Chalet vacation rentals in Pennington County

Find and book unique chalets on Airbnb

Top-rated chalet rentals in Pennington County

Guests agree: these chalets are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Top guest favorite

A scenic view captures snow-covered cliffs framed by evergreen trees. Wisps of mist rise from the mountainous terrain, contrasting with the clear blue sky. The landscape showcases the natural beauty of Spearfish Canyon, highlighting its tranquil winter atmosphere.

Chalet in Lead

4.97 out of 5 average rating, 250 reviews

Spearfish Canyon Skye lodge

Skyelodge is located in the heart of Spearfish Canyon. Located on a cliff wall . A 750 Sq. Ft. apartment on the top floor of a private vacation home. Spearfish Falls and Roughlock Falls one mile away can be accessed by hiking trails. FANTASTIC VIEWS! ( DEER, ELK, BALD EAGLES, PEREGINE FALCONS, OSPREYS, VULTURES ARE YOUR NEIGHBORS) HIKING, BIKING, ROCK CLIMBING, PHOTOGRAPHY, TROUT FISHING, OR JUST HANGING OUT. THE STARS AT NIGHT. GREAT COUPLES RETREAT!

Top guest favorite

The exterior of the home showcases a two-stall garage made of stone, with wooden accents. A spacious upper deck with railings overlooks the surrounding natural landscape, featuring tall pine trees and open grassy areas. Large windows allow for ample natural light.

Chalet in Lead

5 out of 5 average rating, 11 reviews

“Chalet Meyer” In the Black Hills walk to Ski

This stunning home offers views of the ski area on one side and the Black Hills forest on the other. Located within walking distance of Terry Peak’s main ski lodge, Chalet Meyer is cozy yet spacious, with fantastic amenities. Enter through the 2-stall garage with a laundry room on the lower level. The main level features a full kitchen, open living/dining area, sunroom, and a deck with exceptional views—perfect for relaxing, dining, or enjoying morning coffee while watching wildlife etc.

Top guest favorite

The image presents a collage of Sheep Hill Chalet's exterior and interior spaces. The chalet's rustic facade is complemented by large windows. Inside, a cozy living area is furnished with circular tables and comfortable seating. A modern kitchen showcases sleek appliances and ample counter space.

Chalet in Lead

4.96 out of 5 average rating, 189 reviews

Secluded Modern Mountain Rustic Chalet on 10 acres

Sheep Hill Chalet is a Black Hills-inspired rustic modern cabin located in beautiful Lead, South Dakota. Newly built in the heart of nature, on a plot of over 10 acres and bordered by the Black Hills National Forest, this 3 bed, 2.5 bath rental cabin will charm you with its modern architecture and antique rustic touches. Enjoy cozy luxury in the living room with 16 ft windows and double sided stone fireplace! Gourmet kitchen, hot tub, and open living areas - perfect for your gathering!

Top guest favorite

A charming home with a wraparound porch features a metal roof and a wooden exterior painted in shades of green. The front is flanked by large windows, allowing ample natural light, while a small decorative sign adds character to the porch area.

Chalet in Lead

4.94 out of 5 average rating, 158 reviews

Tucked Away Chalet minutes to Deadwood and Skiing

PLEASE READ THE ENTIRE LISTING DESCRIPTION, REVIEW ALL FEATURES, AND VIEW ALL PICTURES TO KNOW EXACTLY WHAT TO EXPECT! Conveniently located in the northern Black Hills in the City of Lead, central to all that it has to offer. Minutes to historic Deadwood and Terry Peak ski area. Snowmobile trails, mountain biking and hiking trails minutes away. Visit the many local breweries and restaurants while taking in all the history of this historic mining town. Please enjoy and respect our home!

Superhost

Chalet in Lead

New place to stay

Peaceful Paradise found at Spearfish Canyon!

Over 25 acres in the scenic Spearfish Canyon area, this 4BR 3BA retreat is 3,200+ sqft of rustic charm & comfort. Vaulted ceilings, wood and tile flooring, two cozy fireplaces—one in the grand primary suite w/ walk-in shower & tub. Large living room, a loft-style billiards room, & chef-ready kitchen w/ all major appliances. Outside, relax on an open patio with outdoor fireplace, bluff views, rock landscaping, and wooded privacy. This is your perfect private getaway in the Black Hills.

Guest favorite

A spacious chalet features a wooden exterior, large windows, and a welcoming deck. The surrounding landscape includes tall pine trees and a grassy area. A parked white vehicle is visible nearby, offering convenient access to the property.

Chalet in Keystone

4.94 out of 5 average rating, 49 reviews

Chalet with View of Mount Rushmore!!

Park your car and walk to all the shops and restaurants along the main strip in Keystone. With a view of Mount Rushmore, a beautiful yard and a huge deck with BBQ grill, your entire family will experience the Black Hills like never before. PLEASE TAKE NOTE, helicopters to Mount Rushmore fly over the chalet about 9am on sunny days and are finished by 7pm. Otherwise, the tranquil and serene setting will make you feel secluded even though Keystone is just a short walk down the hill.

The living room features a stone fireplace as a focal point, surrounded by dark leather couches. Natural light filters in through large windows above a decorative area rug on the wooden floor. A wooden staircase leads to the upper level, accented by handrails.

Chalet in North Lawrence

4.33 out of 5 average rating, 6 reviews

Holy Terror Chalet at Terry Peak Ski Resort

Terry Peak Chalets provides executive level lodging for families, businesses and special events including weddings, retreats, reunions and conferences. Our goal is to create an atmosphere that duplicates your home away from home with countless amenities that you cannot experience anywhere else in the Northern Black Hills. Exciting News! Skiing Season is officially open! Embrace the thrill of winter in South Dakota! Tickets available at the lodge.

A spacious living area features wooden beams and a cozy sofa set, complemented by a decorative coffee table. The open layout includes a dining space and a kitchen area with modern appliances, while a wooden staircase leads to an upper level with a railing.

Chalet in Lead

4 out of 5 average rating, 4 reviews

Homestake Chalet at Terry Peak Ski Resort

A rustic double sink vanity features two white basin sinks placed on a wooden countertop. Above, two decorative mirrors are mounted, reflecting the warm tones of the space. A gray hand towel is neatly hung on a towel ring, complementing the minimalist design.

Chalet in Lead

4.79 out of 5 average rating, 19 reviews

Little Hope Chalet at Terry Peak Ski Resort

A charming chalet features a rustic wooden exterior with a sloped roof and decorative beams. Snow blankets the ground, creating a serene winter scene. A covered balcony extends from the upper level, with a hot tub visible below, adding to the welcoming atmosphere.

Chalet in Lead

5 out of 5 average rating, 3 reviews

Kussy Chalet at Terry Peak Ski Resort

Guest favorite

The Chalet's exterior is warmly illuminated in the evening light, showcasing its wood paneling and A-frame design. Soft light spills from the windows, while the front porch features a welcoming entrance with railings and plants lining the steps.

Chalet in Black Hawk

4.92 out of 5 average rating, 12 reviews

The Chalet on High Meadows

The Chalet on High Meadows is an artistically designed European-styled Chalet nestled in a high meadow of the Black Hills in western South Dakota. It graces a peaceful meadow and overlooks the Black Hills National Forest. It is conveniently located approximately 10 miles NW of Rapid City. Enjoy the openness of the floor plan, the closeness to nature and the simple beauty that surrounds The Chalet.

Guest favorite

A spacious living area features high wooden ceilings and large windows that welcome natural light. Comfortable seating arrangements, including a pair of armchairs, are positioned around a stone fireplace. Indoor plants add a touch of greenery, while a large rug centers the room, enhancing its cozy ambiance.

Chalet in Deadwood

4.95 out of 5 average rating, 87 reviews

Gold Dust Manor-beauty, serenity, privacy for all

One mile to the historic town of Deadwood., the city center, parks, art and culture, great views, restaurants and dining. You’ll love your stay at this luxury mountain home in the beautiful Black Hills. With comfy beds, well equipped kitchen, coziness, high ceilings and views. Great for couples, families (with kids), and large groups. ***Ask me about special Winter and Spring offers.