Holiday rentals in Upton

Spearfish Canyon Skye lodge

Skyelodge is located in the heart of Spearfish Canyon. Located on a cliff wall . A 750 Sq. Ft. apartment on the top floor of a private vacation home. Spearfish Falls and Roughlock Falls one mile away can be accessed by hiking trails. FANTASTIC VIEWS! ( DEER, ELK, BALD EAGLES, PEREGINE FALCONS, OSPREYS, VULTURES ARE YOUR NEIGHBORS) HIKING, BIKING, ROCK CLIMBING, PHOTOGRAPHY, TROUT FISHING, OR JUST HANGING OUT. THE STARS AT NIGHT. GREAT COUPLES RETREAT!

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!

Southern Hills Tiny Home

Sleep soundly in a beautiful country setting. Awake refreshed just minutes from many Black Hills attractions. Mt. Rushmore 41 mi. Custer 20 mi. Hot Springs 18 mi. Custer State Park 24 mi. Wind Cave 17 mi. Adjacent to the Mickelson Trail and minutes from hundreds of miles of Black Hills National Forest trails. Wildlife is abundant in the Southern Hills, including deer, turkeys and elk. Or just sit back and relax as you watch the horses graze in the pasture or take in the endless night sky.

Condo Across from Terry Peak*Hot tub*Spacious

Welcome to Story Blu Summit, a newly updated 2BR/2Bath condo within steps of Terry Peak and the use of all the amenities Barefoot Resort. ★ Located across from Terry Peak Ski Hill ★ Gorgeous Views ★ 6 miles to Deadwood, SD ★Minutes to downtown Lead ★ Ski, hike, bike, snowmobile trails all close by ★ Large Smart TV's in each bedroom ★ King Bed in Master ★ High-speed internet ★Remote work friendly ★ Use of communal private Hot Tub x3, heated indoor pools x2, exercise room and sauna

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.

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.

Black Hills Condo

Welcome to Black Hills Condo! Come and enjoy this beautiful and sparkly-clean, two-bedroom, two-bath condo! Enjoy main-floor living with private entrance and front of condo parking! Located minutes from Deadwood, Terry Peak, and Sturgis, this condo offers convenience and comfortable living for up to six guests! Amenities include: Private patio, patio grill, pack-and-play, iron/board, and many kitchen amenities and conveniences. Come and enjoy all the Black Hills has to offer!

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!

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.

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!