Vacation rentals in Pennington County

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Top-rated vacation rentals in Pennington County

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Top guest favorite

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

Superhost

The kitchen features natural wood cabinetry and countertops, complemented by a stainless steel microwave and coffee maker. A window allows for a view of the surrounding trees, enhancing the bright and airy space. A decorative coffee pod holder adds a functional touch.

Bungalow in Custer

4.85 out of 5 average rating, 27 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.

Superhost

Condo in Lead

4.81 out of 5 average rating, 217 reviews

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!

Guest favorite

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 favorite

A hot tub is situated under a wooden deck, surrounded by tall pine trees. The tranquil setting is complemented by a clear blue sky, inviting relaxation and connection with nature.

Cabin in Deadwood

4.94 out of 5 average rating, 35 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 favorite

Home in Rapid City

4.97 out of 5 average rating, 96 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 favorite

A serene view of Rapid Creek flows gently past the property, surrounded by lush greenery and well-maintained lawns. A comfortable chair and small table are positioned on a wooden deck, inviting relaxation while enjoying the natural setting.

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

An interior view of a communal sauna features smooth wooden benches on either side and a natural wood-paneled arch overhead. A stone heater is centered along the back wall, with a woven basket positioned to one side. Views of greenery are visible through the rounded window.

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 favorite

A vibrant sunset casts warm hues across the horizon, with streaks of orange and yellow visible in the sky. The cabin with a porch is partially framed by tall trees, and the surrounding landscape features gentle slopes, enhancing the scenic view.

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 favorite

Cabin in Lead

4.97 out of 5 average rating, 30 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 favorite

A modern cabin features a steeply pitched roof, wood and concrete accents. A spacious deck is supported by black beams and includes seating, while steps lead to the entrance. Surrounding greenery offers a natural backdrop, enhancing the secluded atmosphere of the retreat.

Cabin in Lead

4.97 out of 5 average rating, 38 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 favorite

A hot tub is positioned under a covered area, overlooking a serene lakeside view. Flower planters hang above, adding touches of color. Lush greenery encircles the scene, providing a sense of nature's tranquility nearby.

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.