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 hot tub is situated under a covered porch, providing serene views of a vibrant sunset over the expansive landscape. The sky showcases hues of orange and purple, while the peaceful surroundings feature rolling hills and an open horizon.
Flat in Box Elder
4.99 out of 5 average rating, 112 reviews

Welcome to Case Place! A spacious quiet retreat!

Welcome! This relaxing & unique a space sets the stage for beautiful views of the Black Hills & gorgeous sunrises & sunsets right from the hot tub! Case Place is 15 minutes from Rapid City and 30-40 minutes from Mt. Rushmore, Custer & Keystone, & Sturgis. Box Elder is growing & a has public golf course, Ellsworth Air Force Base/Museum! Guests often take in the unique experience of seeing & hearing the sound of freedom from the majestic B-1's! Honeymooners /Anniversaries ❤️ Inquire w/ options.

Top guest favourite
A spacious home is nestled among tall trees, overlooking a gently flowing creek. The property features a large deck and stonework, blending harmoniously with the natural surroundings, while vibrant greenery enhances the serene environment.
Home in Rapid City
4.97 out of 5 average rating, 117 reviews

Creekside Sanctuary

Creekside Sanctuary is a 6+ acre paradise for families, friends, celebrations or retreats. Naming this property was not easy, not only is this a Sanctuary for relaxation and rejuvenation, guests can also enjoy the popular site seeing and abundant wildlife native to our beautiful Black Hills. Whether winter or summer, there are activates nearby - fishing, hiking, skiing, snowmobiling, ice skating. The large yard is host to deer and turkey, an ideal gathering spot for celebration, fun and games.

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, 513 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.

Guest favourite
An outdoor seating area is showcased, featuring four wicker chairs arranged around a circular stone firepit. A wooden bench is positioned nearby, surrounded by lush green grass and natural foliage. A wooden fence adds privacy to the space.
Cabin in Rapid City
4.93 out of 5 average rating, 166 reviews

❖Charming Log Cabin❖Firepit❖Great Deck with Grill❖

Stay at our charming log cabin. It is secluded and private but still only minutes from town. ✔824 sq ft w/free parking & private entrance ✔Self check-in via door code ✔Dog friendly ✔Firepit and complimentary firewood ✔Great deck with grill ✔Close to Canyon Lake Park and a dog park ✔36 minute drive to Mt. Rushmore ✔1 hour drive to Badlands National Park ✔47 minute drive to Custer State Park ✔Full kitchen ✔Fast Wi-Fi ✔In-suite laundry Approved by Pennington County License Number COVHRLIC24-0019

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, 267 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 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, 339 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
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, 123 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, 240 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
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, 386 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
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, 115 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 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, 162 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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