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
Tower in Rapid City
5.0 out of 5 average rating, 56 reviews

Allard Tower

Perched dramatically on the edge of a quartzite cliff and surrounded by towering pines, this two-story rustic tower offers an unforgettable Black Hills escape. With panoramic views stretching across the forest and mountains, it’s the perfect hideaway for those seeking solitude, romance, and a deep connection with nature. Inside, you’ll find everything you need for a comfortable stay. The tower features 1 bedroom, 1 and 1/2 bathroom, and a fully equipped kitchenette—all styled with a warm touch.

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, 526 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
The game room features a classic wooden pool table with a blue felt surface, surrounded by a carpeted floor. A wall of brick showcases various framed memorabilia and decorative items, enhancing the recreational atmosphere. Two high-top chairs are positioned nearby.
Guest house in Rapid City
4.91 out of 5 average rating, 740 reviews

Priceless Black Hills View!

Two Large Furnished Bedrooms, new Queen Beds Pool Table and Darts Large Living Room with sofa sleeper 65'' UHD Smart TV Netflix, Prime, HD/Local Channels Pool and Rec facilities, seasonal WIFI Highspeed Internet Newly remodeled bathroom Outdoor patio area with gas grill Pool table and darts Full size fridge/freezer Convection oven Induction cooktop Microwave Keurig coffee and breakfast snacks Washer/Dryer Close to Rapid City shopping and dining Nature and wild life Amazing stars out at night!

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, 273 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
A panoramic view reveals a verdant canyon surrounded by towering pine trees. Jagged rock formations line the cliffs, with splashes of green foliage contrasting against the earthy tones. The sky, filled with soft clouds, adds a serene backdrop to this natural landscape.
Flat in Hermosa
4.96 out of 5 average rating, 55 reviews

Peaceful Canyon Retreat | Luxe Apt + Wildlife

Enjoy the perfect summer escape—warm days, open skies, and peaceful canyon views. Just 11 miles from the historic Game Lodge and the start of the famous Wildlife Loop. Nestled beside the stunning Box Canyon, our newly built 1-bedroom, 1-bathroom apartment offers a quiet retreat in one of the most breathtaking corners of the Black Hills. Spend your days exploring scenic drives, iconic landmarks, and endless trails, then return to unwind, and take in the natural beauty that surrounds you.

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
4.89 out of 5 average rating, 355 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 Keystone
5.0 out of 5 average rating, 8 reviews

Grizzly Bear Creek- Mt Rushmore Views- w/ Hot tub

Welcome to your perfect Black Hills getaway! Surrounded by breathtaking views, fresh mountain air, and a rustic setting that captures the true spirit of the Black Hills, this home is your ideal escape into nature. Best highlights of the property: 👉 Stunning VIEW of Mt. Rushmore RIGHT from the property 👉 Enjoy a peaceful walking path by the creek and gather around the fire pit to watch the Mount Rushmore lighting ceremony —creating unforgettable memories during your stay.

Guest favourite
Home in Rapid City
4.96 out of 5 average rating, 135 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
4.98 out of 5 average rating, 126 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
5.0 out of 5 average rating, 245 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!

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, 391 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 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, 208 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.

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