Holiday rentals in Chester

4.94 out of 5 average rating, 17 reviews

Cabin 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 *

4.97 out of 5 average rating, 135 reviews

Cozy Flat - near hospitals & universities

Cozy, clean and chic apartment down a flight of stairs in lower level of triplex near Augustana University, University of Sioux Falls, North American Seminary, Sanford & Avera Hospitals, and Midco Aquatics Center. Centrally located close to downtown & an easy drive to Empire Mall & Great Plains Zoo. Electric fireplace. Access to deck with bistro lighting and fire pit in backyard. Clean and safe neighborhood. Same floor laundry access. WiFi and ChromeCast streaming. On street parking available.

4.97 out of 5 average rating, 619 reviews

Guest suite in Brandon

Private Studio Apartment With Private Entrance

Private studio apartment with separate entrance 1/2 mile off I-90. NOTE: DETOUR for I-90 EAST IS IN EFFECT. 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.

4.84 out of 5 average rating, 353 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!

4.96 out of 5 average rating, 126 reviews

Suite Spot

Central location close to Avera, Sanford & VA Hospitals, Augustana & Univ of Sioux Falls, Midco Aquatics & Hockey Complexes, straight shot down Phillips Ave to Downtown, restaurants & Pavilion, close to grocery store, fast food restaurants, coffee shops, bakery & drug store. Quiet & safe neighborhood, driveway parking, private side entrance down 12 steps to lower level apartment with full windows. Perfect for visiting nurses & medical professionals. Hosts Iive on main level. Shared laundry.

4.96 out of 5 average rating, 250 reviews

Home in Renner

RIVER VALLEY RETREAT

“RVR” is 5 peaceful acres in the country overlooking the Sioux River valley, just 3 mi north of the Sioux Falls city limits & I-29/I-90; 4 & 5 mi straight north of the Sanford Pentagon & Premier Center. Guests enjoy a SUNRISE each morning from all 5 bedrooms, the 30’x40’ common area Great Room/Kitchen, lower level British pub & parlor, 14’x40’ patio, 12’x40’ deck, covered deck, enclosed porch, & the 12’x16’ back deck. The last breath of every SUNSET is seen from half of those areas! Enjoy!

4.97 out of 5 average rating, 126 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.

Treehouse in Valley Springs

4.9 out of 5 average rating, 295 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.

Superhost

Barn in Madison

4.91 out of 5 average rating, 103 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.

4.98 out of 5 average rating, 576 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.

4.94 out of 5 average rating, 196 reviews

Loft in Flandreau

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!

4.94 out of 5 average rating, 230 reviews

Tree House: 2-story sunroom, 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 -Saltwater Hot tub (available year-round), firepit, grill, outdoor toys + playset -Local murals + artwork around every corner of the house -Baby/kid amenities: toys, pack-n-play, booster seat + kids' dinnerware

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Other great holiday rentals in Chester

4.89 out of 5 average rating, 36 reviews

The Bird's Nest

Binti URating, 5 stars3 weeks ago

I loved my stay at Regina’s place. It was cozy, calm, and clean. She communicated very well and it was an overall great experience. I recommend this place.

5 out of 5 average rating, 11 reviews

Home in Madison

Enjoy Our Newly Renovated Home: Summit Splendor

MegRating, 5 stars3 weeks ago

Jeanne and Mark were welcoming and responsive. The home appears to be recently redone and the craftsmanship and attention to detail were amazing. Our family felt right at home! Thanks for the impeccable hospitality, Jeanne!

4.92 out of 5 average rating, 12 reviews

Northwest Sioux Falls-New Home 2 bed/2 bath!

Jan MarieRating, 5 stars4 weeks ago

The house was perfect for our 4 night stay!Amy responded quickly with my questions before we arrived. The house was well stocked and the location was perfect! Would love to return to Amy’s place!

5 out of 5 average rating, 15 reviews

Home in Hartford

Under The Oak Tree 2BR Home & Garage in Hartford

ErinRating, 5 stars1 week ago

My boyfriend and I were passing through and needed a place to stay. It was a perfect location, safe neighborhood and Whitney was amazing! Great directions and helpful tips.

4.96 out of 5 average rating, 56 reviews

Guest suite in Brandon

Serene farm stay guest suite

NicholasRating, 5 stars3 days ago

By far one of the best AirBnb's I have stayed at. Stephanie was super helpful and greeted us when we pulled up. It was a scorcher of a day and the unit was nice and cold for us to cool off when we checked in. The property was beautiful and the unit was clean. Will definitely rebook if we ever find our selves back out that way.

Superhost

4.7 out of 5 average rating, 27 reviews

Studio close to downtown

BrittanyRating, 5 stars4 days ago

My friend and I stayed here on our road trip to badlands, it was perfect for what we needed! Tim was responsive and flexible with us, which we greatly appreciated. I’d definitely recommend staying here!

5 out of 5 average rating, 50 reviews

Home in Larchwood

A River House Near Sioux Falls

MrsRating, 5 stars2 weeks ago

My siblings and I take a trip every year, they really love fishing so I had to reserve a house on the lake. Fishing was great, some fish weighed 8 to 10 pounds; This was our biggest haul ever. We caught buffalo, carp, and of course, catfish. It was like heaven. The Home was beautiful, beds were comfortable, plenty of extra lien and everything was clean. The kitchen was a common area, we cooked every day, breakfast and dinner. The island sat 8 to 10 People marble countertops, with great lighting that led into the living room. The open space allowed everyone to be seen collectively. We ate dinner at the dining table nightly, the eight seats accommodated everyone. Bedrooms were spacious, three full bathrooms, television’s everywhere all 4K. Did I say it was absolutely amazing. We are glad we selected this home and would love to revisit. Our host Holly gave great recommendations, guided us, responded expeditiously, and was very professional. I will give this 10 stars if I could.