Oakpark Holiday Rentals
House
- Charlottesville
- ·
- Madison
- 2.57 mi to center
10.0Exceptional
(18 Reviews)
1 Bedroom
1 Bath
4 Guests
800 ft²
Parking
Kitchen
Air Conditioner
Internet
CA $350/Night
7 Nights - CA $2,452
Bed & Breakfast
10.0Exceptional
(53 Reviews)
3 Bedrooms
3 Baths
8 Guests
161.46 ft²
- Parking
Balcony/Terrace- Air Conditioner
- Internet
CA $222/Night
7 Nights - CA $1,556
Bed & Breakfast
- Charlottesville
- ·
- Locust Dale
- 0.81 mi to center
9.2Exceptional
(169 Reviews)
1 Bedroom
1 Bath
Breakfast- Parking
- Balcony/Terrace
- Kitchen
CA $335/Night
7 Nights - CA $2,348
House
10.0Exceptional
(7 Reviews)
2 Bedrooms
2 Baths
6 Guests
Hot Tub- Parking
- Balcony/Terrace
- Kitchen
CA $601/Night
7 Nights - CA $4,211
House
- Charlottesville
- ·
- Pratts
- 0.47 mi to center
10.0Exceptional
(10 Reviews)
3 Bedrooms
2 Baths
6 Guests
1496.18 ft²
- Parking
- Balcony/Terrace
View- Air Conditioner
CA $383/Night
7 Nights - CA $2,684
Apartment
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
4 Guests
800 ft²
- Hot Tub
- Parking
Pool- Balcony/Terrace
CA $276/Night
7 Nights - CA $1,934
Apartment
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
2 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
CA $173/Night
7 Nights - CA $1,213
Cottage
- Culpeper
- ·
- Cedar Mountain
- 4.66 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
- Air Conditioner
Pet Friendly
Child Friendly
Laundry
CA $313/Night
7 Nights - CA $2,192
Cabin
9.4Exceptional
(22 Reviews)
1 Bedroom
1 Bath
4 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
CA $406/Night
7 Nights - CA $2,844
Luxury Holiday Rentals in Oakpark
Over 44+ Luxury Holiday Rentals in or Near Oakpark
House
9.8Exceptional
(9 Reviews)
4 Bedrooms
4 Baths
12 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
CA $2,094/Night
7 Nights - CA $14,660
House
- Culpeper
- ·
- Cedar Mountain
- 4.85 mi to center
8 Bedrooms
5 Baths
16 Guests
6200 ft²
- Hot Tub
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $1,500/Night
7 Nights - CA $10,498
House
10.0Exceptional
(2 Reviews)
6 Bedrooms
4 Baths
16 Guests
4413 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $1,442/Night
7 Nights - CA $10,094
House
- Culpeper
- ·
- Cedar Mountain
- 4.85 mi to center
1 Bedroom
6 Baths
16 Guests
6200.01 ft²
- View
- Air Conditioner
- Internet
- Child Friendly
CA $1,199/Night
7 Nights - CA $8,395
House
10.0Exceptional
(33 Reviews)
7 Bedrooms
4 Baths
14 Guests
3500 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
CA $1,177/Night
7 Nights - CA $8,241
House
- Charlottesville
- ·
- Orange
- 2.8 mi to center
10.0Exceptional
(2 Reviews)
5 Bedrooms
3 Baths
12 Guests
3000 ft²
- Hot Tub
- Parking
Ocean View- Balcony/Terrace
CA $1,093/Night
7 Nights - CA $7,653
House
9.0Exceptional
(4 Reviews)
3 Bedrooms
2 Baths
13 Guests
3000 ft²
Private Pool- Hot Tub
- Parking
- Pool
CA $814/Night
7 Nights - CA $5,696
Cabin
10.0Exceptional
(6 Reviews)
4 Bedrooms
3 Baths
16 Guests
3300 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
CA $793/Night
7 Nights - CA $5,553
House
- Culpeper
- ·
- Cedar Mountain
- 4.85 mi to center
5 Bedrooms
3 Baths
10 Guests
3200 ft²
- Hot Tub
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $726/Night
7 Nights - CA $5,082
Top-Rated Holiday Rentals with a Pool in Oakpark
Over 6+ The Best Private Villas and Holiday Rentals in Oakpark with a Pool
House
8.8Fabulous
(21 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
CA $395/Night
7 Nights - CA $2,764
Ski Chalet
6.8Good
(5 Reviews)
1 Bedroom
1 Bath
2 Guests
398.26 ft²
Oceanfront- Breakfast
- Parking
- Pool
CA $200/Night
7 Nights - CA $1,400
House
3.0Average
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
796.53 ft²
- Oceanfront
- Breakfast
- Parking
- Pool
CA $232/Night
7 Nights - CA $1,624
House
3 Bedrooms
2 Baths
13 Guests
3003.13 ft²
- Pool
- View
- Air Conditioner
- Internet
CA $671/Night
7 Nights - CA $4,700
House
- Virginia
- ·
- Brightwood
- 0.71 mi to center
10.0Exceptional
(183 Reviews)
6 Bedrooms
3 Baths
18 Guests
4000 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
CA $1,009/Night
7 Nights - CA $7,061
House
- Virginia
- ·
- Brightwood
- 0.76 mi to center
5.0Average
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Internet
CA $193/Night
7 Nights - CA $1,352
Pet-Friendly Holiday Rentals in Oakpark
Over 9+ Pet-Friendly Holiday Rentals in or Near Oakpark
House
10.0Exceptional
(12 Reviews)
4 Bedrooms
2 Baths
11 Guests
2000 ft²
- Breakfast
- Parking
- Balcony/Terrace
- Kitchen
CA $551/Night
7 Nights - CA $3,855
Hotel
- Charlottesville
- ·
- Locust Dale
- 0.77 mi to center
8.1Excellent
(48 Reviews)
10 Baths
423.02 ft²
- Breakfast
EV Charge Station- Parking
- Balcony/Terrace
CA $462/Night
7 Nights - CA $3,231
House
- Charlottesville
- ·
- Madison
- 3.67 mi to center
10.0Exceptional
(3 Reviews)
4 Bedrooms
2 Baths
9 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
CA $609/Night
7 Nights - CA $4,265
House
- Charlottesville
- ·
- Madison
- 2.58 mi to center
10.0Exceptional
(2 Reviews)
4 Bedrooms
3 Baths
10 Guests
3172 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $482/Night
7 Nights - CA $3,372
Cabin
- Charlottesville
- ·
- Pratts
- 0.57 mi to center
9.0Exceptional
(2 Reviews)
4 Bedrooms
3 Baths
8 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
CA $647/Night
7 Nights - CA $4,533
New
Cabin
3 Bedrooms
3 Baths
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $525/Night
7 Nights - CA $3,679
Cottage
- Virginia
- ·
- Brightwood
- 2.39 mi to center
2 Bedrooms
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $228/Night
7 Nights - CA $1,593
House
10.0Exceptional
(1 Review)
4 Bedrooms
3 Baths
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $651/Night
7 Nights - CA $4,559
House
- Culpeper
- ·
- Cedar Mountain
- 1.14 mi to center
4 Bedrooms
3 Baths
6 Guests
2865 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $138/Night
7 Nights - CA $964
Large Holiday Rentals and Private Villas in Oakpark
Over 2+ Large Holiday Rentals and Private Villas in or Near Oakpark
House
5.0Average
(85 Reviews)
4 Bedrooms
4 Baths
10 Guests
- Kitchen
- Air Conditioner
- Child Friendly
- Laundry
CA $285/Night
7 Nights - CA $1,993
House
- Culpeper
- ·
- Cedar Mountain
- 4.85 mi to center
5 Bedrooms
4 Baths
10 Guests
3196.88 ft²
- View
- Air Conditioner
- Internet
- Child Friendly
CA $533/Night
7 Nights - CA $3,727
Oakpark Private Villas and Holiday Homes Under $200
Over 6+ Oakpark Private Villas and Holiday Homes Under $200
Cottage
- Charlottesville
- ·
- Madison
- 3.36 mi to center
9.4Exceptional
(8 Reviews)
3 Bedrooms
2 Baths
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $277/Night
7 Nights - CA $1,941
Apartment
- Charlottesville
- ·
- Madison
- 3.14 mi to center
9.3Exceptional
(41 Reviews)
1 Bedroom
1 Bath
4 Guests
925.7 ft²
- Parking
- Balcony/Terrace
- View
- Air Conditioner
CA $200/Night
7 Nights - CA $1,400
House
5.0Average
(2 Reviews)
3 Bedrooms
3 Baths
8 Guests
2000 ft²
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
CA $264/Night
7 Nights - CA $1,848
House
- Virginia
- ·
- Brightwood
- 0.76 mi to center
5.0Average
(1 Review)
1 Bedroom
1 Bath
2 Guests
- Child Friendly
CA $168/Night
7 Nights - CA $1,177
House
- Culpeper
- ·
- Cedar Mountain
- 5.53 mi to center
2 Bedrooms
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $165/Night
7 Nights - CA $1,152
Apartment
- Charlottesville
- ·
- Orange
- 4.41 mi to center
1 Bedroom
1 Bath
3 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Child Friendly
CA $118/Night
7 Nights - CA $827
Instantly Bookable Holiday Homes in Oakpark
Over 8+ Instantly Bookable Holiday Homes in or Near Oakpark
Ski Chalet
- Virginia
- ·
- Brightwood
- 0.86 mi to center
10.0Exceptional
(38 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $383/Night
7 Nights - CA $2,684
House
10.0Exceptional
(7 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $629/Night
7 Nights - CA $4,402
Other
- Charlottesville
- ·
- Pratts
- 0.47 mi to center
10.0Exceptional
(17 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $400/Night
7 Nights - CA $2,796
Other
- Charlottesville
- ·
- Madison
- 2.90 mi to center
4 Bedrooms
2 Baths
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $567/Night
7 Nights - CA $3,969
House
2 Bedrooms
2 Baths
4 Guests
- Hot Tub
- Parking
- Kitchen
- Air Conditioner
CA $555/Night
7 Nights - CA $3,888
House
10.0Exceptional
(11 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
CA $306/Night
7 Nights - CA $2,145
House
10.0Exceptional
(10 Reviews)
4 Bedrooms
3 Baths
8 Guests
3520 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $516/Night
7 Nights - CA $3,615
New
House
- Charlottesville
- ·
- Madison
- 3.08 mi to center
4 Bedrooms
2 Baths
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $437/Night
7 Nights - CA $3,056
Book a Last Minute Place to Stay in Oakpark
About Casai's Private Villas and Holiday Rentals in Oakpark
Discover more than 53 vacation rentals available in Oakpark. 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 Oakpark.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Oakpark, 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 Oakpark. On average, places to stay near Oakpark offer 1176.81 ft², with nightly prices averaging CA $541.
With Casai, finding and comparing holiday rentals in Oakpark 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 Oakpark
| Type | Count |
|---|---|
| Vacation Homes | 31 |
| Holiday Apartments | 8 |
| Cottages | 3 |
Use these Quick Filters to Find a Holiday Rental in Oakpark
★ 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 Oakpark.
Weather in Oakpark, VA
View the weather forecast for Oakpark before booking your Oakpark 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
Frequently Asked Questions About Oakpark?
What are the top holiday rentals in Oakpark?
With numerous options available in Oakpark, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Oakpark:
- Hill of Content B&B
- New pickel ball court! basketball and putt putt too!
- Beautiful home with mountain and river views.
- Historic Madison Eagle Inn
- Farmhouse close to Wedding venues, Wineries, breweries, shops. Dogs welcome!
- Iconic Virginia Farmhouse with Furnished Silo and Scottish Highland Cows
- Farm living at it's best!
- Country Retreat Near Shenandoah & Old Rag - Family Friendly Getaway
- Mid-Century Modern Woodland Retreat with Hot Tub, Cold Water Plunge, & Fire Pit!
- Breathe deep, stay cozy — spacious log cabin living on 30 acres in Aroda, VA
How many Casai.ca holiday rentals are available in Oakpark?
As of 2026, Casai boasts over 53 properties listed in the Oakpark area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Oakpark.
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