Family-friendly holiday rentals in Dickinson

Private Apt, welcoming Short & Long Term Stays #3

Unwind in this spacious 1 Bed 1 Bath rental with updated appliances and a homey feel. This brick building offers a cozy and secluded space. Our bedroom offers a large closet space and a modern bedroom set to allow for plenty of room to unpack during your stay. Our living area has an open concept that includes a TV with Firestick to allow for personal streaming on your usual devices. A coffee bar and several other amenities available for use. This apt is setup to welcome short and long term stays

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.

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.

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.

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!

Happy Camper’s RV

You won’t forget the great surroundings of this unique destination. Just a few minutes from Lake Sakakawea. Right inside Beulah ND. This is a great budget option for a fun place to stay! It is an RV, however, we’ve added a few things to make it feel more like home. First, a tankless water heater. Second, full water and sewer hookups. We also are continuing to upgrade!

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!