Vacation rentals in South Billings

Lovely 2-bedroom loft w/fireplace & chef’s kitchen

Located in the heart of downtown Dickinson our loft is the perfect place to call your home away from home. Whether you’re in town to visit friends and family or need a place to relax after visiting Medora and the North Dakota badlands, you can cozy up in our two bedroom two bath loft. Our loft also has a beautiful chef’s kitchen where you can prepare home cooked meals if you like to cook or is in walking distance to several great places to eat if you want someone to do the cooking for you.

Cozy Medora home for family gatherings and fun!!

Bring your entire family and your friends to this cozy, 4 bedroom, 3 bathroom home, furnished with an additional 3 sets of bunkbeds! Nestled in the historic streets of beautiful Medora, ND, dining, shopping, and various forms of entertainment are all a short stroll from your front door. Enjoy a dip in the hot tub, cook out on the BBQ grill, or with a cup of coffee in your hand, enjoy the beautiful sunrises and sunsets from the patio in the large backyard that borders the beautiful Badlands.

Boots Bison Cabin 2 BR 1 B Sleeps 6

Fully furnished cabin has everything you need for an easy stay. Enjoy awe inspiring views of the badlands from the front porch. This 2BR comfortably sleeps 6 with 1 queen size bed, 2 twin beds and a pull out queen sofa. Guests share 1B with shower/tub combo. Kitchen comes with daily essentials. Minutes to everything Medora has to offer. Bring your horse, bike, and golf clubs. We look forward to your visit! This cabin is in an RV Campground. There may be a camper parked close to the cabin.

Guest Favorite Gladstone Valley, two bedroom B&B

This stylish country place is close to the enchanted Hwy, which has 70 to 80 ' high sculptures along the road. When you take the I-94 Gladstone exit you will see the 80 ' high "Birds in Flight" sculpture. At the end you will be at the enchanted castle. We are 40 miles from Medora & Roosevelt National Park a must-see destinations. You have a private entrance & patio. A BBQ bar with a pizza oven on the upper deck. Outdoor fire pit & (3) kayaks to use on the Heart River below.

Lakeside Haven

Relax with friends and family at this quaint peaceful cottage nestled between the lake and the golf coarse. Walk out the back door and enjoy the great walleye fishing, boating, swimming or an adventure of your choice. Take a 5 minute drive and explore Dickinson with its many opportunities. Or if you want to see the #1 attraction in North Dakota, visit Medora a short 39 min away. If golf is more your style visit Heart River Golf Course just around the corner.

•Cozy•3•Bedroom• with Hot Tub

**I’ll be adding another property that will be ready Spring 2026– Located across the street from this property!** Just north of downtown, located in the center of Dickinson, this newly remodeled home boasts plenty of natural light, rustic chic decor, and a great backyard with a brand new hot tub. Located about half a mile from the interstate makes for a quick easy trip to Medora, the gateway to the south unit of Theodore Roosevelt National Park.

Medora Cabin - Trailhead of Maah Daah Hey

Escape to a picturesque retreat surrounded by breathtaking natural beauty of the Badlands. Welcome to our charming 3-bedroom, 3-bathroom cabin, ideally situated near Medora and Bully Pulpit Golf Course, with the Maah Daah Hey trailhead right at your patio. With a generous sleeping capacity for 12 guests, this cabin is the perfect haven for families and friends seeking an unforgettable outdoor adventure.

Baker, MT Ranch House Peaceful and Quiet 3bd/1ba

Entire guesthouse, 1650 sq ft. Three bedroom, large living room, private bathroom and kitchenette in the country with beautiful views. There is a large comfortable sectional sofa that guests can sleep on and a 3D TV with DVDs. This space is perfect for families. Private entrance room with tile floor. Great for hunters!

3 bed, 2 bath near TRNP, Medora and Dickinson

Feel at home at this 3 bedroom, 2 bathroom twinhome. There is a fenced yard- so you can bring your animals too (there is a pet fee, please make sure you add you have them coming). This home is in the middle of Medora & Dickinson- so perfect location! Close to national parks and probably hunting too!

Longhorn Lodge

Kick back and relax in this calm, stylish space just 15 minutes southwest of Historic Medora. Breath taking views in a secluded location. Just a quick drive to the Theodore Roosevelt National Park entrance and minutes to the Maah Daah Hey Trail. Great for family or a quiet couples getaway.

The Lodge

The Lodge is a large A-Frame house with an open floor plan that is decorated with hunting and rustic decor. It is located 4.5 miles east of exit 64 in Dickinson. It is a perfect place for a quiet get away or for a family get together.

Miller Cabin - near TRNP, Medora, and Dickinson

Fifteen minutes from Medora. Relax with the whole family at this peaceful place to stay. Also perfect to use as a hunting cabin during the winter. There is a lot to do nearby and Dickinson is 20 minutes away.