Vacation rentals in Pennington County

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Top-rated vacation rentals in Pennington County

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

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Top guest favorite
Chalet in Lead
4.97 out of 5 average rating, 258 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
Cabin in Lead
4.98 out of 5 average rating, 213 reviews

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

Top guest favorite
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, 501 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.

Top guest favorite
A scenic view showcases the cabin nestled amongst tall pine trees, surrounded by expansive green meadows. A winding gravel driveway leads to the property, with a seasonal pond visible in the foreground, reflecting the clear blue sky.
Home in Hill City
4.99 out of 5 average rating, 269 reviews

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!

Guest favorite
A scenic view of rolling hills and dense tree cover is captured from the outdoor patio area. Lush green grass and a variety of shrubs provide a natural border, while an expansive sky with scattered clouds completes the tranquil landscape.
Guesthouse in Rapid City
4.91 out of 5 average rating, 732 reviews

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!

Guest favorite
Cabin in Custer
4.94 out of 5 average rating, 202 reviews

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.

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, 255 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.

Top guest favorite
Cabin in Spearfish
4.9 out of 5 average rating, 130 reviews

Charming 1890's Log cabin 3

Featured in 605 magazine, this log cabin originates back to the late 1800's and is centrally located in the heart of Spearfish and at the northern tip of the Black Hills. Several restaurants are located within walking distance from the home and city bike and hiking trails can be found within a few blocks. Within a 15 mile radius, you will find and abundance of outdoor adventure including; mountain biking, hiking, rock climbing, skiing, snowmobiling, snowshoeing, sightseeing, etc...

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, 124 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 modern fire lookout tower is showcased, elevated on flared metal beams. Surrounded by tall pine trees, the structure features a spacious patio below and a welcoming deck above, designed for enjoying beautiful views. Warm ambient lighting enhances the exterior at dusk.
Tower in Custer
4.98 out of 5 average rating, 112 reviews

Fire Lookout Tower Next to Custer State Park

Enjoy this newly built 2023, modern Fire Lookout Tower. Suspended in the air over welded metal flared beams. Located just 5 minutes to Custer State Park. Experience some of the most unique views of rock formations while you drink your morning coffee. Open floor plan with 1.5 bathrooms all to yourself. Great area to hike, bike, see the fluffy buffalo. Just a 2 minute drive to downtown Custer. Feel refreshed when you stay in style at this cozy rustic gem.

Top guest favorite
The rustic cabin is nestled among trees, showcasing a wooden exterior with large windows and a deck. Sunlight filters through the branches, highlighting the natural materials of the structure. A gentle slope leads to the entrance surrounded by a lush forest.
Cabin in Spearfish
4.97 out of 5 average rating, 380 reviews

Secluded Cabin - Coyote Ridge Lodge

A unique, secluded, rustic cabin nestled on 10 acres of Ponderosa pine forest. Enjoy morning coffee on the sunny, spacious deck, afternoon picnics by the creek, a cozy wood fire in the evening and a sky full of stars at night. Only 12 minutes from great food and cafes in Spearfish; 20 minutes to Deadwood. The cabin is best for couples, families and groups of close friends. Note limited privacy; there are no bedrooms with doors you can close.

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, 154 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