Vacation rentals in Pennington County

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Top-rated vacation rentals in Pennington County

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Top guest favorite
A vibrant sunset paints the sky in shades of orange and pink, silhouetting the surrounding pine trees and snow-covered landscape. The horizon features rolling hills, creating a serene and picturesque backdrop for the tranquil scene.
Home in Custer
4.96 out of 5 average rating, 134 reviews

Custer Blue Bird Haven in Beautiful Valley Setting

"Bluebird House -guests have entire house-3 bedrooms, 2 bathrooms, 2 living rooms, a full kitchen with a good dishwasher. There’s a Kitchenette in the lower level. Also, a Gas Fire Pit on lower level deck- available to guests, UNLESS Fire Danger’s high- will be removed. There’s a total of 3 queen-sized beds & 4 single beds, in the new expanded Blue Bird Haven, which can sleep 10 guests. Basic de'cor- relaxing! Enjoy Incredible sun sets & solitude in the beautiful Black Hills “Valley” setting!

Top guest favorite
Chalet in Lead
4.97 out of 5 average rating, 254 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 favorite
A modern living area is presented with a brown leather sofa and two green chairs. A round coffee table sits in the center on a patterned rug. Art prints adorn the walls, and large glass doors provide views of the surrounding trees.
Home in Spearfish
4.98 out of 5 average rating, 61 reviews

Spearfish 2bd1ba/Bonus RV Spot

Brand new modern cabin on private acreage nestled in the pine trees. Enjoy a quiet stay 10 minutes from Spearfish. -1 Bedroom w/ queen bed -1 bedroom w/ king bed -Full Bathroom -Washer/Dryer Starlink internet is provided which allows for remote working and streaming services on the TV. Traveling with someone with a camper? A bonus RV spot is located next to the cabin with full electric/water/sewer hookups for an extra fee. Please message before booking for camper pricing details/restrictions.

Top guest favorite
The loft features a cozy sleeping area with a spacious bed dressed in a light blanket. Bright pillows add a pop of color. Natural light fills the room from a large window with red curtains, and a smaller window enhances the airy feel. A decorative feature stands nearby.
Loft in Lead
4.98 out of 5 average rating, 683 reviews

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.

Guest favorite
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
4.96 out of 5 average rating, 249 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.

Superhost
Guesthouse in Rapid City
4.76 out of 5 average rating, 141 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!

Top guest favorite
An open-concept living space features a modern kitchen with wooden cabinetry and white appliances. A dining table for four is positioned next to a cozy seating area with a stylish chair and gray couch. Natural light fills the room from a skylight above.
Apartment in Rapid City
4.95 out of 5 average rating, 168 reviews

118 Main - Apt. 6

Central down town location? Check! Private covered parking? Check! Washer and Dryer? Check! A hard to beat base camp for a South Dakota adventure. See the Black Hills and Badlands by day, park the car and walk to restaurants and entertainment for the evening. Bring your mountain bike and hit the urban trails, or make your way to the bike path along Rapid Creek for a peaceful in town ride. 1 bedroom apartment will sleep 4, that is 2 people on the bed and 2 on the sleeper sofa.

Guest favorite
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, 118 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 favorite
A welcoming entrance is highlighted by steps leading up to a green cottage with a dark door. Colorful chairs in orange and green are positioned on the porch, surrounded by potted plants with vibrant flowers, enhancing the inviting entryway.
Farm stay in Sturgis
5 out of 5 average rating, 102 reviews

Peaceful Farm Stay at Edge of Black Hills!

The Cottage at Bear Butte Gardens is located on a farm alongside beautiful Bear Butte State Park just outside of Sturgis. This private studio space has all of the amenities and easy access just off Highway 79. Guests can enjoy morning sunrises, tea or coffee on the front porch, bird watching during the day, and star gazing at night uninhibited by street lights. Located on the edge of the Black Hills with easy access to trails, scenic drives, hiking, skiing, and fishing!

Guest favorite
The exterior features a newly remodeled wooden facade with a welcoming entrance. A set of steps leads to a deck with a simple railing, providing access to large windows that illuminate the interior.
Guest suite in Rapid City
4.93 out of 5 average rating, 101 reviews

Modern Luxury | 2BR/1BA | Minutes from Downtown

Experience upscale comfort in this newly remodeled, 2 King Bedroom, modern-luxury unit—just minutes from downtown. Enjoy a private entrance, serene deck with wildlife views, full gourmet kitchen, spa-style walk-in shower, washer/dryer, and high-speed Wi-Fi. Peaceful, quiet, and close to top tourist spots. Note: Steps required for access. This is a secondary unit. The property is split into two units, with this unit being on the upper level.

Top guest favorite
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, 159 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 favorite
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, 146 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.

Popular amenities for Pennington County vacation rentals