Holiday rentals in Chester

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.

Walk to the Lake 2 Bedroom. 2 Bath.

Relax with the whole family at this peaceful retreat. This 2 bedroom, 2 bath will be your home away from home. Fully stocked and ready for your stay! This peaceful home is located so close to so much...You cannot be bored. Unless you want to be! Grab a book and hit the hammock, or drop your boat into beautiful Lake Madison, just a half mile away. Whatever you may choose to do, we'll be ready for you! Please note: This home is not directly on the water. We are a 3 minute walk away.

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.

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.

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.