Vacation rentals in Winner

Entire house for fishing, hunting, or passing by!

Perfect location for the outstanding fishing on the Missouri River and the great deer and pheasant hunting that Gregory county is known for! Within 15 to 25 minutes of four different boat ramps on the river! Double carport to keep your boat or vehicles under cover! Located on five lots so plenty of room to park or just enjoy the outdoor room. Quiet small town with extremely friendly residents! Also perfect for anyone just passing by for the night! “N0”TV in house or Wi-Fi but great cell service.

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.

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.

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.

Barn overlooking the Niobrara River

Get away from it all when you stay under the stars at Lucky Creek Barn. With beautiful views of the Niobrara River and Pine Ridge, you are fully immersed in nature. Sip your coffee while listening to song birds and watching whitetail deer or turkeys in their natural habitat. You can splash and play around in the Niobrara River right within walking distance or take a day trip to tube or kayak further upstream. Come explore the Niobrara River Valley in this ultra relaxing setting!

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.

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.

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.

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!

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.

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.

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.