Vacation rentals in Chester

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Top-rated vacation rentals in Chester

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

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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, 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.

Guest favourite

The living room features midcentury modern furniture, including a sofa facing a 55" Smart TV. Natural light floods in from large windows. A wooden coffee table is complemented by decorative accents. The open layout leads to a dining area visible in the background, enhancing the inviting space.

Home in Sioux Falls

4.95 out of 5 average rating, 150 reviews

Downtown Apt | Completely Private | Extended Stay

Spend your time in Sioux Falls at one of the highest rated Airbnb’s! Located in the heart of town within walking distance to Downtown, Phillips Avenue, Starbucks, nightlife, excellent restaurants, and more! EXCELLENT REVIEWS! Explore the entire city as we are centrally-located. Minutes away from Airport, Falls Park, Avera & Sanford hospitals, The VA, Sanford Sports Complex, Premier Center, USF, and Augustana. Experienced hosts who strive to give you the best stay possible! Inquire today!

Top guest favourite

A spacious living area is furnished with a light brown couch adorned with red accent pillows, complemented by a wooden coffee table. The room features a dark accent wall, framed pictures, and ample natural light from a nearby window, creating a comfortable setting.

Apartment in Sioux Falls

4.94 out of 5 average rating, 150 reviews

Suite Spot

Central location close to Avera, Sanford & VA Hospitals, Augustana & Univ of Sioux Falls, Midco Aquatics & Hockey Complexes, straight shot down Phillips Ave to Downtown, restaurants & Pavilion, close to grocery store, fast food restaurants, coffee shops, bakery & drug store. Quiet & safe neighborhood, driveway parking, private side entrance down 12 steps to lower level apartment with full windows. Perfect for visiting nurses & medical professionals. Hosts Iive on main level. Shared laundry.

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 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.

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

4.97 out of 5 average rating, 32 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)

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, 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, 24 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!

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 out of 5 average rating, 58 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.