Family-friendly holiday rentals in West Pennington

Spearfish Canyon Retreat (Valhalla)

A lovely log home located in spectacular Spearfish Canyon. Situated between Spearfish and Deadwood. Wi-Fi/cell /internet. Northern Black Hills Attractions and Activities: Spearfish Falls Bridal Veil Falls Roughlock Falls Fishing Rock Climbing Hiking Snowmobiling Skiing Many fine restaurants 15 mins to Spearfish 1/2 hour to Lead and Deadwood. 1 hour to Rapid City and Devil’s Tower. 1 1/2 hours to Mt. Rushmore or Badlands. 1 3/4 hours to Crazy Horse, Custer and Custer State Park

Quiet private suite with garage bay & kitchenette

Quiet private bedroom and kitchenette isolated from the main house with common use sun room between. Rural setting off Hwy 44 just minutes from Rapid City Airport. Tesla 11kw destination charging outlet in your garage bay directly accessible from the suite. Starlink 150mbps internet. Pet friendly to friendly pets with pet door from the suite out to the fenced back yard & patio isolated from our dog & cat. Private bath has in-floor heat and endless hot water with continuous flow water heater.

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!

Priceless Black Hills View!

Two Large Furnished Bedrooms, new Queen Beds Pool Table and Darts Large living room with new sofa sleeper Newly remodeled bathroom 65'' UHD Smart TV, Dish DVR, Bluray Pool and Rec facilities, seasonal WIFI Highspeed Internet Outdoor patio area with seating Gas grill Pool table and darts Full size fridge/freezer Convection oven Induction cooktop Microwave Keurig coffee and breakfast snacks Washer and dryer Close to Rapid City shopping and dining Nature and wild life Amazing stars out at night!

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.

★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.

Southern Hills Tiny Home

Sleep soundly in a beautiful country setting. Awake refreshed just minutes from many Black Hills attractions. Mt. Rushmore 41 mi. Custer 20 mi. Hot Springs 18 mi. Custer State Park 24 mi. Wind Cave 17 mi. Adjacent to the Mickelson Trail and minutes from hundreds of miles of Black Hills National Forest trails. Wildlife is abundant in the Southern Hills, including deer, turkeys and elk. Or just sit back and relax as you watch the horses graze in the pasture or take in the endless night sky.

Pine Mountain Rest

Come find a restful space in the Heart of the Hills. After a busy day exploring all that the Black Hills have to offer you will find a quiet place to relax, fix your meals and rest for another day of adventure. Relax on the deck and listen to the Hill City 1880 train whistle as it returns from its final run. Located in Hill City we are in the heart of everything you want to do. Mickelson Bike Trail runs through town. Mount Rushmore and Crazy Horse are within 15 miles.

The Mercantile at Mad Peak Lodging, sleeps four

The Mercantile at Mad Peak Lodging is part of our Old West–inspired collection of vacation rentals, blending historic character with modern comfort in the heart of the Black Hills. Surrounded by mountain scenery, this inviting retreat offers a peaceful setting with easy access to outdoor adventure, local attractions, and scenic drives. Whether you’re exploring the Hills or unwinding after a full day out, the Mercantile is a comfortable and memorable place to stay.

Modern A-Frame Cabin Next to Custer State Park

Enjoy this spacious modern A-Frame Cabin. Located just 5 minutes to Custer State Park. Experience views of the Needles Highway and Black Elk Peak while you drink your morning coffee! You will have access to the entire house all to yourself! Great area to hike, bike, see the fluffy buffalo. Just a two minute drive to downtown Custer. This area has great ATV and kayak, trail ride rentals near by! Feel refreshed when you stay in this rustic gem.

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