Holiday houses in Winner

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Top-rated holiday rentals in Winner

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Top Guest favourite
A spacious exterior of the cabin is presented, featuring a light gray façade with large garage doors. A gravel driveway leads to the entrance, while a well-maintained lawn and clear blue skies complete the serene landscape.
Cabin in Chamberlain
4.97 out of 5 average rating, 77 reviews

Chamberlain 2 Bdrm Cabin, with Man Cave, sleep 4-6

2 bedroom cabin connected to the heated man cave includes a kitchen, dining table, microwave, sink, refrig, oven; 1 bedroom with queen bed, 1 bedroom with bunk beds , a pull-out sofa in living room, and full bathroom. Washer & dryer available. Large gravel parking lot pull thru Cabin sits on 3-acre lot with wildlife, impeccable views of Missouri River and the sunset. The property is quiet, away from crowds, offers easy access from Hwy 50, Close to American Creek Marina, downtown Chamberlain

Top Guest favourite
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 out of 5 average rating, 65 reviews

The Log Cabin

Log cabin just minutes away from the Missouri River, public beach, marina & airport. Plenty of indoor and outdoor space for entertaining. Perfect for family gatherings, fishing and hunting trips. This This three-story cabin can sleep up to 14, includes 5 bedrooms, 10 beds and 3 bathrooms. Fully loaded kitchen with plenty of seating, front/rear decks and walkout basement. Large loft. Garage has game room with mini pool table & foosball. Outdoor propane grill, large yard, swing set & playhouse.

Guest favourite
A spacious living room is presented with a brown leather sectional sofa, a comfortable armchair, and a patterned area rug. A dining table with chairs is visible in the background, complemented by natural light from nearby windows.
Home in Valentine
4.87 out of 5 average rating, 94 reviews

Valentine’s Tourist Tenure

Valentine’s Tourist Tenure is Located right off HWY 97 on your way to Merritt Dam. We would love to host you during your time in the Heart City! Our cozy little space has all that you will need for time away and we aim to make you to feel right at home. It is located close to the Bait shop and all of the restaurants, gas stations, Scotty’s Ranchland Foods, and more. There is plenty of room on the property for parking your RV, trailer, or boat as well. We can’t wait to host you for you stay!

Guest favourite
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
4.94 out of 5 average rating, 18 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.

Guest favourite
The two-story green house, built in a traditional style, displays a well-kept front yard with a manicured lawn. A white picket fence frames the entrance. Distinctive architectural details on the upper level, including large windows and decorative trim, highlight the home's charming character.
Home in Valentine
4.86 out of 5 average rating, 14 reviews

Annie's House

This lovely home was built in 1890 for Mr. Charles Hiram Cornell. He was a Nebraska State Senator in 1888 and was also the Founder of the First National Bank in Valentine, as well as Cornell Dam With a great central location, the house is within walking distance to local restaurants, coffee shops, and shopping. Owned by one family since the 1950’s, it is named for my mother Annie, who loved living here. Please enjoy making your own memories in this home, and in the Heart City!

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, 8 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.

Top Guest favourite
A covered patio area features a mix of red and green outdoor seating options, inviting relaxation. The exterior of the dwelling is a muted green with a metal roof, surrounded by natural landscaping. A light-colored concrete surface is visible in front of the entrance.
Tiny home in Platte
4.99 out of 5 average rating, 150 reviews

Carriage House - Private Dwelling. 3 beds, 1 bath

The Carriage House is a private, separate dwelling located on the property of Molly's Manor B&B. Unique and comfortable, 525 sq. ft. No step entry. Main floor includes a bedroom with one Queen-size bed, a cozy living room, fully equipped kitchen with appliances and cookware, and bathroom with a large shower; W/D. Two full-size beds in the upstairs loft, including a futon. Non-smoking, pet-free. Minisplit for AC/heat, Smart TV and WiFi. Plenty of parking for vehicles/boat.

Guest favourite
The exterior of a modern duplex is highlighted, featuring a wooden facade and large windows. A gravel driveway is visible, with ample outdoor space surrounded by fencing and trees. The entrance is adorned with a welcoming sign, inviting guests into the property.
Townhouse in Pukwana
4.99 out of 5 average rating, 71 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
A modern river cabin is pictured from the front, featuring a metal roof, wood siding, and a spacious porch with a railing. A gravel driveway leads up to the attached garage, surrounded by grassy areas and trees, under a cloudy sky.
Cabin in Platte
4.93 out of 5 average rating, 56 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
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
4.99 out of 5 average rating, 74 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 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, 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
A spacious living area showcases a mix of comfortable seating and a dining space that accommodates six. Natural wood accents offer a warm ambiance, complemented by decorative wall-mounted animal mounts. The open layout includes a well-equipped kitchen, enhancing the inviting setting.
Home in Chamberlain
4.99 out of 5 average rating, 170 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.

Popular amenities for Winner holiday rentals

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