
Cottage vacation rentals in Pennington County
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Top-rated cottage rentals in Pennington County
Guests agree: these cottages are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Pennington County cottage rentals
Cottage rentals with a hot tub

Cottage #7 - Spearfish Orchard Creek Cottages
The personalized text message if any help was necessary sets this place and owner apart!

Cottage #2 - Spearfish Orchard Creek Cottages
Cottage #2 was a perfect tiny home to stay in. The first day I was there it was 70°. The next day it was 30° and snowing. The fireplace made the tiny house so cozy. My host was quick to respond to any questions I had. I would stay again!

Cottage #5 - Spearfish Orchard Creek Cottages
A good place to stay - very clean and cozy.

Cottage#6 - Spearfish Orchard Creek Cottages
Great place definitely would go back!

Cottage #1 - Spearfish Orchard Creek Cottages
When I first arrived someone was occupying the cottage I had booked. I messaged the host and they responded right away and had solved the issue in under 30 minutes. The cottage was pristine, cozy, and comfortable. It worked great for me and my dog to stay for a night.

Cottage #3 - Spearfish Orchard Creek Cottages
Perfect size for my wife and I to stay here. We felt like it was a big tiny house and had so much more room to spread out and relax. Well furnished too! I stayed in these cottages as a young child and their much more updated since then! Fun fact my grandparents used to own these wayyyy back until they sold in the 70's.

Cottage #4 - Spearfish Orchard Creek Cottages
We had a wonderful stay at JAckie's charming cottage! The space was spotless, and Jackie was incredibly responsive and helpful throughout our visit. We loved exploring the beautiful town of Spearfish. We'd absolutely stay here again and highly recommend it to others!

Bullock Cottage at First Deadwood Cottages
Highly recommend Wayne's place!! Great location for walking to/from restaurants and casinos. This was a sxs trip for us; plenty of space to park our trailer onsite and great location for jumping on the trails right from the house. The house was nice and spacious for three couples and enjoyed the hot tub after a long day of riding. We hope to be back!!
Pet-friendly cottage rentals

Cottage #7 - Spearfish Orchard Creek Cottages
The personalized text message if any help was necessary sets this place and owner apart!

Cottage #9 Spearfish Orchard Creek Cottages
We really enjoyed our stay! It was super cozy

Wild Bill Cottage at First Deadwood Cottages
Wayne’s place is charming and cozy and comfortable. Loved the decor and old west Deadwood photos and feel. We enjoyed the at home feeling. We had a great experience! Can’t wait to go back

Pet-Friendly Custer Cottage Steps from Downtown
Perfect place for our stay. Fenced in yard was perfect for dog. Great location to all parks/ attractions/ Restaurants & shopping too!

Cottage #3 - Spearfish Orchard Creek Cottages
Perfect size for my wife and I to stay here. We felt like it was a big tiny house and had so much more room to spread out and relax. Well furnished too! I stayed in these cottages as a young child and their much more updated since then! Fun fact my grandparents used to own these wayyyy back until they sold in the 70's.

Cottage #4 - Spearfish Orchard Creek Cottages
We had a wonderful stay at JAckie's charming cottage! The space was spotless, and Jackie was incredibly responsive and helpful throughout our visit. We loved exploring the beautiful town of Spearfish. We'd absolutely stay here again and highly recommend it to others!

Bullock Cottage at First Deadwood Cottages
Highly recommend Wayne's place!! Great location for walking to/from restaurants and casinos. This was a sxs trip for us; plenty of space to park our trailer onsite and great location for jumping on the trails right from the house. The house was nice and spacious for three couples and enjoyed the hot tub after a long day of riding. We hope to be back!!

The Rock and Block house
We stayed for a couple nights on our way to Yellowstone. The house was everything we hoped for. Clean, quiet, and close to the Badlands. We were able to come back and relax after a day of hiking. The board games were an extra perk! So much fun. We would definitely stay again. Thank you!
Private cottage rentals

Cottage #7 - Spearfish Orchard Creek Cottages
The personalized text message if any help was necessary sets this place and owner apart!

Cozy Creekside Cottage
This was a beautiful place. The kids loved the park next door and so did we. 😆 We walked into town each day to a different ice cream place. The house was clean and very well organized. Definitely would go back!!

Cottage #9 Spearfish Orchard Creek Cottages
We really enjoyed our stay! It was super cozy

Cottage #3 - Spearfish Orchard Creek Cottages
Perfect size for my wife and I to stay here. We felt like it was a big tiny house and had so much more room to spread out and relax. Well furnished too! I stayed in these cottages as a young child and their much more updated since then! Fun fact my grandparents used to own these wayyyy back until they sold in the 70's.

Cottage #4 - Spearfish Orchard Creek Cottages
We had a wonderful stay at JAckie's charming cottage! The space was spotless, and Jackie was incredibly responsive and helpful throughout our visit. We loved exploring the beautiful town of Spearfish. We'd absolutely stay here again and highly recommend it to others!

Mystic Road Cottage… -Peaceful -Private -Hot tub
(5 Stars – The Perfect Honeymoon Getaway!) Our stay at Mystic Rd Cottage in Hill City, SD was everything we could have hoped for and more for our honeymoon. The cabin was clean, cozy, private, and tucked away in the perfect spot—what more could newlyweds from North Carolina ask for while exploring the beautiful Black Hills? The location was unbeatable—just a short drive to Mount Rushmore and Crazy Horse, with the scenic Needles Highway practically in the backyard. Even Badlands National Park was only a couple hours away and made for a perfect day trip. Bonnie and her husband were absolutely wonderful—so kind and welcoming. You can really feel the warmth of the locals here, which made our trip even more special. We couldn’t have picked a better place to celebrate this special chapter in our lives. Highly recommend Mystic Rd Cottage to anyone looking for a peaceful and memorable stay in the Black Hills!

Best little house in Deadwood
Perfect place for our small group. Clean and exactly as described. It is an easy walk to downtown Deadwood.

The Rock and Block house
We stayed for a couple nights on our way to Yellowstone. The house was everything we hoped for. Clean, quiet, and close to the Badlands. We were able to come back and relax after a day of hiking. The board games were an extra perk! So much fun. We would definitely stay again. Thank you!
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