Holiday houses in Madison

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Top-rated holiday rentals in Madison

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Top Guest favourite
A spacious bedroom features a large bed with a navy blue comforter and yellow throw pillows. Nightstands with lamps are placed on either side. A red area rug adds warmth to the wood-style flooring, while a blue accent wall complements the neutral tones.
Guesthouse in Sioux Falls
4.96 out of 5 average rating, 279 reviews

Downtown Cozy Basement Aparment with King Bed

Welcome to our freshly remodeled cozy basement apartment located near downtown Sioux Falls! Our primary goal is to offer you an impeccably clean, comfortable, and thoroughly enjoyable stay. This one-bedroom, one-bathroom basement apartment is the perfect place for couples or solo travelers looking to experience the charm of our city. We're walking distance to Downtown Sioux Falls, beautiful McKennan Park, and Sioux Falls Co-op Grocery Store. Located between Sanford and Avera Medical Centers.

Guest favourite
A cozy living room features a large leather sofa adorned with decorative pillows, complemented by a light wooden coffee table. Natural light fills the space through multiple windows, highlighting the textured area rug beneath. Decorative plants add a touch of greenery to the inviting atmosphere.
Guest suite in Sioux Falls
4.96 out of 5 average rating, 693 reviews

Casalona: Cozy Designer-Curated Central Retreat

Charming mid-century home in the heart of Sioux Falls, steps from Augustana and close to Sanford and downtown. Guests have private access to the front of the house, including two bedrooms, a spacious living room, and full bath. With natural light, cozy furnishings, and greenery, the space feels inviting. Styled with vintage, Moroccan, Japanese, and Scandinavian influences, this thoughtfully designed home offers a peaceful, inspiring place to stay for travelers seeking comfort, style, and home.

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, 433 reviews

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

Spacious 2 bdrm/2 bath town home on west side Sioux Falls! Nice big picture window in the living room overlooking the large pond. Remote controlled exterior awning over the patio & exterior shade on living room window for added privacy! Nice kitchen w/plenty of counter top & cabinet space! Master BdRm w/ a King Bed, hosts a very nice bath with in floor heat, standard closet plus a walk in closet! Second BdRm w/ Queen Bed & bath are nicely sized. Amazing two stall garage and fenced backyard!

Top Guest favourite
Guest suite in Sioux Falls
4.92 out of 5 average rating, 133 reviews

Wildflower Suite w/ Full Kitchen close to Sanford

Arched windows, wrought iron railing & sandy colored stucco define this 1920's Spanish style 2-story bungalow where you have the entire main level. Hot water, cozy clean linens, & excellent WiFi are appreciated throughout this distinctive home on a peaceful side street. Close to Sanford USD Medical Center, USF & Augustana universities, FSD airport, golf course, Midco Aquatics, & Great Plains Zoo. Prime location near vibrant & expanding downtown with sculpture walk, breweries, & live music.

Superhost
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
4.92 out of 5 average rating, 104 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

Top Guest favourite
A spacious living area features polished cement flooring and features a wooden dining table with white chairs. A comfortable futon is positioned nearby with a soft blanket draped over it. Sliding barn doors add rustic charm, and a ceiling fan contributes to airflow.
Home in Sioux Falls
4.97 out of 5 average rating, 189 reviews

Secluded getaway, 10 min from SF

Get away from the busyness just outside of Sioux Falls. A full private apt in a new home in a country neighborhood. Parking spot and private walkway to a separate entrance on the lower level walkout. Relax with a split king adjustable bed and warm up with a steam shower for two. Full kitchen, Sitting area w/a futon bed, Carpet free, Polished cement with in-floor heat, Central Air & Ceiling Fans, Wooded backyard. Good Earth State Park 1/2 mile, Dntn Sioux Falls 10 miles, I-90 10miles.

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, 108 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, 394 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!

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, 358 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
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, 211 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!

Guest favourite
A spacious backyard features a circular stone fire pit surrounded by multiple outdoor chairs. A hot tub is positioned nearby, with a patio area presenting a blend of grass and concrete. The home’s exterior is painted in a soft gray, complemented by well-kept landscaping.
Home in Sioux Falls
4.94 out of 5 average rating, 289 reviews

Beautiful Family Home - Perfect for Large Groups!

Welcome to your spacious 5-bed, 3-bath haven! Embrace family fun with a pool, Transformer Pinball, and a basketball court in the expansive driveway. Fully equipped kitchen awaits your culinary adventures. Conveniently close to 41st street corridor, Lake Lorraine, Empire Mall, and the District. Your perfect retreat awaits! Looking for fun at the house?! Enjoy a garage converted into a game room, that is free with booking!

Popular amenities for Madison holiday rentals

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