Guesthouse holiday rentals in Pennington County

The exterior of the home features a rustic wooden facade with large windows that allow natural light to enter. A spacious driveway leads to a two-car garage, surrounded by a landscape of trees and greenery, creating a serene outdoor setting.

4.91 out of 5 average rating, 79 reviews

Modern Smart House | 2BR/2BA | 2 Patios + Fire Pit

Luxurious 2BR/2BA smart home minutes from downtown & top Black Hills attractions like Mount Rushmore, Custer State Park, & Deadwood. Enjoy smart appliances, digital rain shower, voice-controlled lighting, and 2 private patios w/ fire pits and a grill. Surrounded by peaceful nature and frequent wildlife. Includes 2-car garage, fast Wi-Fi, & upscale finishes—your refined retreat in the Black Hills. Note: The property is split into two units, with this unit being larger on both main & upper level.

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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.

4.91 out of 5 average rating, 745 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!

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4.97 out of 5 average rating, 79 reviews

A cozy guest house is set against a backdrop of lush trees, featuring a covered patio area with large glass doors. A fire pit with several red chairs is arranged in front, inviting gatherings. A gravel outdoor space surrounds the property, enhancing the natural setting.

Guesthouse in Custer

Custer Cozy Guest House

Cozy guest house centrally located in the southern Black Hills on five acres. Enjoy beautiful sunsets from the shared fire pit just steps from the guest house. Located 5 miles from the town of Custer. Enjoy your days visiting nearby Custer State Park, Crazy Horse Memorial, Mt. Rushmore, Wind Cave Nat'l Park, Jewell Cave. Walk, bike or run on the 109 mi Mickelson trail. We are also 2 hours from Badlands Nat'l Park. This area is rich in beauty and history so be sure to get out and explore!

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A gravel driveway winds through green grass and tall trees, leading to Stoneridge Ranch. A sign marks the entrance, and buildings are visible in the background, set against a clear blue sky.

4.92 out of 5 average rating, 236 reviews

Stoneridge Ranch

Stoneridge Ranch’s name came from previous owner & isn’t currently a ranch. It is something off the beaten path for some peace & quiet. We’re tucked away in the beautiful Black Hills only 30min from Rapid City & several local attractions: Mt Rushmore, Reptile Gardens, Bear Country, Needles Highway, Rushmore Caves + many more. Opportunities to see plenty of wildlife(deer/turkeys), our horse, pony, 2 dogs & 2 cats. Walk/runners take advantage of the gravel/paved roads for a lovely stroll.

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Superhost

4.75 out of 5 average rating, 167 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!

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4.92 out of 5 average rating, 166 reviews

A warm living space features a four-poster bed with neatly arranged towels on the bedding. A leather couch complements a wooden coffee table, while a dining area is visible. Natural light flows through large windows, and a kitchen area is in the background, enhancing the open layout.

Guesthouse in Spearfish

Cottage 10-Modern Farmhouse

Come and stay in this Modern, Elegant Farmhouse! This beautiful cottage has all the amenities for a great stay. Amenities: -Fully Equipped Kitchen -Tile Shower with Unlimited Hot Water! -Coffee and Essentials -Hot tub (shared with other guests) Location: Downtown Spearfish. Three blocks from BHSU or Main Street! 1 hr to Mt Rushmore & Rapid City Airport. WE ALLOW UP TO TWO DOGS ONLY. PET FEE APPLICABLE. NO CATS. PLEASE MESSAGE ME FOR DETAILS. *No smoking allowed on the property*

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4.96 out of 5 average rating, 165 reviews

The living area features a modern design with a large flat-screen TV mounted on a textured wall. A vibrant blue retro refrigerator complements the kitchen space, which includes stylish cabinetry and a black countertop. A contemporary electric fireplace adds warmth, while a coffee table sits centrally on the floor.

Guesthouse in Sturgis

Hidden Gem in Historic Home

Newly renovated Airbnb duplex, nestled in a quaint small town setting. This charming 400 square foot space is ideal for two people, yet comfortably accommodates up to four with a queen pull-out couch in the living room. Enjoy the convenience of a kitchenette for preparing meals and snacks during your stay. This home is a duplex. The otherside of the duplex is rented out by a young family. Experience the charm of small-town living and book your stay in our inviting Airbnb today!

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4.99 out of 5 average rating, 161 reviews

The entrance features a welcoming red door framed by neutral siding, with a small wooden step area leading up to it. A gravel pathway leads to the doorway, complemented by a decorative pot with greenery visible beside the door.

Guesthouse in Whitewood

Country Lodge ~Where the Prairie Meets the Pines

Our space started as my husbands "man cave." A place to display his hunting accomplishments and do all things manly. Yet, as the project progressed it turned into a lovely rustic lodge that we'd like to share with you. Just 5 miles North of Sturgis we provide a space that is minutes away from Bear Butte State park, the beautiful Black Hills and sits on a quiet valley acreage. It would be ideal for anyone visiting the area who enjoys fresh country air and a bit of rustic charm.

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4.98 out of 5 average rating, 171 reviews

The exterior of the Mercantile features blue siding and a red sign, showcasing a traditional design. A covered porch is present, furnished with a small table and two chairs. Windows allow natural light to fill the space, while trees surround the property, enhancing privacy.

Guesthouse in Deadwood

The Mercantile at Mad Peak Lodging, sleeps four

The Mercantile at Mad Peak Lodging is part of our Old West–inspired collection of vacation rentals, blending historic character with modern comfort in the heart of the Black Hills. Surrounded by mountain scenery, this inviting retreat offers a peaceful setting with easy access to outdoor adventure, local attractions, and scenic drives. Whether you’re exploring the Hills or unwinding after a full day out, the Mercantile is a comfortable and memorable place to stay.

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4.88 out of 5 average rating, 208 reviews

A cozy sitting area features a brown love seat positioned next to a window, with a small table and decorative items nearby. The kitchen area, visible in the background, includes a white refrigerator and stove, and charming cabinetry enhances the space.

Guesthouse in Spearfish

Adorable loft carriage house with hot tub

This is the original carriage house from 1892 that has been converted into living quarters with a small fenced in outdoor space. The cozy cottage is made up of two levels. On the floor level, is a small kitchen, bathroom, and sitting area with gas fire place (love seat pulls out to a single bed). On the second level, via a narrow steep hayloft staircase, is a king bed, tv, and private balcony. This quaint space is the perfect get away.

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4.94 out of 5 average rating, 131 reviews

A charming exterior of a cottage is framed by lush green grass and trees. The yellow door stands out against the muted tones of the building, inviting guests inside. A split rail fence is visible in the foreground, completing the rustic countryside feel.

Guesthouse in Hermosa

Black Hills Bungalow

A comfortable gathering place for families and small groups, yet cozy enough for a couples getaway. Minutes from the Southern Black Hills, Badlands, Crazy Horse, Mount Rushmore, Custer State Park, Rapid City, Hill City, and many hiking trails and fun! This is a Native American decor and beautiful area around the place! ***Please note-there are NOT nine beds, only five people may stay. Air BnB will not change it. 😉

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