Best Vacation Homes in Madison County
Cabin
10.0(54 Reviews)
2 Bedrooms
2 Baths
4 Guests
2200 ft²
Fireplace/Heating
Balcony/Terrace
Kitchen
Parking
R5,507/Night
7 Nights - R38,541
House
10.0(10 Reviews)
3 Bedrooms
2 Baths
6 Guests
1496.18 ft²
- Fireplace/Heating
- Balcony/Terrace
View
Pet Friendly
R4,462/Night
7 Nights - R31,234
Bed & Breakfast
9.2(165 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Balcony/Terrace
Breakfast- Kitchen
R5,229/Night
7 Nights - R36,601
Cottage
10.0(18 Reviews)
2 Bedrooms
2 Baths
7 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
Air Conditioner
R3,251/Night
7 Nights - R22,762
House
9.5(4 Reviews)
1 Bedroom
1 Bath
4 Guests
398.26 ft²
- Fireplace/Heating
- Parking
- Air Conditioner
Internet
R3,718/Night
7 Nights - R26,028
Cabin
10.0(17 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R1,694/Night
7 Nights - R11,866
House
10.0(13 Reviews)
2 Bedrooms
2 Baths
8 Guests
Spa- Fireplace/Heating
- Balcony/Terrace
- Kitchen
R3,848/Night
7 Nights - R26,933
Cabin
10.0(11 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R3,489/Night
7 Nights - R24,428
Madison County Luxury Rentals
House
10.0(2 Reviews)
4 Bedrooms
2 Baths
3500 ft²
Hot Tub- Fireplace/Heating
Ocean View- Balcony/Terrace
R155,478/Night
7 Nights - R1,088,348
House
10.0(1 Review)
8 Bedrooms
9 Baths
30 Guests
- Fireplace/Heating
Pool- Balcony/Terrace
- Pet Friendly
R69,512/Night
7 Nights - R486,581
House
10.0(3 Reviews)
5 Bedrooms
5 Baths
14 Guests
- Fireplace/Heating
- Pet Friendly
- Internet
Child Friendly
R14,133/Night
7 Nights - R98,939
Cabin
9.4(96 Reviews)
6 Bedrooms
4 Baths
16 Guests
4400 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
R13,971/Night
7 Nights - R97,791
House
10.0(2 Reviews)
5 Bedrooms
3 Baths
14 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R9,831/Night
7 Nights - R68,821
House
10.0(30 Reviews)
5 Bedrooms
3 Baths
10 Guests
3000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R7,784/Night
7 Nights - R54,481
House
10.0(148 Reviews)
4 Bedrooms
3 Baths
8 Guests
2500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R7,489/Night
7 Nights - R52,428
Cabin
10.0(1 Review)
3 Bedrooms
2 Baths
6 Guests
2630 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R7,057/Night
7 Nights - R49,405
Madison County Pet Friendly Vacation Rentals
Cabin
10.0(11 Reviews)
1 Bedroom
1 Bath
4 Guests
1289 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R3,271/Night
7 Nights - R22,892
Cabin
8.4(402 Reviews)
71 Bedrooms
29 Baths
143 Guests
1200.43 ft²
Oceanfront- Fireplace/Heating
- Pool
- Ocean View
R1,681/Night
7 Nights - R11,769
Apartment
10.0(7 Reviews)
1 Bedroom
1 Bath
2 Guests
- Balcony/Terrace
- Pet Friendly
- Internet
- Child Friendly
R5,308/Night
7 Nights - R37,151
Hotel
8.1(48 Reviews)
10 Baths
423.02 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Breakfast
R5,373/Night
7 Nights - R37,603
Cottage
10.0(2 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R3,572/Night
7 Nights - R25,010
Cabin
9.8(54 Reviews)
2 Bedrooms
1 Bath
4 Guests
680 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
R5,029/Night
7 Nights - R35,195
Cottage
9.8(46 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R2,943/Night
7 Nights - R20,596
House
9.8(6 Reviews)
2 Bedrooms
1 Bath
6 Guests
1100 ft²
- Spa
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
R2,989/Night
7 Nights - R20,920
Madison County Large Vacation Homes
House
10.0(2 Reviews)
4 Bedrooms
3 Baths
10 Guests
3172 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
R5,252/Night
7 Nights - R36,763
Cabin
10.0(2 Reviews)
4 Bedrooms
2 Baths
10 Guests
Private Pool- Fireplace/Heating
- Pool
- Pet Friendly
R14,854/Night
7 Nights - R103,983
House
9.4(72 Reviews)
5 Bedrooms
3 Baths
12 Guests
4000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R11,725/Night
7 Nights - R82,078
House
10.0(183 Reviews)
6 Bedrooms
3 Baths
18 Guests
4000 ft²
- Private Pool
- Hot Tub
- Spa
- Fireplace/Heating
R11,739/Night
7 Nights - R82,175
Cottage
10.0(15 Reviews)
3 Bedrooms
2 Baths
11 Guests
1900 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
R4,672/Night
7 Nights - R32,705
House
10.0(3 Reviews)
10 Bedrooms
11 Baths
24 Guests
13993 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
R26,173/Night
7 Nights - R183,215
House
10.0(1 Review)
4 Bedrooms
4 Baths
13 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R4,682/Night
7 Nights - R32,770
Cottage
5.0(1 Review)
3 Bedrooms
2 Baths
10 Guests
1200 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R3,233/Night
7 Nights - R22,633
Why Choose Rent By Owner for your Madison County Vacation Rental Homes?
What makes our Vacation Rentals 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.
Best Times to Visit Madison County
When should you plan your Vacation Rentals stay?
Timing your visit to this charming destination can enhance your experience, and choosing the right season ensures you enjoy all that the region has to offer during your stay in Madison County.
Peak Season Highlights
Spring (March to May)
During spring, the area comes alive with vibrant scenery, making it an ideal time for outdoor activities and exploring the scenic landscape.
Average Temperature Daytime: 60°F to 75°F - Nighttime: 40°F to 55°F
Fall (September to November)
Autumn offers stunning foliage views that attract visitors seeking picturesque landscapes and a peaceful atmosphere.
Average Temperature Daytime: 65°F to 70°F - Nighttime: 45°F to 50°F
Off-Season Highlights
Winter (December to February)
Winters feature a quieter environment, perfect for those looking to enjoy the tranquility of this destination without the crowds.
Average Temperature Daytime: 40°F to 50°F - Nighttime: 25°F to 35°F
Summer (June to August)
While summer can be warm, it remains less crowded, offering a calm retreat for those visiting in the warmer months.
Average Temperature Daytime: 80°F to 85°F - Nighttime: 60°F to 65°F
Weekly Weather Forecast for Madison County
How to Book Your Madison County Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. 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 Madison County
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals 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
Outdoor Amenities
- Enjoy a spacious outdoor patio, perfect for relaxing and entertaining amidst the scenic landscape.
- Take advantage of a private backyard area with lush greenery and space for outdoor activities.
- Benefit from access to scenic hiking trails nearby, allowing you to explore the natural beauty of the region.
- Relax in a charming porch or veranda that offers picturesque views of the countryside.
- Make use of an outdoor fireplace or fire pit, ideal for cozy evenings under the stars.
- Utilize well-maintained picnic areas equipped for alfresco dining in the fresh air.
- Take a dip in an outdoor swimming pool if available, providing a refreshing retreat during your stay here.
Top Attractions Around Madison County
What attractions are nearby?
While staying here, you'll find a variety of outdoor activities and scenic attractions nearby, allowing you to explore the natural beauty and charming spots of Madison County and its surrounding region.
Family Activities
- Skyline Drive: Embark on a scenic drive through Shenandoah National Park, where you can enjoy breathtaking views and family-friendly hiking trails within the region.
- Local Wineries and Farms: Explore the area’s family-oriented wineries and farms that offer engaging tours and tastings suitable for visitors of all ages.
- Madison County Historical Museum: Discover local history through engaging exhibits and interactive displays that make learning fun for children and adults alike.
- Hiking and Nature Trails: Experience outdoor adventures by exploring numerous trails around here that cater to family outings and nature appreciation.
Adult Activities
- Wine Tasting Tours: Explore the region's renowned wineries and savor local wines that showcase the area's rich viticultural heritage.
- Hiking and Nature Walks: Discover scenic trails through the rolling hills and lush landscapes, perfect for immersing yourself in the natural beauty of the region.
- Historic Landmark Visits: Delve into local history by touring notable sites that highlight the area’s cultural and historical significance.
- Farmers Markets and Artisan Shops: Experience the vibrant local scene by browsing handcrafted goods and fresh produce in nearby markets.
Other Places to Stay in Madison County, VA
Rose River Falls
Wolftown
Madison
Brightwood
Pratts
Big Meadows
Rochelle
Locust Dale
Madison County Travel Tips
How Can You Make the Most of Your Stay?
- Explore local outdoor activities: Take advantage of the area's scenic landscapes and outdoor adventures to fully immerse yourself in the natural beauty of Madison County.
- Visit nearby wineries and farms: Experience the region’s rich agricultural heritage by touring local wineries and farms during your stay.
- Plan your trip around seasonal events: Check the calendar for seasonal festivals and events that showcase the area’s culture and community spirit.
- Choose a well-located vacation rental: Select a property that offers easy access to key attractions and outdoor spots, ensuring a more enjoyable and convenient visit.
Transportation Options
- Madison County Transit: You can rely on local buses to conveniently navigate the area and explore its scenic surroundings.
- Rental Cars: Car rental services offer flexibility for you to discover hidden gems and enjoy the natural beauty of the region at your own pace.
- Taxi Services: Taxis provide quick and direct transportation, making it easy to reach dining, shopping, or outdoor destinations nearby.
- Ride-Sharing Options: Popular ride-sharing platforms are available here, offering an affordable and efficient way to move around the area comfortably.
Local Customs Options
- Southern Hospitality: You can expect warm welcomes and friendly interactions that showcase the area's renowned Southern hospitality during your stay.
Embrace the local culture by experiencing traditional folk music sessions, which are a cherished part of this destination’s community gatherings. - Farmer’s Markets: Engaging with the region's vibrant farmer’s markets provides a glimpse into local produce and artisanal crafts, reflecting the area's agricultural roots.
- Historical Celebrations: Participating in seasonal festivals and historical reenactments allows you to connect with the rich history that shapes the area’s unique identity.
Frequently Asked Questions About Madison County?
1. What are the top vacation rentals in Madison County?
There are a lot of options in Madison County. If you plan on staying in the Madison County area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Madison County:
- Incredible Old Rag and Shenandoah Panoramas from this Lovely, Peaceful Retreat
- Modern Cabin on 30 Private Acres near Old Rag & Shenandoah Nat Park - Fiber Wifi
- New pickel ball court! basketball and putt putt too!
- Spacious, Beautiful, Quiet Home with Amazing Old Rag Views
- Sleeps 6, custom, gorgeous home on 180 acres, amazing views of Old Rag Mountain
- Charming 2-bedroom cottage in lovely Madison with WiFi, AC
- Pop's Place on the Rapidan River.
- Farmhouse close to Wedding venues, Wineries, breweries, shops. Dogs welcome!
- Charming 2-bedroom barn with WiFi, AC in brilliant Etlan, minutes from Old Rag.
- Modern, unique cabin minutes away from Old Rag Mountain
2. Which vacation homes in Madison County are best for families?
If you are looking for a family-friendly vacation home in Madison County, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Madison County:
3. How many Rentbyowner vacation rentals are available in Madison County?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 80 in the Madison County area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Madison County.
4. What is the cancellation policy for vacation rentals in Madison County, Virginia?
Cancellation policies vary by property, so it’s important to review the specific listing details or contact the property owner directly to understand the terms and any applicable fees before booking.
5. Are there any specific check-in and check-out times for vacation rentals in this area?
Check-in and check-out times are determined by each host. Please refer to the individual listing or reach out to the property owner to confirm the schedule for your stay.
6. How do I know if a vacation rental in the region is suitable for my group size and needs?
Each listing provides details about maximum occupancy, amenities, and suitability. Be sure to review these details carefully and contact the property owner if you have additional questions.
7. What should I do if I encounter any issues during my stay at a vacation rental in the area?
In case of problems, contact the property owner or local support team listed on the booking page. Most hosts are eager to assist and ensure your experience is enjoyable.
8. Are pets allowed in vacation rentals around here, and are there any restrictions I should be aware of?
Pet policies vary by property. To avoid surprises, review the listing's pet policy and contact the owner for clarification if needed before confirming your reservation.
Madison County Top Rated Vacation Rentals
Cabin
9.0(387 Reviews)
1 Bedroom
1 Bath
- Spa
- Fireplace/Heating
- Pool
- Balcony/Terrace
R3,306/Night
7 Nights - R23,134
House
5.0(2 Reviews)
1 Bedroom
1 Bath
2 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Internet
R2,247/Night
7 Nights - R15,730
House
4 Bedrooms
6 Baths
12000 ft²
- Hot Tub
- Pool
- Pet Friendly
- Kitchen
R15,488/Night
7 Nights - R108,413
House
1 Bedroom
2 Baths
4 Guests
600 ft²
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
R2,764/Night
7 Nights - R19,351
