2-Level Modern Home on 25 Wooded Acres with Amazing Mountain Views
Afton, VA
8% off
Price is NZ$5,490
NZ$5,490
NZ$784 per night
includes taxes & fees
Find spaces that suit your style
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Find properties near top attractions in Monticello
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Postcard Cabins Shenandoah
Sleeps 2 · 1 bedroom
1010 out of 10
Exceptionalexceptional
6 reviews(6 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
71 reviews(71 reviews)
Glade Cottage at White Lotus Eco Spa Retreat
Sleeps 2 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
11 reviews(11 reviews)
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Sleeps 4 · 2 bedrooms · 2 bathrooms
9.09.0 out of 10
Wonderfulwonderful
270 reviews(270 reviews)
The Natchez - quiet front porch & rockers.
Sleeps 4 · 2 bedrooms · 1+ bathroom
1010 out of 10
Exceptionalexceptional
124 reviews(124 reviews)
Numerous On-Site Trails: Earlysville Wooded Cabin
Sleeps 2 · 1 bathroom
1010 out of 10
Exceptionalexceptional
65 reviews(65 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