Holiday rentals with a pool in Pennington County

4.87 out of 5 average rating, 79 reviews

A loft-style bedroom features wooden paneling and a slanted ceiling. A spacious bed with a quilted blue and white coverlet is paired with decorative pillows. A comfortable chair sits in the corner, creating a cozy seating area. Natural light filters through a nearby window.

Cabin in Rapid City

Silver Lining Cabin in the Black Hills near Mount

Welcome to Silver Mountain Resort and Cabins. Solving Lining Canin is one of seven cabins that our on country property. Silver Lining Cabin is an air-conditioned suite built in knotty pine. A unique upper floor loft with slanted ceilings, and very comfortable. This charming space has it's own entrance facing the back meadow and pool. It includes 1 queen bed plus a large comfortable chair that transforms into a small bed and a trifold sleeping mat (both ideal for smaller children). It has one b

4.91 out of 5 average rating, 711 reviews

A scenic view reveals a snow-covered landscape, with tall evergreen trees dotting the foreground. The distant hills and valleys can be seen under a clear blue sky, creating a serene winter atmosphere.

Guesthouse in Rapid City

Priceless Black Hills View!

Two Large Furnished Bedrooms, new Queen Beds Pool Table and Darts Large living room with new sofa sleeper Newly remodeled bathroom 65'' UHD Smart TV, Dish DVR, Bluray Pool and Rec facilities, seasonal WIFI Highspeed Internet Outdoor patio area with seating Gas grill Pool table and darts Full size fridge/freezer Convection oven Induction cooktop Microwave Keurig coffee and breakfast snacks Washer and dryer Close to Rapid City shopping and dining Nature and wild life Amazing stars out at night!

5 out of 5 average rating, 11 reviews

DogFriendly*KingEnsuite*Trlr Parking*Garage*HotTub

Holiday Discounts!!! Relax in a spacious 5BR/3BA cabin in Powder House Pass with clubhouse and pool access. Enjoy the best parking for trailers, ATVs & snowmobiles. Main floor king ensuite, hot tub, 80" TV, air hockey, retro arcade & gas firepit. View Terry Peak from the front porch. Just 1 min to ATV & Mickelson trails, and minutes to skiing & Deadwood. Perfect for family or friends looking to unwind, explore, and make lasting memories in the Black Hills. One minute to the snowmobile trails!

5 out of 5 average rating, 149 reviews

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.

Home in Rapid City

Private Pool! Great Rapid City Location!

*Please be sure to read all house information! Welcome to Mary Jo's Place, a charming 1950s Rapid City home! Sleeping six with two bedrooms and two bathrooms. Located near the Historic West Boulevard in the center of Rapid City! A great location with nearby parks, walking and hiking trails, grocery, and restaurants. Also, easily access Mount Rushmore Road and Interstate 90. This home has recently been updated and is ready for your stay! Did we mention there is a private heated indoor pool!

5 out of 5 average rating, 97 reviews

A comfortable living area features a brown leather sofa adorned with patterned cushions. Above it, woven wall art is displayed, accompanied by hanging pendant lights. A rustic wooden ladder leans against the wall, and small side tables sit beside the sofa.

Condo in Lead

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

Superhost

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.

Home in Rapid City

4.81 out of 5 average rating, 112 reviews

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

Beautiful home in a residential neighborhood on the West Side of Rapid City. Perfect for families and gatherings. You will have access to a two car garage, above ground pool, trampoline, large outdoor deck, fire pit, and a grill that’s available when the weather permits. The house is almost 80 years old and there are some features that are still from the 50s and we like those. We don't plan on changing them so if you're looking for a totally updated house this house might not be for you.

Superhost

A green cabin is positioned among tall trees, surrounded by a grassy area. A stone fire pit is visible, accompanied by six metal chairs arranged around it, suggesting a place for gathering. Natural light illuminates the scene under a partly cloudy sky.

Cabin in Keystone

4.79 out of 5 average rating, 19 reviews

The Spokane Cabin

Welcome to Spokane Cabin where memories await! With 2 bedrooms/2 baths, an inviting living room, full kitchen, and 6 person dining area this is the perfect place for a family gatherings. At night relax around the outdoor fire pit complete with complimentary smore's. Enjoy a swim at our community pool (open seasonally). You will feel complete on this 8 acre property surrounded by National Forest while also being mins away from Mt Rushmore (2.4 miles) and Custer State Park (15 mins).

Guest suite in Rapid City

A private guest suite features a spacious bed with a textured gray blanket. A small round table and two chairs offer a cozy seating area. A flat-screen television is mounted on the wall, and a compact kitchenette is positioned beside a bathroom door. Natural light enters through the window with dark curtains.

4.86 out of 5 average rating, 44 reviews

Red Rock Private Guest Suite

Cozy, private guest suite in a newer apartment community, on the edge of the beautiful Black Hills of Rapid City, SD near the Red Rock Golf Course. Inside the space you will enjoy a queen size bed, private bathroom, washer & dryer, mini fridge, microwave, kuerig, TV, and small dining table. In the shared space of the apartment community guests will have access to a full kitchen, fitness center, pool table, shuffleboard, and swimming pool (Memorial Day to Labor Day only).

The exterior of the mountain modern cabin showcases a blend of wood and metal siding, complemented by large windows. The driveway leads to a three-stall garage, surrounded by snow-dusted pines. The home features multiple levels under a cloudy sky, highlighting its spacious design.

4.89 out of 5 average rating, 132 reviews

44° North Lodge- Luxury Cabin in Powder House Pass

Mountain Modern Cabin with Stunning Views of Terry Peak, Sleeps 26. The crown jewel of the Northern Black Hills. Escape to our beautiful NEW retreat nestled in the pines and aspens of the Black Hills. You will enjoy this immaculate home located in the prestigious Powder House Pass. This luxury mountain modern home features three levels of wonderful amenities with a great floor plan for large groups. It is ideal for family reunions or celebrations with friends.

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.

4.97 out of 5 average rating, 99 reviews

Moonlight Pines-Happy Little Cabin

Moonlight Pines (n.) a place where memories are made. Hello, we are so happy you’re here! Relax, unwind, + consume all the beauty + positive energy our space offers. Steps away from trails + slopes, have fun exploring our beautiful backyard knowing a cozy fire, a game of backgammon, a glass of wine, + a soak in the hot tub await (#hygge)! Connect with the peacefulness of nature and, of course, enjoy the moonlight shining down on all the pines!

4.87 out of 5 average rating, 79 reviews

Iron Horse Cabin

Located near Terry Peak & Deadwood.Quiet ATV/UTV friendly community located on a paved road with parking for up to 3 trucks with 3 trailers or 6 vehicles. The Iron Horse Cabin is in the Gilded Mountain Community & in additional to a private hot tub, Guests have access to a shared salt water pool (heated year-round!), 2 additional hot tubs, exercise room, pool table, sauna & a large space for gatherings at the Community's Clubhouse.