
Holiday rentals with a pool in Pennington County
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Top-rated rentals with a pool in Pennington County
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Popular amenities for Pennington County rentals with a pool
House rentals with a pool

Crescent Moon Retreat
We had a wonderful stay here! The home was comfortable and beautiful. It was close to Terry Peak, which was wonderful for our two days of skiing. The hot tub was a perfect way to end the days. The only issue we had was lack of hot water. It wouldn’t last to even fill the master bathroom tub. Other than that we were so impressed! Would highly recommend this home!

Timber Trails: Pet-Friendly Haven for Adventurers
We booked the cabin for our annual family ski trip! We loved the space and loved that we could bring our furry friend! The home was just as described. We enjoyed the hot tub! The kids enjoyed the ping pong table in garage! What a wonderful location, will definitely book again.

Dog-friendly 3BR house with swimming pool access!
We enjoyed our stay. The host are very responsive if you have any issues. It is very quiet and private. Beautiful deck and lots of space. There were a few little things like the grill was very dirty, the dishwasher was broken and hard to make work, one pull out couch is broken and there was damage to some of the other furniture etc. However, none of it really affected our stay. The driveway is steep and there isn't a lot of yard space, but the home is very large and well stocked with what you need. The Wi-Fi was amazingly fast. There was soap/shampoo etc. in each bathroom, laundry soap, dishsoap, cleaning supplies, spices, coffee etc. The location is on a gravel road and is very close to Custer and pretty centrally located for the area. It was nice to have access to the KOA pools etc. There were two large TV's, a Fooseball table, a full wet bar/kitchen downstairs and an amazing spa tub room. Also, stero through the home and deck. We would definitely recommend the property!

Dwntwn Custer Farmhouse on Main St. with Hot Tub
We really enjoyed or stay at Sarah's Airbnb. Everything you need is within walking distance, which was quite enjoyable. Although, it is on the edge of downtown, we had no issue with road noise, which was nice relative to the location. There is a grocery store across the street, so it was easy to walk over and buy food to prepare in the well equipped kitchen. The Pizza Mill restaurant was also across the street and there pizzas were outstanding. I would highly recommend this impendent and locally owned business. We also walked a block to breakfast one morning and ate at the Our Place restaurant. This locally owned breakfast diner was also a gem and had a wonderful hometown atmosphere. Further down the main street were several other shops and places to eat. The only negative issue with Sarah's pace was the narrow, steep, and winding stairwell to the second floor. None of our group over 50 felt comfortable staying upstairs. All and all a good stay.

Kickback Shack, Powderhouse Pass, Black Hills, SD
The Kickback Shack was a great place to stay for a quick getaway to ride snowmobiles. House was super nice and love the location - easy access to trails, restaurants and town. Highly recommended!

Summer Swimming Retreat
We had a wonderful stay and a memorable week! The house was very clean and had everything we needed. The front porch and back deck, patio, and pool where fantastic for relaxing after a busy day of hiking and site seeing. The set up of the house is great for multiple families (the cushy sectional on the garage level was my favorite!). The house is a short drive to restaurants and downtown Rapid City. We were able to Door Dash on nights when we didn't feel like cooking or going out. We were not successful in getting Uber or Lyft the one time we tried. The house is near the base so there is the very occasional rumble of a large plane nearby, but otherwise the neighborhood is nice and quiet. We didn't need to contact the owner for much, but when we did Jennifer was very responsive. I highly recommend!

Chalet Mt Rushmore VIEWS Hot Tub
We had a great time in the Keystone area and were happy to have this cute AirBnB to come back to after a long day of exploring…and the hot tub was a hit with the kids. My only suggestion would be to add 1-2 more lamps in the sitting/tv area.

Wind Dance Lodge w/ HOT TUB Large Shop garage
An amazing spot- Met up with a total of 8 people and had plenty of space to spread out. The kitchen was great for making food for us all and the table was fun to play games. LOVED the hot tub and game room. Right off a main road but still felt private and secluded.
Apartment rentals with a pool

Roomy Condo on the Mountain
Great place stayed here to go snowmobiling. There was not direct access to the snowmobile trail from the condo but it is possible to ride from the condo

A3- Spacious 2bd/2ba condo w/ hot tub, walk to ski
beautiful location and lodg. it was perfect for our family to stay 2 bedrooms and baths. we spent the days at different attractions and then came home to a nice little space. no a/c, but it was always cool in the evening, so it was perfect. hot tubs were a great way to end the day. we stayed over the week of the 4th. it was just perfect.

Kindred Pines At Terry Peak
Very much enjoyed our stay at Kindred pines, and having the pool and hot tub made the stay extra enjoyable!

A8- Bright lodge feel 1bd/1ba walk to ski, w/ view
short walk to the ski lift and got to relax in the pool, hot tub and sauna! would highly recommend and hope to stay again soon!

A4-Bright 2bd/2ba main floor corner unit
We liked it even more than the photos. It was so nice to have two bathrooms. Living on the ground floor was easy for carrying our gear. We loved the hot tub! (Sadly our first night it was cold, so check before arrival if they will heat it). Nice to have access to pool table and extremely nice to walk to Terry Peak just across the street! (Tip buy lift tickets in advance for New Year’s Eve! Pick up passes night before so you can get right in gear rental lines). Hosts were very responsive. Nice to cook our own food.

*New* Across from Terry Peak*Hot tub*Spacious
Always love being able to stop in, such an incredible space and scenery!

B3 classy updated 1bd/1ba, walk to ski, w/ pool
The rooms are perfect for short stay where you came to ski. The pool and hot tubs are great to loosen up in after a day on the slopes
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