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 favourite
Chalet in Lead
4.97 out of 5 average rating, 260 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
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 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, 503 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 favourite
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, 270 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!

Top guest favourite
A log cabin in a lush, green landscape is highlighted by a spacious wooden deck that wraps around the home. The structure features a sloped roof and multiple chimney stacks. Vibrant autumn foliage adds warmth to the exterior, creating a serene outdoor environment.
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 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, 125 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
A cozy living area is shown, featuring two patterned armchairs and a comfortable sofa. A wooden table with a vase of flowers sits near a window that brings in natural light. A clock and a lamp add to the welcoming ambiance.
Guest suite in Hill City
4.99 out of 5 average rating, 185 reviews

Pine Mountain Rest

Come find a restful space in the Heart of the Hills. After a busy day exploring all that the Black Hills have to offer you will find a quiet place to relax, fix your meals and rest for another day of adventure. Relax on the deck and listen to the Hill City 1880 train whistle as it returns from its final run. Located in Hill City we are in the heart of everything you want to do. Mickelson Bike Trail runs through town. Mount Rushmore and Crazy Horse are within 15 miles.

Top guest favourite
A wooden deck is seen overlooking a green golf course, surrounded by tall pine trees under a clear blue sky. The sunlight casts shadows on the deck's surface, enhancing the natural beauty of the setting.
Guest suite in Custer
4.95 out of 5 average rating, 365 reviews

The View at Bear Rock Two (Top Unit)

Relax in our charming guest suite featuring a private rooftop deck with serene views of Rocky Knolls Golf Course. Enjoy a comfortable queen bed, a renovated bathroom with a modern shower, and convenient amenities like a mini-fridge, microwave, cable TV, and Wi-Fi. Located just minutes from local dining, bars, and major attractions including Mount Rushmore, Crazy Horse Memorial, and Custer State Park, our suite offers the perfect base for your Black Hills adventure.

Top guest favourite
The A-frame cabin is framed by tall pine trees, showcasing a blend of wood and metal in its exterior design. Warm lights illuminate the structure, highlighting the large windows and inviting entrance. A stairway leads to the deck, enhancing accessibility to the cozy retreat.
Tiny homes in Custer
4.99 out of 5 average rating, 198 reviews

Modern A-Frame Cabin Next to Custer State Park

Enjoy this spacious modern A-Frame Cabin. Located just 5 minutes to Custer State Park. Experience views of the Needles Highway and Black Elk Peak 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 and kayak, trail ride rentals near by! Feel refreshed when you stay in this rustic gem.

Top guest favourite
Cottage in Spearfish
4.96 out of 5 average rating, 268 reviews

Off-Grid Cottage at Granny Flats

Welcome! Cappie, Star of Building Outside the Lines on Magnolia Network, built this adorable off-grid cottage as his own, but now you have the opportunity to stay! This beautiful 3-acre property, once the Swisher Farm, is today a working homestead, dozens of chickens, and a large garden. This cottage is handmade, from the bespoke front door to the custom 2-headed shower. We know you'll appreciate the details!

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 homes in Lead
4.98 out of 5 average rating, 156 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
A vibrant field of purple flowers stretches across the landscape, surrounded by green grasses. Pine trees are visible in the background, creating a harmonious blend with the clear blue sky above.
Apartment in Custer
4.96 out of 5 average rating, 327 reviews

Journeys End cozy Apartment attached to house

Cozy apartment attached to the main house, queen bed, full sized couch bed, large shower, mini kitchen with sink, microwave, refrigerator, coffee pot, toaster. Deck outside--gas grill and patio furniture. Located on 26 acres of pine forest, meadow and mt. Rock shop on property. Lots of space for rest, relaxation, or hiking. Access to children's playground, mountaintop deck and hiking trails.

Popular amenities for Pennington County vacation rentals