Holiday rentals near Monticello
We found 1,527 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:3 Oct - 10 Oct
Image gallery for “The Suite”. at Chase Cottage - Private Entrance! Luxury accommodations.
1010 out of 10 rating
Exceptional
(32 reviews)
“The Suite”. at Chase Cottage - Private Entrance! Luxury accommodations.
Gordonsville, VA
8% off
Price is AU$2,876
AU$2,876
AU$411 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$15,251
AU$15,251
AU$2,179 per night
includes taxes & fees
Image gallery for Piedmont Place 303| Lux Vineyard & Brewery Getaway in the Heart of Crozet | Pet Friendly
9.89.8 out of 10 rating
Exceptional
(47 reviews)
Piedmont Place 303| Lux Vineyard & Brewery Getaway in the Heart of Crozet | Pet Friendly
Crozet, VA
7% off
Price is AU$3,128
AU$3,128
AU$447 per night
includes taxes & fees
Image gallery for Secluded 20+ Acre Retreat Near Brew & Wine Trails
9.89.8 out of 10 rating
Exceptional
(7 reviews)
Secluded 20+ Acre Retreat Near Brew & Wine Trails
Afton, VA
7% off
Price is AU$3,748
AU$3,748
AU$535 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$2,060
AU$2,060
AU$294 per night
includes taxes & fees
Image gallery for Luxury Log Cabin Getaway: Near Wintergreen Resort & Shenandoah Valley
1010 out of 10 rating
Exceptional
(12 reviews)
Luxury Log Cabin Getaway: Near Wintergreen Resort & Shenandoah Valley
Shipman, VA
12% off
Price is AU$3,052
AU$3,052
AU$436 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$1,997
AU$1,997
AU$285 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
7% off
Price is AU$5,937
AU$5,937
AU$848 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$4,294
AU$4,294
AU$613 per night
includes taxes & fees
Image gallery for Sip 'n Dip: Hot Tub Foosball Pool Table Ping Pong
9.29.2 out of 10 rating
Wonderful
(7 reviews)
Sip 'n Dip: Hot Tub Foosball Pool Table Ping Pong
Nellysford, VA
7% off
Price is AU$4,750
AU$4,750
AU$679 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$1,975
AU$1,975
AU$282 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$2,374
AU$2,374
AU$339 per night
includes taxes & fees
Image gallery for 5 BR Wintergreen House w/ Game Room, 75” TV, Ping Pong, Foosball, Wet Bar & Deck
1010 out of 10 rating
Exceptional
(12 reviews)
5 BR Wintergreen House w/ Game Room, 75” TV, Ping Pong, Foosball, Wet Bar & Deck
Nellysford, VA
8% off
Price is AU$8,594
AU$8,594
AU$1,228 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$3,971
AU$3,971
AU$567 per night
includes taxes & fees
Image gallery for Upscale Wintergreen Getaway. Golf View Deck, Pool, and Modern Comforts
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Upscale Wintergreen Getaway. Golf View Deck, Pool, and Modern Comforts
Nellysford, VA
7% off
Price is AU$1,900
AU$1,900
AU$271 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
(106 reviews)
Berry Hill Lake - Cabin w/ NEW Infinity Pool - Pet Friendly - Private Lake
Nellysford, VA
8% off
Price is AU$11,976
AU$11,976
AU$1,711 per night
includes taxes & fees
Image gallery for The "Small" House
1010 out of 10 rating
Exceptional
(6 reviews)
The "Small" House
Nellysford, VA
8% off
Price is AU$3,685
AU$3,685
AU$526 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$2,610
AU$2,610
AU$373 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$2,536
AU$2,536
AU$362 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$3,677
AU$3,677
AU$525 per night
includes taxes & fees
Image gallery for Gorgeous Tiny Home on Cliff's Edge - 4WD/AWD Access Only
1010 out of 10 rating
Exceptional
(13 reviews)
Gorgeous Tiny Home on Cliff's Edge - 4WD/AWD Access Only
Rockfish, VA
8% off
Price is AU$3,380
AU$3,380
AU$483 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
22% off
Price is AU$4,702
AU$4,702
AU$672 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$8,522
AU$8,522
AU$1,217 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$3,233
AU$3,233
AU$462 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
15 reviews(15 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)
Briarpatch - Luxury 4BR House - in Wintergreen Retreat Collection of fine Homes!
Sleeps 10 · 4 bedrooms · 2+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
132 reviews(132 reviews)
Charming Lakefront Cabin: Fish, Hike & More!
Sleeps 5 · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
29 reviews(29 reviews)
Numerous On-Site Trails: Earlysville Wooded Cabin
Sleeps 2 · 1 bathroom
1010 out of 10
Exceptionalexceptional
71 reviews(71 reviews)
1700"s Summer Kitchen Cottage #147 Pool & Spa
Sleeps 4 · 1 bedroom · 1 bathroom
9.89.8 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