Holiday rentals 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 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, 510 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
Flat in Rapid City
4.92 out of 5 average rating, 249 reviews

Lovely Basement Apartment, 1 Bdrm, private entry

Bring friends or family to this great place with lots of room for 4 ppl with private entry, 1000 sq ft cozy basement, apartment w/ 1 bdrm, Queen bed, 1 full size hide a bed sofa. New large sectional with 3 loungers, kitchen table. Discount for traveling nurses, etc, Oct-May, two people on long stays. 1/2 hour to Mt Rushmore, Keystone, and Sturgis and 40 min to Hill City. 1 hour to Badlands. 2 Minutes to downtown. Kitchen and Livingroom, full bath Lg Bdrm, Coffee bar, 2 lg Roku Tv's. 😊 ENJOY

Top guest favourite
Home in Spearfish
4.98 out of 5 average rating, 279 reviews

Falsebottom Hide-away

This is a great place to relax and enjoy the sounds of nature after a long day vacationing. Sleeps six with a secure fenced yard for the safety of your pets. Located in beautiful Maitland Canyon with seasonal Falsebottom Creek right off the private back deck featuring a BBQ and outdoor table. We have lived here for 40 years and are still amazed with the beauty of the Northern Black Hills. Close to so much, but with a real connection to the pristine nature that the Black Hills are famous for.

Top guest favourite
A spacious sleeping area is surrounded by tall wooden bookshelves filled with numerous books. A bed with a colorful quilt featuring floral patterns occupies the center, complemented by two pillows. Natural light may filter through nearby windows, providing a cozy atmosphere.
Guest suite in Custer
4.93 out of 5 average rating, 143 reviews

Journeys End--Guest house in the Black Hills

Guest house perfect for a quiet relaxing stay in the middle of pine trees, mountains, and meadows. Relax with us in the quiet beauty of the Black Hills. Deer, turkeys, rabbits, chipmunks are seen on the property--often right out your window. Children's playground, deck on mountaintop and 26 acres of meadow/forest to roam. 3 miles outside Custer Rock shop at our home and welcome rock-hounds. Guest house is in the back of our shop--separate from the house. Private concrete covered patio.

Guest favourite
Cabin in Sturgis
4.95 out of 5 average rating, 266 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 favourite
Tiny home in Wasta
4.88 out of 5 average rating, 338 reviews

The tiny house of Wasta with lots of character

Kick back and relax in this calm, stylish space. The tiny house is not an actual tiny house, a one bedroom with 1 queen bed, bathroom, kitchen/living room. Lazy boy reclining love seat, and a lazy boy recliner (very comfortable) for watching a movie in front of a faux fireplace. The kitchen is furnished with everything you need to prepare a home cooked meal. The microwave is air fryer/microwave. Enjoy your evening/morning sitting on the covered porch with your favorite beverage.

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
A vibrant sunset casts warm hues across the horizon, with streaks of orange and yellow visible in the sky. The cabin with a porch is partially framed by tall trees, and the surrounding landscape features gentle slopes, enhancing the scenic view.
Home in Rapid City
4.98 out of 5 average rating, 120 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
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
4.94 out of 5 average rating, 108 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 favourite
The exterior of the building features a welcoming entrance with a teal door, surrounded by light-colored brick and neutral wall tones. Flowers and landscaping are present by the entryway, and the design includes awnings above the doors.
Flat in Rapid City
4.97 out of 5 average rating, 111 reviews

118 Main - Apt. 4

A quite place in the heart of Rapid City! Your own designated covered parking spot right outside the door, walking distance to everything you need. Washer and dryer in the apartment, fully equipped kitchen, your own WiFi network and smart TV. A great place for a night, or all the comforts of home if you want to stay a month or two! Furniture is all new and the sleeper sofa has a foam mattress (it's actually comfortable.)

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, 168 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
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, 159 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 holiday rentals

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