Vacation rentals in Tripp County

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Top-rated vacation rentals in Tripp County

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Guest favorite

The exterior of the dwelling features a blue-grey facade with white trim and a welcoming front porch. A sign reading 'HOME' is displayed prominently, and potted flowers add a touch of color. The entrance is approached by wooden steps, surrounded by landscaped gravel and foliage.

Home in Winner

4.93 out of 5 average rating, 81 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 large sign reading 'Shippy Rodeo Bulls' is prominently displayed, with an American flag gently waving beside it. The scene is set against a wide, open sky, with a gravel pathway visible leading into the ranch area. Fenced pens can be seen in the background.

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 wooden deck leads to a home entrance, bordered by vibrant flowers and decorative planters. A red umbrella provides shade over outdoor seating, while bicycle accents and gardening tools are placed nearby. Lush greenery enhances the inviting outdoor space.

Private room in Winner

4.8 out of 5 average rating, 5 reviews

Mabel's apartment

Quiet neighborhood, cleanrooms, comfortable beds, affordable price. Living area is a basement apartment with private entrance through the garage. We can sleep up to eight people comfortably. There is a small kitchen with refrigerator, stove, sink, microwave, coffee pot, toaster and dishes. Washer and dryer for using when needed. We do require a deposit of one night stay of $100.

Top guest favorite

A modern building with a blue and white exterior features double doors leading to a patio. The structure is set against a clear blue sky, with a spacious gravel area surrounding it, enhancing the open and rural surroundings.

Guesthouse in Winner

4.98 out of 5 average rating, 50 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 tranquil landscape is depicted, featuring a serene pond surrounded by tall grasses and golden vegetation. Rolling hills extend in the background, with a clear blue sky overhead and a few scattered trees dotting the scene.

Guest suite in Winner

4.95 out of 5 average rating, 133 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.