Family-friendly vacation rentals in Deadwood

Deadwood Vacation Rental Apartment

The home is located in the Historic Deadwood Presidential neighborhood, that sets on the side of the cliff overlooking Deadwood, with magnificent mountain views. Walking distance to all attractions - , restaurants, casinos, concerts, nightlife, museums and fitness center. Just steps away from everything Deadwood has to offer - literally - 116 steps down into the gulch. The Deadwood City Rec & Aquatics fitness center is located at the base of the stairs, and stones throw from the apartment.

Cabin on 20 acres w/ horses, goats, & mini donkey

Enjoy country living close to town! Two bedrooms w/ queen size beds and loft w/ queen size pullout sofa allow you to comfortably sleep 6! Just 4 miles from downtown Hill City. Sits on 20 beautiful acres surrounded on 3 sides by Forest Service! Enjoy beautiful surroundings - a seasonal pond outside your cabin (water level varies), horses, mini donkey, mini goats and chickens. Enjoy private setting with the convenience of the owners just 1/4 mile up the driveway to take care of your needs!

Harley Court Loft

Cozy loft in the Lead, SD. Moments from downtown, but secluded. Minutes to outdoor activities, skiing, snowshoeing, hiking, biking, or snowmobiling. Winter months, all wheel / 4 wheel drive vehicle is a must!! Close to restaurants, brew pub, and night life!! Kitchenette: microwave, coffee maker, toaster, hot plate, (with pans), and small frig. The loft has electric heat and portable AC. There are 18 steps to get to the loft, for two people. Not kid proof. No pets accepted.

Falsebottom Hide-away

This is a great place to relax and enjoy the sounds of nature after a long day vacationing. Sleeps six with a secure fenced yard for the safety of your pets. Located in beautiful Maitland Canyon with seasonal Falsebottom Creek right off the private back deck featuring a BBQ and outdoor table. We have lived here for 40 years and are still amazed with the beauty of the Northern Black Hills. Close to so much, but with a real connection to the pristine nature that the Black Hills are famous for.

Aggies 1895 Saloon & Brothel Deadwood Main Street

The former Ayres Hardware (founded 1876) Store, loaded with history and charm! One of the few merchants who would not sell or convert to a casino when the gambling boom began in Deadwood. Walking distance to Saloon #10, Kevin Costner's Midnight Star, Franklin Hotel and many other historic Deadwood attractions. You’ll love the location and coziness. Perfect for couples, solo adventurers, business travelers, and families (with kids).Aggies is a restored 2 1/2 bed apt/brothel all inclusive .

Treehouse Yurt Lead Black Hills SD Mickelson Trail

Off grid yurt in the pines, with great view of mystic miner and Terry peak above, on mile 100 of beautiful Mickelson trail. Get away to nature (with style and a unique stay)....goulay. not for non-outdoorsy as there is only a half bathroom outhouse, no running water (you get to port it in, great spring pump at nearby Englewood trail-head on Mickelson and running stream for a dip at bottom of hill), no electricity, and a great little wood stove. BEFORE RENTING read other things to note.

Modern 5-bed cabin with Hot Tub, King size beds

Conveniently located only 2 miles outside of historic Deadwood, 11 miles outside legendary Sturgis, and 8 miles from Terry Peak ski lodge, this secluded modern cabin is nestled amongst the pines and a young aspen grove. Large picture windows highlight the living spaces, and the rough sawn deck reflects the perfect mountain escape for enjoying your morning coffee amongst the bent oak trees. Enjoy the wildlife that frequent this peaceful property while relaxing in the brand new hot tub.

Castle in the Sky

Are you looking for a luxurious, unique place to stay? This house sits overlooking Rapid City with incredible skyline views, every evening is as picture perfect as the glowing city lights. This unique house is a fun mix of eclectic and fancy. Originally built as a local builder's "Coup de Grande", he ended up only finishing the guest house. You will find high-end finishes mixed with eclectic choices. We promise this will be one of the most memorable places you'll ever stay!

Arn Barn Cabin

Great cabin with lovely views from the covered porch in the Terry Peak area. Two bedrooms, both containing queen beds, one of these adjustable, the other with a fold-out chair for extra space if needed. One level, open floor plan with a large comfortable sectional that will also pull out into a bed if additional sleeping space is needed. Outdoor fire pit and grill available for your use. Fully stocked kitchen to make you feel right at home while enjoying the Black Hills.

The Mercantile at Mad Peak Lodging, sleeps four

The Mercantile at Mad Peak Lodging is part of our Old West–inspired collection of vacation rentals, blending historic character with modern comfort in the heart of the Black Hills. Surrounded by mountain scenery, this inviting retreat offers a peaceful setting with easy access to outdoor adventure, local attractions, and scenic drives. Whether you’re exploring the Hills or unwinding after a full day out, the Mercantile is a comfortable and memorable place to stay.

Darby's Cabin in the Woods

Kick back and relax in our cozy cabin. Built in 2021 and decorated with love to make you feel at home in the woods! Includes two bedrooms, two bathrooms, living room, full kitchen, loft with two queen-size beds, porch, and fire-pit. Enjoy sitting outside on the porch or share a drink and camp stories around the fire-pit. Books, TV and board games are available for in-home entertainment. If you're looking for a peaceful getaway, Darby’s Cabin is the place for you!

Stay in the Heart of Deadwood at the Jordan's!

This home, is on Deadwoods Historic Registery and located on Historic Main Street, just a couple blocks from the action! Features include a full kitchen, full bath, queen sized bed, laundry facilities, and a nice front deck. There is high speed wifi and a 40" Roku capable TV. Parking is in a private lot. We think you will love coming back to this cozy home and quiet neighborhood after enjoying all Deadwood and the Black Hills have to offer!