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

Charming Cottage - by hospitals & universities

Enjoy a charming Cottage Christmas this year! Great location in a safe & quiet neighborhood by Augustana Univ & Sioux Falls Seminary & a short drive to Midco Aquatics Center, Univ of Sioux Falls, & Sanford & Avera Hospitals. Easy walk to Breadsmith, Bagel Boy, Caribou Coffee, Lewis Drug & HyVee Grocery. 2 bedrooms with comfy queen & standard beds. Large dining room. Deck with grille, patio set, fire pit & bistro lights. Nearby street parking. Dishwasher. Keurig coffeemaker. On-site free laundry.

The Historic Haunted Dairy Coach House (Sept/Oct)

During Sept/Oct we embrace local folklore and turn into the haunted dairy coach house ( enjoy our many creepy antiques) Centrally located in the sleepy town of Colton just minutes away from prime hunting and fishing and just a stones throw away from the biggest city in the state. The cabin sits on the same property as Tellberg's Gym LLC, which guests will also have access to. Forget some essentials for your trip? We are close to retailers. Need a bite to eat? There are several nearby places.

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.

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)

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.

Terrace Park #3

The perfect place to stay for work or play (or a stopover through town)! Curl up in front of the fireplace on the full-sized couch and stream your favorite shows on the 48” LED TV (Netflix only, no cable) or take a break from relaxing and get some work done on the desk. Eat takeout on the high-top table in the kitchen or make your own meal with the full-sized kitchen. The place is fully stocked, from dishes and silverware, fresh towels and sheets, to soap and shampoo.

Private Studio Apartment With Private Entrance

Private studio apartment with separate entrance 1/2 mile off I-90. NOTE: Busy street during business hours, but the apartment is quiet. Fast food, restaurants, grocery store nearby. Features Murphy queen bed, full futon with top bunk, kitchenette w/small sink, microwave, full fridge/freezer, Keurig, toaster, & induction stovetop. Separate bathroom, SMART TV, wifi, AC, heater, coffee and tea, as well as snacks. Towels, washcloths, and toiletries.

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!