
Holiday rentals in Pennington County
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Top-rated holiday rentals in Pennington County
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Welcome to Case Place! A spacious quiet retreat!
Welcome! This relaxing & unique a space sets the stage for beautiful views of the Black Hills & gorgeous sunrises & sunsets right from the hot tub! Case Place is 15 minutes from Rapid City and 30-40 minutes from Mt. Rushmore, Custer & Keystone, & Sturgis. Box Elder is growing & a has public golf course, Ellsworth Air Force Base/Museum! Guests often take in the unique experience of seeing & hearing the sound of freedom from the majestic B-1's! Honeymooners /Anniversaries ❤️ Inquire w/ options.

Spearfish Canyon Skye lodge
Skyelodge is located in the heart of Spearfish Canyon. Located on a cliff wall . A 750 Sq. Ft. apartment on the top floor of a private vacation home. Spearfish Falls and Roughlock Falls one mile away can be accessed by hiking trails. FANTASTIC VIEWS! ( DEER, ELK, BALD EAGLES, PEREGINE FALCONS, OSPREYS, VULTURES ARE YOUR NEIGHBORS) HIKING, BIKING, ROCK CLIMBING, PHOTOGRAPHY, TROUT FISHING, OR JUST HANGING OUT. THE STARS AT NIGHT. GREAT COUPLES RETREAT!

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.

Bear Butte Luxury Retreat~ Hot Tub~ 10 Mins to DT
This 3-bedroom house is in a prime location & has EVERYTHING you need for an amazing vacation in Sturgis, South Dakota! • Private New Construction Home w/ Amazing Views of Bear Butte Mtn! • 2 Miles Away from Buffalo Chip Campground, 7 miles to Bear Butte State Park • 3 bed/2 bath-Sleeps 12 • Pool Table, Ping Pong & Skeeball • Indoor Fireplace • Hot Tub • RV/ATV/UTV Parking Spaces w/ Electric Hookup • Corn Hole and Giant Connect 4 • Card and Board Games! • Family Friendly- Pack n Play & High Cha

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.

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.

*4Bed*Beautifully updated home*Close to airport!
Kick back and relax in this beautifully decorated home. This stunning 4 bed, 2 bath home offers comfort and convenience, located just 8 minutes from Rapid City Regional Airport, 10 minutes from Rushmore Crossing (Shopping Center & Restaurants), 3 minutes from Black Hills Speedway, 10 minutes from Hwy 16 for Black Hills attractions, and 5 minutes from I-90 for a trip to Deadwood’s casinos or the Sturgis Motorcycle Rally. Perfect for families, groups, or solo travelers exploring the area!

Mid-Century Modern Living in the Black Hills
Upper two levels of my four level mid-century modern home with private entrances! Located in a quiet cul-de-sac near the foothills of the Black Hills and ~10 min from downtown Rapid City. This property features ample living space, a fully equipped kitchen with complimentary breakfast, plenty of natural light and a spacious back yard. It includes two bedrooms and one bathroom. I live on the completely separated lower levels of the home so you can enjoy the upper levels all to yourself!

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!

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.

Deadwood Two Bit Cabin on the Creek
Escape to our peaceful 2-bedroom Black Hills cabin on 4 private acres just minutes from historic Deadwood. A gentle creek runs through the property where guests often see deer, wild turkeys, and other wildlife. Enjoy quiet forest surroundings while being only 4 miles from Deadwood, 10 miles from Sturgis, and 13 miles from Terry Peak. Perfect for couples, families, and anyone looking for a relaxing Black Hills getaway close to hiking, skiing, and adventure.
Popular amenities for Pennington County holiday rentals
Other great holiday rentals in Pennington County

Modern Smart House | 2BR/2BA | 2 Patios + Fire Pit

Safari Tent at HTR Black Hills

Luxury Escape w/Hot Tub, Firepit and Barrel Sauna

Peaceful Canyon Retreat | Luxe Apt + Wildlife

Rustic Cabin

Spacious 4BR/3BA | Near Ellsworth AFB + Rapid City

Coffee Bar & Movie Room, 2 King Suites, Firepit

Glass Lodge- SD Bucket List to Stay
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