Holiday rentals in Tripp County

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.

Sign Inn Colome

Welcome to the Sign Inn located on Main Street Colome, South Dakota. Take a step back in time and enjoy the eclectic style of the Sign Inn, which is fully decorated with vintage items and it’s signature local signs, many of which has local roots to the central South Dakota area. Each room and area of the Sign Inn has been curated to tell a story while also providing an updated and comfortable stay to guests. We welcome all guests - hunters and travelers to join us at the Sign Inn.

Robbins Retreats S.A. House

Welcome to your quiet escape in central South Dakota! Step inside to an open living/kitchen area, two bedrooms, and two full bathrooms. Central heat and air keep it comfortable year-round, and all the little touches make it feel like a home away from home. Located just 15 miles outside of Winner, your stay is perfectly positioned for exploring the Missouri River, hunting or just soaking in the serenity. Book now, spots fill fast! Sleeps 5 comfortably | Pet-friendly on request

3 bed Hunter/Cowboy Bunk house in Country

Book this for your family/hunting trip! Older simple house with 3 beds, a couch hide-a-bed, w enough room in one bedroom to add an air mattress. 1 bathroom. Full Kitchen with stove, fridge, micro & dishes. Window AC. Large yard. We even have pens for your horses/cattle and an indoor arena to ride in for additional fees. Dogs welcome but must be kenneled outside. NO smoking. If you want new & fancy, this place is not for you. We offer clean beds in a great rural setting.

Retro Chic Getaway

What do you get when the ’70s and ’90s have a love child? This apartment. Just off Main St in Winner, SD, this 2-bedroom throwback delivers bold vibes with all the essentials. It’s clean, affordable, and perched above a local tech company (tech troubles? Yep—we know a guy). You’ll be steps from restaurants, bars, and—shameless plug—one of the best tattoo shops in the Midwest. Step inside, soak up the patterns, and let nostalgia run wild. Welcome to your vintage getaway!

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 bunks (4 twins) in bedroom #2. Sleeps up to 6.

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!

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.

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.

The Ranch

A little piece of heaven centered right in the heart of pheasant country. This property can house up to 16 people if needed and is very quit and secluded. It sets on a 160 acres of rural property. This site is great for larger family's that like to be outside and there is plenty of room for parking any sized vehicles.

The Boar's Tusk Lodge

Create your own South Dakota adventure at the Boar's Tusk Lodge. This recently finished lodge is all new and set-up to handle sizeable groups and their gear. Every detail has been thought through to provide for an enjoyable stay for guests looking for an elevated experience.

Hidden Creek Lodging #2

We welcome traveling nurses, Construction workers, or just relax with the whole family at this peaceful place to stay! Just a short distance from the hospital, drive in movie theatre, and shopping. RV sites and additional lodging units available.