Vacation rentals with outdoor seating in Deadwood

Rare Hideaway on Main, Retro unit

Charming 50s-Themed Main Street Apartment in Deadwood Located just blocks from downtown, this unique Main Street apartment is the perfect choice for a weekend getaway with friends, a family vacation, or a couples' retreat. We are proud new owners of this historic 1920s building and have lovingly remodeled it to offer a blend of vintage charm and modern comfort, with a fun 50s theme throughout. Guests are also welcome to enjoy the backyard space for outdoor relaxation or activities. Our propert

Lead me to Adventure

Let us Lead you to Adventure in this 2 bedroom, 1 bath condo in the beautiful Black Hills. Sleeps up to 6 and is perfect for those looking for a relaxing getaway. We welcome all! Get your adventure on at the nearby Mickelson trail, the 3,000+ miles of ATV trails with access in every direction. Minutes from Historic Deadwood, Terry Peak Ski Area, Spearfish Canyon, and Sturgis. Mount Rushmore and Custer State Park are within driving distance. We welcome any questions ahead of & during your stay.

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.

The Hills Hütte on Terry Peak

The Hills Hütte on Terry Peak is a quaint 2 bedroom 1 bath space with large vaulted ceilings for an airy, spacious feel. This new build is situated with panoramic views from the front porch while you sip your coffee and meditate. Just minutes to the ski resort and direct access to off road trails, this property is sure to please anyone's adventurous side, no matter the season! With a nod to cozy Alpine huts, the Hütte is the only place for a couples trip or family getaway. Please join us!

Summit Trails Lodge | Cozy, Hot Tub, Trail Access

Summit Trails Lodge offers the ultimate nature escape: a warm and spacious knotty pine cabin crafted for comfort, connection, and outdoor adventure. Whether you're gathering with family or friends, it's the perfect place to relax, recharge, and explore. *Mountain views *Private hot tub *3-level cabin, lots of privacy *Minutes to skiing, ATV and hiking trails, and horseback riding *Lead 3mi / Deadwood 8mi / Sturgis 20mi *Easy day trips to Mt. Rushmore, Crazy Horse, and Custer State Park

Guest Suite with Beautiful Views and Hot Tub

Keep it simple at this peaceful and centrally-located guest suite. Located half a mile from downtown, this unit has it all! Enjoy your coffee with a view of the incredible Black Hills and the winding Spearfish Creek below. This guest unit overlooks the Spearfish city park campground and recreation paths. This guest suite is the lower level of our home and has no shared indoor spaces. Outside you’ll be greeted with beautiful views and a shared hot tub for an unmatched in town experience.

Private Farmhouse Studio

Private Hot Tub!! Enjoy a stylish experience at our modern studio, located within walking distance to a Mexican eatery, brewery, farmer's market, bike path and Spearfish creek! Two sisters with a love for design renovated a small cabin into this cozy space for guests intending to explore the beautiful Black Hills. With a fully-equipped kitchen, this charming home is full of custom touches including a handcrafted barn door. Dogs allowed by PREAPPROVAL ONLY, please message for details.

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.

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!

Newly remodeled in the Heart of Deadwood

This newly remodeled, comfortable apartment is right in the heart of Deadwood! This home, built in the early 1900's is on Deadwood's Historical Registery, and is located on famous Main Street just a couple blocks from the action. It is a one bedroom apartment with one bath and a full kitchen. Laundry facilities are available. You'll love coming back to this cozy space with all the comforts of home, after enjoying all Deadwood and the Black Hills has to offer!

Secluded Cabin - Coyote Ridge Lodge

A unique, secluded, rustic cabin nestled on 10 acres of Ponderosa pine forest. Enjoy morning coffee on the sunny, spacious deck, afternoon picnics by the creek, a cozy wood fire in the evening and a sky full of stars at night. Only 12 minutes from great food and cafes in Spearfish; 20 minutes to Deadwood. The cabin is best for couples, families and groups of close friends. Note limited privacy; there are no bedrooms with doors you can close.

Aces & Eights, 1 mile to Deadwood, Hot tub

Keep it simple at this peaceful and centrally-located place. Located 1 mile from Deadwood, South Dakota in the Black Hills. Aces and Eights is a studio style cabin set for that perfect getaway. Grab a cab to town or order a pizza right to your doorstep. This lodge is adjoining with a second similar cabin called Dakota Lodge. Each side has its own deck, hot tub, space. This cabin is set up in perfect historic, rustic Deadwood Style.