Holiday rentals with outdoor seating in Deadwood

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!

Secluded Modern Mountain Rustic Chalet on 10 acres

Sheep Hill Chalet is a Black Hills-inspired rustic modern cabin located in beautiful Lead, South Dakota. Newly built in the heart of nature, on a plot of over 10 acres and bordered by the Black Hills National Forest, this 3 bed, 2.5 bath rental cabin will charm you with its modern architecture and antique rustic touches. Enjoy cozy luxury in the living room with 16 ft windows and double sided stone fireplace! Gourmet kitchen, hot tub, and open living areas - perfect for your gathering!

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.

The Daning Main Floor Suite

Blocks away from the closest casino and all Historic Main Street has to offer the french doors of this Historic Victorian Style home still hang and greets guests to the newly renovated Main Floor Suite. Six (6) guests can enjoy all the amenities of home including Washer/Dryer, Private Outdoor Space, Full Kitchen, Newly Renovated Bathroom, HDTV, and Wi-Fi all minutes away from downtown Historic Deadwood. Live like a local and play like one too at The Daning Main Floor Suite.

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!

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!

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.

Adorable loft carriage house with hot tub

This is the original carriage house from 1892 that has been converted into living quarters with a small fenced in outdoor space. The cozy cottage is made up of two levels. On the floor level, is a small kitchen, bathroom, and sitting area with gas fire place (love seat pulls out to a single bed). On the second level, via a narrow steep hayloft staircase, is a king bed, tv, and private balcony. This quaint space is the perfect get away.