Madison holiday homes

We found 73 holiday rentals — enter your dates for availability
Discover a selection of 23 homes and other holiday rentals in Madison that are perfect for your trip. Whether you're staying in a holiday rental with friends, family or even just your pets, you'll find the best amenities for hanging out with the people that matter most, including air conditioning and Wi-Fi. You'll be able to choose a property to rent that has what everyone needs, including places that are non-smoking or accessible.

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Why people love visiting rustic Madison

Enjoy the history and other features of Madison. This relaxing and scenic city entices travellers with its hiking and mountain views. A holiday 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 attractions to visit while you're in town? Venture out of your holiday home and check out everything that makes Madison a fun place to get away to. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • 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)
  • Old House Vineyards (20 mi / 32.2 km)
  • Castle Hill Cider (20.1 mi / 32.4 km)
  • Keswick Vineyards and Winery (20.9 mi / 33.6 km)

Exploring the natural landscape of Madison

Whether you're an active traveller or just want to appreciate the scenery, Madison is a great place to get outside. Here are a few of the area's most stunning sights, all within 30 miles (48.2 km) of the city centre:

  • Shenandoah National Park (13.6 mi / 21.9 km)
  • Luray Caverns (23.1 mi / 37.2 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)

How to get to and around Madison

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

Frequently asked questions

Where are the best Madison ski resort rentals?
For skiing near Madison, Virginia, the closest ski resort is located at Massanutten, which is approximately a one-hour drive from the town. Visitors looking for ski resort rentals should consider options in the Massanutten area, where a variety of accommodations are available. Many of the properties here are ski-in/ski-out condos or cabins that offer direct access to the slopes, great for avid skiers and snowboarders.These rentals typically feature amenities such as fully equipped kitchens, fireplaces for a cosy atmosphere after a day on the mountain, and access to communal facilities like hot tubs and pools. Additionally, some properties offer stunning mountain views and outdoor spaces for enjoying the fresh air.In the nearby towns of McGaheysville and Elkton, travellers can find charming lodges and holiday homes that provide a more secluded experience while still being conveniently located for easy access to the ski resort. These accommodations often include modern conveniences such as Wi-Fi, laundry facilities, and spacious living areas, making them suitable for families or groups looking to enjoy both skiing and the local scenery.Beyond the slopes, the region is rich in outdoor activities, including hiking trails and nature parks, allowing guests to explore the beautiful landscapes of the Shenandoah Valley.
What is the most popular type of holiday rental accomodation in Madison?
In Madison, holiday houses are the most popular type of holiday rental, with about 57 available in the area. These properties typically provide ample space, featuring multiple bedrooms, fully equipped kitchens, and spacious living areas, making them ideal for families or groups. Many also include outdoor spaces such as decks or gardens, superb for relaxing after a day of exploring the local countryside. Additionally, there are around 12 charming cottages available, which offer a cozier atmosphere and often come with unique character and rustic decor. A few apartments and cabins can also be found, providing diverse options for travellers seeking different experiences.
Are there any family house rentals in Madison?
In Madison, Virginia, there are numerous family-friendly house rentals available, with around 22 options to choose from. This charming area offers a blend of natural beauty and small-town charm, making it an ideal destination for families seeking a getaway. Many of these properties feature spacious living areas, fully equipped kitchens superb for preparing family meals, and outdoor spaces where children can play safely.Visitors can enjoy the local scenery, with nearby attractions such as Shenandoah National Park, which provides a wealth of hiking trails and stunning vistas. Additionally, the historic sites in the vicinity offer insight into the region's rich past.
Can I rent a holiday home with a pool or hot tub in Madison?
In Madison, Virginia, there are several holiday homes available for rent that feature pools and hot tubs. This picturesque area, located in the foothills of the Blue Ridge Mountains, provides a tranquil setting for a relaxing getaway. Many of these properties come with amenities such as private pools, outdoor patios, and hot tubs, superb for unwinding after a day of exploring the local countryside.Travellers can expect well-equipped kitchens for self-catering, along with spacious living areas that are ideal for family gatherings or group retreats. The serene surroundings offer opportunities for outdoor activities, including hiking in the nearby mountains and enjoying the scenic beauty of Virginia's wine country.
Are there pet-friendly house rentals in Madison?
In Madison, Virginia, there are several pet-friendly house rentals available, with a total of 17 options for travellers seeking a comfortable stay. Many of these rentals feature spacious layouts, fully equipped kitchens, and outdoor spaces, making them ideal for families or groups travelling with pets. You can expect amenities such as fenced yards, barbecue grills, and sometimes even fire pits, allowing for enjoyable evenings outdoors.The area surrounding Madison is rich in natural beauty, with opportunities for hiking and exploring the countryside. Nearby attractions like the Shenandoah National Park offer trails that are suitable for pets, and the picturesque landscapes provide a tranquil setting for your holiday.
Are there any remote work holiday rentals in Madison?
In Madison, Virginia, there is a good selection of remote work holiday rentals, with around 78 options available. This charming area offers a peaceful environment ideal for those looking to combine work and relaxation. Many of the properties come equipped with essential amenities for remote work, such as high-speed Wi-Fi and designated workspaces, ensuring a productive stay.Travellers can expect to find comfortable living spaces featuring modern conveniences like fully equipped kitchens, which are superb for preparing meals during longer stays. Additionally, many rentals offer outdoor areas where guests can unwind after a day's work, taking in the scenic beauty of the surrounding countryside.The town itself is surrounded by picturesque landscapes and offers access to local attractions, including the nearby Shenandoah National Park, superb for outdoor enthusiasts. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Madison?
In Madison, Virginia, popular rental amenities include well-equipped kitchens, allowing guests to prepare their own meals during their stay. Many properties also feature decks or patios, providing lovely outdoor spaces to relax and enjoy the surrounding countryside. For those who appreciate a warm beverage, coffee and tea makers are commonly available in the rentals. Onsite parking is another convenient amenity, ensuring that guests have easy access to their vehicles. Additionally, many rentals come with fireplaces, adding a cosy touch to the accommodations, particularly during the cooler months.
When is the best time to visit Madison for a holiday rental?
April marks the beginning of the peak travel season in Madison, Virginia, drawing visitors eager to immerse themselves in the area's rich history and stunning natural scenery. From April through June, the region comes alive with vibrant blooms and outdoor activities, making it an ideal time for those looking to explore the picturesque landscapes and local attractions.During April, temperatures are typically mild, ranging from 5 to 20 degrees Celsius, providing a comfortable climate for sightseeing and outdoor adventures. Springtime in Madison is particularly lovely, as the gardens and vineyards awaken, offering opportunities for leisurely strolls and wine tastings in the nearby wineries.For those seeking a more budget-friendly experience, December is a wonderful time to visit. While it's considered the low season, the charm of Madison during the winter months is enchanting. You can enjoy a quieter atmosphere, cosy accommodations, and the festive spirit of the holiday season, all while finding great deals on holiday rentals.Ultimately, the best time to visit Madison for a holiday rental depends on your preferences. If you crave the buzz of spring and summer activities, April through June is perfect. However, if you prefer a peaceful retreat with seasonal charm, then December is an excellent choice.
What are the top attractions in Madison?
In Madison, Virginia, visitors can enjoy a range of attractions that highlight the area's natural beauty and rich history. The nearby Shenandoah National Park offers stunning views, hiking trails, and opportunities for wildlife observation, making it a superb spot for outdoor enthusiasts. The park's Skyline Drive provides a scenic route that showcases the breathtaking Blue Ridge Mountains.In the heart of Madison, the historic downtown area features charming shops and local eateries, allowing visitors to experience the small-town atmosphere. The Madison County Historical Society offers insights into the region's past, with exhibits that celebrate local heritage.Additionally, the surrounding countryside is dotted with wineries and vineyards, offering tastings and beautiful views of the rolling hills.
Are all fees included in the Madison holiday homes prices shown on Bookabach?
Bookabach 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.
Are there any Madison holiday homes with parking?
Bookabach offers a wide selection of holiday homes 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 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.
Are there any discounts for Madison holiday homes?
You can find great discounts on holiday homes in Madison on Bookabach, 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.
Can I change or cancel my Madison holiday home booking on Bookabach?
To find Madison holiday rentals with free cancellation, just use Bookabach'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". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Madison?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising 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 favourites, and build the perfect itinerary together.
How early should I book a Madison holiday home?
Book your Madison holiday home 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 Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Madison?
Prices for holiday homes 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. Bookabach offers something for every taste and budget, from affordable homes in Madison to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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.
Why should I join Bookabach as a host?
Joining Bookabach 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, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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