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, 507 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 charming yellow cabin is framed by lush greenery, with a wooden deck leading to the entrance. The path is bordered by plants, and a lantern-style fixture adds to the tranquil setting. Sunlight filters through the surrounding trees, highlighting the welcoming entrance.
Home in Spearfish
4.98 out of 5 average rating, 278 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.

Guest favourite
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
4.95 out of 5 average rating, 265 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.

Guest favourite
Guest house in Rapid City
4.77 out of 5 average rating, 154 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 favourite
A cozy bedroom features a queen bed adorned with a blue and brown patterned quilt. Soft lighting is provided by a bedside lamp, and natural light enters through two windows with dark blinds. The ceiling fan adds a practical touch to the airy ambiance.
Tiny home in Wasta
4.88 out of 5 average rating, 336 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
Home in Rapid City
4.96 out of 5 average rating, 129 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
The exterior of the guesthouse is showcased, featuring a light-colored façade and a welcoming front porch. A covered carport and landscaped lawn enhance the entrance, while trees provide natural shade alongside the walkway. The driveway is spacious, allowing for convenient access.
Home in Rapid City
4.97 out of 5 average rating, 117 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 of a modern guesthouse displays a blend of wood and stone accents, framed by a well-maintained lawn. A small tree and a rock landscaping feature are visible, while the sky above showcases a clear evening hue.
Farm stay in Rapid City
5 out of 5 average rating, 236 reviews

Luxury Ranch Stay

Be our guest on 40 private and fully gated acres. From all windows of the house you can watch 2 horses and cattle grazing through the meadow. The evening sunsets are magical with deer & turkeys wandering through. Relax under the stars at our fire pit (all supplies provided). Let your kids run wild with water guns & a water fall pond to refill at! Located right off HWY 16 makes you only 10 minutes to downtown Rapid City and 20 minutes to Mt. Rushmore!

Guest favourite
A charming creek-side home is featured, showcasing rustic wooden siding and a welcoming entrance. A pathway leads to a wooden deck, with a flagpole prominently displaying the American flag. Vibrant green grass and a fire pit with red chairs enrich the outdoor space, surrounded by natural hills.
Cabin in Rapid City
4.83 out of 5 average rating, 385 reviews

Creek-side Cabin | Hot Tub + Trout Fishing

Wake up to the sound of a babbling creek, sip your morning coffee on the deck while bighorn sheep graze on the hillside, and spend your evenings soaking in the hot tub under a sky full of stars. This beautifully furnished 3-bedroom Black Hills cabin sits right on the water — perfect for trout fishing, family gatherings, romantic getaways, or simply unplugging from the world. With stunning creek and mountain views, This is a Complete Black Hills retreat.

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, 158 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.

Top guest favourite
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.
Flat 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.

Top guest favourite
A spacious outdoor area features a comfortable swing set with striped cushions, positioned on well-maintained grass. In the background, a cabin with a green roof is surrounded by tall trees, providing a serene setting for relaxation.
Cabin in Hermosa
4.94 out of 5 average rating, 210 reviews

Beautiful Black Hills Cabin Centrally Located.

Beautiful Black Hills Cabin Centrally located on Hwy 40 West in Hermosa SD. This property is within 30 min of Keystone/Mt Rushmore, Hill City, Custer/Crazy Horse. Enjoy the Amazing views of the Hills and the abundance of wildlife from the covered patio. Two Bedrooms with Queen Beds. One large bathroom with walk in shower. Fully Furnished kitchen with all amenities, and Washer and Dryer.

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