Cunningham Holiday Rentals
House
10.0Exceptional
(18 Reviews)
2 Bedrooms
2 Baths
4 Guests
1000 ft²
Kitchen
Air Conditioner
Internet
Laundry
US $397/Night
7 Nights - US $2,781
Apartment
- Charlottesville
- ·
- Scottsville
- 0.91 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
5 Guests
1496.18 ft²
Parking
Balcony/Terrace- Internet
Security/Safety
US $265/Night
7 Nights - US $1,855
Bed & Breakfast
10.0Exceptional
(57 Reviews)
1 Bedroom
1 Bath
Breakfast- Parking
Pool- Balcony/Terrace
US $285/Night
7 Nights - US $1,992
Apartment
- Virginia
- ·
- Boyd Tavern
- 3.98 mi to center
10.0Exceptional
(12 Reviews)
1 Bedroom
1 Bath
2 Guests
425 ft²
- Parking
- Pool
Ocean View- Balcony/Terrace
US $294/Night
7 Nights - US $2,056
House
- Virginia
- ·
- Zion Crossroads
- 1.49 mi to center
7 Bedrooms
4 Baths
19 Guests
2400.35 ft²
- Parking
Spa- Internet
Pet Friendly
US $743/Night
7 Nights - US $5,203
House
- Virginia
- ·
- Charlottesville
- 3.90 mi to center
9.6Exceptional
(65 Reviews)
1 Bedroom
1 Bath
2 Guests
544 ft²
Private Pool
Hot Tub- Parking
- Pool
US $311/Night
7 Nights - US $2,176
Cottage
- Virginia
- ·
- Charlottesville
- 3.88 mi to center
9.6Exceptional
(34 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $311/Night
7 Nights - US $2,176
Cottage
- Virginia
- ·
- Charlottesville
- 4.09 mi to center
9.4Exceptional
(111 Reviews)
1 Bedroom
1 Bath
2 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $311/Night
7 Nights - US $2,176
Cottage
- Virginia
- ·
- Boyd Tavern
- 4.07 mi to center
8.8Fabulous
(14 Reviews)
1 Bedroom
1 Bath
4 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $293/Night
7 Nights - US $2,048
Luxury Holiday Rentals in Cunningham
Over 97+ Luxury Holiday Rentals in or Near Cunningham
House
- Charlottesville
- ·
- Scottsville
- 6.02 mi to center
6 Bedrooms
5 Baths
12 Guests
- Air Conditioner
- Internet
Child Friendly- Laundry
US $3,060/Night
7 Nights - US $21,418
Cabin
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
8 Guests
- Air Conditioner
- Internet
- Child Friendly
- Laundry
US $1,550/Night
7 Nights - US $10,847
House
- Virginia
- ·
- Charlottesville
- 3.56 mi to center
9.6Exceptional
(14 Reviews)
5 Bedrooms
5 Baths
10 Guests
5500 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $1,510/Night
7 Nights - US $10,571
House
- Virginia
- ·
- Zion Crossroads
- 3.92 mi to center
10.0Exceptional
(7 Reviews)
4 Bedrooms
3 Baths
10 Guests
3860 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $1,484/Night
7 Nights - US $10,388
House
- Virginia
- ·
- Boyd Tavern
- 0.42 mi to center
1 Bedroom
1 Bath
- Parking
- Internet
- Child Friendly
- Security/Safety
US $943/Night
7 Nights - US $6,601
House
2 Bedrooms
1 Bath
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $889/Night
7 Nights - US $6,220
House
- Virginia
- ·
- Boyd Tavern
- 0.42 mi to center
4 Bedrooms
3 Baths
6 Guests
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $856/Night
7 Nights - US $5,992
House
- Virginia
- ·
- Boyd Tavern
- 0.42 mi to center
4 Bedrooms
3 Baths
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $844/Night
7 Nights - US $5,911
House
- Virginia
- ·
- Zion Crossroads
- 1.86 mi to center
9.4Exceptional
(24 Reviews)
4 Bedrooms
3 Baths
13 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $730/Night
7 Nights - US $5,111
Top-Rated Holiday Rentals with a Pool in Cunningham
Over 10+ The Best Private Villas and Holiday Rentals in Cunningham with a Pool
Hotel
9.6Exceptional
(143 Reviews)
1 Bath
- Hot Tub
- Breakfast
- Parking
- Pool
US $649/Night
7 Nights - US $4,543
New
Other
- Charlottesville
- ·
- Scottsville
- 0.80 mi to center
3 Bedrooms
3 Baths
10 Guests
2000 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $514/Night
7 Nights - US $3,598
New
Other
- Charlottesville
- ·
- Scottsville
- 0.71 mi to center
1 Bedroom
2 Baths
4 Guests
900 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $241/Night
7 Nights - US $1,690
Apartment
- Virginia
- ·
- Boyd Tavern
- 4.01 mi to center
10.0Exceptional
(79 Reviews)
1 Bedroom
1 Bath
2 Guests
700 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $297/Night
7 Nights - US $2,080
House
- Virginia
- ·
- Boyd Tavern
- 3.20 mi to center
10.0Exceptional
(12 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $554/Night
7 Nights - US $3,881
House
10.0Exceptional
(3 Reviews)
5 Bedrooms
4 Baths
12 Guests
- Private Pool
- Pool
- Balcony/Terrace
- Air Conditioner
US $2,835/Night
7 Nights - US $19,845
House
- Virginia
- ·
- Charlottesville
- 4.09 mi to center
10.0Exceptional
(3 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $686/Night
7 Nights - US $4,801
Hotel
- Virginia
- ·
- Boyd Tavern
- 3.45 mi to center
9.0Exceptional
(125 Reviews)
1 Bath
- Hot Tub
- Pool
- Spa
- Balcony/Terrace
US $305/Night
7 Nights - US $2,132
House
- Virginia
- ·
- Zion Crossroads
- 3.93 mi to center
1 Bedroom
1 Bath
- Pool
- Balcony/Terrace
- Internet
- Child Friendly
US $1,533/Night
7 Nights - US $10,733
Pet-Friendly Holiday Rentals in Cunningham
Over 36+ Pet-Friendly Holiday Rentals in or Near Cunningham
Cottage
- Charlottesville
- ·
- Lake Monticello
- 1.21 mi to center
10.0Exceptional
(47 Reviews)
1 Bedroom
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $266/Night
7 Nights - US $1,861
House
- Charlottesville
- ·
- Lake Monticello
- 1.26 mi to center
1 Bedroom
2 Baths
5 Guests
968.75 ft²
Oceanfront- Parking
- Ocean View
View
US $183/Night
7 Nights - US $1,278
Cottage
- Charlottesville
- ·
- Lake Monticello
- 1.21 mi to center
10.0Exceptional
(42 Reviews)
1 Bedroom
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $269/Night
7 Nights - US $1,881
House
10.0Exceptional
(9 Reviews)
1 Bedroom
1 Bath
2 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $245/Night
7 Nights - US $1,716
Bed & Breakfast
- Virginia
- ·
- Charlottesville
- 5.09 mi to center
5 Bedrooms
3 Baths
6 Guests
129.17 ft²
- Breakfast
- Parking
- Balcony/Terrace
- View
US $352/Night
7 Nights - US $2,464
Cabin
10.0Exceptional
(6 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $407/Night
7 Nights - US $2,847
House
- Charlottesville
- ·
- Lake Monticello
- 1.26 mi to center
9.8Exceptional
(15 Reviews)
1 Bedroom
1 Bath
5 Guests
965 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $235/Night
7 Nights - US $1,642
Apartment
- Virginia
- ·
- Zion Crossroads
- 1.86 mi to center
9.4Exceptional
(6 Reviews)
1 Bedroom
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $245/Night
7 Nights - US $1,714
Cottage
- Virginia
- ·
- Zion Crossroads
- 1.85 mi to center
9.2Exceptional
(149 Reviews)
2 Bedrooms
1 Bath
7 Guests
1100 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $213/Night
7 Nights - US $1,490
Large Holiday Rentals and Private Villas in Cunningham
Over 8+ Large Holiday Rentals and Private Villas in or Near Cunningham
House
- Virginia
- ·
- Zion Crossroads
- 1.49 mi to center
9.6Exceptional
(11 Reviews)
7 Bedrooms
3 Baths
19 Guests
2400 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $724/Night
7 Nights - US $5,065
House
- Charlottesville
- ·
- Palmyra
- 2.26 mi to center
5 Bedrooms
4 Baths
12 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $539/Night
7 Nights - US $3,774
House
- Charlottesville
- ·
- Scottsville
- 4.21 mi to center
10.0Exceptional
(23 Reviews)
5 Bedrooms
3 Baths
10 Guests
5600 ft²
- Parking
- Spa
- Balcony/Terrace
- Kitchen
US $864/Night
7 Nights - US $6,048
House
- Charlottesville
- ·
- Keswick
- 1.75 mi to center
10.0Exceptional
(3 Reviews)
5 Bedrooms
5 Baths
15 Guests
4600 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,329/Night
7 Nights - US $9,302
House
- Charlottesville
- ·
- Royal Acres
- 0.21 mi to center
10.0Exceptional
(3 Reviews)
5 Bedrooms
4 Baths
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,181/Night
7 Nights - US $8,264
House
- Charlottesville
- ·
- Scottsville
- 1.96 mi to center
4.6Average
(9 Reviews)
12 Bedrooms
14 Baths
36 Guests
7500 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $1,503/Night
7 Nights - US $10,521
House
9 Bedrooms
7 Baths
18 Guests
- Hot Tub
- Balcony/Terrace
- Kitchen
- Internet
US $3,240/Night
7 Nights - US $22,683
House
- Charlottesville
- ·
- Keswick
- 1.11 mi to center
4 Bedrooms
3 Baths
14 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Laundry
US $213/Night
7 Nights - US $1,488
Wheelchair Accessible Holiday Homes in Cunningham
Over 2+ Wheelchair Accessible Holiday Homes in or Near Cunningham
Cottage
- Charlottesville
- ·
- Scottsville
- 0.63 mi to center
9.8Exceptional
(39 Reviews)
1 Bedroom
1 Bath
4 Guests
800 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $200/Night
7 Nights - US $1,400
House
- Virginia
- ·
- Boyd Tavern
- 1.49 mi to center
1.8Average
(5 Reviews)
2 Bedrooms
1 Bath
5 Guests
1350 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $171/Night
7 Nights - US $1,197
Cunningham Private Villas and Holiday Homes Under $200
Over 22+ Cunningham Private Villas and Holiday Homes Under $200
Cottage
1 Bedroom
1 Bath
2 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $190/Night
7 Nights - US $1,332
Bed & Breakfast
1 Bedroom
2 Baths
6 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $177/Night
7 Nights - US $1,236
Cottage
- Charlottesville
- ·
- Scottsville
- 1.67 mi to center
9.4Exceptional
(9 Reviews)
1 Bedroom
1 Bath
2 Guests
1000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $146/Night
7 Nights - US $1,023
House
- Virginia
- ·
- Boyd Tavern
- 6.97 mi to center
3 Bedrooms
1 Bath
5 Guests
2450 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $125/Night
7 Nights - US $873
Cottage
10.0Exceptional
(30 Reviews)
1 Bedroom
1 Bath
2 Guests
1015 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $198/Night
7 Nights - US $1,388
Cottage
10.0Exceptional
(5 Reviews)
1 Bedroom
1 Bath
2 Guests
1400 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $175/Night
7 Nights - US $1,228
House
- Virginia
- ·
- Boyd Tavern
- 4.76 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $76/Night
7 Nights - US $531
House
- Virginia
- ·
- Charlottesville
- 2.90 mi to center
1 Bedroom
1 Bath
2 Guests
2400 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $75/Night
7 Nights - US $528
Cottage
10.0Exceptional
(78 Reviews)
2 Bedrooms
1 Bath
4 Guests
900 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $185/Night
7 Nights - US $1,292
Instantly Bookable Holiday Homes in Cunningham
Over 31+ Instantly Bookable Holiday Homes in or Near Cunningham
Cottage
- Charlottesville
- ·
- Lake Monticello
- 1.21 mi to center
10.0Exceptional
(62 Reviews)
1 Bedroom
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $292/Night
7 Nights - US $2,046
House
- Charlottesville
- ·
- Scottsville
- 0.71 mi to center
10.0Exceptional
(58 Reviews)
2 Bedrooms
1 Bath
6 Guests
1200 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $269/Night
7 Nights - US $1,885
Cabin
- Charlottesville
- ·
- Palmyra
- 2.54 mi to center
8.4Excellent
(5 Reviews)
1 Bedroom
1 Bath
3 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $359/Night
7 Nights - US $2,513
House
- Virginia
- ·
- Zion Crossroads
- 1.86 mi to center
9.4Exceptional
(11 Reviews)
3 Bedrooms
2 Baths
9 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $561/Night
7 Nights - US $3,930
House
- Charlottesville
- ·
- Scottsville
- 5.80 mi to center
9.4Exceptional
(6 Reviews)
3 Bedrooms
2 Baths
6 Guests
1329 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $346/Night
7 Nights - US $2,421
House
- Virginia
- ·
- Boyd Tavern
- 4.36 mi to center
10.0Exceptional
(52 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $467/Night
7 Nights - US $3,269
House
- Virginia
- ·
- Charlottesville
- 3.47 mi to center
9.2Exceptional
(23 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $457/Night
7 Nights - US $3,200
New
Apartment
- Virginia
- ·
- Charlottesville
- 4.12 mi to center
10.0Exceptional
(19 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $287/Night
7 Nights - US $2,011
House
10.0Exceptional
(19 Reviews)
2 Bedrooms
1 Bath
4 Guests
1100 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $394/Night
7 Nights - US $2,755
Book a Last Minute Place to Stay in Cunningham
About Casai's Private Villas and Holiday Rentals in Cunningham
Discover more than 106 vacation rentals available in Cunningham. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Cunningham.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Cunningham, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Cunningham. On average, places to stay near Cunningham offer 728.09 ft², with nightly prices averaging US $501.
With Casai, finding and comparing holiday rentals in Cunningham is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
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Top Accommodation Types in Cunningham
| Type | Count |
|---|---|
| Vacation Homes | 57 |
| Cottages | 19 |
| Holiday Apartments | 12 |
Use these Quick Filters to Find a Holiday Rental in Cunningham
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Cunningham.
Weather in Cunningham, VA
View the weather forecast for Cunningham before booking your Cunningham Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Top Attractions Around Cunningham, VA
Casai offers a large selection of top attractions around Cunningham . Research things to do on your vacation before you visit Cunningham.
Frequently Asked Questions About Cunningham?
What are the top holiday rentals in Cunningham?
With numerous options available in Cunningham, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Cunningham:
- Private Retreat on 10 Acres Minutes from Monticello, Wineries & Charlottesville!
- Bluebird Cottage B: Quiet, Firepit, Patio, Games
- 106 acre Farm with Animals, River & Private Pond, near Wineries and Breweries
- Woodville Bed and Breakfast
- Farmhouse On 14 Acres. Close to Monticello & Ash Lawn Highland
- Bluebird Cottage A: Across from Lake Monticello, Near Charlottesville, 1 Dog Ok
- Cottage at Deer Ridge Farm
- Charming Historic Carriage House Studio Apartment
- Entire Cottage on Equestrian Farm with Zebras
- Barn Studio in country setting but close to town
Which holiday homes in Cunningham are best for families?
If you're searching for a family-friendly holiday home in Cunningham, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Cunningham:
- Charlottesville Farmhouse Dream Oasis w Pool
- Charming bed & breakfast with 2 bedrooms and AC in lovely Arvonia
- Two-Bedroom, One Bathroom Cottage on 250-Acre Cattle Farm for Getaway near Richmond, Virginia
How many Casai.com holiday rentals are available in Cunningham?
As of 2026, Casai boasts over 106 properties listed in the Cunningham area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Cunningham.
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