Vacation rentals in Tripp County

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Top-rated vacation rentals in Tripp County

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

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Superhost

The exterior of the house features a charming two-story design with a dark blue facade. A set of wooden stairs leads to a welcoming entryway, adorned with a small flower planter. Lush greenery surrounds the property, providing a serene atmosphere.

Home in Winner

4.86 out of 5 average rating, 92 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.

A lively common area showcases vintage decor and unique local signs. A bar area is illuminated by a neon beer sign, while various framed pictures and posters adorn the wooden walls. The space is complemented by a mix of seating options, inviting guests to relax and socialize.

Home in Colome

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.

Guest favorite

A simple one-story house with a metal roof is set on a grassy yard. The front features a small wooden deck with black railings and a single entrance door. Two windows are visible on the facade, enhancing the home’s rural appeal.

Home in Colome

4.93 out of 5 average rating, 14 reviews

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.

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, 3 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. 2 bedroom 1 bath. Full bed in bedroom #1 and a set of bunks (4 twins) in bedroom #2. Sleeps up to 6.

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

4.98 out of 5 average rating, 65 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!

Top 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, 96 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 cozy sitting area is highlighted by a plush sofa adorned with decorative pillows. A small round table is positioned in front, complemented by a patterned area rug. Wall accents include framed artwork and stylish light fixtures that add a warm glow.

Guest suite in Winner

4.95 out of 5 average rating, 147 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.

Superhost

A rustic exterior of a wooden cabin showcases a blend of natural wood and green siding. A flagpole stands prominently in front, with a flag gently waving. Surrounding greenery includes trees and well-kept grass, enhancing the peaceful rural setting.

Cabin in Dallas

4.69 out of 5 average rating, 39 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.