Holiday rentals 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 *

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

Lakeside Getaway Just West of Sioux Falls

A hidden gem tucked into the inlet of Wall Lake, just 10 minutes west of Sioux Falls, SD! Not only a fishermen’s paradise, it’s also great for a calm kayak or paddle board ride, or venture straight out into the lake to enjoy a swim. At night enjoy roasting marshmallows by the fire and lounging in a hammock. The sunsets over the farmland will take your breath away. In the winter, enjoy your own private ice skating rink. The perfect getaway for a family and stocked with baby gear if needed.

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.

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)

Luxury Suite • Private Yard • Hot Tub • King Bed

Welcome to The Chic Suite — a fully private, luxury guest suite designed for rest, convenience, and quiet comfort. Featuring a plush king bed, rainfall tile shower, secluded fenced yard, and your own hot tub, this space is perfect for business travelers, quick overnight stays, and couples looking for a peaceful retreat in northwest Sioux Falls. Tucked behind the main home garage with its own entrance, walkway, and outdoor space — you’ll have complete privacy during your stay.

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.

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.

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!