Vacation rentals in Winner

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Top-rated vacation rentals in Winner

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite

The spacious living area features vaulted ceilings with wooden beams and large windows allowing natural light. A stone fireplace is located at the center, and a flat-screen TV is mounted above. Two sets of sliding glass doors lead to outdoor views.

Cabin in Chamberlain

5.0 out of 5 average rating, 82 reviews

The Log Cabin

Log cabin just minutes away from the Missouri River, public beach, marina & airport. Plenty of indoor & outdoor space for entertaining. Perfect for family gatherings, fishing & hunting trips. This three-story cabin sleeps up to 15, includes 5 bedrooms, 10 beds, 2 folding beds & 3 bathrooms. Fully loaded kitchen with plenty of seating, front/rear decks and walkout basement. Large loft. Garage game room with mini pool table & foosball. Blackstone Griddle, large yard, swing set & playhouse.

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Superhost

The exterior of the house features a charming two-story design with a dark blue facade. A set of wooden stairs leads to a welcoming entryway, adorned with a small flower planter. Lush greenery surrounds the property, providing a serene atmosphere.

Home in Winner

4.84 out of 5 average rating, 119 reviews

Cozy Little Getaway

*if calendar does not show availability for your desired dates please direct message me regarding availability Relax with the whole family at this peaceful place to stay. Great location, centrally located in Winner. 5 bedroom 1.5 bathroom. Fully stocked with anything & everything you may need for your stay. *Pets are allowed with $50 non-refundable fee. This will be added to your invoice. Pets are allowed in heated laundry room, or in the front porch, not in the main part of the house.

LocationFamilyGrill

Top guest favorite

A cozy living room features a combination of soft furnishings, including a pair of recliners and a mix of sofas. Lighting is provided by side lamps, and artwork adorns the walls, including a mounted deer head. A patterned area rug adds color to the neutral space.

Home in Gregory

4.95 out of 5 average rating, 22 reviews

The Lodge

Located on the Edge of town in Gregory, South Dakota. pop 1250. A great place to stay when visiting the area or family. Large grassy yard, easy to find, clean and comfortable. We have an outdoor space with tables and a grill. Gregory County is in the Pheasant Triangle, Known for Big Whitetail, and is 35 mins from the Missouri River. Pets are allowed Outdoors in the kennel area. Please no pets indoors. Please send us a message if you have any questions or need help with a booking.

LocationFamilyHospitality

Top guest favorite

A rustic living space features a leather sofa, adorned with a decorative blanket. A wooden coffee table, decorated with greenery, sits in front. Exposed wooden beams and a corrugated metal ceiling are visible, along with stairs leading to an upper level.

Barn in Colome

5.0 out of 5 average rating, 26 reviews

The Old Hayloft

Adventure awaits you in this rustic getaway. Just a short drive off of HWY 183 south of Colome to stay in this super cute old hayloft that had been renovated as guest quarters. Stair access externally. This is not handicap accessible and very rustic. It is on the second story. 2 bedroom 1 bath. Full bed in bedroom #1 and a set of twin beds in bedroom 2 and the third bedroom is an open loft (no door up steeper stairs) with another set of twin beds. Total guests is up to 6.

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Superhost

Apartment in Winner

4.89 out of 5 average rating, 9 reviews

Retro Chic Getaway

What do you get when the ’70s and ’90s have a love child? This apartment. Just off Main St in Winner, SD, this 2-bedroom throwback delivers bold vibes with all the essentials. It’s clean, affordable, and perched above a local tech company (tech troubles? Yep—we know a guy). You’ll be steps from restaurants, bars, and—shameless plug—one of the best tattoo shops in the Midwest. Step inside, soak up the patterns, and let nostalgia run wild. Welcome to your vintage getaway!

LocationFamilyIndoor spaces

Superhost

Tiny home in Dallas

N1- Spacious Cottage Getaway |Sleep 8 |Near Dining

The Cottages feature two identical, well-appointed rental units, each sleeping up to 8 guests—ideal for families, friends, or group stays. Enjoy a comfortable, hassle-free visit with all bedding, towels, and home essentials provided. Located just 4 miles west of Gregory, close to local favorites like Frank’s Days and Runors Fine Dining. Units may be booked individually or together. Stay a full week and receive one complimentary night!

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Guest favorite

Home in Chamberlain

4.87 out of 5 average rating, 15 reviews

Welcome to our cozy escape "The Bunkhouse"

Discover your perfect rural retreat in our charming and cozy bunkhouse. Surrounded by the gentle rhythm of farm life and the natural beauty of the open fields. This rustic escape offers a truly peaceful setting to unwind and recharge. Gaze out over endless farm fields, breathe in the fresh country air, and let the quiet, starlit nights wash your worries away.

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Top guest favorite

The living room is arranged with two cozy sofas in various sizes, complemented by decorative cushions. A neutral-toned area rug is placed on the floor, and a flat-screen TV is mounted on the wall. Natural light enters through the window, adorned with simple curtains.

Guesthouse in Winner

4.98 out of 5 average rating, 82 reviews

The Rustic MP6

Relax with the whole family at this peaceful place to stay. two bedrooms one queen bed other full bed. the living room has two sofas with beds in them. they are full size and queen size beds. Just recently added two rollaway beds (twin size) can host up to 5-10 people if you don't mind sharing a bed. no smoking or no pets inside. beautiful view!

ValueFamilyBathroom

Guest favorite

A charming farmhouse exterior is framed by tall trees and a white picket fence. The house features a pitched roof and a porch with large windows, inviting natural light. Grass surrounds the property, creating a serene rural setting.

Home in Winner

4.95 out of 5 average rating, 109 reviews

Grandma’s House - peaceful, 28 miles to Niobrara

Enjoy the peace and quiet of this quaint old farmhouse on a working farm/ranch in the country, 28 miles to Niobrara River in Nebraska, 26 miles to Sparks, for tubing and canoeing, 45 miles to Valentine, Nebraska, 28 miles from Winner, SD. Ask about a camper hookup, outdoor arena for riding, weather permitting, and pens for your horses.

FamilyValueLong stay

Top guest favorite

A cozy sitting area is highlighted by a plush sofa adorned with decorative pillows. A small round table is positioned in front, complemented by a patterned area rug. Wall accents include framed artwork and stylish light fixtures that add a warm glow.

Guest suite in Winner

4.94 out of 5 average rating, 180 reviews

The Hide-A-Way

Have fun in the heart of pheasant country on the east edge of Winner, South Dakota. This newly remodeled space has been converted from an old lumber yard into a homey and comfortable space. It's less than a mile from town and is conveniently located on Us Highway 18. Within walking distance to the drive-in theater and local museum.

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A rustic exterior of a wooden cabin showcases a blend of natural wood and green siding. A flagpole stands prominently in front, with a flag gently waving. Surrounding greenery includes trees and well-kept grass, enhancing the peaceful rural setting.

Cabin in Dallas

4.73 out of 5 average rating, 44 reviews

The Ranch

A little piece of heaven centered right in the heart of pheasant country. This property can house up to 16 people if needed and is very quit and secluded. It sets on a 160 acres of rural property. This site is great for larger family's that like to be outside and there is plenty of room for parking any sized vehicles.

ValueFamilyOutdoor spaces

Top guest favorite

Home in Colome

4.92 out of 5 average rating, 101 reviews

Farmhouse

Farmhouse is in the country. You will be 5 miles from Colome. You will have 3 miles of gravel road that is well maintained. The farmhouse was built in the 1940’s and has old charm. The woodwork is original. There may be some cattle nearby. You will be able to see Buffalo down the road.

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