Holiday houses in Madison

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Top-rated holiday rentals in Madison

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Top Guest favourite
The exterior of a spacious house is illuminated by soft outdoor lighting, highlighting the inviting features of the structure against a twilight sky. A large deck wraps around the home, offering ample space for relaxation. Lush greenery surrounds the property, enhancing the tranquil setting.
Home in Renner
4.96 out of 5 average rating, 272 reviews

RIVER VALLEY RETREAT

“RVR” is 5 peaceful acres in the country overlooking the Sioux River valley, just 3 mi north of the Sioux Falls city limits & I-29/I-90; 4 & 5 mi straight north of the Sanford Pentagon & Premier Center. Guests enjoy a SUNRISE each morning from all 5 bedrooms, the 30’x40’ common area Great Room/Kitchen, lower level British pub & parlor, 14’x40’ patio, 12’x40’ deck, covered deck, enclosed porch, & the 12’x16’ back deck. The last breath of every SUNSET is seen from half of those areas! Enjoy!

Guest favourite
The exterior of a rustic log cabin is presented, featuring a spacious deck with outdoor furniture. A manicured lawn extends in front, bordered by a line of smooth stones. Large windows reflect the surrounding greenery, while the driveway and garage are visible to the right.
Home in Madison
4.93 out of 5 average rating, 109 reviews

Black Bear Lodge Lake Madison

Rustic, cozy Log Cabin designed to accommodate larger families. Sleeps 15 No bachelor/bachelorette parties. House highlights: - Log Timber finishes - Gas Fireplace - Extra fridge/freezer space - Basement wet bar - Poker/Bumper pool table - Electric Fireplace - Garage Wet bar - Dart Board - Cornhole/Bean Bags - Tables w/ Benches and chairs - Concession bar to serve food and drinks to 1,000 square foot paver patio - Fire pit - Hot tub - Outdoor movie - Hammock - Swinging Chairs

Guest favourite
A spacious backyard is showcased, featuring a large blue kayak and a green paddle board resting on the grass. The two-story home, with numerous windows, displays a deck accessed by stairs. A hammock is seen hanging, surrounded by lush greenery.
Home in Hartford
4.89 out of 5 average rating, 140 reviews

Lakeside Getaway Just West of Sioux Falls

A hidden gem tucked into the inlet of Wall Lake, just 10 minutes west of Sioux Falls, SD! Not only a fishermen’s paradise, it’s also great for a calm kayak or paddle board ride, or venture straight out into the lake to enjoy a swim. At night enjoy roasting marshmallows by the fire and lounging in a hammock. The sunsets over the farmland will take your breath away. In the winter, enjoy your own private ice skating rink. The perfect getaway for a family and stocked with baby gear if needed.

Top Guest favourite
A newly renovated cabin is framed by tall trees and lush green grass, showcasing a vibrant red roof. The exterior features large windows and double doors that provide a welcoming entrance. The landscape reflects a tranquil setting in a peaceful neighborhood.
Holiday home in Lake Preston
4.97 out of 5 average rating, 109 reviews

Peaceful and quiet small town cabin

Come and enjoy our freshly renovated cabin located in the peaceful little town of Lake Preston, SD. We are located right in the heart of pheasant country! Our cabin is a wonderful base for your fishing outings. Lake Whitewood - 3 miles away; Lake Thompson - 4 miles; L. Poinsett - 20 miles; L. Henry- 21 miles; Dry Lake #2 - 27 miles. We have plenty of room for your boat/camper. Laura Ingall's Wilder's home is 9 miles away. Enjoy a very peaceful spot with the amenities of a small town.

Top Guest favourite
A shaded gazebo is featured with a circular fire pit at its center, surrounded by cushioned seating. The expansive deck offers a view of the lake, while the shoreline and water are visible in the background, providing a serene setting for relaxation.
Cabin in Wentworth
4.99 out of 5 average rating, 105 reviews

Intimate lake-side cabin with cozy outdoor space

Relax in this newly renovated, modern cabin. An easy 40 minutes from Sioux Falls, its truly lakeside location lets you wake up to the sound of crashing waves just outside your bedroom window. Enjoy a peaceful morning coffee on the deck, then explore the lake via kayak, and finish your day by coming up to a romantic fire under the gazebo. Perfect for a couple’s getaway. Convenience store and Hillside restaurant located within walking distance. Lakes Golf Course is 1.4 miles away.

Top Guest favourite
A private hot tub is surrounded by charming outdoor seating, with a ceiling fan above for comfort. Soft lighting illuminates the space, enhancing its inviting atmosphere. The entrance to an exterior patio is visible, providing easy access to the outdoors.
Home in Sioux Falls
4.97 out of 5 average rating, 400 reviews

Inspiration Ranch-HOT TUB/lower unit/SUPER CLEAN!!

PLEASE READ!! Welcome to Inspiration Ranch, located in a safe, new neighborhood with quick access to restaurants, shopping, and stores. This private lower unit has its own entrance via the garage stairs. Enjoy full access to the entire space featuring tall ceilings, large windows, and an open, inviting layout. You’ll feel right at home the moment you arrive—perfect for relaxing or exploring the area! Guests are always happy and comfortable here! ✨ PLEASE READ MY REVIEWS!

Top Guest favourite
The treehouse is elevated on a sturdy platform, surrounded by snow-covered landscape and trees. The structure features a wraparound deck with a metal railing and a sloped roof, allowing for unobstructed views of the environment. Morning light casts a soft glow over the scene.
Treehouse in Valley Springs
4.91 out of 5 average rating, 382 reviews

Lookout Loft Treehouse

Welcome to the Lookout Loft Treehouse! Find a retreat in this peaceful hilltop oasis just a short 20 min drive out of Sioux Falls, SD. Sleep in the clouds on your dreamy pillow top mattress, wake up to stunning 360 degree views overlooking the surrounding countryside. Enjoy a cup of coffee on the wraparound deck, a propane fire on the mid-level deck and a dip in the hot tub at ground-level. Space includes a kitchenette, bathroom, and sleeping quarters, with AC and heat.

Top Guest favourite
The exterior of a ranch-style home is showcased, featuring a well-maintained lawn with green grass and decorative landscaping. A wide driveway leads to a two-stall garage with multiple windows. The house is framed by trees and shrubbery, offering a welcoming presence.
Home in Sioux Falls
4.97 out of 5 average rating, 396 reviews

3 Bed/2 Bath Southside executive manor

Welcome to your peaceful Southside retreat! This 1,488 sq ft ranch offers comfort and convenience with 2 king bedrooms, 2 baths, and a business suite with twin bed and Wi-Fi. Enjoy a cozy living room with 65” TV, fenced yard, deck, and 2-stall garage. Dogs welcome (max 2; see rules under "Other Details to Note"). Sleeps 5 max — 5th guest +$50/night. Ideal for families, professionals, and travelers seeking quiet relaxation near Sioux Falls attractions.

Top Guest favourite
A stack of dark blue plates is arranged neatly next to a rustic ceramic mug. The mug features an embossed design, highlighting the name 'RETRAT AT THE RIVER.'. The arrangement is placed on a wooden surface, providing a warm contrast.
Loft in Flandreau
4.95 out of 5 average rating, 218 reviews

Bend In the River AirBnB

A little rest, a little Rock & Roll. Historic Downtown Flandreau is in undergoing a series of renovations and reinvestments in properties, we are proud to be among them! Downstairs we are expanding The Merc - our boutique Mercantile, Taproom, Liquor Store, Coffee Shop and Live Music venue. Upstairs you'll find our historic 2-bedroom loft retreat a simple, clean, spacious, and fun place to stay. We hope you'll find it restful and inspiring as well!

Top Guest favourite
A well-appointed bedroom features a spacious bed with a padded headboard, flanked by two bedside tables with lamps. A decorative bench sits at the foot of the bed, and a soft area rug covers the floor. The walls are painted in a calming gray hue.
Home in Sioux Falls
4.95 out of 5 average rating, 274 reviews

The Cozy Place

Welcome to our Cozy Place, close to everything in Sioux Falls. When you step into this basement apartment style unit, you can’t help but appreciate the fresh and updated look with a warm and inviting feel. This house is built as a triplex therefore is separated into 3 apartments that operate as Airbnb stays. This listing is for the newly remodeled basement unit / apartment, and you will have your privacy and enjoy the comforts it provides.

Guest favourite
An aerial view captures the vineyard home surrounded by rows of grapevines, with protective nets covering the crops. The spacious property features a combination of open fields and wooded areas. The house showcases multiple levels, with large windows overlooking the scenic landscape.
Home in Volga
4.91 out of 5 average rating, 112 reviews

4 bedroom vineyard home near Brookings, SD

Enjoy a get-away in a vineyard home. Beautifully decorated inside and out! Walk through the grape vines, sample the grapes, taste the wine and relax! The spacious 4 bedroom home has plenty of room for large groups. Open concept and multiple levels allow for your guests to come together and enjoy meals and conversation. A huge 800 sq ft patio makes for amazing outdoor entertaining. Enjoy the sunset over the vines.

Top Guest favourite
A spacious townhome exterior is highlighted, showcasing a two-stall garage with a well-maintained facade. Lush green grass surrounds the home, complemented by decorative plants along the pathway. The sky displays soft hues of pink and orange, indicating either dawn or dusk.
Townhouse in Sioux Falls
4.97 out of 5 average rating, 465 reviews

The Marybeth - 2Bdrm/2Bath Townhouse w/Garage

Spacious 2BR/2BA townhome on the west side of Sioux Falls! Enjoy a large picture window overlooking the pond, a remote-controlled patio awning, and an exterior shade for added privacy. Kitchen offers plenty of counter and cabinet space. Master bedroom features a King bed, in-floor-heated bath, and walk-in closet. Second bedroom has a Queen bed with a nicely sized bath. Includes a two-stall garage and fenced backyard!

Popular amenities for Madison holiday rentals

  1. Airbnb
  2. United States
  3. South Dakota
  4. Lake County
  5. Madison