Holiday houses in Chester

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Top-rated holiday rentals in Chester

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

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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

4.97 out of 5 average rating, 290 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!

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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, 118 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, 126 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, 42 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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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, 427 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

Home in Beaver Creek

4.97 out of 5 average rating, 124 reviews

Country Escape: Large Family Home near Sioux Falls

Welcome to Country Escape! Relax with the whole family at this peaceful getaway in the country. Located near the small town of Beaver Creek, MN, this home away from home will provide a quiet respite from the busyness of life. Surrounded by corn and soybean fields, you will get a taste of true country life. About 1 mile south of Interstate 90, and just across the Minnesota/South Dakota border, it's a short 20 minute drive to/from East Sioux Falls, SD.

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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, 239 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!

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Top Guest favourite

Guest suite in Madison

4.98 out of 5 average rating, 63 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, 30 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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Top Guest favourite

A spacious lakeside property is set against a clear blue sky, featuring a deck lined with seating. A boat dock is visible in the water, accompanied by a canopy. Towering trees provide shade, enhancing the natural environment surrounding the home.

Home in Chester

5.0 out of 5 average rating, 65 reviews

Brant Lake Escape

Get away from it all at the Brant Lake Escape! Enjoy all the luxurious amenities at the property. Including a game room, hot tub and 90 inch tv ready to stream! Enjoy the South Dakota fresh air and relax on the lily pad or splash around with numerous floats. Get active with the kayaks, stand up paddle board or fishing poles. Make s’mores at either of the two outdoor fireplaces (gas or wood burning). Dock is in the lake seasonally.

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Guest favourite

A spacious two-story house is depicted with an expansive deck overlooking rolling hills. A gravel driveway leads up to the home, which features a mix of wood and stone accents. Multiple entrances are visible along the side of the building, accessible via a few steps.

Home in Baltic

4.93 out of 5 average rating, 81 reviews

Ranch House: 70 Acres, Horses, Hot tub, Sleeps 15

Enjoy your peaceful getaway at The Ranch House! • 70-acre horse ranch 20 minutes from Sioux Falls • Large group ready - sleeps 15 people • Experience ranch life with horses • Two kitchens + bonus kitchenette • Two large living rooms • Hot Tub under the stars! • Five smart TV's throughout the house • 5 bedrooms + 5 bathrooms • Perfect for retreats or multi-family trips! Book your your stay before this one fills up!

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