Family-friendly vacation rentals in West Pennington

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Top-rated family-friendly rentals in West Pennington

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

A charming red house is surrounded by lush green grass and tall trees, with a sloped hill rising in the background. A small deck with white chairs is visible at the front, offering a welcoming outdoor space.

Cabin in Hill City

4.94 out of 5 average rating, 113 reviews

Grandma's House in the Heart of the Black Hills

Grandma's House is in the heart of the Black Hills, located 1 mile from Hill City, it is minutes away from Mt. Rushmore, Crazy Horse, Custer State Park and more. It sits alone on the edge of a meadow with hills directly behind it and a small, bubbly creek in front of the house. It has plenty of room for kids to run and play outside, and a cozy, quaint inside for families to enjoy each other's company. Grandma’s House is available for extended stays November thru April. Contact host for details

Guest favorite

A spacious living area features large windows that allow natural light to fill the room. Comfortable seating options, including brown armchairs and a cozy couch, surround a round coffee table. The dining area has a long table, and sliding doors open to a private deck with outdoor seating.

Cabin in Custer

4.94 out of 5 average rating, 190 reviews

★Nature Stay with Views Like No Where Else★

This home is magazine worthy and one of a kind! Modernly furnished to an excellent standard. It is the ideal retreat for a secluded & nature-bound stay. You can open the windows and let the sounds of the creek make you feel like you are in paradise. It is Conveniently located near Mount Rushmore, Crazy Horse, Custer State Park, and other major tourist destinations. It's less than 5 minutes to Hill City! We believe it is the ultimate location to immerse yourself in the beauty of the Black Hills.

Top guest favorite

A scenic view showcases the cabin nestled amongst tall pine trees, surrounded by expansive green meadows. A winding gravel driveway leads to the property, with a seasonal pond visible in the foreground, reflecting the clear blue sky.

Home in Hill City

4.99 out of 5 average rating, 252 reviews

Cabin on 20 acres w/ horses, goats, mini donkey

Enjoy country living close to town! Two bedrooms w/ queen size beds and loft w/ queen size pullout sofa allow you to comfortably sleep 6! Just 4 miles from downtown Hill City. Sits on 20 beautiful acres surrounded on 3 sides by Forest Service! Enjoy beautiful surroundings - a seasonal pond outside your cabin (water level varies), horses, mini donkey, mini goats and chickens. Enjoy private setting with the convenience of the owners just 1/4 mile up the driveway to take care of your needs!

Top guest favorite

A geodesic dome structure is situated on a grassy hillside, surrounded by natural scenery. Wooden posts with string lights provide ambient lighting, while gray outdoor seating invites relaxation. The clear sky and distant trees complement the tranquil outdoor setting.

Dome in Hermosa

4.97 out of 5 average rating, 122 reviews

Ponderosa Dome

Furnished with King bed, dual twin beds, coffee-bar, and breakfast table. Private outdoor seating area with lighting, gas and wood fire pit. Wood for purchase. Restroom-guest fav, a few minutes’ walk and located in a shared building, not in unit, pictures in listing. AC in summer (June 1) and electric heater in winter. Non aggressive dogs. No bathroom in unit! Self-check in. Directions are sent the morning of arrival. If your unit requires a passcode, that will be sent upon booking. No WIFI

Top guest favorite

The loft features a cozy sleeping area with a spacious bed dressed in a light blanket. Bright pillows add a pop of color. Natural light fills the room from a large window with red curtains, and a smaller window enhances the airy feel. A decorative feature stands nearby.

Loft in Lead

4.98 out of 5 average rating, 655 reviews

Harley Court Loft

Cozy loft in the Lead, SD. Moments from downtown, but secluded. Minutes to outdoor activities, skiing, snowshoeing, hiking, biking, or snowmobiling. Winter months, all wheel / 4 wheel drive vehicle is a must!! Close to restaurants, brew pub, and night life!! Kitchenette: microwave, coffee maker, toaster, hot plate, (with pans), and small frig. The loft has electric heat and portable AC. There are 18 steps to get to the loft, for two people. Not kid proof. No pets accepted.

Guest favorite

A rustic cabin is nestled among tall trees, displaying a stone facade and a green roof. The surrounding grassy area creates an inviting outdoor space. A gravel driveway leads to an adjacent structure, enhancing accessibility to the property.

Cabin in Hill City

4.87 out of 5 average rating, 103 reviews

Black Hills Get-Away

The Black Hills Get-Away is truly a retreat from the hustle and bustle. The star gazing is amazing. Towels and linens are provided and the kitchen is fully equipped. Two TV's with satellite service and DVD. Their is an outside patio with a picnic table and a charcoal grill. Stream fed trout pond on site with catch and release fishing. The cabin is located 3 miles from historic Rochford and the Moonshine Gulch Saloon. It is 1.5 miles from the Mickelson bike and hiking trailhead.

Top guest favorite

A quaint cabin exterior is showcased, featuring a wooden facade with a red metal roof. A small porch with two chairs is set under a shaded tree. Colorful planters and a decorative feature can be seen in the background, contributing to the inviting outdoor space.

Tiny home in Four Corners

4.98 out of 5 average rating, 172 reviews

KK, tiny cabin close to beauty of Black Hills SD

A 10 x 32 tiny cabin conveniently located 1 mile off paved Hwy 585. Our working ranch has cattle, goats, horses. Beautiful scenery with frequent sightings of elk, deer, turkeys. This unique cabin features: WIFI, TV with DVD player only, microwave, retro fridge, bathroom with shower, twin bunk beds, and a queen bed. Experience the beauty and serenity of Wyoming and closeness of Black Hills attractions; and simple ranch life! Quiet and off the grid. Beautiful sunsets, too.

Guest favorite

A covered porch is displayed with two wooden chairs positioned in front. Large glass doors reveal a spacious dining area and kitchen, featuring dark cabinetry and modern appliances. The floor appears polished and reflects the warm lighting from overhead fixtures.

Home in Hill City

4.95 out of 5 average rating, 194 reviews

Hill City Hideaway on the Mickelson Trail

Location, location, location. Hill City is located in the center of the Black Hills and this house is within walking distance of the best parts of Hill City. 40 feet to the world famous Mickelson Trail, 1/2 a block to the 1880s steam train, and 3 blocks to the best restaurant in South Dakota. This home is not too big and not too small. Whether you are doing a couples get away, traveling with kids or your friends this home may be "just right" for you.

Guest favorite

The cabin interior features natural wood paneling, creating a warm environment. A queen bed is displayed with neatly arranged linens, alongside a set of twin bunk beds. A wooden chair and a small desk are visible, with a map of Hill City adorning the wall.

Cabin in Hill City

4.86 out of 5 average rating, 194 reviews

Hip Hill City Cabin near Mt. Rushmore

Rustic pine sleeper cabin in the beautiful Black Hills. One queen bed with twin bunk beds (three beds in total). Cabins do not include a shower, bathroom or running water inside. Showers and bathrooms are available for free use in main guest shower house. A great base for touring the area, with quick access to lakes, Mickelson Trail and a 20 minute drive to Mt. Rushmore. Featuring an award-winning bistro, wine and beer tasting room.

Top guest favorite

A modern tiny cabin features reflective walls, blending into the surrounding nature. Tall trees and a blue sky are mirrored on the surface, creating a seamless connection with the forest. The cabin's structure is set among rocky terrain, emphasizing its unique design.

Tiny home in Lead

4.98 out of 5 average rating, 106 reviews

Mirror Cabin in the Black Hills

You'll love this unique and romantic escape. This tiny mirror cabin, REFLECT+RECONNECT, is nestled in the serene beauty of the Black Hills of South Dakota. It creates a rejuvenating and memorable experience. This unique retreat is designed to offer you a chance to disconnect from the hustle and bustle of everyday life and reconnect with the special person in your life, yourself, and the surrounding nature.

Guest favorite

A private hot tub is situated on a covered patio, surrounded by lush greenery. The calming waters reflect the natural light filtering through the canopy of trees. Nearby, a wooden bench and a swing add to the serene outdoor setting.

Cabin in Custer

4.92 out of 5 average rating, 169 reviews

Tenderfoot Creek Retreat

Welcome to Tenderfoot Creek Retreat! You will find yourself surrounded by towering evergreens of the Black Hills National Forest, and steps from the Mickelson Trail. You will occupy the entire main or 2nd floor of this rustic residence. Close to all the major Black Hills attractions yet you will feel at one with nature. Tenderfoot Creek can lull you to sleep or greet the morning with its soothing chatter.

Top guest favorite

A single-story house is depicted with a wooden exterior in a soft grey shade. Large glass sliding doors offer views of the interior, framed by two side windows. A small seating area with two chairs is visible on the porch, surrounded by grassy grounds and pine trees.

Cottage in Hill City

5 out of 5 average rating, 201 reviews

Mystic Road Cottage… -Peaceful -Private -Hot tub

Kick back and relax in this calm, stylish space. Conveniently located adjacent to the Mickelson Trail and UTV Trails. If you enjoy water adventures, Deerfield Lake, Sheridan Lake and Pactola Lake are only a short drive away. Come enjoy nature and explore the Black Hills. End your day relaxing in the hot tub gazing at the stars.