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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Top 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, 119 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

Top guest favorite
Cabin in Keystone
4.98 out of 5 average rating, 125 reviews

The Winsome Cabin - Hinterwood Inn & Cabins

The Winsome Cabin is part of Hinterwood Inn & Cabins, situated 60 ft. from National Forest. Enjoy hiking and wildlife sightings from your front door! The cabin has 2 bedrooms, each with a queen bed, a queen murphy bed in the living room, a bathroom with a shower (no tub), and an apartment size kitchen w/ essentials. Custom built by the owners, enjoy the beautiful stump accent wall, vaulted ceilings, and large windows. Includes a private deck with a gas grill, private fire pit area, and more!

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, 275 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 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, 180 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. Deck/fire pit. 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 spacious hot tub with lights is positioned on a wooden deck, surrounded by a protective wall. Snow covers the steps leading to the tub, while a small side table is visible next to it. Warm ambient lighting highlights the tub's inviting surface.
Cabin in Sturgis
4.95 out of 5 average rating, 266 reviews

Pet friendly 2 bedroom log cabin with hot tub.

This beautiful large 2 bedroom cabin nestled right outside of Sturgis SD can comfortably accommodate several guests, as it has 2 bedrooms as well as 2 living rooms. One of the living rooms has 2 fold out twin beds. 7 person hot tub! patio furniture as well. This cabin gives you the privacy you need yet the comforts of being 5 mins from a grocery store. Gorgeous views of the Black Hills. Fully furnished home. BBQ grill. We have a few different airbnbs and the cabin is completely private.

Top guest favorite
The exterior of the guesthouse is showcased, featuring a light-colored façade and a welcoming front porch. A covered carport and landscaped lawn enhance the entrance, while trees provide natural shade alongside the walkway. The driveway is spacious, allowing for convenient access.
Home in Rapid City
4.98 out of 5 average rating, 120 reviews

Enchantment hills retreat guesthouse.

This is a guesthouse beautiful Black Hills of South Dakota. Incredible views . 25 minutes from Mount Rushmore and all of Black Hills. Centrally located. Enjoy watching the deer ,wild turkeys , foxes and other wildlife wandering through. Use as a locum's medical professional, couples retreat or business executive . Approximately 700 sq/ft, and exquisitely decorated. Driveway private. Stunning views overlooking enchantment Canyon and the beautiful prairies.

Top guest favorite
Cabin in Custer
4.99 out of 5 average rating, 310 reviews

CABIN @ redblue - King bed - near parks & trails

Enjoy your stay in a private, rustic cabin with all the comforts of home. King bed! Steps from Black Hills National Forest & Michelson Trail, this location is centrally located to Wind Cave National Park, Jewel Cave National Monument, Crazy Horse Memorial & Mount Rushmore National Memorial. Bring your hiking shoes. Bring your bikes. Adventure is yours! Also on the property is the redblue RIDGE and OUTLAW units. Perfect for family reun

Top guest favorite
Cabin in Custer
4.97 out of 5 average rating, 116 reviews

Elk Ridge-Fire Place-Custer

Imagine yourself in the quiet and peaceful Black Hills Forest on Elk Ridge. The serenity of the forest and the warm pine smell will instantly bring you back to nature. The five-bedroom, three-bath cabin sits on a secluded piece of property that is close (6 miles) to Jewel Cave National Park, one of South Dakota’s most popular attractions. A large private back patio, gazebo, and a nice-sized hot tub with tons of outdoor space.

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, 178 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 vibrant field of purple flowers stretches across the landscape, surrounded by green grasses. Pine trees are visible in the background, creating a harmonious blend with the clear blue sky above.
Apartment in Custer
4.96 out of 5 average rating, 328 reviews

Journeys End cozy Apartment attached to house

Cozy apartment attached to the main house, queen bed, full sized couch bed, large shower, mini kitchen with sink, microwave, refrigerator, coffee pot, toaster. Deck outside--gas grill and patio furniture. Located on 26 acres of pine forest, meadow and mt. Rock shop on property. Lots of space for rest, relaxation, or hiking. Access to children's playground, mountaintop deck and hiking trails.

Top guest favorite
A gravel road is framed by tall pine trees, leading to a spacious area under a clear blue sky. The entrance features wooden posts with a sign overhead, creating a welcoming access point to the hillside property.
Guest suite in Piedmont
4.96 out of 5 average rating, 112 reviews

Lower level apartment in mountain setting

This is a comfortable, quiet and cool lower level apartment at the end of a road in the hills between Rapid City and Sturgis. A kitchen with utensils and a coffee pot with coffee are provided. Large private bath and a comfortable size bedroom. An exercise room with recumbent bicycle is available along with a laundry room. There is a private entrance and plenty room to park.

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
4.99 out of 5 average rating, 232 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.

Popular amenities for West Pennington family-friendly rentals