Holiday houses in Madison
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Top-rated holiday rentals in Madison
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The Artist’s A-Frame
Get away and enjoy the comfort and convenience of this unique, newly remodeled A-Frame home nestled in a quiet, safe, upscale neighborhood, minutes from Clifty Falls State Park (10 min. drive), Historic Downtown (5 min. drive), hilltop shopping (5 min. drive): Hanover College (15 min. drive) •Fast Wi-Fi •Electric Fireplace .Two 55” Roku TVs, Complimentary YouTube TV for local and cable stations •Keurig & Drip Coffee, K-cups, local coffee, tea, bottled water .Paved driveway parking .Gas BBQ grill
ValueFamilyAir conditioning
Studio apartment above Garage in downtown Madison
This special place is located in downtown Madison. It's steps from restaurants and walking distance across all of downtown Madison. This above the garage apartment overlooks a koi pond and beautiful backyard of one of Madison's historic homes. Enjoy the beautiful balcony views and relax in this studio efficiency apartment with a pull out couch. Walking distance to gorgeous hiking destinations, including Clifty Falls State Park and the Heritage Trail. Come enjoy all that Madison has to offer!
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The Book Haven - A Book Lover's getaway near Main
Spacious & stylish period home furnished like you’re traveling back in time - or escaping it. With an eclectic mix of decor from antique federalist style to fun MCM, the owners designed it to feel like a cozy library. Ready to see historic Madison? Walk 3 mins to Main St where you’ll find the Attic, Mad Love, Trolley Barn, & Olde Tyme. On Saturday mornings, take a 7-min stroll through Madison’s most stately brick homes down Third through Mill, Vine, Elm, and Broadway to the Farmer’s Market.
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Glenda’s Overlook
Situated just one and a half blocks from the iconic Milton-Madison Bridge spanning the picturesque Ohio River, Glenda's Overlook offers the perfect retreat for you and your loved ones. Our home is located merely a few walking blocks, or short golf cart ride, from the historic district, and offers easy access to the city's charming wineries, shops, restaurants, Crystal Beach and vibrant festivals that Madison has to offer. Additionally, we are only a short drive to Clifty Falls State Park.
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Cozy downtown home with patio. Walk to everything.
Your family will be close to everything in downtown Madison when you stay at this conveniently located, updated home built in 1880. First floor open concept floor plan includes living room equipped w/electric fireplace and an eat-in kitchen w/bar stool seating for 4. Upstairs offers two bedrooms and full bath w/shower and old old-fashioned soaker tub. Enjoy nice weather on the fenced back patio. Note: This property contains stairs and is not recommended for guests with mobility issues.
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Historic Madison Spa Retreat perfect location
Highlighted on Madison Loft Tours. 1800s historic 3rd story charming Loft offers a spa retreat & private deck. In the midst of Madison’s shopping, dining, festivals & nightlife. Located between Main St and the river. Antique furnishings and beautiful woodwork highlighted. Sip local coffee from our private deck or relax in a jacuzzi tub after touring the sights. Wineries, bars, Mad Paddle Brewery and great restaurants surround us. Hanover College & Clifty Park are minutes away.
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Riverview Historical Retreat
Full time Airbnb home in Historic Downtown Madison. This two bed, two bath home overlooks the Ohio River and includes a fully stocked kitchen, washer/dryer, screened in back porch, internet, keyless entry, and more Centrally located next to Bicentennial Park, enjoy one of the many restaurants, bars, parks, and local events, or enjoy a quiet weekend away with a weekly Music/Movie by the river, a local farmers market, and shops. There is something for everyone to enjoy in Madison
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The Treehouse - Hot Tub - Indoor Pool Get Away!
The Treehouse is a perfect retreat! It is secluded by the hills surrounding Madison. Complete privacy, yet 5 minutes from downtown, or hilltop. Year-round views of the beautiful hills of Kentucky. Winter views of the Ohio River and downtown. The house has stunning ceilings made from coastal cedar off an island near Vancouver, British Columbia and beautiful skylights in the studio and indoor pool area. This is an Adults only property. 2-night min.
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Cozy Farmhouse Retreat in Historic District
Located in the Historic District in Madison! Lisa and Richard co-own and co-host this recently updated cottage. Welcome to our cozy, chic Farmhouse Retreat. It is one block from Main Street, featuring so many charming shops, restaurants, and historic buildings for which Madison is famous. Only three blocks from the mighty Ohio and a short five-minute drive to Clifty Falls State Park. We fell in love with Madison and know you will, too.
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Hilltop Dome, 42 secluded acres in nature
Our Geodome is tucked away on 42 private acres exclusively for you and your guest Enjoy the stars at night, fire pit, hot tub, high speed internet, washer dryer, and smart TV . The Dome is equipped with a 2 ton mini split that will keep you warm in the winter and cool in the summer We are conveniently located within 15 miles of Madison, IN, Vevay, IN, Clifty Falls, Belterra Casino, also within 62 miles of Cincinnati and Louisville.
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Carole's Cottage
Quaint cottage located in downtown Madison. A short walk to all shops & restaurants and beautiful riverfront. Guests have entire home including a screened in back porch to enjoy your morning coffee or just relax and read a book. Master bedroom has a king size bed and 2nd bedroom has a futon. Our kitchen is fully equipped, including stove, refrigerator, microwave and keurig coffee maker.
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Watchmaker Place in Historic Madison District
This historic home is in the heart of downtown Madison. Watchmaker Place has been completely renovated while retaining its charm and elegance throughout. Located on beautiful West 2nd Street, less than two blocks from the river, restaurants, brewery, wineries, and downtown shopping. Convenient for festival activities or just a weekend away from it all.
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Popular amenities for Madison holiday rentals
Other great holiday rentals in Madison
The Magnolia on Main hosted by Swell Stay
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The Jefferson Street Retreat - Prime Location
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2King Beds+1Block to MainSt+Privacy Fence+Walkable
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Clean Hilltop 4BR | Near Clifty Falls | Sleeps 8
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Mulberry Manor*Walkable*8 Guests*4 Bed/2.5 Bath
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3-suite cottage spa (aaaah!) house
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The Olive House
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Little Pink House - North
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When is the best time to visit Madison?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $247 NZD | $254 NZD | $256 NZD | $254 NZD | $254 NZD | $247 NZD | $269 NZD | $263 NZD | $281 NZD | $261 NZD | $259 NZD | $261 NZD |
| Avg. temp | 2°C | 4°C | 9°C | 15°C | 20°C | 25°C | 27°C | 26°C | 22°C | 16°C | 9°C | 4°C |
Frequently Asked Questions
What are the best places to stay in Madison?
Historic downtown is known for character-rich lodgings and easy access to shops, galleries, and the riverfront. Vacation rentals are also found in quiet neighborhoods around Madison, appealing to travelers seeking a local feel.
What are the best things to do in Madison with kids?
Kids enjoy interactive museums, riverside parks, and nature trails in Clifty Falls State Park. Seasonal events feature activities like petting zoos, craft fairs, and guided tours around the historic downtown.
What are some of the best things to do in Madison?
Explore Madison’s historic downtown, wander scenic riverfront trails, and visit Clifty Falls State Park for nature hikes. Art galleries, community festivals, and local museums add to the area’s appeal.
How is the weather in Madison?
Madison’s winters average 28–44°F (-2–6°C) and summers warm to 71–89°F (22–32°C), with moderate rainfall throughout the year. Spring and fall have milder temperatures and are often chosen for outdoor activities.
When is the best time to visit Madison?
Late spring and early fall are often recommended for comfortable temperatures and active community events. Summer brings warmer weather and outdoor festivals, while winter draws visitors for historic tours and quieter scenery.
What are the best places to visit in Madison?
Madison has a historic downtown, the riverfront, Clifty Falls State Park, and the Lanier Mansion, which includes interpretation of the era’s history. Museums, art galleries, and scenic parks are frequently suggested stops.
What are some hiking trails in Madison?
Madison has hiking trails in Clifty Falls State Park, including forested paths and waterfalls. Additional walking trails can be found in local parks and along the riverfront area.
What are some family activities we can do in Madison?
Families often explore the riverfront, enjoy local parks, or visit nearby museums for interactive exhibits. Seasonal festivals, petting zoos, and guided nature walks are frequently suggested options around Madison.
What are some of the best day trip ideas from Madison?
Day trip options include exploring nearby wineries, visiting regional nature preserves, and touring historic towns with local markets. Outdoor adventure areas and cultural sites in the region attract visitors looking for new experiences.
Are there any pet friendly accommodations available in Madison?
Many vacation rentals around Madison welcome pets, especially in downtown or near the riverfront. Several parks and trails make it easy to enjoy outdoor time with dogs.
What are some local tips for visiting Madison?
Madison has a walkable historic downtown lined with shops and eateries; comfortable shoes are helpful for exploring. The riverfront is popular for scenic strolls, and advance reservations can be useful at busy restaurants during event weekends.
What is Madison known for?
Madison is known for its well-preserved historic downtown, scenic riverfront, and vibrant arts scene. Clifty Falls State Park, local festivals, and heritage sites reflecting nineteenth-century history are frequently mentioned.
What are the best hidden gems to explore in Madison?
Look for tucked-away antique shops, historic gardens, and locally owned cafes in Madison’s downtown. Some visitors discover less-known walking trails and art galleries in quieter neighborhoods around the city.
What are the best foods to try in Madison?
Madison’s food scene features locally rooted comfort dishes like fried chicken, barbecue, and hearty sandwiches, alongside seasonal produce from nearby farms. The area is also known for homemade pies, craft beers, and classic Midwest desserts.
What should I bring for a trip to Madison?
Pack layers to handle changing temperatures; winters dip to 28°F (-2°C) while summers reach nearly 89°F (32°C). Comfortable shoes work well for historic downtown strolls, and a rain jacket is useful due to occasional rainfall year-round.
What is the nightlife in Madison like?
Madison has a laid-back nightlife with live music venues, riverside bars, and cafes open late. Downtown is frequently suggested for evening strolls, casual drinks, and local entertainment.
What are the most popular events or festivals in Madison?
Madison has annual events such as the Madison Regatta, which features hydroplane boat races, and Madison Chautauqua Festival of Art, celebrating regional artists and crafts. Community traditions frequently highlight music, food, and the town’s historic riverfront.
Are there family friendly vacation rentals in Madison?
Madison has family-friendly vacation rentals, especially near historic and downtown neighborhoods. Many are close to parks and local attractions, providing inviting spaces for groups traveling with children.
Quick stats about holiday rentals in Madison
Total holiday rentals
Explore 130 holiday rentals in Madison
Nightly prices starting at
Madison holiday rentals start at $51 NZD per night before taxes and fees
Verified guest reviews
Over 9,680 verified reviews to help you choose
Family-friendly holiday rentals
80 properties offer extra space and kid-friendly amenities
Pet-friendly accommodation
Find 30 rentals that welcome pets
Rentals with dedicated workspaces
60 properties have a dedicated workspace
Wi-Fi availability
130 of Madison holiday rentals include Wi-Fi access
Popular amenities for guests
Guests love Gym, BBQ grill and Laptop-friendly workspace across Madison rentals
4.9 Average rating
Madison stays are highly rated by guests—averaging 4.9 out of 5!
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