Holiday rentals in Upton

4.91 out of 5 average rating, 46 reviews

Home in Lead

Minutes from Deadwood & Terry Peak Ski Area

Spacious 4 bedroom, 3 full-bath home in the center of The Black Hills. Off street parking with room for several cars/trailer/side by sides. A short drive from Deadwood, Spearfish Canyon, Sturgis and Terry Peak Ski Area. Walking distance to grocery store, hardware store, local coffee/gift shops and Mickelson Trail. Two comfortable living rooms greet you on the first and second floor with the bedrooms on the second and third floor. Fireplace on the main floor along with a large deck with a view.

Top guest favourite

Home in Custer

4.93 out of 5 average rating, 28 reviews

Cozy Cottage: Family-Friendly, SD Charm, Bar, Deck

Welcome to The Green Door Cottage in Custer! This cozy 3BR, 2BA home, filled with South Dakota charm, is just steps from local dining, shops, and bars. Relax on the spacious back deck or unwind at the small bar downstairs. Inside, enjoy a rustic atmosphere with plenty of local decor. Perfect for families or small groups, it’s a great base for exploring the Black Hills. ☀ 10 Min to Custer State Park ☀ 15 Min to Sylvan Lake ☀ 30 Min to Mt. Rushmore Experience Custer With Us and Learn More Below

5 out of 5 average rating, 12 reviews

Gold Pan Cabin - NEW Cabin in Terry Peak!

NEW Cabin located in Terry Peak. Minutes from the slopes, snowmobile trails, ATV trails, Michelson trail, multiple golf courses, many site seeing attractions and so much more! This is a 3-level spacious 5 bedroom, 3.5 bath cabin that sleeps 14. Enjoy king and queen beds, NO bunk beds here! Enjoy your time soaking in the hot tub, relax by the outdoor gas fire pit on the large wrap around deck, or just take in the stunning views of the beautiful Black Hills! Enjoy shuffleboard and dartboard!

4.85 out of 5 average rating, 26 reviews

Bungalow in Custer

Red Roof Cottage in Custer walkable to downtown!

New listing in Custer, South Dakota! 2 bedroom quaint cottage with many custom finishes. Only 8 minutes to Custer State Park, 20 minutes to Mount Rushmore, 16 minutes to Jewel Cave, 15 minutes to Crazy Horse Memorial, and 21 minutes to Wind Cave! Full kitchen, BBQ grill, air conditioning, bunk room, and a fully fenced yard for privacy. Walking distance to downtown restaurants, shops, and museums. Free off-street parking and additional parking are available for large vehicles and trailers.

4.84 out of 5 average rating, 273 reviews

Yurt in South Lawrence

Treehouse Yurt Lead Black Hills SD Mickelson Trail

Off grid yurt in the pines, with great view of mystic miner and Terry peak above, on mile 100 of beautiful Mickelson trail. Get away to nature (with style and a unique stay)....goulay. not for non-outdoorsy as there is only a half bathroom outhouse, no running water (you get to port it in, great spring pump at nearby Englewood trail-head on Mickelson and running stream for a dip at bottom of hill), no electricity, and a great little wood stove. BEFORE RENTING read other things to note.

4.81 out of 5 average rating, 217 reviews

Apartment in Lead

Black Hills Stay Walk to Brewery 3mi 2Deadwood Ski

Stay at our charming 2-bedroom condo in downtown Lead, just minutes from skiing and 3 miles to Deadwood! With over 209 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!

4.91 out of 5 average rating, 142 reviews

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

4.94 out of 5 average rating, 35 reviews

Cabin in Deadwood

HilltopHaven, Deadwood, Hot tub, Paved Roads

Hilltop Haven overlooks the Historic Town of Deadwood, SD. This 4 bedroom 3 bath cabin is your home for your trip to the Black Hills. The deck at this home allows you to wake with the sun shining on the Hills and enjoy the sunset with the twinkle of the lights of Deadwood. Mount Rushmore, Custer State Park, Crazy Horse can be discovered with a short hour drive down scenic Hwy 385. We want you to experience the hills by staying Black Hills Premier Vacation Homes; Hilltop Haven Cabin

4.9 out of 5 average rating, 153 reviews

Apartment in Lead

Condo in the Hills #1 | Minutes to Deadwood

Cozy condo in the Northern Black Hills with all the luxuries you'll want. This property is near the most beautiful places in South Dakota - Spearfish Canyon, Sturgis, Deadwood, waterfalls, lakes, gambling, hunting, ATV riding, snowmobiling, skiing and endless outdoor adventures! Enjoy the cozy, clean, and rustic décor of the wild west in our fully furnished condo. Perfect for couples, solo adventurers, business travelers, or families.

4.97 out of 5 average rating, 29 reviews

The Last Chance Getaway - Terry Peak Area

This beautiful cabin is located in the Terry Peak Ski Development and is just a few minutes away from the ski slopes and miles of trails. The huge windows create a frame of amazing views! Last Chance provides you with ease of off-road parking with plenty of space to maneuver a trailer, hot tub after your day of taking in the sites of the Black Hills and all everything needed to ensure you have a comfortable, relaxing stay!

Top guest favourite

4.97 out of 5 average rating, 37 reviews

BS Retreat - Brand New Construction - Hot Tub !

A luxury retreat with all the modern conveniences to help you escape the daily routine, while still connecting to those you love. A perfect layout for any group. Something to do in every season. Instant access to skiing, hiking, atv trails, and more! Hot tub/EV charger/baby gates/huge deck/luxury linens and beds/custom lighting/massive fireplace/Keurig Commercial coffee maker….you name it, we thought of it!