Holiday rentals in Pennington County

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Top-rated holiday rentals in Pennington County

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Top guest favourite
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 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, 500 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 spacious studio area features a king-sized bed with decorative pillows and a headboard made of wood. Alongside, a cozy seating arrangement with a large leather couch and colorful throw pillows creates a comfortable atmosphere, complemented by a ceiling fan and warm lighting.
Flat in Rapid City
4.97 out of 5 average rating, 114 reviews

Oversized studio on a 5 acre wooded lot with views

This stylish, 800 sq. ft studio has beautiful views of the Black Hills and is surrounded by national forest. It's a short 10 minute drive to Rapid City on the scenic Rimrock Highway. Amazing hikes and a scenic overlook are a short distance away. There's a private entry to the walk out lower level on a 6 acre lot. Studio has king sized bed, full bathroom, kitchenette w/ lg. fridge, microwave,toaster oven, coffee maker, etc . Outdoor parking or covered parking is available in inclement weather.

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, 268 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
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, 685 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 favourite
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.

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, 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 favourite
A cozy bedroom features a queen-sized bed adorned with a colorful patterned quilt and decorative pillows. A bedside lamp provides soft lighting, and a wooden dresser and a ladder-style chair add character to the space. Natural light filters through sheer curtains.
Apartment in Rapid City
4.97 out of 5 average rating, 168 reviews

Grandma's House

This is my townhome in west Rapid City. I invite to you my welcoming downstairs, air conditioned, basement bedroom, bath, and living room with a smart TV, microwave, mini fridge, coffee, tea, blender and toaster area. Snacks included. Ground floor and NO STAIRS. I live in a small town home community that enjoys its quiet privacy, and you are most welcome here. I am your host and am very excited to welcome you to stay in my clean, quiet, safe, cute and comfortable home.

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 home 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
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.

Popular amenities for Pennington County holiday rentals