Madison Holiday Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Madison

Fridge, microwave, oven, stovetop
Cornfield Country House
The price is NZ$491
includes taxes & fees
2 Jun - 3 Jun
Cornfield Country House
Property grounds
Beautifully updated 4 bedroom Lake Home
10.0 out of 10, Exceptional, (17)
"We booked a stay for a family wedding. This was a perfect property for multigenerational stay. Very clean and comfortable. Everything we needed was there. If in the area we absolutely would book again. Thank you!"
Beautifully updated 4 bedroom Lake Home
Fridge, microwave, oven, stovetop
Sportsman's Country Lodge: The Roost
9.4 out of 10, Exceptional, (14)
"Nice place"
The price is NZ$328
includes taxes & fees
2 Jun - 3 Jun
Sportsman's Country Lodge: The Roost
Save an average of 15% on thousands of hotels when you're signed in
Pool
Waterfront Big Stone Lake Home w/Dock & Views
10.0 out of 10, Exceptional, (87)
"making this our annual rental."
Waterfront Big Stone Lake Home w/Dock & Views
Interior
1BR cabin on Big Stone Lake
10.0 out of 10, Exceptional, (1)
"This was a great, quiet place to stay on Big Stone. It was a garage with a living quarters. The host was responsive and helpful."
1BR cabin on Big Stone Lake
Interior
Cozy Appleton Getaway w/ Screened-In Porch + Yard!
9.8 out of 10, Exceptional, (19)
"Very impressed...wasn't expecting for it to be as pretty and clean as it was. Will stay again now that we know about it."
Cozy Appleton Getaway w/ Screened-In Porch + Yard!
Property grounds
Year round cabin on level lot with dock
9.8 out of 10, Exceptional, (7)
"This is a perfect place to stay and enjoy the lake."
Year round cabin on level lot with dock
Property grounds
Enjoy this peaceful house on Big Stone Lake!
10.0 out of 10, Exceptional, (5)
"Very very nice accommodations! Excellent communication with Host. We had a very nice time and the lakeview was terrific. Would definitely recommend."
Enjoy this peaceful house on Big Stone Lake!
Beach
The Mulberry House near the south shore of Big Stone Lake
10.0 out of 10, Exceptional, (10)
"House was amazing, checkin was easy. Communication very fast response would stay here again"
The Mulberry House near the south shore of Big Stone Lake
Interior
Sportsman's Country Lodge: The Bluegill
The price is NZ$268
includes taxes & fees
2 Jun - 3 Jun
Sportsman's Country Lodge: The Bluegill
Exterior
Odessa Lodge 3bd/2ba-Close to hunting, fishing, hiking and Lake Fun
10.0 out of 10, Exceptional, (5)
"It’s a nice place to stay."
The price is NZ$417
includes taxes & fees
30 May - 31 May
Odessa Lodge 3bd/2ba-Close to hunting, fishing, hiking and Lake Fun
Exterior
Spacious home with a large deck and ample space for beautiful sunset viewing!
10.0 out of 10, Exceptional, (4)
"Had a great stay at this place access to big stone was right there for our fishing and John was a great host! Will stay again for sure"
Spacious home with a large deck and ample space for beautiful sunset viewing!
4 bedrooms, WiFi, bed sheets
Large Private Lodge located in the middle of a hunters paradise
9.8 out of 10, Exceptional, (16)
"Great place to gather with friends after a day in the field hunting."
Large Private Lodge located in the middle of a hunters paradise
Interior
Cozy Appleton Getaway w/ Screened-in Porch + Yard!
3.5 star property
Cozy Appleton Getaway w/ Screened-in Porch + Yard!
Fridge, microwave, oven, stovetop
4 Bedroom 2 Bath Lodge overlooking river bottoms with fabulous views
10.0 out of 10, Exceptional, (12)
"We had family in town for a wedding at a local venue and this spot worked great! Would definitely recommend."
4 Bedroom 2 Bath Lodge overlooking river bottoms with fabulous views
Don't see what you're looking for?
See all available properties in Madison
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Madison you may be interested in

Fridge, microwave, oven, stovetop
Cornfield Country House
The price is NZ$491
includes taxes & fees
2 Jun - 3 Jun
Cornfield Country House
Individually decorated, desk, blackout curtains, free cots/infant beds
Super 8 by Wyndham Milbank SD
2.0 star property
7.4 out of 10, Good, (167)
"Safe, clean and quiet!"
The price is NZ$125
includes taxes & fees
16 Jun - 17 Jun
Super 8 by Wyndham Milbank SD
Lobby sitting area
Grandstay Hotel and Suites Milbank
2.5 star property
9.6 out of 10, Exceptional, (175)
"Staff was super friendly and helpful! Property was very clean and well kept."
The price is NZ$263
includes taxes & fees
2 Jun - 3 Jun
Grandstay Hotel and Suites Milbank
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Madison holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Madison. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Madison. Seeing all the best attractions is bound to make you fall in love with Madison. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Madison short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Madison?

Yes, there are holiday rentals close to the most popular sights in Madison, or you can select a more secluded option if you're looking for a relaxing stay. Madison is known for its entertainment choices and theatres. Make sure you have time to check out the museums while you're in the area.

What are some of the best holiday rentals that Madison has to offer?

Sportsman's Country Lodge: The Roost: This holiday home rental outside of Madison is equipped with a BBQ, air conditioning and laundry facilities to help you feel comfortable during your stay. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

What can I see and do in Madison?

While you're exploring the area, Lac qui Parle State Park and Lac qui Parle Wildlife Management Area are a couple of picturesque spots to get outside and enjoy nature. Big Stone National Wildlife Refuge and Odessa Boulder are a couple of places you'll find in the wider area.

What’s a holiday rental in Madison like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Madison. Holiday rentals feature amenities such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from public hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for family trips or small group gatherings.