Best Vacation Homes in Madison
Cabin
10.0(211 Reviews)
1 Bedroom
1 Bath
4 Guests
Fireplace/Heating
Ocean View
Balcony/Terrace
View
US $201/Night
7 Nights - US $1,409
House
10.0(4 Reviews)
1 Bedroom
2 Baths
6 Guests
1399.31 ft²
Hot Tub- Fireplace/Heating
- Balcony/Terrace
Parking
US $176/Night
7 Nights - US $1,232
Hotel
10.0(149 Reviews)
1 Bath
- Fireplace/Heating
Kitchen- Parking
Air Conditioner
US $189/Night
7 Nights - US $1,325
Cabin
10.0(114 Reviews)
2 Bedrooms
1 Bath
5 Guests
800 ft²
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $179/Night
7 Nights - US $1,256
Apartment
10.0(3 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
Child Friendly
Security/Safety
US $177/Night
7 Nights - US $1,239
Apartment
10.0(75 Reviews)
2 Bedrooms
2 Baths
4 Guests
1500 ft²
- Fireplace/Heating
- Ocean View
- View
- Kitchen
US $220/Night
7 Nights - US $1,538
House
10.0(66 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
Pool- Balcony/Terrace
- Kitchen
US $243/Night
7 Nights - US $1,703
House
10.0(47 Reviews)
3 Bedrooms
1 Bath
4 Guests
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $250/Night
7 Nights - US $1,752
Madison Luxury Rentals
House
10.0(1 Review)
5 Bedrooms
4 Baths
16 Guests
3270 ft²
- Fireplace/Heating
Pet Friendly- Kitchen
- Parking
US $716/Night
7 Nights - US $5,015
New
Cabin
4 Bedrooms
3 Baths
14 Guests
1617 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $539/Night
7 Nights - US $3,774
House
10.0(1 Review)
3 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $522/Night
7 Nights - US $3,652
House
10.0(61 Reviews)
4 Bedrooms
3 Baths
12 Guests
3500 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $504/Night
7 Nights - US $3,529
New
House
1 Bedroom
4 Baths
14 Guests
1614.59 ft²
- Fireplace/Heating
- Air Conditioner
Internet- Child Friendly
US $472/Night
7 Nights - US $3,305
House
9.8(10 Reviews)
4 Bedrooms
4 Baths
8 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
US $439/Night
7 Nights - US $3,076
House
10.0(2 Reviews)
3 Bedrooms
2 Baths
6 Guests
3175 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $436/Night
7 Nights - US $3,051
Apartment
9.8(9 Reviews)
1 Bedroom
1 Bath
2 Guests
510 ft²
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $421/Night
7 Nights - US $2,946
Madison Pet Friendly Vacation Rentals
Apartment
10.0(32 Reviews)
1 Bedroom
1 Bath
5 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $162/Night
7 Nights - US $1,135
House
10.0(1 Review)
2 Bedrooms
2 Baths
4 Guests
1162.5 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Internet
US $288/Night
7 Nights - US $2,014
Hotel
8.8(694 Reviews)
1 Bath
- Fireplace/Heating
- Pool
Breakfast- Pet Friendly
US $150/Night
7 Nights - US $1,051
House
10.0(20 Reviews)
2 Bedrooms
1 Bath
4 Guests
1166 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $219/Night
7 Nights - US $1,530
House
8.0(1 Review)
2 Bedrooms
1 Bath
4 Guests
699.65 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Pet Friendly
US $252/Night
7 Nights - US $1,765
House
10.0(16 Reviews)
3 Bedrooms
2 Baths
8 Guests
1635 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $355/Night
7 Nights - US $2,488
House
10.0(2 Reviews)
2 Bedrooms
1 Bath
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $313/Night
7 Nights - US $2,192
House
10.0(2 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $290/Night
7 Nights - US $2,032
Madison Large Vacation Homes
House
10.0(67 Reviews)
5 Bedrooms
3 Baths
10 Guests
2200 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $377/Night
7 Nights - US $2,642
Apartment
6.5(2 Reviews)
5 Bedrooms
8 Baths
20 Guests
1407.92 ft²
- Fireplace/Heating
- Parking
- Air Conditioner
- Internet
US $216/Night
7 Nights - US $1,513
Cabin
10.0(63 Reviews)
4 Bedrooms
2 Baths
12 Guests
2040 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $228/Night
7 Nights - US $1,597
House
10.0(39 Reviews)
5 Bedrooms
3 Baths
10 Guests
2200 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $337/Night
7 Nights - US $2,358
House
3 Bedrooms
4 Baths
10 Guests
2800 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $348/Night
7 Nights - US $2,439
House
10.0(125 Reviews)
6 Bedrooms
2 Baths
12 Guests
1900 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $255/Night
7 Nights - US $1,787
Cabin
10.0(42 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $243/Night
7 Nights - US $1,699
Cabin
9.4(38 Reviews)
2 Bedrooms
1 Bath
100 Guests
1200 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $172/Night
7 Nights - US $1,202
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?
To make the most of your stay in Madison, Indiana, USA, consider visiting during the local shoulder seasons when the region's natural beauty and charming atmosphere are at their peak, offering a more relaxed and authentic experience for those seeking the perfect vacation rental here.
Peak Season Highlights
Spring (March to May)
During springtime, this destination comes alive with vibrant scenery and pleasant weather, making it an ideal period for outdoor exploration. Expect moderate daytime temperatures, perfect for enjoying the area's unique charm.
Average Temperature Daytime: 60-75°F - Nighttime: 45-55°F
Fall (September to November)
Autumn offers stunning fall foliage and comfortable temperatures, encouraging memorable outdoor activities. It's a popular season for visitors seeking to experience the region’s natural beauty at its peak.
Average Temperature Daytime: 65-70°F - Nighttime: 45-50°F
Off-Season Highlights
Winter (December to February)
The winter months bring colder weather and fewer tourists, providing a peaceful escape. This is a good time for visitors wanting to enjoy the cozy side of the area in quieter surroundings.
Average Temperature Daytime: 40-50°F - Nighttime: 25-35°F
Summer (June to August)
While summer can be busy with vacationers taking advantage of warmer weather, the region still offers opportunities for relaxation and outdoor activities. It’s especially suitable if you prefer lively atmospheres and longer days.
Average Temperature Daytime: 80-90°F - Nighttime: 60-70°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 outdoor dining areas perfect for al fresco meals and gatherings.
- Relax in private patios or decks offering scenic views of the surrounding landscape.
- Take advantage of well-maintained gardens or landscaped yards for leisurely strolls.
- Make use of outdoor fire pits to cozy up during cool evenings.
- Utilize shared or private swimming pools available in select properties.
- Explore nearby walking trails or nature paths for outdoor adventures.
- Experience the convenience of outdoor parking spaces tailored for your vehicle.
Top Attractions Around Madison
What attractions are nearby?
In this charming destination, you can enjoy a variety of outdoor activities, explore local shops and galleries, or take in scenic river views, all conveniently close to your vacation rental for a memorable stay.
Family Activities
- Madison Riverfront Park: Enjoy a family picnic and leisure time along the scenic river, perfect for relaxed afternoons during your stay in the area.
- Clifty Falls State Park: Explore beautiful waterfalls, hiking trails, and nature activities that make this park an ideal outdoor destination for families visiting here.
- Historic Downtown Madison: Discover charming shops, local eateries, and historic sites that provide a fun and educational experience for all ages.
- The Madison Railroad: Take a nostalgic train ride through the region, offering memorable adventures within a short drive from your vacation rental here.
Adult Activities
- Historic Downtown Madison Walking Tour: Discover charming architecture and local history as you stroll through the area's well-preserved streets.
- Madison Brewing Company Tour: Enjoy sampling locally brewed beers in a vibrant setting that captures the region’s rich brewing heritage.
- Clifty Falls State Park Exploration: Immerse yourself in natural beauty with scenic hikes, waterfalls, and breathtaking views just outside the city center.
- Art and Museum Visits: Engage with the region's vibrant arts scene by exploring galleries and museums showcasing local talent and historical artifacts.
Other Places to Stay in Madison, IN
Brooksburg
Hanover
Historic Eleutherian College
King's Daughters' Health
Jefferson County
Austin
Switzerland County
Florence
Scott County
Scottsburg
Madison Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Dining and Shops: Take advantage of the region’s charming local eateries and boutiques to immerse yourself in the area's authentic atmosphere.
- Plan Outdoor Activities: Make the most of nearby parks and scenic spots for outdoor adventures that showcase the natural beauty here.
- Discover Cultural Heritage: Engage with the area's rich history by visiting museums or historical landmarks to deepen your understanding of this destination.
- Book Early for Popular Vacation Rentals: Secure your preferred property ahead of time to ensure a comfortable stay in this sought-after region.
Transportation Options
- Madison Transit Authority: Local bus services offer convenient transportation within the city and to surrounding areas, making it easy to explore this charming destination.
- Rental Cars: Renting a car provides flexibility for visiting nearby attractions and discovering the scenic region at your own pace.
- Taxi Services: Taxi options are readily available here, offering quick and reliable transfers around the area when you need them.
- Bike Rentals: Biking is a popular way to enjoy the scenic views and historic districts of Madison, with bike rentals accessible for all ages and levels.
Local Customs Options
- Southern Hospitality: In this area, welcoming gestures and friendly interactions are deeply rooted in local customs, making your stay feel warm and inviting.
- The region values handcrafted goods and traditional crafts, offering you an authentic experience of local artistry during your visit.
- Participating in seasonal festivals and community events is a cherished tradition that provides insight into the area's vibrant cultural identity.
- Preservation of natural beauty is important here, so you'll find that outdoor etiquette and environmental consciousness shape daily life.
Madison Vacation Rental Frequently Asked Questions
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:
- 1800’s restored log cabin on 26 private rolling wooded acres with sunset views
- The Chandler Hotel
- Secluded Country Home in Historic Hoosier Hills
- Stoney Creek - Sit back and unwind
- Best downtown location! Stablemasters Quarters is awarded winning! Come see why…
- #209 Kings, River View, Deck, Bicentennial Park
- The Wadsworth in National Historic District of Madison, Indiana.
- Rustic cabin just outside of Madison!
- Luxurious 4 Bedroom Home in Heart of Historic Madison's Downtown
- Beautiful and spacious 3BR historic home centrally located in downtown, Madison.
2. How many vacation rentals have private pools in Madison?
There are 3 vacation rentals with private pools near Madison. Top-rated RBO homes that have access to a swimming pool include:
3. 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:
4. How many Rentbyowner vacation rentals are available in Madison?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 184 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.
5. What is the cancellation policy for vacation rentals in Madison, Indiana?
The cancellation policy varies depending on the host. You should review the specific listing details or contact the property owner directly to understand the options and any fees associated with cancellations.
6. How do I ensure my booking in Madison, Indiana is secure?
Bookings are secured through a trusted platform that offers secure payment methods. It’s recommended to communicate with the host through the platform’s messaging system and review their verification status for added confidence.
7. Are there any house rules I should be aware of when staying in this region?
Each vacation rental has its own house rules set by the host. Be sure to read the rental description thoroughly and contact the host if you have questions about specific policies or requirements.
8. Can I modify or extend my reservation in the area once it's booked?
Modifications or extensions depend on the host’s approval and the availability of the property. Contact the host as soon as possible to discuss your plans and receive confirmation before making changes.
9. What amenities are typically included in vacation rentals near Madison, Indiana?
Most listings offer essential amenities such as Wi-Fi, kitchen facilities, and parking. Check the specific property’s listing details for a comprehensive list of what’s available during your stay.
Madison Top Rated Vacation Rentals
House
9.8(84 Reviews)
2 Bedrooms
2 Baths
5 Guests
900 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $218/Night
7 Nights - US $1,523
Hotel
9.4(113 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
US $103/Night
7 Nights - US $720
Hotel
8.8(692 Reviews)
1 Bath
Spa- Pool
- Balcony/Terrace
- Breakfast
US $113/Night
7 Nights - US $794
Hotel
8.8(152 Reviews)
11 Baths
322.92 ft²
Private Pool- Fireplace/Heating
- Pool
- Balcony/Terrace
US $120/Night
7 Nights - US $839
Hotel
8.7(152 Reviews)
1 Bath
348.04 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $169/Night
7 Nights - US $1,180
US $173/Night
7 Nights - US $1,210
Hotel
8.6(988 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Breakfast
- Kitchen
US $159/Night
7 Nights - US $1,111
Hotel
8.6(282 Reviews)
11 Baths
172.22 ft²
Oceanfront- Fireplace/Heating
- Pool
- Ocean View
US $140/Night
7 Nights - US $980
