Family-friendly vacation rentals in Dickinson

5.0 out of 5 average rating, 168 reviews

The exterior of a two-story building is shown, featuring a blend of stone and smooth surfaces. Large windows with black frames allow natural light to enter. A pair of double doors at the entrance are centered beneath a decorative overhang, offering easy access.

Loft in Dickinson

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.

Indoor spacesKitchenLong stay

4.88 out of 5 average rating, 224 reviews

A comfortable seating area features a dark grey sofa adorned with decorative cushions. Light is allowed to enter through large windows, providing a view of the outdoor scenery. Nearby, a wooden dining table with chairs complements the space, enhancing the homey atmosphere.

Camper/RV in Medora

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/gift shop in our garage.

FamilyKitchenWifi

4.79 out of 5 average rating, 24 reviews

HillStay Hideaway

Welcome to your peaceful getaway in Dickinson! A warm, and inviting retreat just under an hour from Theodore Roosevelt National Park. Whether you’re exploring the Badlands, driving the scenic loops, or simply looking to relax. Perfect for couples, families, or solo travelers looking for calm, comfort, and quick access to the park. This split level home has three bedrooms and two full baths . Your home away from home in the North Dakota Badlands awaits. Relax, recharge, and explore.

Indoor spacesFamilyAmenities

4.88 out of 5 average rating, 369 reviews

A covered outdoor patio features two metal chairs with mesh backs, set around a small table. The view overlooks rolling hills and a distant farm, surrounded by greenery, creating a serene environment for relaxation.

Guest suite in Gladstone

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.

KitchenFamilyCheck-in

An open-plan living area features a stylish white sofa with blue and red accent pillows. A dining table with black chairs sits nearby, and a kitchen area is equipped with modern appliances. A lofted space overlooks the room, enhancing the sense of height and openness.

4.97 out of 5 average rating, 33 reviews

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.

Indoor spacesKitchenComfort

4.92 out of 5 average rating, 120 reviews

Apartment in Dickinson

Granny's Corner Suite

Welcome the TR Presidential Library and relax in a private 2 bdr suite with supplied linens, towels, soaps, breakfast foods/snacks, WIFI, ROKU TV for your streams or free channels. There are many nearby restaurants, shops, 2 playgrounds in this walkable university area just 10 blocks away from the hospital. The stocked shared laundry is just behind your back door. Seasonal Medora Musical and year-round Theodore Roosevelt National Park are 35 minutes West.

Indoor spacesFamilyParks

A two-story building is depicted, characterized by a mix of siding materials. A wooden deck with steps leads up to the entrance. Windows are evenly spaced, providing natural light, while greenery surrounds the base, creating an inviting outdoor space.

5.0 out of 5 average rating, 21 reviews

•Beautiful Downtown Home•Close To Everything•

Welcome to Affinity on 1st! You will have all the comforts of home at this unique downtown property, originally constructed in 1921. Steps away from bars, restaurants, shopping, groceries, Legacy Square 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.

FamilyIndoor spacesSleep quality

5.0 out of 5 average rating, 21 reviews

A Meadowlark Stay

Cozy 3-bedroom prairie home in a quiet Dickinson neighborhood with a large fenced backyard and easy interstate access. Minutes from downtown, Walmart, August House wedding venue, and a short drive to Medora and Theodore Roosevelt attractions. Features handmade quilts, vintage charm, oak furnishings, and calm neutral decor throughout. Ideal for families, wedding guests, sports travel, and remote work. Clean, peaceful, and welcoming.

Indoor spacesKitchenQuiet

4.86 out of 5 average rating, 14 reviews

Condo in Dickinson

Rest and Renew across from DSU - The Olive Branch

Step inside this warm and inviting retreat just a short walk from Dickinson State University, Biesiot Activity Center, local restaurants, and coffee shops. Cozy mid-century charm meets modern comfort with wood-beam ceilings, cozy brick asthetics, spacious living areas, and restful bedrooms. Whether you’re here to unwind, explore, or visit loved ones, The Olive Branch welcomes you with peace, comfort, and connection.

FamilyKitchenDecor

4.89 out of 5 average rating, 47 reviews

Townhouse in Dickinson

Hideaway at Water Tower Hill

Bright, spacious split-level near Water Tower Hill. Upstairs you will 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!

Indoor spacesKitchenWalkability

4.93 out of 5 average rating, 14 reviews

A cozy living area is presented with soft carpet flooring and gray walls. A comfortable beige sofa is positioned with a decorative throw draped over one arm. A small round marble-top coffee table is centered on the floor, and a TV stands on a black unit against the wall.

Apartment in Dickinson

Cami-cozy home

Experience a comfortable and convenient family getaway at this inviting accommodation. Ideally located near downtown Dickinson, the college, and various entertainment options, this property provides easy access to key destinations. Walmart is accessible within a 9-minute drive, while Medora is approximately 35 minutes away by car, and the Paragon Bowl Champs Sports complex is a mere 5-minute walk.

FamilyKitchenAccuracy

A spacious living area features a sectional sofa arranged to promote conversation, accompanied by a cozy armchair. A large area rug lies beneath, and natural light enters through dual windows. Wall art complements the rich wood ceiling and dark accent walls, enhancing the room's modern style.