Family-friendly holiday rentals in Dickinson

Grandpa’s Attic

Take a break in this tranquil loft getaway. Grandpa’s Attic is an open-space studio that offers a kitchenette for a dorm-like retreat. There is one twin-size and one queen bed to rest and gaze into the hint of indoor twinkling summer Dakota skies. The private bathroom is fully stocked (towels, soap, etc) with a shower, toilet, sink. Get cozy in the corner to watch TV, read, or enjoy a walk in the peaceful surroundings. Be sure to enjoy the local fares and sights before continuing your journey!

Country in the Middle of Town

Enjoy this spacious 3,600 sq. ft. home on a 0.63-acre yard, blending country tranquility with town convenience. Sleeps 12 comfortably with 4 bedrooms(6 beds) and 4 bathrooms. Futon, cot, and couches also available. Dogs are welcome. The fenced backyard features a trampoline perfect for kids. Located just 4 blocks from the Rec Center, 3 minutes from restaurants, and 35 minutes from Medora and the Badlands. A perfect getaway location for all. Vacation, hunt or fish, this is the place for you.

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.

Boots Hunter Cabin Medora ND 2 BR 1 B Sleeps 6

Fully furnished cabin has everything you need for an easy stay. Enjoy awe inspiring badlands from the front porch. This 2BR cabin 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.

King's Guest Ranch Vacation Heaven

Our ranch is close to Theodore Roosevelt National Park, Medora, Medora Musical, Maah Daah Hey trail and restaurants. We offer a different experience than you will get it Medora. The ranch is a peaceful retreat while being an easy 8 mile drive from town. Guests routinely tell us the ranch rivals the national park for scenery and its right out their door. An added bonus, the drive to town is spectacular. If you need Wifi we have free Wifi in our guest lounge in our garage.

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.

•Cozy•3•Bedroom• with Hot Tub

**I’ll be adding two more properties that will be ready Spring 2026– Located directly behind, and 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.

Roosevelt Chalet

This modern, art-filled guesthouse is Medora’s most stylish stay—just minutes from the Maah Daah Hey Trail, Bully Pulpit Golf Course, and Theodore Roosevelt National Park. With two serene queen bedrooms, a fully equipped kitchen, spacious living areas, and a lower level with four twin XL murphy beds and a ping pong table, it’s designed for high-comfort living. Thoughtful family amenities and sweeping Badlands views make it a perfect place to relax and recharge.

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.

•Beautiful Downtown Home•Close To Everything•

Welcome to Affinity on 1st! You will have all the comforts of home at this downtown property. Just steps away from bars, restaurants, shopping, groceries, a playground and more. Theodore Rosevelt National Park is a 40-minute drive. Dickinson State University is just minutes away. There is also a large private parking lot to accommodate multiple or large vehicles and green space for your four legged companions.

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.

Hideaway at Water Tower Hill

Bright, spacious split-level near Water Tower Hill. Enjoy a bright living room with games, dining room opening to a deck with BBQ, and convenient laundry. Downstairs features large bedrooms and a full bath. Detached garage and off-street parking. Just a short, scenic drive to the historic town of Medora and the stunning Badlands- perfect for combining relaxation with adventure!