
Ski-in/Ski-out holiday rentals in Pennington County
Find and book unique ski-in/out homes on Airbnb
Top-rated ski-in/out rentals in Pennington County
Guests agree: these ski-in/out homes are highly rated for location, cleanliness and more.

Remodeled Condo at Terry Peak SD
At 6500 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. No added Cleaning Fee when booking reservation.

Remodeled Condo at Terry Peak SD
At 6500 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. No added Cleaning Fee when booking reservation.

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!

Remodeled Condo at Terry Peak SD
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.the whole family at this peaceful place to stay.

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!

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

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.

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.

Remodeled Condo at Terry Peak SD
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.

Remodeled Condo at Terry Peak SD
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.

Kussy 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.

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.
Popular amenities for Pennington County ski-in/out rentals
Ski-in/out house rentals

Black Hills Hideaway w/ Wraparound Deck & Hot Tub!

6BR Ski In/Out Skiview Black Hills Ski In/Out

Lead/Deadwood, Pet friendly. Central location

Hillside Haven

Hillside Haven
Family-friendly, ski-in/out home rentals

Remodeled Condo at Terry Peak SD

Lead/Deadwood, Pet friendly. Central location

Scenic Lead Cabin: Steps to Terry Peak Ski Area!

Spacious Lodge on Terry Peak w/ Hot Tub!

Remodeled Condo at Terry Peak SD

Turtle House Getaway | Black Hills Basecamp

Tenderfoot Creek Retreat

Deer Pass Lodge
Ski-in/out cabin rentals

Scenic Lead Cabin: Steps to Terry Peak Ski Area!

Spacious Lodge on Terry Peak w/ Hot Tub!

Tenderfoot Creek Retreat

Deer Pass Lodge
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