Vacation rentals in Tripp County

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.

4.92 out of 5 average rating, 86 reviews

Cozy Little Getaway

KristaRating, 5 stars3 weeks ago

Katlyn’s rental was a great stop for us on our road trip to CO. The listing was as described and Katlyn was flexible with our checkout time with an unexpected work meeting was scheduled. If we are ever in Winner again we wouldn’t hesitate to stay here!

A rural scene depicts a gravel road curving through open fields, bordered by sparse trees. A white house is visible in the distance, with an expansive cloudy sky overhead. The textured clouds create a unique atmospheric effect, adding a sense of tranquility to the setting.

4.93 out of 5 average rating, 14 reviews

3 bed Hunter/Cowboy Bunk house in Country

WrenettaRating, 5 stars19 months ago

My father, grandfather and I stayed in this Airbnb for a hunting trip. It was perfect for our group there was lots of space and it had a homey feel to it. We are planning to use it again next year. Jennie was very nice and checked up with us to make sure that we didn’t need anything. It is definitely a rustic cowboy style home as described. 10/10 we loved it!

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.

Vacation rentals for every style

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Popular amenities for Tripp County vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Tripp County

A rustic bar area is showcased, featuring wooden walls adorned with framed artwork and memorabilia. A neon Miller Lite sign illuminates the space. An inviting dining table and chairs provide seating, while the open layout reveals a staircase leading to an upper seating area.

LeahAnnRating, 5 stars1 week ago

Sign Inn eclectic main lodge

This was a great space! We were in the area for a wedding and making a short family vacation around it. Loved what they've done with the interior. We're collectors and I'm someone who refinishes old spaces so this was a perfect fit. Loved the coffee bar. The place was clean and we didn't have any issues.

Top guest favorite

Double doors with large glass panels provide access to the outdoor area. A sleek handle and a keypad lock are visible on one door. Reflections of the surroundings can be seen in the glass, while light curtains suggest connectivity to the interior.

Guesthouse in Winner

4.98 out of 5 average rating, 55 reviews

The Rustic MP6

CynthiaRating, 5 stars5 days ago

The place made our vacation so much more enjoyable than a motel stay. We had more quality family time and room to enjoy our evenings. Had everything we needed. This was our first experience with an airbnb. Thanks.

A cozy living area features a neutral-colored couch with two small dogs nestled beside a child. A comfortable chair offers additional seating. A television is mounted on the wall opposite a dark cabinet. Natural light enters through a window adorned with light curtains.

4.92 out of 5 average rating, 12 reviews

The Quiet House

KathrynRating, 5 stars1 week ago

We enjoyed our stay while we were in town for a wedding.

AnalisaRating, 5 stars3 weeks ago

Sign Inn Colome

What a fun place to explore

4.92 out of 5 average rating, 86 reviews

Cozy Little Getaway

KristaRating, 5 stars3 weeks ago

Katlyn’s rental was a great stop for us on our road trip to CO. The listing was as described and Katlyn was flexible with our checkout time with an unexpected work meeting was scheduled. If we are ever in Winner again we wouldn’t hesitate to stay here!

Top guest favorite

A well-organized bathroom features a clean, modern design with grey walls. A stylish mirror reflects light above a white sink. Shelves display decorative signs and toiletries, while neatly stacked towels are placed on a wooden stool. A plush mat lies on the floor beside the toilet.

Guest suite in Winner

4.94 out of 5 average rating, 136 reviews

The Hide-A-Way

KyleRating, 5 stars2 weeks ago

This was a repeat stay for me. And I’d keep staying here or recommending it to others. She is very responsive. A very minor issue with the toilet handle occurred, and she fixed it promptly before I needed it again.

4.93 out of 5 average rating, 14 reviews

3 bed Hunter/Cowboy Bunk house in Country

WrenettaRating, 5 stars19 months ago

My father, grandfather and I stayed in this Airbnb for a hunting trip. It was perfect for our group there was lots of space and it had a homey feel to it. We are planning to use it again next year. Jennie was very nice and checked up with us to make sure that we didn’t need anything. It is definitely a rustic cowboy style home as described. 10/10 we loved it!

A functional bathroom is presented with a bathtub, toilet, and a small vanity unit. A window allows natural light, covered with a patterned curtain. A woven rug adds color to the hardwood floor, while toiletries are organized on the vanity.