Vacation rentals in Chester

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Top-rated vacation rentals in Chester

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Top guest favorite

A spacious townhome exterior is highlighted, showcasing a two-stall garage with a well-maintained facade. Lush green grass surrounds the home, complemented by decorative plants along the pathway. The sky displays soft hues of pink and orange, indicating either dawn or dusk.

Townhouse in Sioux Falls

4.97 out of 5 average rating, 412 reviews

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!

Guest favorite

Tiny home in Colton

4.73 out of 5 average rating, 133 reviews

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.

Superhost

A charming two-story house is presented with a light-colored exterior and dark shutters. The welcoming front door, adorned with a decorative mold, is flanked by two green windows. A neat driveway leads up to the home, bordered by fresh landscaping.

Home in Sioux Falls

4.84 out of 5 average rating, 361 reviews

Cozy Chalet without the Mountains

Have you ever heard the phrase, "Tiny, but Mighty"? That is this house! The bedroom is an open loft that can be found at the top of the spiral staircase on the 2nd floor. There is fast wifi, off street parking for 2 vehicles, a fireplace, desk and washer/dryer combo. We are centrally located near downtown shopping and nightlife, 7 minutes from the airport, 3 minutes to Sanford PREMIER Center, and under 10 minutes from both hospitals. The house has all you need...you may never want to leave!

Superhost

The exterior of a rustic log cabin is presented, featuring a spacious deck with outdoor furniture. A manicured lawn extends in front, bordered by a line of smooth stones. Large windows reflect the surrounding greenery, while the driveway and garage are visible to the right.

Home in Madison

4.92 out of 5 average rating, 100 reviews

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

Top guest favorite

A spacious living area features polished cement flooring and features a wooden dining table with white chairs. A comfortable futon is positioned nearby with a soft blanket draped over it. Sliding barn doors add rustic charm, and a ceiling fan contributes to airflow.

Home in Sioux Falls

4.97 out of 5 average rating, 162 reviews

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.

Guest favorite

A cozy living room features a large leather sofa adorned with decorative pillows, complemented by a light wooden coffee table. Natural light fills the space through multiple windows, highlighting the textured area rug beneath. Decorative plants add a touch of greenery to the inviting atmosphere.

Home in Sioux Falls

4.96 out of 5 average rating, 673 reviews

Casalona | Central • Boho, Mid-Mod Stay w/ Sunroom

Charming mid-century home in the heart of Sioux Falls, perfectly located steps from Augustana University, close to Sanford, downtown, and Falls Park. This stylish retreat features a bright sunroom overlooking native wildflower gardens, lush plants, cozy living spaces, and a movie projector for relaxing nights in. Designed with thoughtful details and a unique blend of vintage, Moroccan, Japanese, and Scandinavian styles, it’s a peaceful, inspiring place to call home during your stay.

Guest favorite

The treehouse is elevated on a sturdy platform, surrounded by snow-covered landscape and trees. The structure features a wraparound deck with a metal railing and a sloped roof, allowing for unobstructed views of the environment. Morning light casts a soft glow over the scene.

Treehouse in Valley Springs

4.91 out of 5 average rating, 326 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.

Top guest favorite

A charming house is displayed beneath a clear blue sky, featuring distinctive architectural details such as decorative wooden trim and large windows. The exterior is painted in light colors, complemented by red brick accents at the base, surrounded by well-maintained lawns and greenery.

Guest suite in Madison

5 out of 5 average rating, 17 reviews

715 N Egan Residence

Welcome to your cozy retreat in the heart of Madison! This private entry/exclusive 1-bedroom, 1-bathroom unit offers a comfortable and convenient stay just across the street from Dakota State University. Private entry with code lock access ensures smooth check-in. Perfect for visiting parents, professors, or students. Whether you’re here for a weekend visit or an extended stay, this Airbnb provides a peaceful home base for your adventures. We look forward to hosting you!

Superhost

The exterior of a barn-style building is presented, featuring a light grey facade with a metallic roof. Three large garage doors are visible, providing access to the lower level. A decorative quilt block hangs on the side, and a stone marker by the entrance displays 'Sunda Farm.'

Barn in Madison

4.89 out of 5 average rating, 109 reviews

Farm Barn Loft

Located in a farming community in Eastern South Dakota. Just a few minutes from Madison, stay in our barn loft. 1300 sq ft. space includes a private bedroom, bathroom, couch, bar area, and game table. You can also enjoy a game of ping pong, pool/snooker (adults only), and coin-operated pinballs. While on the farm you're welcome to see our animals. This is a working farm and you will get to experience the daily activities. Come see this unique setting.

Top guest favorite

An outdoor seating area features a small patio with a table and two chairs, surrounded by planters of vibrant flowers. The entrance to the building is flanked by two large windows, providing natural light to the space. The grass offers a green backdrop.

Apartment in Sioux Falls

4.98 out of 5 average rating, 595 reviews

Private Home for your rest and leisure!

My place is close to the airport and right off of interstate I-90.. You’ll love my place because of the coziness, the location, and the family friendly neighborhood.. My place is good for couples, solo adventurers, families (with kids),I live in the country so my WIFI is a MIFI JET PACK .. so it’s not perfect so if you need to work or depend on wifi it may not be a good fit unless you have unlimited WIFI . and as of 2022 i am no longer allowing pets.

Top guest favorite

The exterior of a newer house is presented, featuring a light-colored facade with stone accents and a spacious driveway leading to a closed garage door. A wooden deck is visible at the entrance, surrounded by grassy areas and partly cloudy skies.

Apartment in Sioux Falls

4.97 out of 5 average rating, 391 reviews

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.

Top guest favorite

A cozy living area features a comfortable futon and a twin-sized bunk above, adorned with colorful patterned pillows. A television is mounted on a white media console, complemented by a decorative rug and vibrant curtains. Soft seating is provided by a beige armchair.

Guest suite in Brandon

4.97 out of 5 average rating, 642 reviews

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.