Vacation rentals in Chester

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

Cozy Flat - near hospitals & universities

Cozy, clean and chic apartment down a flight of stairs in lower level of triplex near Augustana University, University of Sioux Falls, North American Seminary, Sanford & Avera Hospitals, and Midco Aquatics Center. Centrally located close to downtown & an easy drive to Empire Mall & Great Plains Zoo. Electric fireplace. Access to deck with bistro lighting and fire pit in backyard. Clean and safe neighborhood. Same floor laundry access. WiFi and ChromeCast streaming. On street parking available.

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.

Casalona: Cozy Designer-Curated Central Retreat

Charming mid-century home in the heart of Sioux Falls, steps from Augustana and close to Sanford and downtown. Guests have private access to the front of the house, including two bedrooms, a spacious living room, and full bath. With natural light, cozy furnishings, and greenery, the space feels inviting. Styled with vintage, Moroccan, Japanese, and Scandinavian influences, this thoughtfully designed home offers a peaceful, inspiring place to stay for travelers seeking comfort, style, and home.

McKennan Park Cottage/Patio fireplace and hot tub.

We offer you a beautiful garden cottage setting with a guest apartment (w/ private access) in the lower level of our home. Guests have private access to hot tub, fire place and backyard garden patio until 11 pm. Walking distance to downtown. Our home is a safe space for folks from all minority and marginalized groups. We welcome guests of all races, faiths, genders, and sexual orientations. ***Note that we only accept guests with good reviews/no red flags from previous AirBnB hosts.

Cozy Chalet without the Mountains

Have you ever heard the phrase, "Tiny, but Mighty"? That is this house! The bedroom is an open loft that can be found at the top of the spiral staircase on the 2nd floor. There is fast wifi, off street parking for 2 vehicles, a fireplace, desk and washer/dryer combo. We are centrally located near downtown shopping and nightlife, 7 minutes from the airport, 3 minutes to Sanford PREMIER Center, and under 10 minutes from both hospitals. The house has all you need...you may never want to leave!

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.

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.

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, Midco Aquatics, & Premier Event Center. Prime location near vibrant & expanding downtown with sculpture walk, breweries, & live music.

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.

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.

Home away from home

Newer house in a nice residential neighborhood. Close to skiing and car race track NO CLEANING FEES Space available for Airbnb rental is the main part of the house. Owner has a separate apartment in the basement with a separate entrance. There is a lock on both sides of the door going to the basement at the bottom of the stairs. I will always try to be respectful of your privacy. If you do need anything let me know and I will make myself available.