Holiday houses 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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Guest favourite

Home in Madison

5.0 out of 5 average rating, 9 reviews

3+ night special | King Bed | Dog friendly + Fence

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, convenience, and Bulldog pride! Easy One level Living Kin

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Superhost

A spacious living area is furnished with a sectional couch, accentuated by decorative pillows. Natural light filters through two windows, highlighting a minimalistic coffee table. A television is placed on a console against the wall, with a small side chair and rug completing the inviting setting.

Home in Madison

4.83 out of 5 average rating, 30 reviews

Lake House • Water Views • Fire Pit • Dog Friendly

Experience lake life in this 2-bedroom, 1-bathroom home with lake views. This recently updated home has spacious living areas and offers natural light throughout. Conveniently located on the Northwest corner of Lake Madison you have easy access to the highway, the lake and Madison, SD. 7 minutes to the town of Madison 4 minutes to public water access 7 minutes to Dakota State University 10 minutes to Hillside Resort There are endless things to do at the Lake and in the town of Madison, SD!

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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 Wentworth

4.92 out of 5 average rating, 115 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

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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

4.98 out of 5 average rating, 121 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.

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Guest favourite

A wooden dock extends over the calm surface of Lake Madison, with two chairs positioned at the end. A single, fluffy cloud reflects in the water, complementing the serene blue sky and the tranquil surroundings.

Home in Wentworth

4.95 out of 5 average rating, 39 reviews

Lakeside getaway on Lake Madison

Escape to our serene lakeside retreat on Lake Madison! Enjoy fishing, boating, and relaxing by the water. Our cozy house offers 2 bedrooms (sleeps 5), a spacious living room, and a four seasons room with stunning views. Conveniently located near local attractions, it's the perfect getaway for unforgettable memories! SUMMER BOOKINGS include a detached garage with kitchenette, full bathroom, 3 additional beds (sleeps additional 4 people), a game table, and living space! (AC only)

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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

5.0 out of 5 average rating, 30 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.

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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, 418 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.

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Top Guest favourite

Guest suite in Madison

4.98 out of 5 average rating, 59 reviews

715 N Egan Residence

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

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Top Guest favourite

Home in Madison

5.0 out of 5 average rating, 25 reviews

The Ranch!

Escape to the country and enjoy a relaxing stay in our spacious shouse. Perfect for family getaways, hunting and fishing trips, work stays, reunions, graduation parties, and special events. With plenty of room to gather, comfortable amenities, beautiful sunsets, and peaceful surroundings, you'll find everything you need for a memorable stay. Your home away from home awaits! 2 Camper Spots (Only available May-October) (w/ Additional fee)

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Guest favourite

The exterior of a single-story house features a light-colored facade with a welcoming front porch. A small garage with a star decoration is visible to the right. Lush green grass surrounds the property, complemented by trees in the background.

Home in Brookings

4.91 out of 5 average rating, 194 reviews

Brookings Haven

This home will be all yours when you book! There are three beds, two bathrooms and two different living room areas with TVs to unwind after a long day of sports or work. This house is located near the Hillcrest Aquatic Center so you will be pretty well centrally located. The property has a large patio with a charcoal and gas grill available for guest use and two different kitchen areas.

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Guest favourite

Four lounge chairs are positioned on lush green grass, facing a serene lake scene. The calm water reflects the sky, while boats can be seen in the distance. Trees provide shade, creating a peaceful spot to relax and enjoy the view.

Cabin in Madison

4.92 out of 5 average rating, 99 reviews

Salty Pirate Cabin on Lake Madison

Welcome to The Salty Pirate, a cozy year-round lakefront cabin on beautiful Lake Madison. Enjoy stunning water views, a fully equipped kitchen, washer and dryer, and comfortable furnishings. Relax on the private deck, grill on the patio, or gather around the fire pit in the spacious yard. Perfect for fishing trips, family getaways, or peaceful weekends on lake time.

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Guest favourite

An airy living area showcases large windows that offer sweeping views of Lake Herman. A sleek sofa is positioned to provide comfort, while a modern chandelier hangs from the high ceiling, enhancing the open atmosphere. A stone fireplace adds a cozy touch to the space.

Home in Madison

5.0 out of 5 average rating, 12 reviews

Skeet’s Retreat: Lake Herman Madison, SD Sleeps 8

Relax at Skeet’s Retreat, a remodeled lakefront getaway on Lake Herman near Madison, SD. Sleeps 8 with beautiful lake views, spectacular sunsets, direct shoreline access, a fire pit, Blackstone grill, seasonal dock, and 300 feet of shoreline. Close to Lake Herman State Park, DSU, Lake Madison, local events, fishing, hunting, and Madison-area attractions.

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