Madison vacation rentals

We found 72 vacation rentals — enter your dates for availability

Discover a selection of 22 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.

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Find out more about Madison

Why visit Madison

  • Outdoor Adventures: Enjoy hiking and exploring stunning mountains and captivating waterfalls in Madison's natural beauty.
  • Family-Friendly Atmosphere: Experience a welcoming environment with activities suitable for all ages, perfect for family outings.
  • Amish Craftsmanship: Discover the charm of local Amish craftsmanship while exploring the picturesque neighborhoods.
  • Cozy Accommodations: Choose from cozy cabins and charming cottages that provide comfort and convenience for your stay.
  • Secluded Serenity: Find relaxing vibes in secluded spots, ideal for unwinding and creating lasting memories.

Popular types of accommodation in Madison

Planning a getaway to Madison? The excitement begins with selecting the perfect accommodation. From cozy cabins and houses to charming cottages, there are plenty of options to suit every traveler. Explore available room options and discover house rentals or apartments that fit your needs. Madison rentals offer the ideal blend of comfort and convenience, ensuring an unforgettable stay in this vibrant destination.

  • Cabins: Experience the charm of nature with cozy cabins that are the top choice for travelers seeking a rustic retreat in Madison.
  • Houses: Enjoy spacious and comfortable private homes, ideal for families and groups looking for a home-away-from-home experience.
  • Cottages: Delight in quaint and inviting cottages that provide a perfect blend of comfort and charm for your stay.
  • Apartments: Opt for convenient apartments that offer a modern living space with easy access to local amenities.
  • Condos: Choose stylish condos that combine luxury and comfort, perfect for an upscale vacation experience in Madison.**

Top attractions near Madison

Madison, Virginia, is perfect for outdoor enthusiasts and adventure seekers, offering stunning scenery and a variety of attractions. Visitors can explore beautiful mountains, captivating waterfalls, and historic homes, making it an ideal destination for families and those looking to immerse themselves in nature. Whether you're hiking or enjoying a family outing, Madison has something for everyone to create lasting memories.

  • Old Rag Mountain: A popular destination for outdoor enthusiasts, Old Rag Mountain offers thrilling hiking trails with stunning vistas. The challenging ascent rewards adventurers with breathtaking panoramic views of the Blue Ridge Mountains, making it a perfect spot for nature lovers.
  • Rapidan River: This picturesque river is perfect for a day of relaxation or adventure. Enjoy kayaking or fishing along its scenic banks, or simply take a leisurely stroll to soak in the tranquil surroundings.
  • James Madison's Montpelier: Explore the historic estate of the fourth U.S. President, James Madison. This beautifully preserved plantation provides insight into early American history and culture, with guided tours showcasing its rich heritage.

Things to do recommended for couples

For a romantic getaway in Madison, explore Early Mountain Vineyards for a cozy wine tasting. Just 12 miles away, Sharp Rock Vineyards offers stunning views and a charming atmosphere. Don't miss Honah Lee Vineyard, 15 miles from Madison, perfect for an outdoor escape and delightful drinks.

Things to do recommended for families

Families visiting Madison, Virginia can enjoy a refreshing day at Preddy Creek Trail Park, located 15 miles away. This recreational area offers wellness and relaxation vibes, perfect for family activities like hiking and picnicking amidst nature.

Things to do recommended for groups

Enjoy a day on the greens at Green Hills Golf Course, just 9 miles from Madison. For a unique experience, visit Belmont Farms Distillery, 15 miles away, for tastings with a romantic atmosphere. Don't forget to stop by the Barboursville Gift Gallery, located 14 miles from Madison, for local treasures.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Madison

If you're planning a trip with a group, family, pets, or considering extended stays, be sure to use the appropriate filters to match your needs. Here are some helpful Vrbo booking tips for you.

  • Traveling to Madison with a group: Think about how many bedrooms you'll require, as well as features like a full kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Madison with young kids: Traveling with young kids can be quite a task. It's important to prioritize their comfort and safety, along with suitable amenities like a private pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Madison: For many families, a trip isn’t truly enjoyable without their furry companion. If you can relate, explore Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Madison: If you're in search of vacation rentals that offer great deals for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can easily discover and save on monthly rentals. Don't forget to include additional features in your search, such as parking, a well-equipped kitchen, or a private pool.

Where to stay in and around Madison

Madison, Virginia, offers a perfect blend of outdoor adventure and serene scenery for travelers. Explore the nearby neighborhoods and immerse yourself in the family-friendly atmosphere, where the warmth of friendly locals enhances your experience. Discover the beauty of natural meadows and the charm of Amish craftsmanship as you venture through this picturesque region. With its relaxing vibes and secluded spots, Madison promises a memorable getaway for all vacationers.

  • Pratts: Located a mere 2 miles from Madison, Pratts is a charming city that offers a delightful escape into nature. Known for its stunning scenery, it's the perfect destination for outdoor enthusiasts and couples seeking a romantic getaway. Visitors can enjoy various recreational activities in the nearby national state park and national park, where hiking and picnicking are popular pastimes. The serene lake in the area provides opportunities for fishing and boating, making Pratts a picturesque spot for nature lovers.
  • Graves Mill: Nestled within the Madison area, Graves Mill is a quaint village that promises adventure and scenic beauty. This hidden gem attracts travelers looking for outdoor experiences, including skiing at the nearby ski fields during the winter months. The village is conveniently located near both national and state parks, offering ample opportunities for hiking, wildlife watching, and exploring visitor centers that provide insight into the local ecology and history. Whether you're an avid skier or a nature explorer, Graves Mill has something for everyone.
  • Wolftown: Wolftown, another lovely village near Madison, is celebrated for its blend of outdoor activities and entertainment. This charming community is a fantastic choice for those seeking a romantic getaway or a fun-filled day out. With easy access to recreational areas, visitors can enjoy hiking and biking trails that wind through the scenic landscape. Additionally, the proximity to a national state park and other fascinating museums offers a unique cultural experience, ensuring that your visit to Wolftown is both relaxing and enriching.

Best time to go to Madison

If you're planning a trip to Madison, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April to May and September, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January34.5°F (1.4°C)Light RainMostly SunnySlightly LowSlightly Low
February38.1°F (3.4°C)Light RainMostly SunnyAverageSlightly Low
March45.3°F (7.4°C)Light RainMostly SunnyAverageSlightly Low
April55.8°F (13.2°C)Light RainMostly SunnySlightly HighAverage
May64.9°F (18.3°C)Light RainMostly SunnySlightly HighAverage
June73.2°F (22.9°C)Light RainMostly SunnyAverageSlightly High
July77.9°F (25.5°C)Light RainMostly SunnyAverageSlightly High
August75.6°F (24.2°C)Light RainMostly SunnyAverageSlightly High
September69.3°F (20.7°C)Light RainMostly SunnySlightly HighAverage
October58.3°F (14.6°C)Light RainMostly SunnyAverageAverage
November46.2°F (7.9°C)Light RainMostly SunnySlightly LowAverage
December39.6°F (4.2°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is a breeze

Are you hoping to save money on your upcoming trip? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, consider booking a longer stay, as this can lead to substantial savings. To discover a Vrbo property that aligns with your budget, utilize our filters to narrow down options by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a user-friendly area where you can easily create new trips, continue from where you last left off, or manage your travel plans. You can find your saved or booked properties neatly organized under Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

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)
  • Wisteria Farm and Vineyard (17.8 mi / 28.6 km)
  • Stone Mountain Vineyards (19.1 mi / 30.7 km)
  • Old House Vineyards (20 mi / 32.2 km)
  • Keswick Vineyards and Winery (20.9 mi / 33.6 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:

  • Shenandoah National Park (13.6 mi / 21.9 km)
  • Old Rag Mountain (12.3 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)
  • Stony Man (16.3 mi / 26.3 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, Virginia, United States of America when booking a vacation rental?
When considering a vacation rental in Madison, Virginia, the area around the charming downtown offers a delightful mix of comfort and convenience. This neighborhood is known for its historic atmosphere and is close to some of the town's top attractions, including the beautiful Shenandoah National Park, which provides stunning views and outdoor activities, great for nature enthusiasts. Another highlight is the local wineries and vineyards that dot the landscape, offering tastings and scenic tours that showcase the region's rich agricultural heritage.

Additionally, the downtown area features a selection of properties that cater to various tastes and budgets, making it a versatile option for visitors. You'll find a warm and welcoming community vibe here, with easy access to local shops and eateries.
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 traveling 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. To get the best value, book early and take advantage of Vrbo's free rewards program.
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.
Where are the best Madison ski resort rentals?
For ski resort rentals near Madison, Virginia, travelers should consider the nearby Wintergreen Resort, located about 30 miles away in the Blue Ridge Mountains. This area offers a variety of vacation rentals, including cozy cabins and townhomes that cater to different group sizes. Many of these properties come equipped with modern amenities such as fully equipped kitchens, spacious living areas, and sometimes even fireplaces, providing a warm and welcoming atmosphere after a day on the slopes.

Within the Wintergreen Resort area, visitors can find ski-in/ski-out options that allow for quick access to the ski lifts and slopes. These rentals often feature additional amenities like hot tubs, outdoor decks with stunning mountain views, and access to resort facilities including a spa and dining options.

Furthermore, the surrounding Nelson County offers charming rural cottages and lodges that provide a rustic experience, often with picturesque views of the mountains and valleys. These accommodations are superb for those looking to combine skiing with a peaceful retreat in nature. The region also boasts hiking trails and opportunities for other outdoor activities, making it a well-rounded destination for winter sports enthusiasts.
What is the most popular type of vacation rental accomodation in Madison?
In Madison, Virginia, vacation houses are the most popular type of rental accommodation, with about 19 available throughout the area. These homes often feature spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor spaces superb for enjoying the beautiful Virginia countryside. Additionally, there are several cottages, apartments, and cabins available, each offering unique amenities that cater to different preferences. Cottages typically provide a cozy atmosphere, while cabins may offer a more rustic experience, often located closer to nature.
Are there any family house rentals in Madison?
In Madison, Virginia, families will find a variety of house rentals—about 22 options available throughout the area. This charming locale is surrounded by beautiful countryside and offers a peaceful retreat for visitors. Many of these homes feature spacious living areas, fully equipped kitchens for preparing meals together, and outdoor spaces where children can safely play and explore. Amenities like air conditioning and Wi-Fi ensure a comfortable stay, making it ideal for families.

Additionally, the area is close to attractions such as the scenic Blue Ridge Mountains and various hiking trails, providing ample opportunities for outdoor activities.
Can I rent a vacation home with a pool or hot tub in Madison?
In Madison, Virginia, there are several vacation homes available for rent that feature pools and hot tubs. This charming town, located in the foothills of the Blue Ridge Mountains, offers a peaceful retreat for travelers. Many of the properties with pools and hot tubs come equipped with spacious outdoor areas, great for relaxation and family gatherings, as well as amenities like fully equipped kitchens and cozy living spaces.

The picturesque surroundings provide opportunities for outdoor activities, and the area's wineries and scenic views add to the appeal.
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. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Madison?
In Madison, Virginia, travelers can find a variety of pet-friendly house rentals, with around 17 options available. Many of these homes offer spacious layouts, fully equipped kitchens, and outdoor spaces, making them ideal for families and groups traveling with pets. The properties often feature amenities such as fenced yards, decks, and cozy living areas, ensuring a comfortable stay for both humans and their furry companions.

The scenic countryside surrounding Madison provides plenty of opportunities for outdoor activities, including hiking and exploring the natural beauty of the area. Nearby parks and trails are superb for pet owners looking to enjoy nature while spending quality time with their pets.
Are there any remote work vacation rentals in Madison?
In Madison, Virginia, there are several remote work vacation rentals available, with around 26 options to choose from. Travelers can expect properties equipped with essential amenities for a productive stay, including free Wi-Fi, dedicated workspaces with desk chairs, and comfortable living areas that allow for a pleasant work-life balance. Many rentals also feature cozy interiors and outdoor spaces, making them ideal for unwinding after a day of work.

The scenic backdrop of Madison, with its rolling hills and proximity to attractions like the Shenandoah National Park, provides a serene environment for remote work while allowing easy access to nature and local culture during downtime. 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 travelers 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, popular vacation rental amenities include fully equipped kitchens, allowing guests to prepare their own meals during their stay. Many properties feature decks or patios, superb for enjoying the peaceful surroundings and fresh air. Coffee and tea makers are commonly found in rentals, providing a convenient way to enjoy warm beverages at any time. Onsite parking is also a standard amenity, making it easier for travelers to arrive and explore the area. Additionally, several rentals come with cozy fireplaces, adding a warm and inviting atmosphere, especially during cooler months.
When is the best time to visit Madison for a vacation rental?
April marks the beginning of the peak season in Madison, Virginia, drawing travelers looking to immerse themselves in the region's natural beauty and rich history. From April to June, visitors can enjoy the vibrant spring blooms, making it an ideal time for outdoor activities such as hiking and exploring the scenic landscapes of the Blue Ridge Mountains.

April typically brings mild temperatures, ranging from the low 40s to the upper 60s Fahrenheit, offering comfortable conditions for sightseeing and leisurely strolls through the charming local parks. This is also when the area comes alive with various festivals and events, providing cultural experiences that enhance any visit.

For those seeking a more budget-friendly option, consider visiting in December. While this month is quieter, it presents a unique opportunity to enjoy the peaceful atmosphere and cozy charm of Madison during the winter season. Delightful local shops and eateries offer a warm respite from the cold, making it a wonderful time to relax and recharge.

Ultimately, the best time to visit Madison for a vacation rental depends on your preferences—whether you want to join the lively peak season festivities or enjoy a tranquil getaway in the serene winter months.
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.
What are the top attractions in Madison, Virginia, United States of America?
In Madison, Virginia, visitors can explore a range of attractions that highlight the area's natural beauty and historical significance. The town is surrounded by the picturesque landscapes of the Blue Ridge Mountains, making it ideal for outdoor enthusiasts. Nearby, Shenandoah National Park offers stunning hiking trails, scenic drives along Skyline Drive, and opportunities for wildlife viewing.

The historic Madison Courthouse, located in the town center, is worth a visit for those interested in local history and architecture. Additionally, the nearby Graves Mountain Lodge provides a rustic retreat with access to hiking, fishing, and seasonal events.

For a charming local experience, the town hosts various festivals throughout the year, celebrating its agricultural heritage and community spirit.
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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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