Best Vacation Homes in Madison County
2200 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
R5,352/Night
For 7 Nights R37,467
1496.18 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- View
R4,600/Night
For 7 Nights R32,200
R2,188/Night
For 7 Nights R15,317
1100 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Cabin
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
R4,746/Night
For 7 Nights R33,217
398.26 ft²
4 Guests
1 Bedroom
1 Bathroom
Free Cancellation
House
- Fireplace/Heating
- Parking
- Air Conditioner
R3,833/Night
For 7 Nights R26,834
7 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Cottage
- Fireplace/Heating
- Pet Friendly
- Kitchen
R3,144/Night
For 7 Nights R22,000
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
R1,802/Night
For 7 Nights R12,617
800 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
R4,602/Night
For 7 Nights R32,217
Madison County Luxury Rentals
30 Guests
8 Bedrooms
9 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
R33,696/Night
For 7 Nights R235,869
4400 ft²
16 Guests
6 Bedrooms
4 Bathrooms
Family Friendly
Cabin
- Fireplace/Heating
- Pool
- Balcony/Terrace
R14,404/Night
For 7 Nights R100,818
4000 ft²
12 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
R11,995/Night
For 7 Nights R83,968
3500 ft²
4 Bedrooms
2 Bathrooms
Ocean View
Other
- Hot Tub
- Fireplace/Heating
- Ocean View
R11,238/Night
For 7 Nights R78,668
14 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
R9,916/Night
For 7 Nights R69,417
3000 ft²
10 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
R7,952/Night
For 7 Nights R55,667
14 Guests
5 Bedrooms
5 Bathrooms
Pet Friendly
House
- Fireplace/Heating
- Pet Friendly
- Internet
R7,936/Night
For 7 Nights R55,551
2500 ft²
8 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
R7,721/Night
For 7 Nights R54,051
Madison County Pet Friendly Vacation Rentals
1289 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
R3,424/Night
For 7 Nights R23,967
1200.43 ft²
143 Guests
71 Bedrooms
29 Bathrooms
Free Cancellation
Cabin
- Oceanfront
- Fireplace/Heating
- Pool
R1,733/Night
For 7 Nights R12,133
2 Guests
1 Bedroom
1 Bathroom
Couples Retreat
Apartment
- Balcony/Terrace
- Pet Friendly
- Internet
R5,056/Night
For 7 Nights R35,384
2002.09 ft²
8 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Parking
R5,372/Night
For 7 Nights R37,600
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
R3,394/Night
For 7 Nights R23,750
680 ft²
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
Cabin
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R4,826/Night
For 7 Nights R33,784
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
R3,053/Night
For 7 Nights R21,367
1100 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Spa
- Fireplace/Heating
- Balcony/Terrace
R3,066/Night
For 7 Nights R21,467
Madison County Large Vacation Homes
3172 ft²
10 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
R5,595/Night
For 7 Nights R39,167
10 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
Cabin
- Private Pool
- Fireplace/Heating
- Pool
R15,314/Night
For 7 Nights R107,201
4000 ft²
18 Guests
6 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Hot Tub
- Spa
R12,102/Night
For 7 Nights R84,718
1900 ft²
11 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Cottage
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
R4,817/Night
For 7 Nights R33,717
13993 ft²
24 Guests
10 Bedrooms
11 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
R26,983/Night
For 7 Nights R188,885
13 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
R4,826/Night
For 7 Nights R33,784
1200 ft²
10 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
R3,333/Night
For 7 Nights R23,334
3161 ft²
10 Guests
3 Bedrooms
4 Bathrooms
Family Friendly
House
- Balcony/Terrace
- Kitchen
- Air Conditioner
R6,750/Night
For 7 Nights R47,251
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 Mountain Cabin - 30 Private Acres near Old Rag & the Heart of Shenandoah
- Modern Cabin on Old Rag - Dog-Friendly!
- 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
- Farmhouse close to Wedding venues, Wineries, breweries, shops. Dogs welcome!
- Pop's Place on the Rapidan River.
- Historic Madison Eagle Inn
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
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Pool
- Balcony/Terrace
- Kitchen
R2,317/Night
For 7 Nights R16,217
12000 ft²
4 Bedrooms
6 Bathrooms
Family Friendly
House
- Hot Tub
- Pool
- Pet Friendly
R15,967/Night
For 7 Nights R111,768
600 ft²
4 Guests
1 Bedroom
2 Bathrooms
Family Friendly
House
- Pool
- Balcony/Terrace
- Kitchen
R2,850/Night
For 7 Nights R19,950
