Vacation rentals in Winner

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Top-rated vacation rentals in Winner

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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 out of 5 average rating, 64 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 favorite
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 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
4.94 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 favorite
The exterior of a single-story house is visible, featuring a combination of warm wooden siding and a green metal roof. A patio area with chairs and an umbrella is situated beside the entrance, surrounded by a well-maintained grassy area.
Home in Springview
5 out of 5 average rating, 11 reviews

Where the Wild Things Are

Come visit our house just north of the Niobrara River in the little community of Springview, NE. Where the wild things run - around here you can find antelope, elk, whitetail deer, mule deer and so much more. We offer three bedrooms and two bathrooms, washer/dryer, full kitchen with the necessary cooking utensils, grill, heat/AC, and your own TV in every room. We are finishing up a remodel winter 2024. Family Friendly. Come visit and see all of what northern Nebraska has to offer.

Guest favorite
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
4.85 out of 5 average rating, 13 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 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 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.

Guest favorite
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.

Top guest favorite
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
4.93 out of 5 average rating, 46 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 favorite
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!

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
4.99 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 a rollaway bed (twin size) can host up to 5-9 people if you don't mind sharing a bed. no smoking or no pets inside. beautiful view!

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, 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 favorite
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, 169 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 vacation rentals

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