Photo by Phil Martin

Madison vacation rentals

We found 66 vacation rentals — enter your dates for availability

Discover a selection of 18 homes and other vacation rentals in Madison that are perfect for your trip. Whether you're staying in a vacation rental with friends, family, or just with your pet, you'll find the best amenities for hanging out with the people that matter most, including WiFi and parking. You'll be able to choose a rental for everyone's needs, including places that are non-smoking or accessible.

Vacation rentals with weekly discounts - Madison

Showing deals for:Nov 21 - Nov 28

Image gallery for Charming 2-bedroom cottage in lovely Madison with WiFi, AC

Living area
10 out of 10 rating
Exceptional
(7 reviews)

Charming 2-bedroom cottage in lovely Madison with WiFi, AC

Madison, VA

10% off
Price is CA $209
CA $1,909 total
includes taxes & fees
Charming 2-bedroom cottage in lovely Madison with WiFi, AC

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

Find out more about Madison

Find out more about Madison

Why people love visiting rustic Madison

Enjoy the history and other features of Madison. This relaxing and scenic city entices travelers with its hiking and mountain views. A vacation rental can help make your stay complete. Many rentals come with a full kitchen and laundry facilities.

Activities and attractions in and around Madison

Are you hoping to find things to do in the area? Venture out of your cozy vacation rental and check out everything that makes Madison a fun spot to vacation. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Early Mountain Vineyards (3.5 mi / 5.6 km)
  • Barboursville Vineyards (15.3 mi / 24.6 km)
  • Stone Mountain Vineyards (19.1 mi / 30.7 km)
  • Castle Hill Cider (20.1 mi / 32.4 km)
  • Keswick Vineyards and Winery (20.9 mi / 33.6 km)
  • Glass House Winery (21.3 mi / 34.3 km)

Exploring the natural landscape of Madison

Whether you're an active traveler or just want to appreciate the scenery, Madison is a great place to get out in nature. These are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city center:

  • Luray Caverns (23.1 mi / 37.2 km)
  • Shenandoah National Park (23.7 mi / 38.1 km)
  • Old Rag Mountain (12.2 mi / 19.7 km)
  • Dark Hollow Falls (13.1 mi / 21.1 km)
  • Rose River Falls (13.3 mi / 21.3 km)
  • Swift Run Gap Entrance Shenandoah (15.7 mi / 25.2 km)

How to get to and around Madison

Fly into Charlottesville-Albemarle Airport (CHO), the closest airport, located 19.5 mi (31.5 km) from the city center. If you can't find a flight that's convenient for your trip, you can also fly into Weyers Cave, VA (SHD-Shenandoah Valley Regional), which is 35.7 mi (57.5 km) away.

Frequently asked questions

What is the best area to stay in Madison when booking a vacation rental?
When planning a vacation rental in Madison, Virginia, one of the best areas to consider is the picturesque downtown district. This charming neighbourhood is not only centrally located, making it convenient for exploring the town, but it also boasts a delightful array of shops, cafes, and restaurants. Staying here puts you within easy reach of the Madison County Courthouse, a beautiful historic building that reflects the area's rich heritage. Additionally, the nearby Graves Mountain Lodge offers lovely hiking trails and stunning views of the Blue Ridge Mountains, great for outdoor enthusiasts.
How much does it cost to rent a vacation home in Madison?
Prices for vacation rentals in Madison vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Madison to more spacious homes.
Are there any discounts for Madison vacation house rentals?
You can find great discounts on house rentals in Madison on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of vacation rental accomodation in Madison?
In Madison, vacation houses are the most popular type of rental, with about 16 available throughout the area. These houses typically offer spacious living arrangements, multiple bedrooms, fully equipped kitchens, and outdoor spaces for relaxation, making them ideal for families or larger groups. Additionally, there are several cottages, apartments, and cabins that provide charming alternatives for travellers looking for a more rustic or intimate experience. Many of these rentals are set in picturesque surroundings, allowing guests to enjoy the natural beauty of Virginia while having all the comforts of home.
Are there any family house rentals in Madison?
In Madison, Virginia, there are plenty of family house rentals available, with around 20 options to choose from. The area is known for its picturesque countryside and charming small-town atmosphere, making it an ideal spot for families seeking a peaceful getaway. Many of these homes feature spacious living areas, fully equipped kitchens for home-cooked meals, and outdoor spaces where children can enjoy themselves.
Can I rent a vacation home with a pool or hot tub in Madison?
In Madison, Virginia, several vacation homes are available for rent that feature pools and hot tubs, providing a refreshing option for relaxation during your stay. The area is known for its picturesque landscapes and charming rural setting, making it an ideal retreat. Many of these rentals come equipped with amenities such as spacious outdoor areas, fully equipped kitchens, and comfortable living spaces, ensuring a convenient and enjoyable experience for travellers.
Can I find long-stay vacation rentals in Madison?
A long-stay vacation rental in Madison is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Madison?
In Madison, Virginia, there are several pet-friendly house rentals available, providing a welcoming environment for travellers with furry companions. Many of these properties come equipped with amenities such as spacious yards, fully equipped kitchens, and comfortable living areas, ensuring a pleasant stay for families and groups. The area is known for its scenic beauty, with nearby attractions offering opportunities for outdoor activities, making it ideal for those who enjoy nature alongside their pets.
Are there any remote work vacation rentals in Madison?
In Madison, Virginia, there are numerous remote work vacation rentals available, with around 22 options to choose from. This quaint town, set against the backdrop of the beautiful Blue Ridge Mountains, provides an ideal setting for those looking to blend work and leisure. Many of these properties come equipped with essential amenities for remote work, including desks, Wi-Fi, computer monitors, and comfortable office chairs, ensuring a productive environment. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Madison vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Madison with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Madison?
In Madison, Virginia, popular vacation rentals typically feature essential amenities that cater to travellers' needs. Most properties come equipped with kitchens, allowing guests to prepare their own meals, alongside microwaves and refrigerators for convenient food storage and heating. Additionally, many rentals include stovetops for cooking, making them ideal for those who prefer a self-catering experience.
When is the best time to visit Madison for a vacation rental?
April is the most popular time to visit Madison, Virginia, as the landscape comes alive with vibrant blooms and pleasant weather, greatly suited for outdoor exploration. The peak season stretches from April to June, attracting nature enthusiasts and those eager to immerse themselves in the area's rich history and scenic beauty.

During these spring months, you can enjoy comfortable daytime temperatures averaging in the low to mid-teens Celsius, ideal for hiking the picturesque trails of the nearby Blue Ridge Mountains or exploring the charming local wineries. The vibrant atmosphere of Madison in spring is complemented by community events and festivals that showcase the region's culture.

For those looking for a more budget-friendly option, December presents an opportunity to experience Madison's tranquillity, as the crowds dissipate and you can enjoy the serene winter landscape. The crisp air adds a refreshing quality to outdoor activities like walking and birdwatching.
How early should I book a Madison vacation rental?
Book your Madison vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Madison home rental booking on Vrbo?
To find Madison vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Madison vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
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