Holiday houses in Tripp County

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Top-rated holiday rentals in Tripp County

Guests agree: these stays are highly rated for location, cleanliness and more.

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Cabin in Witten Township
4.33 out of 5 average rating, 3 reviews

Witten Lodge

Discover the charm of Witten Lodge, offering a serene getaway with all the comforts of home. This quirky retreat features 4 bedrooms, 2 bathrooms, and is equipped with essentials for a hassle-free stay. Enjoy modern conveniences like a washing machine, air conditioning, general heating, wireless internet, a fully equipped kitchen with a stove and refrigerator. Perfect for families or groups seeking a peaceful escape in nature. Pet Friendly upon request - only available outside. No Smoking.

Superhost
Home in Winner
4.84 out of 5 average rating, 106 reviews

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.

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, 10 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.

Apartment in Winner
5 out of 5 average rating, 4 reviews

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!

An aerial view of a large white and gray barn with a metal roof, surrounded by green pastures. Adjacent to the barn, a series of pens are visible. Gravel pathways lead to additional structures and parking areas, creating a rural setting.
Place to stay in Colome

RV hookups at Bucking Bull Arena. Pens avail.

We offer 30amp hookups next to our indoor bucking bull facility. Pens available also for additional fee for your horses/livestock. Hookups are on right (east) side of big white and gray barn. There are three separate 30amp plugs. No sewer. There is water if you need to add some to your unit Portapotty on site most of summer. Showers/bathroom available in bunkhouse if not occupied.

Top Guest favourite
Guesthouse in Winner
4.99 out of 5 average rating, 75 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
Guest suite in Winner
4.95 out of 5 average rating, 165 reviews

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.

Cabin in Dallas
4.72 out of 5 average rating, 43 reviews

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.

Cabin in Winner

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.

Superhost
Home in Colome
5 out of 5 average rating, 3 reviews

Home in Colome

Perfectly situated for your next hunting adventure! This charmingly rustic house features 3 bedrooms and 2 full baths, offering ample space for your whole group. While the decor is traditional and simple, it's equipped with all the essentials for a smooth, hassle-free stay.

Superhost
Home in Winner

Hidden Creek RV Park and Lodging #3

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.

Popular amenities for Tripp County holiday rentals