Family-friendly holiday rentals in Pennington County

Farm♡tastic stay @ Hills Roost Farm!

Our farm's only bnb, "The Roost," offers a clean, modern, & fun space to stay. Located in the lower walkout level of our home, it's similar to a suite. Offering 575 sq. ft. of private, clean, well maintained living quarters include, a kitchen, a cozy living space, w/twin sofa bed, & a spacious bed & bathroom. Chickens just outside your door to greet you a "rise & shine" morning & flowers everywhere. Our seasonal gardens are open for you to enjoy picking organic food, along with farm fresh eggs.

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!

Squirrel Hill Cabin - hot tub, gameroom, wi-fi

A hidden gem in the heart of the Black Hills, our cabin is nestled on 3 private acres lovingly named Squirrel Hill. With decks in every direction, you're encouraged to take in the abundance of nature. Watch for deer, turkey, birds and squirrels. Relax under the pines in the hot tub or on the deck featuring a gas firepit and 10-person table. Inside, you'll find everything you need for a well-appointed getaway. Worlds away from the hustle & bustle of real life; just 10 minutes west of Rapid City.

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 sofa sleeper 65'' UHD Smart TV Netflix, Prime, HD/Local Channels Pool and Rec facilities, seasonal WIFI Highspeed Internet Newly remodeled bathroom Outdoor patio area with gas grill Pool table and darts Full size fridge/freezer Convection oven Induction cooktop Microwave Keurig coffee and breakfast snacks Washer/Dryer Close to Rapid City shopping and dining Nature and wild life Amazing stars out at night!

Private Pool! Great Rapid City Location!

*Please be sure to read all house information! Welcome to Mary Jo's Place, a charming 1950s Rapid City home! Sleeping six with two bedrooms and two bathrooms. Located near the Historic West Boulevard in the center of Rapid City! A great location with nearby parks, walking and hiking trails, grocery, and restaurants. Also, easily access Mount Rushmore Road and Interstate 90. This home has recently been updated and is ready for your stay! Did we mention there is a private heated indoor pool!

Treehouse Yurt Lead Black Hills SD Mickelson Trail

Off grid yurt in the pines, with great view of mystic miner and Terry peak above, on mile 100 of beautiful Mickelson trail. Get away to nature (with style and a unique stay)....goulay. not for non-outdoorsy as there is only a half bathroom outhouse, no running water (you get to port it in, great spring pump at nearby Englewood trail-head on Mickelson and running stream for a dip at bottom of hill), no electricity, and a great little wood stove. BEFORE RENTING read other things to note.

lNDOOR POOL! The FUN house

Ready for an unforgettable getaway? Welcome to your 7,000 sq. ft. vacation dream home! Packed with fun for all ages and designed with sustainability in mind, thanks to solar-powered energy! Whether you're splashing down the water slide, soaking in the hot tub, or enjoying a friendly game of foosball, this is where epic memories are made. Everyone in the family will thank you for choosing this one-of-a-kind escape! This property is pet-free and 100% smoke-free – indoors and out.

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!

Classic Monroe, 2 blocks from The Monument Civic

Welcome to our Classic Monroe home. This property features 3 bedrooms and 1 bath. Family fun is just around the corner with an arcade in the basement. Sleeping accommodations include a two queen sized beds, and four twin size beds. Additional features of the home include a full kitchen, a full sized refrigerator, stove, microwave, K-cup maker, & air fryer. This home is located one block off a main street to Downtown and two blocks from The Monument Event Center.

Luxury Ranch Stay

Be our guest on 40 private and fully gated acres. From all windows of the house you can watch 2 horses and cattle grazing through the meadow. The evening sunsets are magical with deer & turkeys wandering through. Relax under the stars at our fire pit (all supplies provided). Let your kids run wild with water guns & a water fall pond to refill at! Located right off HWY 16 makes you only 10 minutes to downtown Rapid City and 20 minutes to Mt. Rushmore!

Creek-side Cabin | Hot Tub + Trout Fishing

Wake up to the sound of a babbling creek, sip your morning coffee on the deck while bighorn sheep graze on the hillside, and spend your evenings soaking in the hot tub under a sky full of stars. This beautifully furnished 3-bedroom Black Hills cabin sits right on the water — perfect for trout fishing, family gatherings, romantic getaways, or simply unplugging from the world. With stunning creek and mountain views, This is a Complete Black Hills retreat.