Holiday rentals in Chester

A studio apartment features a full-sized bed with a light blue comforter. A chair is situated beside the bed, and a small refrigerator is seen next to a television on a stand. Natural light enters through a window, highlighting the neutral-colored walls.

4.91 out of 5 average rating, 125 reviews

Private Little Hideaway

Keep it simple at this peaceful and centrally-located hide-a-way. Be within walking distance from beautiful Downtown Sioux Falls and the Washington Pavillion, but far enough to get away from the hustle and bustle. Only 0.9 miles from Sanford Hospital, 2.0 miles from Avera Hospital, 1.7 miles from the Denny Sanford Premier/Convention Center, & 3.2 miles from the Regional Airport. The host offers transportation to & from the airport for a minimal fee, along with vehicle parking options while gone.

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.

4.84 out of 5 average rating, 185 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

Guest house in Sioux Falls

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.

4.96 out of 5 average rating, 277 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.

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!

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.

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

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.

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.

4.99 out of 5 average rating, 105 reviews

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

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.

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.

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!

Treehouse in Valley Springs

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.

4.91 out of 5 average rating, 355 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.

The exterior of a ranch-style home is showcased, featuring a well-maintained lawn with green grass and decorative landscaping. A wide driveway leads to a two-stall garage with multiple windows. The house is framed by trees and shrubbery, offering a welcoming presence.

4.97 out of 5 average rating, 351 reviews

3 Bed/2 Bath Southside executive manor

Welcome to your peaceful Southside retreat! This 1,488 sq ft ranch offers comfort and convenience with 2 king bedrooms, 2 baths, and a business suite with twin bed and Wi-Fi. Enjoy a cozy living room with 65” TV, fenced yard, deck, and 2-stall garage. Dogs welcome (max 2; see rules under "Other Details to Note"). Sleeps 5 max — 5th guest +$50/night. Ideal for families, professionals, and travelers seeking quiet relaxation near Sioux Falls attractions.

An outdoor seating area features a small patio with a table and two chairs, surrounded by planters of vibrant flowers. The entrance to the building is flanked by two large windows, providing natural light to the space. The grass offers a green backdrop.