Holiday rentals in Upton

Crazy Horse (14' tipi)

Crazy Horse & Custer traveled this way to Devils Tower. This tipi can comfortably sleep 4 adults. Each tipi has as two burner stove, 3 gallons of water, a pot, coffee fixing things, a propane lantern and a solar lantern. There is no electricity on the property and an outdoor solar shower available if desired. Sleeping places (pad, sheets, blankets and pillows) can be set up for a total fee of $30 for 4 payable on arrival; more available for $10. Please request this when making a reservation.

Reato House--Cozy comfort away from home, HOT TUB!

This house is a comfy, cozy, 2 bedroom, 1 bath house built in the early 1900's and recently updated. It is in the heart of the Black Hills, minutes from Deadwood. It is close to skiing and snowmobiling in the winter; hiking, sightseeing and fishing in the summer. The deck overlooking Lead offers a space in the sun or a covered portion for shade. Four person hot tub and fireplace makes the end of day so relaxing! Be aware, there are 32 stairs from street to house. Trailer parking available.

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.

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.

Kara Creek Ranch - Log Cabin

Looking to get away from it all? This cozy log cabin sits alone on a rise overlooking fields of sunflowers, where the deer & antelope graze and Kara Creek runs lazily through the valley. Guests are welcome to hike, fish Kara Creek, or fish the 11 acre pond stocked with trout (many over 20 inches) and large mouth bass. This cabin sits about 4 miles from our ranch headquarters, where we also offer food, horseback riding and other activities from May-Oct. Please contact us for more information!

Charming Cabin in Pine Haven

- 2 bedrooms and 2 bathrooms, sleeps up to 8 - Wifi throughout - Parking for 3 vehicles - Washer / Dryer - On quiet street - 10 minutes from Key Hole marina - Close to Devils Tower, about 40 miles * No smoking permitted on the property. * No pets * Please alert us ahead of your arrival if you plan to use the futon beds. * Sturgis week available. Nightly price of $400 with a minimum 4 nights. * Winter reservations are subject to cancellations due to problems with snow removal/availability.

Black Hills Condo by Brewery 3mi to Deadwood Ski

Stay at our charming 2-bedroom condo in downtown Lead, just minutes from skiing and 3 miles to Deadwood! With over 233 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!

The Lower Hillsview Loft

Retreat to this two story modern apartment home right in the heart of Spearfish. Walking distance from Black Hills State University, these high-end spaces are perfect for those wishing to visit a family students or to simply just explore the area! Beautifully decorated with high-end, local photography, curated modern furniture, and a stunning outlook from the balcony, this Black Hills getaway is a must for visitors through all seasons. *Stairs must be used to access bedrooms.

KK, tiny cabin close to beauty of Black Hills SD

A 10 x 32 tiny cabin conveniently located 1 mile off paved Hwy 585. Our working ranch has cattle, goats, horses. Beautiful scenery with frequent sightings of elk, deer, turkeys. This unique cabin features: WIFI, TV with DVD player only, microwave, retro fridge, bathroom with shower, twin bunk beds, and a queen bed. Experience the beauty and serenity of Wyoming and closeness of Black Hills attractions; and simple ranch life! Quiet and off the grid. Beautiful sunsets, too.

Condo in the Hills #2

Live the perfect Black Hills vacation experience in this cozy and stylish condo! Our fully-furnished home is located in the stunning Black Hills, just a short drive away from some of South Dakota's most picturesque sights. Embark on an array of unforgettable outdoor adventures, from Spearfish Canyon, to Sturgis, and Deadwood. Enjoy the clean, rustic, and luxurious amenities within our comfortable condo, perfect for the whole family.

Boutique Apt- Walk to Downtown - Patio - Laundry

Relax comfortably in our newly remodeled 1BR apartment! Conveniently located off the highway, it's a short walk to downtown Spearfish's dining, coffee, and shopping. Explore nearby parks, trails, and a grocery store, making it an ideal spot for your stay. Start your day with coffee or tea from the fully stocked coffee bar, cook with brand-new appliances or take in views of Lookout Mountain from the front porch.

Off-Grid Cottage at Granny Flats

Welcome! Cappie, Star of Building Outside the Lines on Magnolia Network, built this adorable off-grid cottage as his own, but now you have the opportunity to stay! This beautiful 3-acre property, once the Swisher Farm, is today a working homestead, dozens of chickens, and a large garden. This cottage is handmade, from the bespoke front door to the custom 2-headed shower. We know you'll appreciate the details!