Holiday rentals in Chester

Summit Loft - cozy & centrally located

Centrally located gem! Across street from Augustana Univ, just blocks from the Univ of Sioux Falls, SF Seminary & Caribou, easy drive to Sanford & Avera Hospitals & Midco Aquatics Center. Double bed & futon. Onsite laundry in the lower level. The Loft has its own separate entrance up exterior steps on the 2nd level of a residential home with keyless entry. Hi speed internet & desk & smart TV. Keurig coffee maker. Fire up the grill & relax on the deck surrounded by bistro lights in the evening.

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.

The Marybeth - 2Bdrm/2Bath Townhouse w/Garage

Spacious 2 bdrm/2 bath town home on west side Sioux Falls! Nice big picture window in the living room overlooking the large pond. Remote controlled exterior awning over the patio & exterior shade on living room window for added privacy! Nice kitchen w/plenty of counter top & cabinet space! Master BdRm w/ a King Bed, hosts a very nice bath with in floor heat, standard closet plus a walk in closet! Second BdRm w/ Queen Bed & bath are nicely sized. Amazing two stall garage and fenced backyard!

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

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.

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.

The Tree House: Solarium, Hot Tub, Family-Fun

SoDak Stays is proud to present the one-of-a-kind Tree House! -Two-story solarium perfect for enjoying all the seasons of South Dakota -Sleeps 12 people, perfect for families and groups! -5 min drive to downtown Sioux Falls -Hot tub (available year-round), firepit, grill, outdoor toys + playset -Fully-fenced in backyard (pets welcome!) -Local murals + artwork around every corner of the house -Baby/kid amenities: toys, pack-n-play, booster seat + kids' dinnerware

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.

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!