Holiday rentals in Pennington County

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Top-rated holiday rentals in Pennington County

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Guest favourite

Home in Lead

4.91 out of 5 average rating, 46 reviews

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, 27 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

Superhost

Bungalow in Custer

4.85 out of 5 average rating, 26 reviews

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.

Guest favourite

Cabin in Lead

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

Guest favourite

Cabin in Deadwood

4.94 out of 5 average rating, 34 reviews

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

Top guest favourite

Home in Rapid City

4.98 out of 5 average rating, 91 reviews

Historical Downtown Cottage with Hot Tub

Welcome to your downtown cottage retreat in this renovated 1914 home. After a day of Black Hills adventuring enjoy dinner and a movie with a relaxing soak in the hot tub. Experience luxury mattresses and linens that will leave you feeling refreshed. Located less than a mile from restaurants, coffee shops, shopping, and hiking in the Skyline Wilderness. Minutes from SDSM&T, Monument Health, and the Civic Center. 30-40 mins to Mount Rushmore, Crazy Horse, Custer State Park and more!

Guest favourite

Home in Rapid City

4.93 out of 5 average rating, 90 reviews

Perfectly Located Creekside Vacation Home

LOCATION...LOCATION...LOCATION! Creekside property!!!! This ideally located Black Hills home is nestled in the center of many favorite attractions which are just a scenic drive away! Pick a direction which will lead you to Deadwood, Hill City, Mount Rushmore, Rapid City, Custer...you are in the center of it all! Located just a few miles away is Pactola Lake and Sheridan Lake where you can add to your vacation memories with a pontoon, kayak or other water-related rentals!

Superhost

Cabin in Custer

4.86 out of 5 average rating, 44 reviews

Mountain View Gem: Firepit + Sauna + Wildlife

Nestled among the Ponderosa Pines, our cabin offers breathtaking views of the Needle Spires, providing a truly unique and relaxing getaway. Thoughtfully designed for a home-like feel, our cabins provide all you need for a comfortable stay. Just 5 miles from downtown Custer and conveniently located within minutes' drive to Mount Rushmore, Crazy Horse, Custer State Park, and other major tourist attractions, it's the perfect base to explore the beauty of the Black Hills!

Top guest favourite

Home in Rapid City

4.97 out of 5 average rating, 91 reviews

Enchantment hills retreat guesthouse.

This is a guesthouse beautiful Black Hills of South Dakota. Incredible views . 25 minutes from Mount Rushmore and all of Black Hills. Centrally located. Enjoy watching the deer ,wild turkeys , foxes and other wildlife wandering through. Use as a locum's medical professional, couples retreat or business executive . Approximately 700 sq/ft, and exquisitely decorated. Driveway private. Stunning views overlooking enchantment Canyon and the beautiful prairies.

Guest favourite

Cabin in Lead

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

Cabin in Lead

4.97 out of 5 average rating, 35 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!

Guest favourite

Chalet in Rapid City

4.83 out of 5 average rating, 41 reviews

4. Lakeside Rapid City Home With Views

This is a beautiful lakeside home located on the west side of Rapid City. Huge windows creating a beautiful bright space with lake views. Relax in the hot tub and enjoy the surrounding nature! Location can't be beat. Woodsy oasis right in the city. Please note this is a personal residence when not rented.