Holiday houses in Winner

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Top-rated holiday rentals in Winner

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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.

Top Guest favourite
The lodge is depicted with a two-story exterior featuring light gray siding and white trim. A covered front porch with a small set of steps provides access. A star emblem is visible on the side, and the surrounding area includes gravel landscaping.
Home in Oacoma
4.99 out of 5 average rating, 67 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.

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 welcoming exterior of a single-story home showcases a charming front porch illuminated by soft lights. A pathway leads to the entrance, framed by a neatly manicured lawn. Two chairs and a small table offer a cozy seating area under the roof.
Home in Valentine
4.94 out of 5 average rating, 47 reviews

Heart City Cozy

Welcome to Heart City Cozy, this home is a Guest Favorite and we are Super Hosts. You are close to everything when you stay at this centrally-located home right off downtown. Sleep up to 8 with 3 queen beds and a convertible sofa bed. Full kitchen equipped with pretty much everything you need. Laundry room and iron available too… Make it your place to stay, get Cozy and enjoy your stay in the Heart City.

Top Guest favourite
A living area features two comfortable sofas, complemented by decorative pillows. A round table with a plant is set beside a chair. Natural light enters through the window, highlighting the wood flooring and a wall clock, contributing to a cozy ambiance.
Home in Chamberlain
4.95 out of 5 average rating, 58 reviews

American Creek Retreat

Just a block from the Missouri River and walking distance to boat ramps at American Creek Marina.. it’s a 7 bedroom (14 beds) 3 bath home, with large dining room for gathering, full kitchen featuring double oven range and coffee bar, additional upstairs living room and kitchenette bar area, large mudroom for all of your outdoor adventure equipment, and a separate “poker room” / party room and so much more!

Guest favourite
The spacious kitchen features wood cabinetry, a central island with a sink, and modern appliances, including a dishwasher. Adjacent to the kitchen, a dining area is visible, showcasing a large table with ample seating. Soft pendant lighting illuminates the space.
Home in Valentine
4.88 out of 5 average rating, 17 reviews

The Kozy Kottage

Welcome to The Kozy Kottage, our home away from home. We look forward to hosting you in this space we have created to encourage some of our favorite things - relaxing mornings filled with good coffee, cooking favorite meals together, gathering with family and friends to visit or play games, and nights of peaceful rest. We hope you will feel as comfortable here as we do!

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