Charlottesville holiday rentals
We found 623 holiday rentals — enter your dates for availability
Select the perfect private holiday rental within easy reach of Charlottesville, VA (CHO-Charlottesville-Albemarle). Holiday rentals provide the best amenities for your family, friends or furry companion, including parking and a garden. You'll be sure to find a property to rent to meet everyone's needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Charlottesville, VA (CHO-Charlottesville-Albemarle)
Showing deals for:7 Nov - 14 Nov
Image gallery for 1700"s Summer Kitchen Cottage #147 Pool & Spa
9.89.8 out of 10 rating
Exceptional
(51 reviews)
1700"s Summer Kitchen Cottage #147 Pool & Spa
Gordonsville, VA
8% off
Price is S$1,418
S$1,418
S$203 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 S$1,649
S$1,649
S$236 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 S$1,683
S$1,683
S$240 per night
includes taxes & fees
Image gallery for Secluded Stanardsville Cabin w/ 10 Acres & Hot Tub
1010 out of 10 rating
Exceptional
(101 reviews)
Secluded Stanardsville Cabin w/ 10 Acres & Hot Tub
Stanardsville, VA
14% off
Price is S$3,168
S$3,168
S$453 per night
includes taxes & fees
Image gallery for Charming 2-bedroom cottage in lovely Madison with WiFi, AC
1010 out of 10 rating
Exceptional
(7 reviews)
Charming 2-bedroom cottage in lovely Madison with WiFi, AC
Madison, VA
8% off
Price is S$1,783
S$1,783
S$255 per night
includes taxes & fees
Image gallery for Perfect vacation home! 100+ REVIEWS AND 5 STARS ON AIRBNB
1010 out of 10 rating
Exceptional
(6 reviews)
Perfect vacation home! 100+ REVIEWS AND 5 STARS ON AIRBNB
Earlysville, VA
12% off
Price is S$5,951
S$5,951
S$850 per night
includes taxes & fees
Image gallery for Cottage and working farm in heart of Virginia wine country near UVA & Woodberry
1010 out of 10 rating
Exceptional
(8 reviews)
Cottage and working farm in heart of Virginia wine country near UVA & Woodberry
Gordonsville, VA
8% off
Price is S$3,874
S$3,874
S$553 per night
includes taxes & fees
Image gallery for 1802 cottage once part of Monticello and owned by Thomas Jefferson
9.49.4 out of 10 rating
Exceptional
(81 reviews)
1802 cottage once part of Monticello and owned by Thomas Jefferson
Charlottesville, VA
16% off
Price is S$2,048
S$2,048
S$293 per night
includes taxes & fees
Image gallery for Farmhouse close to Wedding venues, Wineries, breweries, shops. Dogs welcome!
9.89.8 out of 10 rating
Exceptional
(10 reviews)
Farmhouse close to Wedding venues, Wineries, breweries, shops. Dogs welcome!
Madison, VA
8% off
Price is S$3,267
S$3,267
S$467 per night
includes taxes & fees
Image gallery for Cozy Chalet bordering Shenandoah Park near Massanutten Resort and Skyline Drive.
1010 out of 10 rating
Exceptional
(23 reviews)
Cozy Chalet bordering Shenandoah Park near Massanutten Resort and Skyline Drive.
Elkton, VA
8% off
Price is S$1,878
S$1,878
S$268 per night
includes taxes & fees
Image gallery for Shenandoah Mountain Majesty Log Cabin on 15 Acres - Hot Tub-1GB Fiber Internet
9.69.6 out of 10 rating
Exceptional
(11 reviews)
Shenandoah Mountain Majesty Log Cabin on 15 Acres - Hot Tub-1GB Fiber Internet
Stanardsville, VA
8% off
Price is S$4,883
S$4,883
S$698 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 S$2,182
S$2,182
S$312 per night
includes taxes & fees
Image gallery for Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy
1010 out of 10 rating
Exceptional
(36 reviews)
Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy
Charlottesville, VA
8% off
Price is S$4,209
S$4,209
S$601 per night
includes taxes & fees
Image gallery for Relax at 3100 feet and enjoy the peace and tranquility
1010 out of 10 rating
Exceptional
(78 reviews)
Relax at 3100 feet and enjoy the peace and tranquility
Dyke, VA
12% off
Price is S$1,683
S$1,683
S$240 per night
includes taxes & fees
Image gallery for Luxury Stay on Flower Farm by Wineries Near Charlottesville-Pet-Friendly
1010 out of 10 rating
Exceptional
(21 reviews)
Luxury Stay on Flower Farm by Wineries Near Charlottesville-Pet-Friendly
Somerset, VA
8% off
Price is S$3,698
S$3,698
S$528 per night
includes taxes & fees
Image gallery for The Lodge in Sugar Hollow -Charlottesville near Crozet
1010 out of 10 rating
Exceptional
(59 reviews)
The Lodge in Sugar Hollow -Charlottesville near Crozet
Crozet, VA
28% off
Price is S$3,855
S$3,855
S$551 per night
includes taxes & fees
Image gallery for Pete's Place: Forest retreat near wineries, Blue Ridge School, and Shenandoah NP
9.89.8 out of 10 rating
Exceptional
(38 reviews)
Pete's Place: Forest retreat near wineries, Blue Ridge School, and Shenandoah NP
Stanardsville, VA
25% off
Price is S$1,266
S$1,266
S$181 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
(29 reviews)
Escape the City! Plain Outside; Gorgeous Inside; Huge Horse/Cattle Farm
Gordonsville, VA
18% off
Price is S$3,650
S$3,650
S$521 per night
includes taxes & fees
Image gallery for Peaceful mountain farmhouse, close to Shenandoah NP, wineries and more
1010 out of 10 rating
Exceptional
(37 reviews)
Peaceful mountain farmhouse, close to Shenandoah NP, wineries and more
Stanardsville, VA
8% off
Price is S$2,835
S$2,835
S$405 per night
includes taxes & fees
Image gallery for Cottage on quiet farm close to town and wineries
9.69.6 out of 10 rating
Exceptional
(57 reviews)
Cottage on quiet farm close to town and wineries
Charlottesville, VA
8% off
Price is S$2,280
S$2,280
S$326 per night
includes taxes & fees
Image gallery for The Cabin at the Lake
9.89.8 out of 10 rating
Exceptional
(28 reviews)
The Cabin at the Lake
Madison, VA
8% off
Price is S$1,909
S$1,909
S$273 per night
includes taxes & fees
Image gallery for Fairwood Cottage-Exceptional 1BR Cottage Minutes From Charlottesville & Wineries
1010 out of 10 rating
Exceptional
(25 reviews)
Fairwood Cottage-Exceptional 1BR Cottage Minutes From Charlottesville & Wineries
Charlottesville, VA
19% off
Price is S$1,967
S$1,967
S$281 per night
includes taxes & fees
Image gallery for The House in the Holla at the foot of Shenandoah National Park
9.89.8 out of 10 rating
Exceptional
(57 reviews)
The House in the Holla at the foot of Shenandoah National Park
Stanardsville, VA
8% off
Price is S$1,571
S$1,571
S$224 per night
includes taxes & fees
Image gallery for Lovers Lane FarmStay on a working family farm. Horses, cows, sheep, bees & more
8.88.8 out of 10 rating
Excellent
(8 reviews)
Lovers Lane FarmStay on a working family farm. Horses, cows, sheep, bees & more
Gordonsville, VA
17% off
Price is S$999
S$999
S$143 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Charlottesville
Moonfire Farm Shenandoah region cozy getaway
Sleeps 4 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
25 reviews(25 reviews)
Family-friendly single home/Walking distance to shopping center and restaurants
Sleeps 8 · 3 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
29 reviews(29 reviews)
Stunning Mountain Views, Hot Tub, Indoor and Outdoor Fireplace, and Game Room!
Sleeps 10 · 4 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
23 reviews(23 reviews)
Large Country House Near Monticello, UVA, Wineries
Sleeps 8 · 4 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
8 reviews(8 reviews)
Peaceful mountain farmhouse, close to Shenandoah NP, wineries and more
Sleeps 7 · 3 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
37 reviews(37 reviews)
Private Retreat on 10 Acres Minutes from Monticello, Wineries & Charlottesville!
Sleeps 8 · 3 bedrooms · 3+ bathrooms
1010 out of 10
Exceptionalexceptional
356 reviews(356 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