Best Vacation Homes in Madison
Cottage
10.0(42 Reviews)
2 Bedrooms
1 Bath
5 Guests
1300 ft²
Fireplace/Heating
Balcony/Terrace
Pet Friendly
Kitchen
£98/Night
7 Nights - £685
House
10.0(10 Reviews)
3 Bedrooms
2 Baths
6 Guests
1496.18 ft²
- Fireplace/Heating
- Balcony/Terrace
View- Pet Friendly
£206/Night
7 Nights - £1,441
£213/Night
7 Nights - £1,492
House
10.0(21 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
Air Conditioner
Child Friendly
Bedding/Linens
£124/Night
7 Nights - £866
House
9.9(12 Reviews)
1 Bedroom
1 Bath
4 Guests
645.83 ft²
- Fireplace/Heating
- View
Breakfast- Pet Friendly
£92/Night
7 Nights - £642
Cottage
10.0(17 Reviews)
2 Bedrooms
2 Baths
7 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
£147/Night
7 Nights - £1,031
House
10.0(12 Reviews)
1 Bedroom
1 Bath
4 Guests
800 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
Parking
£206/Night
7 Nights - £1,442
Apartment
10.0(3 Reviews)
1 Bedroom
1 Bath
4 Guests
800 ft²
Hot Tub- Fireplace/Heating
Pool- Balcony/Terrace
£107/Night
7 Nights - £752
Madison Luxury Rentals
House
10.0(2 Reviews)
4 Bedrooms
2 Baths
3500 ft²
- Hot Tub
- Fireplace/Heating
Ocean View- Balcony/Terrace
£7,187/Night
7 Nights - £50,308
House
10.0(1 Review)
6 Bedrooms
4 Baths
16 Guests
4413 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
£716/Night
7 Nights - £5,009
House
10.0(33 Reviews)
7 Bedrooms
4 Baths
14 Guests
3500 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
£526/Night
7 Nights - £3,683
Other
10.0(7 Reviews)
6 Bedrooms
3 Baths
12 Guests
3700 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
£467/Night
7 Nights - £3,268
House
10.0(2 Reviews)
5 Bedrooms
3 Baths
14 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
£432/Night
7 Nights - £3,025
Apartment
9.0(4 Reviews)
5 Bedrooms
3 Baths
12 Guests
- Hot Tub
- Fireplace/Heating
- Pet Friendly
- Kitchen
£426/Night
7 Nights - £2,979
Other
4 Bedrooms
4 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
£351/Night
7 Nights - £2,457
£347/Night
7 Nights - £2,426
Madison Pet Friendly Vacation Rentals
Cabin
9.8(54 Reviews)
2 Bedrooms
1 Bath
4 Guests
680 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
£175/Night
7 Nights - £1,224
House
9.6(77 Reviews)
1 Bedroom
2 Baths
4 Guests
904.17 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Pet Friendly
£115/Night
7 Nights - £808
House
9.8(17 Reviews)
1 Bedroom
1 Bath
4 Guests
1400 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
£144/Night
7 Nights - £1,008
Villa
5 Bedrooms
3 Baths
12 Guests
10763.91 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- View
£324/Night
7 Nights - £2,266
House
9.8(7 Reviews)
2 Bedrooms
2 Baths
5 Guests
944 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
£115/Night
7 Nights - £806
House
9.8(6 Reviews)
2 Bedrooms
1 Bath
6 Guests
1100 ft²
Spa- Fireplace/Heating
- Balcony/Terrace
- Breakfast
£141/Night
7 Nights - £989
New
House
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
£109/Night
7 Nights - £761
House
10.0(33 Reviews)
3 Bedrooms
2 Baths
10 Guests
1786 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
£146/Night
7 Nights - £1,021
Madison Large Vacation Homes
House
10.0(1 Review)
4 Bedrooms
3 Baths
10 Guests
3172 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
£250/Night
7 Nights - £1,753
House
9.6(36 Reviews)
3 Bedrooms
2 Baths
10 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
£156/Night
7 Nights - £1,092
House
4 Bedrooms
4 Baths
10 Guests
3692 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
Internet
£319/Night
7 Nights - £2,234
Why Choose Rent By Owner for your Madison 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
When should you plan your Vacation Rentals stay?
Choosing the right time to visit here can ensure you enjoy the region's most favorable weather and local events, making your stay in Madison, Virginia, USA, truly memorable.
Peak Season Highlights
Spring (March to May)
During the spring months, you can enjoy the region's lush landscapes and pleasant weather, making it an ideal time for outdoor activities and sightseeing in Madison.
Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F
Fall (September to November)
The fall season offers vibrant foliage and crisp air, perfect for exploring the area's scenic beauty and enjoying outdoor adventures with comfortable temperatures.
Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F
Off-Season Highlights
Winter (December to February)
In winter, the area tends to be quieter, providing a peaceful getaway amid cooler temperatures that encourage cozy stays at your chosen vacation rental.
Average Temperature Daytime: 40°F to 50°F - Nighttime: 25°F to 35°F
Summer (June to August)
While summer is lively here, it also marks the off-peak period when fewer visitors are around, offering more relaxed access to local attractions and accommodations.
Average Temperature Daytime: 80°F to 90°F - Nighttime: 60°F to 70°F
Weekly Weather Forecast for Madison
How to Book Your Madison 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
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 private outdoor swimming pool to refresh during warm summer days.
- Relax in your own hot tub or spa area, perfect for unwinding after outdoor adventures.
- Take advantage of furnished patios or decks for outdoor dining and gatherings.
- Explore scenic walking trails or nature paths accessible from the property grounds.
- Utilize outdoor grilling facilities to host barbecues and cookouts with friends or family.
- Benefit from spacious yards ideal for outdoor games and activities.
- Admire picturesque views of the surrounding landscape from outdoor seating areas.
Top Attractions Around Madison
What attractions are nearby?
In this charming region, you can enjoy a variety of outdoor activities such as nature walks, local wineries, and scenic views that showcase the area's natural beauty during your stay.
Family Activities
- Madison County Heritage Tour: Discover the region's history with your family through engaging exhibits and historic sites nestled in this charming area.
- Lake Caroline Activities: Enjoy a variety of outdoor fun at the local lake, including fishing, paddle boating, and swimming, perfect for a family day out.
- Hiking at the Blue Ridge Mountain Trails: Explore scenic trails suitable for all ages, offering breathtaking views and a chance to connect with nature here.
- Local Farmers Markets: Experience the region's fresh produce and handcrafted goods while supporting local vendors during your family visit.
Adult Activities
- Wine Tasting Tours: Explore the region’s renowned wineries and enjoy tastings that showcase local varietals, perfect for relaxed adult outings in Madison.
- Northern Virginia Breweries: Visit some of the area's craft breweries to sample unique local brews and learn about the vibrant brewing culture here.
- Historical Sites and Museums: Discover stories of the region's past through well-preserved historic sites and engaging museums that offer an enriching cultural experience.
- Scenic Drives and Nature Walks: Take in the region’s beautiful landscapes on scenic drives or tranquil nature walks, ideal for unwinding during your stay.
Other Places to Stay in Madison, VA
Wolftown
Graves Mill
Early Mountain Vineyards
Madison County
Sweely Estate Winery
Pratts
Madison Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Cuisine: Discover the area's culinary delights by visiting local restaurants and markets to enjoy authentic flavors that highlight regional specialties.
- Engage with Nature: Take advantage of outdoor activities such as hiking or leisurely walks in nearby parks to immerse yourself in the natural beauty of this destination.
- Plan Ahead for Attractions: Prioritize popular sites and plan your visits early to maximize your time and avoid missing out on must-see experiences in the region.
- Connect with Local Events: Check the calendar for community events and festivals to gain a deeper understanding of the local culture during your stay here.
Transportation Options
- Car Rentals: Exploring the area by car offers flexibility and convenience, allowing you to visit nearby attractions with ease during your stay.
- Public Transit: Local bus services provide an economical way to navigate here, connecting key points within the region without the need for personal transportation.
- Taxis and Rideshare Services: Taxis or rideshare options like Uber and Lyft offer quick and hassle-free travel around this destination, perfect for short trips or spontaneous plans.
- Bike Rentals: Renting bikes allows you to enjoy scenic routes and explore the area's charm at a leisurely pace, ideal for outdoor enthusiasts.
Local Customs Options
- Southern Hospitality: Visitors often notice the warm and welcoming attitude that characterizes locals here, reflecting the region’s friendly and inviting nature.
- Engaging with local farmers and understanding traditional farming practices offers insight into the area's rich agricultural history.
- Historic Preservation: Respecting and maintaining historic sites and architecture is a common custom that reflects pride in this destination's heritage.
- Participating in local events and festivals helps you connect with residents and experience the area’s close-knit community spirit.
Frequently Asked Questions About Madison?
1. What are the top vacation rentals in Madison?
There are a lot of options in Madison. If you plan on staying in the Madison 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:
- Robinson River Roost - Country cottage near Shenandoah NP
- Beautiful home with mountain and river views.
- Robinson River Retreat - Near River, SNP & Graves
- Barn Apartment on Farm Near Old Rag and Shenandoah National Park
- Charming 2-bedroom cottage in lovely Madison with WiFi, AC
- Farmhouse close to Wedding venues, Wineries, breweries, shops. Dogs welcome!
- Historic Madison Eagle Inn
- Farm living at it's best!
- Mountains, cows & serenity. Great for celebrations, birthdays & family events
- The Apartment at Dark Run Retreat
2. Which vacation homes in Madison are best for families?
If you are looking for a family-friendly vacation home in Madison, 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:
3. How many Rentbyowner vacation rentals are available in Madison?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 55 in the Madison 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.
4. What is the cancellation policy for vacation rentals in Madison, Virginia?
Cancellation policies vary by property; you should review the specific listing details or contact the owner directly to understand the options and any applicable fees for cancellations.
5. How do I confirm my booking at a vacation rental in Madison, Virginia?
Once you select your preferred property and complete the reservation process, you will receive a confirmation email with all the necessary details. For additional assistance, contacting the property owner is recommended.
6. Are there any amenities or facilities included with vacation rentals in this area?
Amenities depend on the individual property; it's best to check the listing description for details on features such as Wi-Fi, kitchens, outdoor spaces, and other amenities before booking.
7. What should I know about check-in and check-out times for vacation rentals in Madison, Virginia?
Check-in and check-out times are specified in each listing. You may need to communicate directly with the property owner for any special requests or adjustments to the standard times.
8. Is it possible to modify or cancel my reservation after booking a vacation rental here?
Modifications and cancellations are subject to the property's policies. Review the specific listing for terms or contact the owner directly to discuss any changes to your reservation.
Madison Top Rated Vacation Rentals
Apartment
10.0(3 Reviews)
1 Bedroom
1 Bath
2 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
£69/Night
7 Nights - £485
House
5.0(2 Reviews)
1 Bedroom
1 Bath
2 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Internet
£104/Night
7 Nights - £726
