Cunningham Resorts
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
AU $250/Night
For 7 Nights AU $1,752
1496.18 ft²
5 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Parking
- Internet
AU $369/Night
For 7 Nights AU $2,585
1 Bedroom
1 Bathroom
Family Friendly
Bed & Breakfast
- Fireplace/Heating
- Pool
- Balcony/Terrace
AU $397/Night
For 7 Nights AU $2,776
1200 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
AU $303/Night
For 7 Nights AU $2,120
2400.35 ft²
19 Guests
7 Bedrooms
4 Bathrooms
Family Friendly
House
- Spa
- Fireplace/Heating
- Pet Friendly
AU $1,839/Night
For 7 Nights AU $12,876
1000 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
AU $315/Night
For 7 Nights AU $2,206
968.75 ft²
5 Guests
1 Bedroom
2 Bathrooms
Free Cancellation
House
- Oceanfront
- Fireplace/Heating
- Ocean View
AU $254/Night
For 7 Nights AU $1,781
500 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
AU $196/Night
For 7 Nights AU $1,371
1200 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Cabin
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
AU $441/Night
For 7 Nights AU $3,085
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
AU $283/Night
For 7 Nights AU $1,980
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
AU $471/Night
For 7 Nights AU $3,297
400 ft²
2 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Parking
AU $131/Night
For 7 Nights AU $917
Why Choose Rent By Owner for your Cunningham Resorts?
What makes our Resorts special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Weekly Weather Forecast for Cunningham
How to Book Your Cunningham Resorts
What's our booking process?
Our platform allows you to browse a curated selection of resorts. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Cunningham
Common Resorts Amenities
What amenities can you expect?
Our Resorts are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Other Places to Stay in Cunningham, VA
Layz S Ranch
Palmyra
Frequently Asked Questions About Cunningham Resorts
1. What are the top Resorts in Cunningham?
There are a lot of options in Cunningham. If you plan on staying in the Cunningham area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Resorts in Cunningham:
- Private Retreat on 10 Acres Minutes from Monticello, Wineries & Charlottesville!
- WELCOME TO DEER RIDGE CABIN! YOUR PERFECT, PRIVATE AND COZY GETAWAY!
- HIDDEN GEM BARN STUDIO WITH A VIEW near Monticello, wineries, with pool
- Farmhouse On 14 Acres. Close to Monticello & Ash Lawn Highland
- Keelona Cottage 2 BR 2 BA near vineyards
- Charming Historic Carriage House Studio Apartment
- Private Hot Tub, Pool, Firepit 3 Bdrm/2 Bth in Wine Region of Year
- Cottage at Deer Ridge Farm
- Barn Studio in country setting but close to town
- 10 Vineyards Within 10 Mi, EV charger & Mini Goats
2. How many Resorts are available in Cunningham?
Currently, the total number of properties listed by RBO in 2026 is over 103 in the Cunningham area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Resorts in Cunningham.
More Rentals You May Like Near Cunningham
1500 ft²
5 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
AU $580/Night
For 7 Nights AU $4,059
965 ft²
5 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
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4 Guests
1 Bedroom
1 Bathroom
Family Friendly
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- Balcony/Terrace
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AU $338/Night
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1100 ft²
7 Guests
2 Bedrooms
1 Bathroom
Family Friendly
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- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
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3 Guests
1 Bedroom
1 Bathroom
Family Friendly
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- Hot Tub
- Balcony/Terrace
- Kitchen
AU $442/Night
For 7 Nights AU $3,095
4 Guests
2 Bedrooms
2 Bathrooms
Couples Retreat
Bed & Breakfast
- Fireplace/Heating
- Air Conditioner
- Internet
AU $545/Night
For 7 Nights AU $3,814
6 Guests
1 Bedroom
2 Bathrooms
Family Friendly
Bed & Breakfast
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
AU $242/Night
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6 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
AU $1,277/Night
For 7 Nights AU $8,942
2500 ft²
8 Guests
4 Bedrooms
2 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
AU $606/Night
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10 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
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- Private Pool
- Fireplace/Heating
- Pool
AU $2,078/Night
For 7 Nights AU $14,543
2400 ft²
19 Guests
7 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
AU $810/Night
For 7 Nights AU $5,670
13 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
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