Holiday houses in Winner

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Top-rated holiday rentals in Winner

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

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Top Guest favourite
Home in Oacoma
4.99 out of 5 average rating, 70 reviews

River Shore Rentals

Gorgeous views of the Missouri River from the HUGE front porch!! The lodge can host up to 16 people with plenty of living and outdoor space to enjoy your stay. 4 bedrooms, 8 beds, 2 full baths and a beautiful, fully supplied kitchen and dining for 8. Great place for family gatherings, hunting, or fishing!! The lodge sits right across the street from the Cedar Shore Marina and boat ramp. There is a bike path across the street that extends for miles for you to enjoy views of the Missouri River.

Superhost
Home in Winner
4.84 out of 5 average rating, 108 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.

Top Guest favourite
Home in Gregory
4.95 out of 5 average rating, 21 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.

Top Guest favourite
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 out of 5 average rating, 16 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.

Guest favourite
The exterior of a wooden duplex is illuminated at night, showcasing its modern architecture. A large circular window is centered on the front, flanked by two slender trees with soft lighting. A wooden bench sits on a gravel pathway, enhancing the inviting entrance.
Townhouse in Pukwana
4.99 out of 5 average rating, 73 reviews

2 bdrm, 3 bed, fncd pvt yard, no pet fee!

Duplex built in 2016, each unit has their own fenced-in yard, washer/dryer, microwave, A/C. Upstairs unit shown is a 2 bed, 1 full bath, w/ queen Temperpedic bed in master and twin over full bunk bed in 2nd bedroom, leather feather couch, patio table & chairs, firepit. 10 min. to Chamberlain schools, hospital & nursing home. Less than 5 min to Interstate I-90 and highway roads leading to Chamberlain and Ft. Thompson. This unit is upstairs.

Guest favourite
Cabin in Platte
4.93 out of 5 average rating, 59 reviews

Twin Pine River House

Relax with the whole family at this peaceful river cabin. Located on the Missouri River hills near Platte Creek Recreation Area near Platte, SD. Enjoy all this area has to offer: fishing, boating, beaches, hiking, pheasant hunting, deer hunting, turkey hunting, ice fishing. Newly finished garage with air conditioning and heat, very pet friendly. Looking to relax, enjoy the beautiful sunrises on the front porch or sunsets on the back deck.

Top Guest favourite
A panoramic view captures the Niobrara River winding through the expansive valley. Pine trees in the foreground frame the serene landscape, characterized by rolling hills and a vast sky. The image conveys a sense of natural tranquility and open space.
Cabin in Sparks
5 out of 5 average rating, 24 reviews

Muleshoe Creek Guesthouse overlooking the Niobrara

Take it easy at this unique and tranquil getaway. Overlooking the Niobrara River Valley you are minutes away from floating the Niobrara National Scenic River, exploring Smith Falls, hitting up a Norden dance, or golfing one of the many golf courses in north central Nebraska. These are just a few of the adventures that await. Some same day bookings are not available depending on our schedule that day.

Guest favourite
Guesthouse in Winner
4.99 out of 5 average rating, 75 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!

Guest favourite
A charming farmhouse is set amidst tall trees, featuring a white picket fence enclosing a grassy yard. The structure showcases a classic design with a metal roof and windows that reflect the surrounding nature.
Home in Winner
4.95 out of 5 average rating, 103 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.

Top Guest favourite
Home in Chamberlain
4.99 out of 5 average rating, 175 reviews

Racquet on Elm Street

Welcome to Racquet on Elm St. Situated in a quiet neighborhood just minutes from the Missouri River/Lake Francis Case, this lodge-style home is designed for comfort, relaxation and fun. This spacious 3BR/2.5BA home, spanning over 2,400 square feet, was completed in April 2019 and includes its very own private attached racquetball court.

Top Guest favourite
Guest suite in Winner
4.95 out of 5 average rating, 166 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.

Guest favourite
Cabin in Valentine
4.83 out of 5 average rating, 6 reviews

The Cozy Cabin Close to Town

Relax with the peace and quiet at this cozy cabin minutes from downtown Valentine. Enjoy getting away from it all but being conveniently close to everything we have here to do here in the Sandhills. The cabin offers a spa experience with a soaker tub and dry sauna to make relaxation even easier.

Popular amenities for Winner holiday rentals

  1. Airbnb
  2. United States
  3. South Dakota
  4. Tripp County
  5. Winner