Family-friendly holiday rentals in South Dakota

Black Hills Stay Walk to Brewery 3mi 2Deadwood Ski

Stay at our charming 2-bedroom condo in downtown Lead, just minutes from skiing and 3 miles to Deadwood! With over 209 reviews and a nearly perfect 5-star rating, our Superhost property offers two king-sized beds, free Wi-Fi, and all the comforts of home. Walk to bars, restaurants, and a brewery right across the street. Enjoy a cozy living space, well-equipped kitchen, and mountain views. Whether for adventure or relaxation, this fully furnished condo is your perfect Black Hills getaway!

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!

Dewey’s Place is for Hunters/Fisherman/Families

Here's your perfect fishing/hunting destination, with space for all your buddies, big family, and/or dogs too! Located within 10 miles of 7+ lakes including Bitter Lake, Waubay Lake, and Enemy Swim and prime hatch area for waterfowl. Perfect for families visiting or groups of outdoorsman looking for a large space where everyone (or almost everyone) gets a bed! Cozy in the winter, cool in the summer, and homey all year round. Host is an area hunter and fisherman with guide experience.

Haylie's Hideaway

Retreat to your next vacation cabin at Haylie’s Hideaway. Tucked into the hillside, you’ll enjoy a quiet hideaway with breath-taking views of the Black Hills. This cabin is located at Terry Peak Ski Area. With 3 bedrooms and 2 bathrooms, this cozy cabin sleeps 6 and is the perfect size for family, friends or any vacationers. Haylie’s Hideaway is also a pet friendly cabin, so no family member gets left out of your vacation plans.

Comfortable and Quaint Space w/ Hot Tub

A four bedroom home: two rooms have a king (one is in the basement and is available for stays with more than four guests) and the other rooms upstairs have a queen in one and two extended twins in the other. The dining, living, and kitchen areas provide guests with a clean modern space for gathering. The basement has a ping-pong table, laundry and a second full bath room. The house also has a four person hot tub available year round.

Beautiful secluded home!

Our beautiful home is cozy but roomy. It has four spacious bedrooms and three full baths. Located at the base of Skyline Drive, and close to many hiking trails, biking trails, public pool and minutes from restaurants and downtown. Mount Rushmore, Keystone, Needles Highway are a beautiful 30 minute drive. Parklike backyard with a propane fire pit. The wood fire pit isn't available for use due to our dry summers. Perfect getaway!

"Generations" Large Group Vacation Home

Beautiful home nestled just minutes outside of Rapid City right off Interstate 90. The home is located on 5 acres for plenty of room for families and large groups. The home has 7 bedrooms, and several common areas including a bar area, pool table, a dining table that can accommodate large groups or families. Beautiful outdoor patios with grilling area. Flat screen TV's throughout the home.

The Garden House

This beautiful early 1900 historical apartment is great for a family get away. Hot tub open April -December 5am-11pm. Three minutes from airport. Ask us about our park and fly program. Two queen beds, a full size hide-a-bed with memory foam mattress. Full kitchen, two patios, one of them being private just for you. Bikes are available for your use. Swimming pool and lake five blocks away.

Finny's Cozy Cottage

Come stay at Finny's Cozy Cottage. Right in the middle of town close to all activities. Close to downtown main street. Newly updated and remodeled House. Grill located in car port with outdoor furniture. Great for families of all ages! Newly updated, new carpet, appliances, and washer and dryer.