Holiday rentals in Pennington County

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Top-rated holiday rentals in Pennington County

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Top guest favourite
A vibrant red barn contrasts with lush green trees and a clear sky, with a colorful rainbow arching above. An inviting hammock is shown in a tranquil setting, while a glimpse of the home's exterior reveals a charming farmhouse next to scenic hills.
Farm stay in Nemo
4.99 out of 5 average rating, 102 reviews

Restored Nemo Farmhouse on Centennial Trail W WiFi

Bring your ATV'S! Plenty of parking. On the Centennial Trail system. Fast wifi, smart TV with Dish channels. We are about 20 minutes from Sturgis, half an hour from Deadwood, and 40 minutes from Rapid City. The nighttime sky is very dark for viewing all the constellations; we have solar lights around the house, but it can be dark without a flashlight. Please keep in mind we are in the forest, and there are bugs, flying insects, and small critters. We work very hard to keep them out of the house!

Guest favourite
A spacious dining area is visible, featuring a dark wood table surrounded by white chairs. A light brown countertop is present in the foreground, while a cozy living space with two brown recliners is shown in the background. Large windows provide natural light, enhancing the welcoming feel.
Home in Rapid City
4.98 out of 5 average rating, 212 reviews

Cheerful 3 bedroom home

Relax with the whole family at this peaceful place to stay. 3 bedroom home, entire main floor. Basement is a separate office unit. Use upper parking with entry to the kitchen. Located close to Rapid City Regional Airport and Black Hills Speedway. Easy access to Highway 16 bypass which ties into I-90 and Highway 16 to Mount Rushmore & the Black Hills. Great view of Black Elk Peak out the living room window! No pets or smoking please. Approved by Pennington County License Number COVHRLIC25-0019

Top guest favourite
A charming red house is surrounded by lush green grass and tall trees, with a sloped hill rising in the background. A small deck with white chairs is visible at the front, offering a welcoming outdoor space.
Cabin in Hill City
4.94 out of 5 average rating, 116 reviews

Grandma's House in the Heart of the Black Hills

Grandma's House is in the heart of the Black Hills, located 1 mile from Hill City, it is minutes away from Mt. Rushmore, Crazy Horse, Custer State Park and more. It sits alone on the edge of a meadow with hills directly behind it and a small, bubbly creek in front of the house. It has plenty of room for kids to run and play outside, and a cozy, quaint inside for families to enjoy each other's company. Grandma’s House is available for extended stays November thru April. Contact host for details

Top guest favourite
A combined kitchen and dining area features a wooden table with four chairs, set against a backdrop of open shelves displaying various dark items. A cozy sleeping area is visible, showcasing a large bed dressed in patterned linens and accented by a black and white wall art piece.
Loft in Sturgis
4.98 out of 5 average rating, 101 reviews

Cozy Sturgis Loft #2

This historic loft is in the heart of Sturgis and has been recently renovated with many thoughtful touches to make your stay as comfortable as possible. This apartment is on the second story next to quiet neighbors with free parking available at the front entrance and also the back entrance of the building. Located 20 min from both Spearfish and from Deadwood and only 60 minutes from Mt Rushmore. Walking distance to several downtown restaurants and bars. Convenient contact-free check-in.

Top guest favourite
A cozy living area features a gray sofa adorned with decorative cushions. A large rug covers the wooden floor, and a fireplace provides a focal point. Art pieces are displayed on the walls, complemented by natural light filtering through sheer curtains.
Home in Rapid City
4.99 out of 5 average rating, 168 reviews

Mid-Century Modern Living in the Black Hills

Upper two levels of my four level mid-century modern home with private entrances! Located in a quiet cul-de-sac near the foothills of the Black Hills and ~10 min from downtown Rapid City. This property features ample living space, a fully equipped kitchen with complimentary breakfast, plenty of natural light and a spacious back yard. It includes two bedrooms and one bathroom. I live on the completely separated lower levels of the home so you can enjoy the upper levels all to yourself!

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, 323 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.

Top guest favourite
The bungalow features a spacious wooden deck with a rail, furnished with four outdoor chairs and a table. Large windows showcase the stone and wood exterior, while the warm lighting highlights the architectural details against the backdrop of trees.
Home in Custer
5 out of 5 average rating, 112 reviews

Beautiful Bungalow Next to Custer State Park

Enjoy this newly built 2023 modern Beautiful Bungalow, 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 style and comfort with amazing accommodations.

Top guest favourite
A charming front porch features a welcoming staircase leading to a red door. Floral decorations hang from the railing, enhancing the entrance's appeal. Comfortable seating is visible on the porch, framed by a well-maintained green lawn and decorative outdoor lighting.
Flat in Deadwood
5 out of 5 average rating, 130 reviews

Newly remodeled in the Heart of Deadwood

This newly remodeled, comfortable apartment is right in the heart of Deadwood! This home, built in the early 1900's is on Deadwood's Historical Registery, and is located on famous Main Street just a couple blocks from the action. It is a one bedroom apartment with one bath and a full kitchen. Laundry facilities are available. You'll love coming back to this cozy space with all the comforts of home, after enjoying all Deadwood and the Black Hills has to offer!

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
4.93 out of 5 average rating, 101 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 entrance door features a welcoming sign stating 'Welcome to Downtown Loft EAST.' Inside, gray walls complement the checkered floor. Natural light filters through large windows, showcasing the warm hardwood flooring and adding dimension to the entryway.
Serviced apartment in Spearfish
4.91 out of 5 average rating, 197 reviews

Downtown Loft East

This apartment is a newly renovated space in a historic building in the heart of Downtown Spearfish! Experience downtown living at its finest! This apartment is within walking distance of all the local hotspots: fine dining, local retailers, Spearfish Brewing, the local bars, and beautiful Spearfish Creek and the City Park! Many local businesses have partnered with us to bring discounts and freebies when you stay with us!

Top guest favourite
The exterior of a handmade strawbale cottage is shown, featuring a wooden facade with large windows. Solar panels are visible on the roof. A spacious driveway leads to a covered parking area, framed by greenery and landscape elements, creating an inviting entrance.
Cottage in Spearfish
4.95 out of 5 average rating, 262 reviews

Off-Grid Cottage at Granny Flats

Welcome! Cappie, Star of Building Outside the Lines on Magnolia Network, built this adorable off-grid cottage as his own, but now you have the opportunity to stay! This beautiful 3-acre property, once the Swisher Farm, is today a working homestead, dozens of chickens, and a large garden. This cottage is handmade, from the bespoke front door to the custom 2-headed shower. We know you'll appreciate the details!

Guest favourite
A modern living area features a large gray sectional sofa paired with two yellow accent chairs. A wooden coffee table is centered on a soft area rug, while a television is mounted on the wall opposite. Art pieces adorn the walls, adding color and interest.
Guest suite in Rapid City
4.89 out of 5 average rating, 341 reviews

Modern Guest Suite conveniently located

Stylish one-bedroom guest suite with private ground-level entrance and dedicated parking. This modern apartment, near the civic center, shopping, and interstate, features a fully equipped kitchen for cooking and a washer/dryer for convenience. Enjoy a comfortable, self-contained space. Note: A separate upper unit may produce some noise.

Popular amenities for Pennington County holiday rentals