Family-friendly holiday rentals in Hill City

A spacious home is nestled among tall trees, overlooking a gently flowing creek. The property features a large deck and stonework, blending harmoniously with the natural surroundings, while vibrant greenery enhances the serene environment.

4.98 out of 5 average rating, 121 reviews

Creekside Sanctuary

Creekside Sanctuary is a 6+ acre paradise for families, friends, celebrations or retreats. Naming this property was not easy, not only is this a Sanctuary for relaxation and rejuvenation, guests can also enjoy the popular site seeing and abundant wildlife native to our beautiful Black Hills. Whether winter or summer, there are activates nearby - fishing, hiking, skiing, snowmobiling, ice skating. The large yard is host to deer and turkey, an ideal gathering spot for celebration, fun and games.

4.94 out of 5 average rating, 125 reviews

A charming red house is surrounded by lush green grass and tall trees, with a sloped hill rising in the background. A small deck with white chairs is visible at the front, offering a welcoming outdoor space.

Cabin in Hill City

Grandma's House in the Heart of the Black Hills

Grandma's House is in the heart of the Black Hills, located 1 mile from Hill City, it is minutes away from Mt. Rushmore, Crazy Horse, Custer State Park and more. It sits alone on the edge of a meadow with hills directly behind it and a small, bubbly creek in front of the house. It has plenty of room for kids to run and play outside, and a cozy, quaint inside for families to enjoy each other's company. Grandma’s House is available for extended stays November thru April. Contact host for details

A scenic view showcases the cabin nestled amongst tall pine trees, surrounded by expansive green meadows. A winding gravel driveway leads to the property, with a seasonal pond visible in the foreground, reflecting the clear blue sky.

4.99 out of 5 average rating, 283 reviews

Cabin on 20 acres w/ horses, goats, & mini donkey

Enjoy country living close to town! Two bedrooms w/ queen size beds and loft w/ queen size pullout sofa allow you to comfortably sleep 6! Just 4 miles from downtown Hill City. Sits on 20 beautiful acres surrounded on 3 sides by Forest Service! Enjoy beautiful surroundings - a seasonal pond outside your cabin (water level varies), horses, mini donkey, mini goats and chickens. Enjoy private setting with the convenience of the owners just 1/4 mile up the driveway to take care of your needs!

4.94 out of 5 average rating, 204 reviews

Cabin in Custer

Nature Stay with Views Like No Where Else

This home is truly one-of-a-kind and straight out of a magazine! Beautifully modern and furnished to an exceptional standard. Open the windows and let the soothing sounds of the nearby creek transport you to your own private paradise. Located close to Mount Rushmore, Crazy Horse Memorial, Custer State Park, and many other top attractions, you’re also just under 5 minutes from Hill City. We truly believe this is the ultimate spot to fully experience the breathtaking beauty of the Black Hills.

4.81 out of 5 average rating, 150 reviews

A wooden cabin is nestled among towering pine trees with expansive windows reflecting the natural surroundings. A wrap-around deck features a private hot tub, and an American flag is displayed proudly outside, contributing to the serene ambiance of the location.

Home in Keystone

Chalet Mt Rushmore VIEWS Hot Tub

You’ll be amazed at the breath-taking view of Mt. Rushmore and the surrounding Black Hills from inside and out of this beautiful air-conditioned cabin situated amidst the quiet whispers of majestic pines in Keystone, SD. The location offers privacy along with comfort as you enjoy the large open deck with gas grill and fire pit, plenty of seating, private hot tub and lots of fresh air. Wrap-around deck with ample dining seating, guest parking and access to the Ramada Mt Rushmore indoor pool!

Superhost

A rustic cabin with wooden siding is seen under a sloped roof. A covered porch is furnished with a wooden picnic table and bright red chairs. Nearby, a small fire pit and grassy areas are visible, while trees line the background.

Cabin in Hill City

4.73 out of 5 average rating, 105 reviews

High Country Guest Ranch - #24 Rodeo

Camping Cabins are perfect for a quick get-a-way for smaller families of 5-6 people! There is a large shared firepit to enjoy!!! Bedding and towels are provided. Mini fridge, microwave, coffee maker and toaster only does NOT have a full kitchen. Coffee and creamer kit provided. Charcoal grill outside, you bring your own supplies. Come enjoy the small cabin feel in the middle of The Black Hills without breaking the bank! Little to NO internet but the store has internet you can use!

4.96 out of 5 average rating, 135 reviews

Castle in the Sky

Are you looking for a luxurious, unique place to stay? This house sits overlooking Rapid City with incredible skyline views, every evening is as picture perfect as the glowing city lights. This unique house is a fun mix of eclectic and fancy. Originally built as a local builder's "Coup de Grande", he ended up only finishing the guest house. You will find high-end finishes mixed with eclectic choices. We promise this will be one of the most memorable places you'll ever stay!

4.99 out of 5 average rating, 194 reviews

A cozy living area is shown, featuring two patterned armchairs and a comfortable sofa. A wooden table with a vase of flowers sits near a window that brings in natural light. A clock and a lamp add to the welcoming ambiance.

Guest suite in Hill City

Pine Mountain Rest

Come find a restful space in the Heart of the Hills. After a busy day exploring all that the Black Hills have to offer you will find a quiet place to relax, fix your meals and rest for another day of adventure. Relax on the deck and listen to the Hill City 1880 train whistle as it returns from its final run. Located in Hill City we are in the heart of everything you want to do. Mickelson Bike Trail runs through town. Mount Rushmore and Crazy Horse are within 15 miles.

4.85 out of 5 average rating, 169 reviews

A small wooden cabin with a blue roof is surrounded by greenery. Flower boxes are placed under the window, complemented by rustic decor elements such as an old wagon wheel and metal barrel. The peaceful country setting is highlighted by the dense trees in the background.

Cabin in Keystone

Hill top Cabin. #4

Small cabin, 2 miles from Mt.Rushmore and walking distance to Keystone, SD shops. Just a queen bed, AC, refrigerator, shower and deck overlooking Battle Creek, 30 feet below. Scenic views of surrounding forest hilltops and canyon. We also have another cozy cabin #5 if this cabin isn't available or if you'd like to book both for a party of 4, just click on our host (Diane's) photo to see both cabin listings. Seasonal openings. June 1- Oct. 11. Not open winter months.

4.95 out of 5 average rating, 390 reviews

A wooden deck is seen overlooking a green golf course, surrounded by tall pine trees under a clear blue sky. The sunlight casts shadows on the deck's surface, enhancing the natural beauty of the setting.

Guest suite in Custer

The View at Bear Rock Two (Top Unit)

Relax in our charming guest suite featuring a private rooftop deck with serene views of Rocky Knolls Golf Course. Enjoy a comfortable queen bed, a renovated bathroom with a modern shower, and convenient amenities like a mini-fridge, microwave, cable TV, and Wi-Fi. Located just minutes from local dining, bars, and major attractions including Mount Rushmore, Crazy Horse Memorial, and Custer State Park, our suite offers the perfect base for your Black Hills adventure.

A covered porch is displayed with two wooden chairs positioned in front. Large glass doors reveal a spacious dining area and kitchen, featuring dark cabinetry and modern appliances. The floor appears polished and reflects the warm lighting from overhead fixtures.

4.96 out of 5 average rating, 213 reviews

Hill City Hideaway on the Mickelson Trail

Location, location, location. Hill City is located in the center of the Black Hills and this house is within walking distance of the best parts of Hill City. 40 feet to the world famous Mickelson Trail, 1/2 a block to the 1880s steam train, and 3 blocks to the best restaurant in South Dakota. This home is not too big and not too small. Whether you are doing a couples get away, traveling with kids or your friends this home may be "just right" for you.

4.99 out of 5 average rating, 206 reviews

The A-frame cabin is framed by tall pine trees, showcasing a blend of wood and metal in its exterior design. Warm lights illuminate the structure, highlighting the large windows and inviting entrance. A stairway leads to the deck, enhancing accessibility to the cozy retreat.

Tiny home in Custer

Modern A-Frame Cabin Next to Custer State Park

Enjoy this spacious modern A-Frame Cabin. Located just 5 minutes to Custer State Park. Experience views of the Needles Highway and Black Elk Peak while you drink your morning coffee! You will have access to the entire house all to yourself! Great area to hike, bike, see the fluffy buffalo. Just a two minute drive to downtown Custer. This area has great ATV and kayak, trail ride rentals near by! Feel refreshed when you stay in this rustic gem.

Popular amenities for Hill City family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.86 out of 5 average rating, 37 reviews

Home in Custer

Rock Face Lodge, Custer SD

A modern cabin with a sloped roof and wooden deck is surrounded by lush greenery. Vibrant wildflowers add color to the scene, while tall pine trees frame the structure. A welcoming sign is visible nearby, enhancing the cabin's rustic charm.

4.98 out of 5 average rating, 125 reviews

Moonlight Pines-Happy Little Cabin

An expansive indoor pool area features a large swimming pool with a water slide. Natural light filters through skylights and large windows. A basketball hoop stands at the side of the pool, while lounge chairs provide space for relaxation.

4.92 out of 5 average rating, 139 reviews

lNDOOR POOL! The FUN house

Superhost

The charming log cottage is set against a stunning natural backdrop, featuring a green metal roof and a spacious porch. A peaceful creek runs alongside the property, while trees and hills frame the view, creating a serene rural setting.

4.75 out of 5 average rating, 28 reviews

Peaceful Pines Retreat - Creekside !

The exterior of the vacation rental features a welcoming entrance with steps leading up to a large glass door. A railing surrounds the steps, and manicured lawns enhance the curb appeal. Trees provide shade, while a nearby building complements the home's design.

5 out of 5 average rating, 17 reviews

Hill City Haven Downtown Main Street

4.99 out of 5 average rating, 310 reviews

The exterior of the cabin showcases a combination of natural wood siding and green accents, framed by tall trees. A welcoming deck extends from the front entrance, and landscaped stone beds add charm. The adjacent structure features a garage and earthy tones, integrating seamlessly with the surroundings.

Cabin in Black Hawk

Squirrel Hill Cabin - hot tub, gameroom, wi-fi

4.83 out of 5 average rating, 388 reviews

A charming creek-side home is featured, showcasing rustic wooden siding and a welcoming entrance. A pathway leads to a wooden deck, with a flagpole prominently displaying the American flag. Vibrant green grass and a fire pit with red chairs enrich the outdoor space, surrounded by natural hills.

Cabin in Rapid City

Creek-side Cabin | Hot Tub + Trout Fishing

5 out of 5 average rating, 10 reviews

Steel Pines Cabin on Maitland rd.

Family- and pet-friendly home rentals

4.96 out of 5 average rating, 54 reviews

A panoramic view reveals a verdant canyon surrounded by towering pine trees. Jagged rock formations line the cliffs, with splashes of green foliage contrasting against the earthy tones. The sky, filled with soft clouds, adds a serene backdrop to this natural landscape.

Apartment in Hermosa

Peaceful Canyon Retreat | Luxe Apt + Wildlife

A spacious mobile home is situated in a winter landscape, surrounded by tall pine trees. Snow blankets the yard, with a wooden staircase leading up to the front entrance. Large windows provide views into the home, enhancing the serene setting.

4.94 out of 5 average rating, 47 reviews

Western Pines

5 out of 5 average rating, 9 reviews

Cabin in Custer

Crazy Horse Lodge - 1 BD Cabin

The exterior of a small home features warm wooden siding and a welcoming entrance with a glass-paneled door. Two patio chairs are positioned on a covered porch, and large windows provide natural light. The surrounding area includes a wooden railing and a paved pathway.

4.88 out of 5 average rating, 24 reviews

Dino's Domo

4.91 out of 5 average rating, 740 reviews

A spacious outdoor pool is visible with clear, turquoise water reflecting the blue sky. A nearby covered seating area provides shade and includes tables and chairs. Fencing surrounds the pool area, adding to its inviting atmosphere.

Guesthouse in Rapid City

Priceless Black Hills View!

4.91 out of 5 average rating, 334 reviews

A stylish tiny house on wheels features a contemporary design with metal siding and a bright yellow door. A small wooden staircase leads to the entrance. The house is set against a backdrop of trees and grass, reflecting a connection to nature.

Tiny home in Custer

Black Hills Rambler-Tiny House

4.88 out of 5 average rating, 59 reviews

The log home features a welcoming exterior with a prominent flag and a covered porch. The structure is surrounded by a lush green lawn, leading to a backdrop of tall trees. A stone wall adds natural texture to the landscape.

Apartment in Hill City

Burro Burrow - Basement Apartment on 8 Acres

4.96 out of 5 average rating, 73 reviews

A spacious tent is positioned on a wooden platform surrounded by trees, with a small fire pit in the foreground. The setting sun casts a warm glow, creating a peaceful atmosphere in the natural landscape.

Tent in Hill City

Hillside Safari Glamping For 2 w/Private Bath 18+

Family-friendly home rentals with a pool

Superhost

A cabin with a wooden facade is surrounded by tall trees and lush green grass. The front deck features a sturdy railing, and multiple windows provide natural light. A stone border outlines the grassy area, contributing to a sense of privacy.

Cabin in Custer

4.82 out of 5 average rating, 11 reviews

French Creek Cabin | Rock Crest Lodge

4.87 out of 5 average rating, 238 reviews

Mineral Mountain Lodge in Gilded Mountain

A private indoor pool features a vibrant blue surface, with a shallow entry area marked with depth indicators. Large windows allow natural light to fill the space, while lounge chairs are positioned along the edges for relaxation. The pool area is designed for guest privacy.

4.99 out of 5 average rating, 176 reviews

Private Pool! Great Rapid City Location!

The home features a single-story brick façade with a well-maintained front yard. A two-car garage is visible on the right, while large windows provide glimpses of the interior. The driveway leads up to the house, bordered by a neat gravel edge.

4.82 out of 5 average rating, 125 reviews

Pool, deck, fire pit, and trampoline!!!

4.94 out of 5 average rating, 72 reviews

An open-concept living area features a spacious sectional sofa facing a modern fireplace. Large windows allow for ample natural light and offer views of the surrounding trees. The kitchen, equipped with contemporary appliances, is positioned in the background, enhancing the inviting atmosphere.

Home in Lead

Timber Trails: Pet-Friendly Haven for Adventurers

4.87 out of 5 average rating, 94 reviews

Iron Horse Cabin

4.82 out of 5 average rating, 529 reviews

A rustic cabin is shown with wooden siding and a green roof. The front porch features two rocking chairs, providing a relaxing spot to enjoy the outdoors. The cabin sits on a gravel area, with grassy surroundings and rolling hills visible in the background.

Cabin in Piedmont

Rustic Cabin