Holiday rentals in Pennington County

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Top-rated holiday rentals in Pennington County

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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 dining area features a white table surrounded by blue chairs, inviting shared meals. A cozy seating area with a brown sofa and a patterned rug complements the space. Natural light flows through large windows adorned with light curtains, enhancing the room's welcoming feel.
Bungalow in Custer
4.99 out of 5 average rating, 161 reviews

The Jasper House: A cheerful downtown bungalow

Named after a local gemstone, The Jasper House is a stylish, centrally-located 1940s bungalow that was newly remodeled in 2022. This cheerful 2-bedroom house sleeps 4 and offers a full kitchen, full bath, fenced back yard with fire pit & grill, and more! -Five minute walk to downtown shopping, award winning restaurants & the Mickelson Trail -Ten minute drive to Custer State Park; twenty minute drives to both Jewel Cave National Monument & Wind Cave National Park -One block from the city pool

Guest favourite
A cozy living area features a gray sofa with a mustard throw, positioned next to a white coffee table. A dark chair adds contrast, and soft natural light fills the space from large windows. An open kitchen is visible in the background, complete with essential appliances.
Home in Wall
4.91 out of 5 average rating, 350 reviews

Cozy Warm Stay. Near Badlands NP. Pets Welcome!

Welcome to Wall – The Gateway to the Badlands Our home is just 3 blocks from Wall Drug Store, 8 miles to Badlands National Park, 20 miles to the Minuteman Missile Site, 77 miles to Mount Rushmore and 94 miles to Wind Cave National Park. Conveniently located near restaurants and gas stations, it's also an easy 8 minute walk to the city park and city pool (Pool opens during summer months) Pets are welcome to stay! Be sure to experience the unforgettable sunrises and sunsets over the Badlands.

Top guest favourite
The interior showcases a rustic stone fireplace wall adorned with buffalo and moose mounts. Exposed wooden beams stretch across a high ceiling, complemented by soft lighting. A framed photograph and a shelf with decorative items add character to the cozy cabin atmosphere.
Cabin in Rapid City
4.96 out of 5 average rating, 176 reviews

Cabin in Hills! Centrally Located! Fully equipped!

Our cozy cabin is located in a quiet neighborhood in the Heart of the Hills. Take in the abundance of nature, smell the fresh pines, and relax after a fun day in the Hills. Inside will be everything you need to make your vacation in the Black Hills a memorable one! Rustic, stone fireplace with buffalo and moose mounts. Fully equipped kitchen. Smoke-free home. 10 minutes from Rapid City, 35 minutes to Mt. Rushmore & Deadwood and 45 minutes to Sturgis or Custer State Park. Paved roads!

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
4.96 out of 5 average rating, 249 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
A warm living space is highlighted by a leather couch and decorative pillows, centered on a wooden coffee table over a patterned area rug. An accent light fixture and artwork adorn the walls, while a small desk and bar seating are visible near the window.
Flat in Rapid City
4.91 out of 5 average rating, 243 reviews

Black Hills Getaway

Rest and recharge at your Black Hills get away in this newly finished apartment. Enjoy the walk-in shower with 2 shower heads and then get a soothing night sleep on the top of the line mattress produced by Nectar. Kick back at the end of your night by trying out the retro arcade game or watching a movie accompanied by your own bucket of popcorn from the popcorn maker and supplies provided. All of this is centrally located within driving distance to all the sites and attractions!

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.

Guest favourite
A single-story house with a neutral exterior is framed by a well-maintained lawn and decorative flower beds. A front porch with steps leads to the main entrance, featuring a white door and large window, while the surrounding landscape is dotted with greenery.
Home in Rapid City
4.94 out of 5 average rating, 566 reviews

Rapid City Black Hills Westside Home 1

The home is in a great location in Rapid City, minutes from downtown, easy access to trails and paths, and a good starting point for exploring the Black Hills! We welcome dogs in our home. No cats! Additional $150 fee will be added if cat is “snuck” into home! There is a nice fully fenced back yard, plenty of off street parking, as well as use of the garage (low clearance). I am happy to help with trail maps and directions as you kick off your adventures in the Black Hills.

Top guest favourite
Home in Rapid City
4.95 out of 5 average rating, 132 reviews

Executive Golf Course Home, Family Friendly

Quiet stay in an exclusive golf course neighborhood entering the Black Hills - 30 minutes to Mount Rushmore, 20 mins to Sheridan Lake, while being a quick 13 mins to downtown. Easy access to Black Hills and Badlands National Park attractions. Locally owned and managed by Rapid City residents! No worrying about a faceless property mgmt company - instead enjoy the attention and timely response from locals who personally care about your experience and stay at their property.

Guest favourite
A serene backyard oasis is depicted, featuring well-maintained grass surrounded by decorative stone pathways and natural rock borders. A covered patio area is visible, illuminated by soft lighting, with comfortable seating arranged under trees, creating a peaceful outdoor retreat.
Home in Rapid City
4.94 out of 5 average rating, 164 reviews

Backyard Oasis in the Heart of Rapid City!

*NO ADDITIONAL PERSON FEE! Entertainer's Delight, newly remodeled Ranch Style Home in a great location close to schools, downtown, and hospital! This 3 bedroom 1 bath home offers many upgrades, stunning backyard oasis with mature trees and perennials, extensive rock work with paths and patios, and a covered concrete patio that leads back into the kitchen and open concept living area. The kitchen has a modern feel, with a bar-top for entertaining. IGB Internet speed!

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, 146 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 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, 199 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.

Popular amenities for Pennington County holiday rentals