Holiday rentals with a kayak in Pennington County

Downtown Legendary Sturgis Loft

Rise 'N Shine brings you a newly updated loft home with 3 bedrooms (3 queen), 2.5BA, huge garage with bar, loads of parking, & 3 sliding glass doors that lead to the 40 foot balcony overlooking Main St Sturgis! This is a super fun and convenient spot that makes for an amazing vacation experience whether you're a family with kids, friend groups, or couples! Proximity to attractions & surrounding towns is impeccable with Mt Rushmore 45min, Deadwood 15min, Spearfish Canyon 15min, & Custer 1hr 15min

Dads 2 Bdr 1 Bath home Hill City 1 car garage

You'll feel at home in the hills nestled in this beautiful fully furnished 2 bdr 1 bath home. Renovated in 2019. Detached garage 1 bay . Sit on the wrap around porch and take in all nature has to offer including a stream, deer and turkeys. Close to all attractions in the Black Hills and Rapid City. Walk to downtown with its restaurants, quaint shops and art galleries. Micolson walking trail is right behind us. Parking galore. Owners occasionally may stay in the studio behind the detached garage

The Whispering Buffalo Condo

Enjoy a unique & exciting experience at a renovated 1800's hotel, turned vacation rental where Calamity Jane frequented. The entire main floor makes up the The Roaming Buffalo including 3BR, 3BA, + murphy's bed. Sleeping space for 8, TVs in every room, private patio, & a hot tub. Grab food and drinks at the bar/restaurant across the street or a cold one at the beer garden. 25min to Rapid, 10min to Spearfish, 15 min to Deadwood. Centrally located to all of your favorite Black Hills attractions!

Cliffside Lodge in Boulder Canyon-Spa-Golf-Private

Vanish into seclusion and serenity in this stunning mountain getaway in Boulder Canyon just outside of Sturgis. Stunning views, a fully stocked kitchen, beds you will melt into, and views of the Boulder Canyon Golf Course directly across from you. This magazine worthy gem offers guests the perfect homebase to explore the Black Hills from a central location and come home to retreat and recharge in a quiet and secluded setting surrounded by soaring pine trees and the stunning beauty of the forest

In the Pines

Welcome to your Black Hills getaway Brand New tiny home. You will be swept away by the swaying of the pine trees, beautiful scenery and abundant wildlife from your very own deck. Enjoy the starry night skies and PEACEFULNESS of being away from the city. Its time to relax, rejuvenate and cozy up in front of the fireplace in the bedroom loft. You are minutes from your next adventure whether it be hiking, biking, kayaking or sight seeing there is something for everyone. * New Starlink internet

Hill City Haven Downtown Main Street

- Located downtown on Main St. Walk to shops + food - Quiet location on main street with plenty of privacy - Hot tub in fenced backyard - plenty of privacy - Fire pit, Grill, Ice Machine, Surround Sound Speaker system - Family friendly space! (and pups too) - Custer State Park pass included with rental for 1 - 20 min to Mt. Rushmore, Crazy Horse, Rapid City, or Custer State Park - UTV/ATV and motorcycle friendly with hoses to wash your toys! - EV Charger - Level 2 Chargepoint Homeflex Charger

French Creek Hideaway. Game room, creek, 10 acres

A wonderful escape. 6 miles to Custer city. 3 miles form Custer State Park Entrance and Stockade lake. 2 mini split AC units for your comfort. French creek flowing on the property for your enjoyment. 4 bedroom house (7 beds total). Includes 18 foot tipi, foos ball table, poker table, arcade, ping pong and 10 acres. Backed up to forest service for endless hiking and exploring. Outdoor decks with seating and a firepit, barbecue and gas grill. Relax and enjoy the beautiful Black Hills

Black Hills Cabin Great Central Location-WIFI

The Black Hills are often underestimated because of the word "Hills". The facts become apparent as you wind your way up hairpin turns high up on Edelweiss Mountain. The 1500 sq. ft. three-bedroom cabin is located at (5600 ft elevation) above sea level in the heart of the Black Hills National Forest. The cabin is located among the pine trees on Edelweiss Mountain just twelve miles north of Hill City South Dakota and three switchback country miles off of the scenic U.S. Highway 385.

DRY Historic China Gulch Cabin

Historic Black Hills cabin offering a true back-to-nature experience near Mount Rushmore and Hill City. Once connected to one of the area’s first doctors, this rustic retreat preserves its original character while providing electricity and cozy accommodations. ⚠️ No running water or indoor plumbing — guests use a traditional outhouse. Conveniently located just off the highway for easy access to attractions. Perfect for travelers seeking a simple, unique, and authentic stay.

Bin2Quinn

Enjoy a one-of-a-kind South Dakota stay in our custom, fully furnished grain bins. One bin features a spiral staircase leading to a queen bed, while the connected bin offers a second bedroom with a queen bed and twin bunk beds. Also a futon and 2 single fold out beds. Includes a bathroom with shower, coffee bar, TV, and modern amenities. Relax outdoors in a seating binzebo with a fire pit and stunning views, or enjoy our private lake with seating and complimentary kayaks.

Black Hills Bungalow

A comfortable gathering place for families and small groups, yet cozy enough for a couples getaway. Minutes from the Southern Black Hills, Badlands, Crazy Horse, Mount Rushmore, Custer State Park, Rapid City, Hill City, and many hiking trails and fun! This is a Native American decor and beautiful area around the place! ***Please note-there are NOT nine beds, only nine people may stay. Air BnB will not change it. 😉

The Iron Keep

Just 1 mile from downtown Sturgis and under 20 minutes to Deadwood, this spacious 5-bedroom home blends rustic, Western, biker, and medieval charm. Perfect for riders, families, bachelorettes, or weekend getaways, it sleeps up to 14 with 8 beds. Enjoy 3 full baths, indoor jetted tub, BBQ, propane fire pit, and a garage for 10+ bikes with lift and air compressor—your ideal home base for rallies and summer events.