
Holiday rentals near Monticello
We found 1,526 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 NZ$3,125
NZ$3,125
NZ$446 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$17,292
NZ$17,292
NZ$2,470 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 NZ$3,396
NZ$3,396
NZ$485 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 NZ$4,071
NZ$4,071
NZ$582 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 NZ$2,208
NZ$2,208
NZ$315 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 NZ$3,313
NZ$3,313
NZ$473 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 NZ$6,432
NZ$6,432
NZ$919 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 NZ$2,141
NZ$2,141
NZ$306 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$4,664
NZ$4,664
NZ$666 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 NZ$5,154
NZ$5,154
NZ$736 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 NZ$2,546
NZ$2,546
NZ$364 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 NZ$2,117
NZ$2,117
NZ$302 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 NZ$9,255
NZ$9,255
NZ$1,322 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 NZ$4,311
NZ$4,311
NZ$616 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 NZ$2,025
NZ$2,025
NZ$289 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 NZ$13,356
NZ$13,356
NZ$1,908 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 NZ$4,007
NZ$4,007
NZ$572 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$2,757
NZ$2,757
NZ$394 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 NZ$2,801
NZ$2,801
NZ$400 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 NZ$4,000
NZ$4,000
NZ$571 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 NZ$3,677
NZ$3,677
NZ$525 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$9,177
NZ$9,177
NZ$1,311 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 NZ$3,519
NZ$3,519
NZ$503 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 NZ$5,102
NZ$5,102
NZ$729 per night
includes taxes & fees
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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