Family-friendly holiday rentals in West Pennington

Restored Nemo Farmhouse on Centennial Trail W WiFi

Bring your ATV'S! Plenty of parking. On the Centennial Trail system. Fast wifi, smart TV with Dish channels. We are about 20 minutes from Sturgis, half an hour from Deadwood, and 40 minutes from Rapid City. The nighttime sky is very dark for viewing all the constellations; we have solar lights around the house, but it can be dark without a flashlight. Please keep in mind we are in the forest, and there are bugs, flying insects, and small critters. We work very hard to keep them out of the house!

Jägerhaus - Mountain Lodge on Private Estate

Our family first crossed this summit in the late '90s. The endless views over cascading pines, harmonious wildlife, and starry skies caused us to settle down and we've been here ever since. Over the years, we've welcomed lovely people from near and far to enjoy the Jägerhaus — join us for your next adventure. If you've stayed with us before, please note some changes + Double-bunk replaced with 1 King bed + House capacity changed from 10 to 8 + Upgraded living room furniture + Repainted spaces

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

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!

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!

Nature Stay with Views Like No Where Else

This home is truly one-of-a-kind and straight out of a magazine! Beautifully modern and furnished to an exceptional standard. Open the windows and let the soothing sounds of the nearby creek transport you to your own private paradise. Located close to Mount Rushmore, Crazy Horse Memorial, Custer State Park, and many other top attractions, you’re also just under 5 minutes from Hill City. We truly believe this is the ultimate spot to fully experience the breathtaking beauty of the Black Hills.

Mirror Cabin in the Black Hills

You'll love this unique and romantic escape. This tiny Mirror Cabin by REFLECT+RECONNECT, is nestled in the serene beauty of the Black Hills. 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. Come for the adventure. Stay for the connection. Leave feeling refreshed, reconnected, and renewed.

Castle in the Sky

Are you looking for a luxurious, unique place to stay? This house sits overlooking Rapid City with incredible skyline views, every evening is as picture perfect as the glowing city lights. This unique house is a fun mix of eclectic and fancy. Originally built as a local builder's "Coup de Grande", he ended up only finishing the guest house. You will find high-end finishes mixed with eclectic choices. We promise this will be one of the most memorable places you'll ever stay!

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.

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.

Cabin @ Bluebird Ridge:Quiet Refuge

If you appreciate beauty, inside and out, our rustic-modern cabin is perfect for you. It's cozy enough for 2 and spacious enough for up to 8. The cabin is surrounded by forest and looks out to the meadows and Hills. If you want comfort, outdoor living space, beauty, peace and quiet, we encourage you to come make yourself at home! Follow us on Insta @bluebirdridge

High Country Guest Ranch - #25 Rodeo

Camping Cabins are perfect for a quick get-a-way for smaller families of 5-6 people! There is a large shared firepit to enjoy!!! Bedding and towels are provided. This cabin does NOT have a full kitchen! Come enjoy the small cabin feel in the middle of The Black Hills without breaking the bank! Little to No internet but the store has internet you can use!!