Ski-in/Ski-out holiday rentals in Pennington County

Spacious Lodge on Terry Peak w/ Hot Tub!

Just a short walk to the Terry Peak Ski Area and only 10 minutes from historic Deadwood, you’ll be in the heart of the Black Hills. Whether you’re carving fresh powder, exploring scenic trails, or trying your luck in Deadwood’s lively casinos, everything you want is right at your fingertips. After your adventures, you and your big crew can relax in the hot tub with the crisp mountain air and small from the pine trees. This isn’t just a stay - it’s a getaway! Time to plan your ski/hiking trip!

Accuracy · Hospitality · Bathroom

Scenic Lead Cabin: Steps to Terry Peak Ski Area!

Nestled among towering Spruce and Aspens on a private half-acre sits an unimposing cabin, nicknamed 'Deep Snow.' This 2-bedroom, 1-bath vacation rental is newly renovated and furnished with modern conveniences, providing a top-notch getaway to lucky travelers. Sit in the bubbling hot tub as you admire the gently sloping mountainside, venture into Black Hills National Forest, and head into Deadwood for gambling and historic sites. Or, pack your camera and head to Mount Rushmore for a day trip!

Location · Family · Condition

Hideaway Cabin for Sturgis Rally

Perfect for Sturgis Rally - This fully furnished four-bedroom private mountain cabin sleeps up to 10 and is close to Deadwood! After all the Rally activities you can relax with a full kitchen, spectacular wood-burning fireplace, amazing deck with private hot tub, dining area, grill and awesome views overlooking the mountains & ski resort. This cabin is complete with a washer/dryer AND a 4 person sauna! This resort has plenty of motorcycle & trailer parking, 2 pools, fitness center & more!

Location · View · Kitchen

Lead/Deadwood, Pet friendly. Central location

Pet friendly!!! Cozy and fully furnished cabin nestled in the serene Black Hills of South Dakota. Features two private bedrooms upstairs, each with a queen bed, plus a spacious open basement with two queen beds and a day bed. Enjoy the new hot tub, a fire pit, and hammock outside. Keurig coffee machine ( coffee provided!). The fully equipped kitchen and grill make mealtime a breeze. Located just minutes from a premier ski resort, you’ll have easy access to outdoor adventures year-round

Family · Location · Skiing

Cozy Mountain Condo • Hot Tubs+Pools • Terry Peak

🌲 Your Mountain Getaway at Barefoot Resort Unwind and breathe a little easier up here at 6,500 ft. This cozy and spacious 2-bedroom condo is the perfect base for skiing, riding, hiking, or just relaxing in the Black Hills. Designed for families, couples, and friend groups, it sleeps 6 comfortably (up to 8 with the pullout). Whether you’re hitting Terry Peak 🎿, gambling in Deadwood 🎰, or cruising Spearfish Canyon 🍂, you’ll love coming back to this warm, peaceful home base.

Value · Family · View

Turtle House Getaway | Black Hills Basecamp

Discover The Turtle House — a peaceful geodesic dome retreat nestled in the Black Hills, just 1.7 miles from downtown Spearfish. Enjoy easy access to hiking, biking, hunting, and skiing at Terry Peak (22 miles), plus iconic spots like Spearfish Canyon and Mount Rushmore. Guests rave about the quiet vibe, spacious yard, gas fireplace, and frequent wildlife sightings. Located within walking distance of the Termesphere Gallery, it’s a perfect getaway in every season.

Location · Value · Bathroom

1 Bed Condo by Terry Peak Summit in South Dakota

At 6,500 feet in elevation, the Barefoot Resort sits among towering pine trees and a rugged, mountainous landscape. With expansive views and a peaceful atmosphere, Barefoot Resort offers the perfect escape from the daily commotion and hectic lifestyle that many are used to. The Barefoot Resort offers an unforgettable experience year-round, so whether you prefer summer, fall, winter, or spring, there is always something to enjoy while you are here.

Location · Value · Cleanliness

2 Bed Condo by Terry Peak Summit in South Dakota

At 6,500 feet in elevation, the Barefoot Resort sits among towering pine trees and a rugged, mountainous landscape. With expansive views and a peaceful atmosphere, Barefoot Resort offers the perfect escape from the daily commotion and hectic lifestyle that many are used to. The Barefoot Resort offers an unforgettable experience year-round, so whether you prefer summer, fall, winter, or spring, there is always something to enjoy while you are here.

Location · Family · Sleep quality

Tenderfoot Creek Retreat

Welcome to Tenderfoot Creek Retreat! You will find yourself surrounded by towering evergreens of the Black Hills National Forest, and steps from the Mickelson Trail. You will occupy the entire main or 2nd floor of this rustic residence. Close to all the major Black Hills attractions yet you will feel at one with nature. Tenderfoot Creek can lull you to sleep or greet the morning with its soothing chatter.

Family · Location · Quiet

B8 Classy and updated 2bd/2ba walk to ski, hot tub

Enjoy the glamour of this stylish, upscale place. With modern updated amenities like the built in fireplace, full kitchen and dining table, this space feels like home with a special touch of class. This 2bd/2ba offers privacy and togetherness all in one. The detail and love put into this pad will leave you coming back for more! Gather where nature meets opulence, in this deluxe experience condo.

Family · Location · Comfort

Great Apt in Historic Deadwood-Lead S.Dakota

Located 3 miles from Historic Deadwood 13 miles from Sturgis . The apt is a block off Main st Lead . 3 bars and restaurants within walking distance and 2 blocks from Homestake Opera House . The Michelson Trail for hiking and biking goes thru Lead. It is about 1 hr and 20 min. To Mt Rushmore and Crazy Horse.

Value · Location · Indoor spaces

Deer Pass Lodge

A true log cabin! Ski and Snowmobile in the winter months, smell the fresh scent of pine in the summer months. Try your luck at gambling in Deadwood or maybe pan for gold at one of the mines. After a long day, come back and relax at Deer Pass Lodge!

Location · Family · Layout