Best Vacation Homes in Madison
9 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Hot Tub
- Fireplace/Heating
- Ocean View
US $188/Night
For 7 Nights US $1,313
301.39 ft²
9 Bathrooms
Free Cancellation
Hotel
- Private Pool
- Hot Tub
- Fireplace/Heating
US $161/Night
For 7 Nights US $1,128
US $153/Night
For 7 Nights US $1,069
8 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $221/Night
For 7 Nights US $1,545
322.92 ft²
8 Bathrooms
Family Friendly
Hotel
- Private Pool
- Fireplace/Heating
- Pool
US $85/Night
For 7 Nights US $595
5 Guests
2 Bedrooms
3 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $210/Night
For 7 Nights US $1,470
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Kitchen
- Air Conditioner
US $273/Night
For 7 Nights US $1,909
850 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $95/Night
For 7 Nights US $666
Madison Luxury Rentals
8 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Hot Tub
- Fireplace/Heating
- Ocean View
US $766/Night
For 7 Nights US $5,364
14 Guests
6 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $649/Night
For 7 Nights US $4,540
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
US $436/Night
For 7 Nights US $3,052
1012 ft²
8 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
US $351/Night
For 7 Nights US $2,459
1800 ft²
8 Guests
4 Bedrooms
2 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $345/Night
For 7 Nights US $2,412
1700 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Group Friendly
House
- Fireplace/Heating
- Air Conditioner
- Internet
US $308/Night
For 7 Nights US $2,155
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $248/Night
For 7 Nights US $1,737
1500 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $211/Night
For 7 Nights US $1,478
Madison Pet Friendly Vacation Rentals
900 ft²
8 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $168/Night
For 7 Nights US $1,179
269.1 ft²
3 Bathrooms
Free Cancellation
Hotel
- Fireplace/Heating
- Pet Friendly
- Parking
US $90/Night
For 7 Nights US $629
7500 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $155/Night
For 7 Nights US $1,082
960 ft²
8 Guests
2 Bedrooms
1 Bathroom
Ocean View
Condo
- Oceanfront
- Fireplace/Heating
- Ocean View
US $198/Night
For 7 Nights US $1,385
Madison Large Vacation Homes
12 Guests
3 Bedrooms
2 Bathrooms
Ocean View
Cabin
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $189/Night
For 7 Nights US $1,320
12 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Hot Tub
- Fireplace/Heating
- Ocean View
US $468/Night
For 7 Nights US $3,278
2000 ft²
10 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Lake View
US $344/Night
For 7 Nights US $2,405
11 Guests
1 Bedroom
2 Bathrooms
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $222/Night
For 7 Nights US $1,552
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?
Choosing the ideal time to visit this destination can enhance your experience and ensure you find the perfect vacation rentals that suit your preferences throughout the year.
Peak Season Highlights
Summer (June to August)
During the warm summer months, this destination sees an influx of visitors seeking outdoor activities and scenic views. You'll find that booking your vacation rentals here during this time ensures a lively atmosphere and plenty of opportunities for exploration.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
Fall (September to November)
The early fall period offers pleasant weather and vibrant natural scenery, making it an ideal time to enjoy your stay in this region. Securing your vacation rentals ahead of the peak season guarantees a comfortable and memorable visit amidst colorful landscapes.
Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F
Off-Season Highlights
Winter (December to February)
During the colder months, the area experiences fewer visitors, providing a tranquil environment for those looking to escape the crowds. Booking your vacation rentals in winter offers a cozy retreat with peaceful surroundings.
Average Temperature Daytime: 20°F to 30°F - Nighttime: 0°F to 15°F
Spring (March to May)
In early spring, the region begins to thaw, and fewer tourists make it an excellent time for flexible travelers seeking quieter accommodations. Planning your stay now ensures a relaxing experience before the busy summer season begins.
Average Temperature Daytime: 45°F to 60°F - Nighttime: 30°F to 40°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 grilling with a fully equipped barbecue area, perfect for gatherings in the region’s scenic surroundings.
- Relax on spacious patios or decks that offer beautiful views and outdoor seating options.
- Take advantage of private yards or gardens to unwind amidst lush greenery, typical of this destination's outdoor charm.
- Make use of outdoor fire pits to cozy up during cooler evenings and enjoy the region’s crisp air.
- Utilize dedicated outdoor dining spaces designed for alfresco meals in this inviting area.
- Explore nearby walking or biking paths easily accessible from your rental, allowing you to experience the region’s natural beauty firsthand.
- Benefit from access to outdoor recreational amenities such as lakeside docks or picnic areas commonly found here.
Top Attractions Around Madison
What attractions are nearby?
During your stay, you can explore a variety of outdoor activities and local attractions that showcase the natural beauty and community charm of this region.
Family Activities
- Madison Dinosaur Museum: Explore fascinating dinosaur exhibits that captivatingly educate children and adults alike about prehistoric history in the area.
- Lake Madison Recreation Area: Enjoy family-friendly activities such as swimming, fishing, or picnicking by the scenic shores of Lake Madison, just moments from local vacation rentals.
- South Dakota State Railroad Museum: Discover the region’s rich transportation heritage with interactive displays and historic trains perfect for a fun day out with the family.
- Wild Water West: Experience thrilling water rides and family-friendly attractions at this nearby water park, ideal for making memories during warm summer days.
Adult Activities
- Madison Antique Shopping Tour: Explore the charming antique stores and collectibles that offer a glimpse into the region’s history and unique craftsmanship.
- Local Art Galleries and Studios: Visit the area’s vibrant art scene by browsing through local galleries showcasing talented regional artists.
- Parks and Nature Reserves: Enjoy leisurely walks, picnics, or birdwatching in the scenic parks and natural preserves surrounding the destination.
- Dining Experiences: Savor authentic South Dakota cuisine at local restaurants, immersing yourself in flavors that reflect the area's rich culinary heritage.
Other Places to Stay in Madison, SD
Lake County
Herman
Lake Herman State Park
Lake County Courthouse
Dakota State University
HealthPoint
Lake View
Madison Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Events and Festivals: Check the regional calendar to align your stay with community events that showcase the area's culture and charm.
- Enjoy Outdoor Activities: Take advantage of nearby parks and trails to experience the natural beauty and outdoor recreation opportunities available here.
- Sample Local Cuisine: Visit popular eateries and food spots to savor the regional flavors and culinary specialties unique to the region.
- Plan Your Transportation: Arrange convenient transportation options or rent a vehicle to comfortably explore all the hidden gems in this destination.
Transportation Options
- Madison Transit System: This regional transit service provides convenient bus routes within the area, making it easy for you to explore local attractions and amenities.
- Madison Regional Airport: Situated just outside the city, this airport connects visitors to major hubs across the country, offering a practical option for travelers arriving by air.
- Rental Cars: Numerous rental agencies in the vicinity offer reliable vehicle options, giving you the freedom to discover the region at your own pace.
- Taxi and Ride-Sharing Services: Available throughout the destination, these services provide quick and hassle-free transportation for your trips around here.
Local Customs Options
- Celebrating Local Heritage: You’ll find that honoring traditions like the region’s Native American history is an important aspect of community life here.
- Participating in Community Events: Engaging in annual gatherings and local festivals offers a glimpse into the area's vibrant cultural scene.
- Respecting Rural Values: The region values hard work and neighborliness, which are reflected in everyday interactions and social norms.
- Observing Local Dining Etiquette: When trying regional cuisine, you'll notice a friendly, laid-back approach to mealtime customs that emphasize hospitality.
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:
- Beautiful Lake Shore Setting!
- Beautiful year round lake home! Sleeps 8 comfortably!
- Lakeside Getaway on Lake Madison. Hot tub with a view of the lake!
- Skeet's Retreat: Lake Herman's Hidden Gem of Adventure and Relaxation! Sleeps 8
- Pristine Lake House on Lake Madison!
- Summit Splendor, a splendid place to stay while in Madison, SD
- 3+ night special | King Bed | Dog friendly + Fenced Yard | 3 TVs
- Lake house on Lake Madison! 4-bedroom, 3-bathroom house on the water!
- Spacious 6BR Lakefront Cabin - Beach Access & Stunning Views on Lake Madison
- 2 Bed 3 Bath in Harbor on Lake Madison
2. 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:
3. How many Rentbyowner vacation rentals are available in Madison?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 33 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.
4. What is the cancellation policy for vacation rentals in Madison, South Dakota?
Cancellation policies vary depending on the specific property listing. To understand the terms and any applicable fees, please review the cancellation details provided in the listing or contact the owner directly before finalizing your booking.
5. Are there any restrictions on the number of guests for vacation rentals here?
Each property has its own guest capacity limits, which are outlined in the listing details. Make sure to verify the maximum occupancy to ensure the rental suits your group's size before completing your reservation.
6. How do I confirm the amenities included in a vacation rental in this area?
Amenities vary from property to property. You can find a detailed list of what’s included in each listing description. Feel free to reach out to the property owner if you need clarification on specific features or facilities.
7. What is the process for checking in and out of vacation rentals in the region?
Check-in and check-out procedures are specified in each property listing. Many owners offer flexible options; contact them in advance to coordinate your arrival and departure times for a smooth experience.
8. Are pets allowed in vacation rentals here, and what are the pet policies?
Pet policies differ among properties. Detailed information about whether pets are permitted and any associated fees or restrictions can be found in the listing details. Always confirm with the owner before bringing pets to ensure compliance.
Madison Top Rated Vacation Rentals
US $115/Night
For 7 Nights US $808
