Holiday houses in Pennington County

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Top-rated holiday rentals in Pennington County

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
A hot tub is situated under a covered porch, providing serene views of a vibrant sunset over the expansive landscape. The sky showcases hues of orange and purple, while the peaceful surroundings feature rolling hills and an open horizon.
Apartment in Box Elder
4.99 out of 5 average rating, 113 reviews

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.

Top Guest favourite
Chalet in Lead
4.97 out of 5 average rating, 265 reviews

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!

Top Guest favourite
A cozy bedroom features a spacious bed covered with a red blanket. Two framed artworks adorn the wall above the bed. A mounted TV is positioned nearby, while a light wood closet with double doors is visible to the right. Natural light enters through a window.
Guest suite in Rapid City
4.98 out of 5 average rating, 513 reviews

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.

Guest favourite
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, 267 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.

Guest favourite
Guesthouse in Rapid City
4.78 out of 5 average rating, 156 reviews

Guest Suite-Hot Tub-Close to Town

Welcome to our charming guest suite with private access and parking, perfect for a relaxing getaway. This unique space offers a hot tub with complete privacy (enclosed by a 6-foot fence), an LED makeup mirror with a defogger, a full-size washer and dryer, and a private patio. Enjoy thoughtful touches and unique details throughout the space. Located near all West Rapid coffee shops and restaurants, it’s also a short drive to major tourist destinations. Book now and enjoy a unique retreat!

Guest favourite
An elegant guest house showcases a unique design with large wooden doors and stone details at the entrance. The exterior features a mix of dark siding and shingle roofing. Surrounding greenery and a rocky hillside complement the peaceful setting.
Home in Rapid City
4.96 out of 5 average rating, 130 reviews

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!

Top Guest favourite
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, 123 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 favourite
Townhouse in Rapid City
4.91 out of 5 average rating, 171 reviews

Modern Townhouse | King Bed | Black Hills Base

A sleek, modern townhouse in Rapid City that checks every box — stylish interiors, a king master bedroom, stunning views of the Black Hills, and an unbeatable location just 7 minutes from the airport and 30 minutes from Mount Rushmore. Whether you're here for a Black Hills adventure, a Sturgis Rally trip, or a business visit, this top-rated space delivers comfort, convenience, and a seamless stay from check-in to checkout.

Top Guest favourite
A modern tiny house features warm wooden siding and a sleek black exterior. A spacious wrap-around deck showcases seating and soft lighting. The surrounding landscape includes distant rock formations under a cloudy sky, providing a serene atmosphere for relaxation.
Tiny home in Custer
4.99 out of 5 average rating, 169 reviews

Rustic Modern Tiny House Next To Custer State Park

Enjoy this modern Tiny House, located just 5 minutes to Custer State Park. Experience unique views of rock formations 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, trail ride and kayak rentals near by! Feel refreshed when you stay in this rustic gem.

Top Guest favourite
Farm stay in Rapid City
5 out of 5 average rating, 10 reviews

Cozy Bunkhouse on bucking bull ranch

Wake up to a rooster’s call and enjoy fresh eggs just steps from your door at our cozy western bunkhouse in the Black Hills. Attached to a working barn, this unique stay lets you feed Highlander cattle, relax by a fire pit with vintage wagon picnic tables, and access nearby ATV trails. Sleeps four with full kitchen, bath, loft, and pull-out couch, perfect for unplugging and experiencing authentic ranch life.

Top Guest favourite
A modern tiny cabin features reflective walls, blending into the surrounding nature. Tall trees and a blue sky are mirrored on the surface, creating a seamless connection with the forest. The cabin's structure is set among rocky terrain, emphasizing its unique design.
Tiny home in Lead
4.98 out of 5 average rating, 162 reviews

Mirror Cabin in the Black Hills

You'll love this unique and romantic escape. This tiny mirror cabin, REFLECT+RECONNECT, is nestled in the serene beauty of the Black Hills of South Dakota. 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.

Superhost
Home in Spearfish
5 out of 5 average rating, 4 reviews

Black Hills View • Deck • Fireplace •DT 4 mins •WD

1,650/3000 ft² family home with expansive deck, outdoor dining area & mountain views. ⥤ Backyard w/ children's play set ⥤ Fully equipped + stocked kitchen ⥤ Dedicated workspace + 1 GB wifi ⥤ Parking → driveway (2-3 cars) ⥤ Keurig + drip coffee maker ⥤ Smart TV + DVD player ⥤ Onsite washer + dryer ⥤ Indoor gas fireplace 4 mins → DT Spearfish (cafes, dining, shopping) 9 mins → Lookout Mountain

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