Chalet vacation rentals in Pennington County

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Top-rated chalet rentals in Pennington County

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Guest favorite

A modern wooden vacation home is set against a backdrop of rocky cliffs and vibrant autumn foliage. Large windows reflect the natural light, while a landscaped area features stones and gravel, creating a rustic entrance. The scene captures the essence of the Spearfish Canyon landscape.

Chalet in Lead

4.97 out of 5 average rating, 236 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

Chalet in Lead

4.95 out of 5 average rating, 169 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!

Guest favorite

A covered porch is featured with a wooden deck and white railings. Two white plastic chairs are placed on the side, providing a spot for relaxation. Nearby, a bicycle leans against the railing, while large windows allow natural light into the interior.

Chalet in Lead

4.94 out of 5 average rating, 144 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!

Chalet in Lead

3.67 out of 5 average rating, 3 reviews

Homestake 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 is visible from a staircase, featuring large windows that invite natural light and showcase views of the outdoor landscape. A modern fireplace complements the cozy seating arrangement, which includes two armchairs and a sofa. Wooden elements enhance the inviting atmosphere.

Chalet in Lead

4.79 out of 5 average rating, 19 reviews

Little Hope Chalet at Terry Peak Ski Resort

An open-concept living area features large windows that allow natural light to fill the space. The room includes a comfortable sectional sofa, a round area rug, and a coffee table, with views of the dining area and kitchen visible in the background.

Chalet in Lead

4.7 out of 5 average rating, 10 reviews

Missing Link 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

5 out of 5 average rating, 6 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.

Top guest favorite

A spacious living area features high ceilings with wood paneling and natural stone accents. Large windows provide views of the surrounding landscape. Comfortable seating is arranged around a stone fireplace, with a dining area visible in the background. Elegant flooring combines tile and carpet textures.

Chalet in Deadwood

4.95 out of 5 average rating, 81 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.

Guest favorite

A hot tub is positioned under a shaded area, with water reflecting the surrounding greenery. Flower pots hang nearby, adding a touch of color, while a pathway and a picturesque backdrop of nature are visible beyond the tub.

Private room in Rapid City

4.93 out of 5 average rating, 77 reviews

2. Lakeside Rapid City Home With Views

This is a beautiful lakeside home located on the west side of Rapid City. Huge windows creating a beautiful bright space with lake views. This room has a California Queen sized bed. This room is for max of 2 people. Relax in the hot tub and enjoy the surrounding nature! Spacious common areas, kitchen and private full bathroom (not ensuite).

Guest favorite

A hot tub is positioned under a covered area, overlooking a serene lakeside view. Flower planters hang above, adding touches of color. Lush greenery encircles the scene, providing a sense of nature's tranquility nearby.

Chalet in Rapid City

4.83 out of 5 average rating, 41 reviews

4. Lakeside Rapid City Home With Views

This is a beautiful lakeside home located on the west side of Rapid City. Huge windows creating a beautiful bright space with lake views. Relax in the hot tub and enjoy the surrounding nature! Location can't be beat. Woodsy oasis right in the city. Please note this is a personal residence when not rented.

Top guest favorite

A hot tub is positioned under a shaded area, reflecting the greenery surrounding it. Hanging planters with purple flowers add a touch of color. A view of a peaceful lakeside path can be seen in the background.

Private room in Rapid City

4.96 out of 5 average rating, 136 reviews

1. Lakeside Rapid City Home With Views

This is a beautiful lakeside home located on the west side of Rapid City. Huge windows creating a beautiful bright space with lake views. Relax in the hot tub and enjoy the surrounding nature! Spacious common areas, kitchen and private half bathroom. This room has a Queen Size bed for a max of 2 people.