Holiday houses in Chester

Relaxing and peaceful Cabin on Brant Lake.

Relax with the whole family at this peaceful cabin on Brant Lake. Fully furnished and ready for you and your family or friends to enjoy some time away! Only 35 minutes from Sioux Falls! Large deck with lots of seating and lower patio for sitting as well. Enjoy watching the sunset from the deck or roasting marshmallows in one of our 3 fire pits. Lots of room to hang out either inside or out. **the dock will not be in the water until Memorial Day and will be out of the water Labor Day weekend *

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.

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.

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.

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, golf course, Midco Aquatics, & Great Plains Zoo. Prime location near vibrant & expanding downtown with sculpture walk, breweries, & live music.

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

3 Bed/2 Bath Southside executive manor

This 1,488 ft², 2+ Bed 2 Bath ranch with business suite accommodates 5 guests and is located in the coveted southside in a quiet neighborhood. Master has a king bed, bath, and walk-in closet. 2nd Bed has king bed. 3rd room has a twin bed and is equipped with desk and, high-speed Wi-Fi. The living room and kitchen with TV, gas fireplace. 2 stall garage. Deck with outdoor eating. Fenced backyard. Dogs welcome here! There is a $50/day charge for 5th guest and one-time $30 pet charge/stay.

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.

Peaceful 2 BR w/ King Bed, 9 Min to Downtown

Clean 2 bedroom with a full kitchen and off-street parking! Blackout curtains, fans & mirrors in each bedroom, door code access, dishwasher & washer/dryer will make your stay comfortable. The entire left side of the duplex is yours to use. You have your own entrance, full kitchen, living area, two bedrooms, bathroom, deck & laundry. The kitchen and living area are on the main floor; bedrooms & bath on the 2nd floor. The kitchen is fully furnished including a Keurig & Instant Pot.

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!

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.