Holiday rentals in Madison

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Top-rated holiday rentals in Madison

Guests agree: these stays are highly rated for location, cleanliness and more.

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Superhost

Home in Madison

5 out of 5 average rating, 3 reviews

Holiday Stay in Madison – Warm & Cozy | Hunters We

Welcome Hunters, message us about our Dog Policy. Welcome to The Dakota – your home away from home in Madison! 3+ Night Specials Just blocks from DSU, our cozy dog-friendly home is perfect for families, fans, and alumni visiting for football, soccer, volleyball and E-Sports. Enjoy a fenced yard, fully stocked kitchen, free laundry, and comfy beds: King in primary suite, Queen in 2nd bedroom, and 3 Twins in kid space. Walkable to DSU and local amenities, The Dakota blends comfort, convenienc

Guest favourite

A spacious living area is highlighted by a large sectional couch and a matching ottoman. A flat-screen television is mounted on the wall, displaying an image of elephants. The open layout leads to a kitchen area, creating a seamless flow throughout the space.

Flat in Sioux Falls

4.84 out of 5 average rating, 186 reviews

The Elephant Suite

Welcome to this one-of-a-kind, majestic elephant themed stay! Newly remodeled, this apartment features a spacious floorplan and inviting atmosphere adorned with subtle elephant motifs. Enjoy lounging on the large sectional couch or a restful night's sleep on the comfy king-sized bed! Conveniently located blocks away from downtown, there are many local attractions, restaurants, and shops within a 5-minute drive. Offering the perfect blend of comfort and convenience for your next Sioux Falls Stay

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.

Guest house in Sioux Falls

4.96 out of 5 average rating, 278 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.

Top guest favourite

Guest suite in Sioux Falls

4.92 out of 5 average rating, 132 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

Guest favourite

A cozy living space is presented with a blue sofa and an upholstered floral chair. Two small ottomans sit in front, complemented by a patterned area rug. Light filters through the windows, enhancing the simplicity of the decor.

Home in Brookings

4.94 out of 5 average rating, 17 reviews

Cozy and Small near DT Brookings

This is a small space in a duplex home near downtown Brookings. It boasts a stand up washer and dryer, and a queen bed! The space is perfect for one person traveling, a couple or a couple of people coming to town to work. The second room has a twin in a very small space, should a second person want a bed or a third person possibly. Our hope is to offer an inexpensive location for people that are traveling to town, working temporarily in town, or need a quick stay on their way somewhere.

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

The exterior of a remodeled house features grey siding with white trim and a welcoming brown front door. Steps lead up to the entrance, flanked by large windows on either side. A manicured lawn surrounds the home, enhancing the inviting curb appeal.

Home in Madison

5 out of 5 average rating, 19 reviews

Enjoy Our Newly Renovated Home: Summit Splendor

Welcome to Summit Splendor, a splendid place to stay while in Madison, SD! This newly remodeled 3+-bedroom, 2 ½ -bathroom house is nestled in a quiet neighborhood, less than 5 minutes from downtown and just a few blocks from Dakota State University, making it a great base while exploring the Madison area. Whether you’re here for a quick getaway or an extended stay, you’ll find comfort and convenience in this charming house. Choosing the best in Madison is only a click away.

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, 356 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.

Guest favourite

A charming house is displayed beneath a clear blue sky, featuring distinctive architectural details such as decorative wooden trim and large windows. The exterior is painted in light colors, complemented by red brick accents at the base, surrounded by well-maintained lawns and greenery.

Guest suite in Madison

5 out of 5 average rating, 25 reviews

715 N Egan Residence

Welcome to your cozy retreat in the heart of Madison! This private entry/exclusive 1-bedroom, 1-bathroom unit offers a comfortable and convenient stay across the street from DSU. Private entry with code lock access ensures smooth check-in. Perfect for visiting parents, professors, or students. Snacks, coffee, and drinks included! Whether you’re here for a weekend visit or an extended stay, this Airbnb provides a peaceful home base for your adventures.

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, 210 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, 288 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!