Cottage vacation rentals in Pennington County

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Popular amenities for Pennington County cottage rentals

Cottage rentals with a hot tub

Guest favorite
Cottage in Spearfish
4.94 out of 5 average rating, 157 reviews

Cottage #7 - Spearfish Orchard Creek Cottages

ShealynRating, 5 stars8 months ago
The personalized text message if any help was necessary sets this place and owner apart!
Top guest favorite
Cottage in Spearfish
4.92 out of 5 average rating, 131 reviews

Cottage #2 - Spearfish Orchard Creek Cottages

DanacaRating, 5 stars2 months ago
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!
Guest favorite
Cottage in Spearfish
4.88 out of 5 average rating, 96 reviews

Cottage #5 - Spearfish Orchard Creek Cottages

EmmaRating, 5 stars5 months ago
A good place to stay - very clean and cozy.
Guest favorite
Cottage in Spearfish
4.95 out of 5 average rating, 161 reviews

Cottage#6 - Spearfish Orchard Creek Cottages

JenniferRating, 5 stars2 weeks ago
Great place definitely would go back!
Guest favorite
Cottage in Spearfish
4.93 out of 5 average rating, 196 reviews

Cottage #1 - Spearfish Orchard Creek Cottages

MeredithRating, 5 stars3 weeks ago
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.
Guest favorite
Cottage in Spearfish
4.95 out of 5 average rating, 165 reviews

Cottage #3 - Spearfish Orchard Creek Cottages

CraigRating, 5 stars2 weeks ago
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.
Guest favorite
Cottage in Spearfish
4.93 out of 5 average rating, 213 reviews

Cottage #4 - Spearfish Orchard Creek Cottages

KallieRating, 5 stars3 weeks ago
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!
Superhost
Cottage in Deadwood
4.78 out of 5 average rating, 32 reviews

Bullock Cottage at First Deadwood Cottages

AlyssaRating, 5 stars9 months ago
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

Guest favorite
Cottage in Spearfish
4.94 out of 5 average rating, 157 reviews

Cottage #7 - Spearfish Orchard Creek Cottages

ShealynRating, 5 stars8 months ago
The personalized text message if any help was necessary sets this place and owner apart!
Guest favorite
Cottage in Spearfish
4.94 out of 5 average rating, 186 reviews

Cottage #9 Spearfish Orchard Creek Cottages

KaeleighRating, 5 stars1 month ago
We really enjoyed our stay! It was super cozy
Guest favorite
Cottage in Deadwood
4.74 out of 5 average rating, 57 reviews

Wild Bill Cottage at First Deadwood Cottages

RavenRating, 5 stars2 months ago
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
Guest favorite
Cottage in Custer
4.96 out of 5 average rating, 73 reviews

Pet-Friendly Custer Cottage Steps from Downtown

MaureenRating, 5 stars1 week ago
Perfect place for our stay. Fenced in yard was perfect for dog. Great location to all parks/ attractions/ Restaurants & shopping too!
Guest favorite
Cottage in Spearfish
4.95 out of 5 average rating, 165 reviews

Cottage #3 - Spearfish Orchard Creek Cottages

CraigRating, 5 stars2 weeks ago
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.
Guest favorite
Cottage in Spearfish
4.93 out of 5 average rating, 213 reviews

Cottage #4 - Spearfish Orchard Creek Cottages

KallieRating, 5 stars3 weeks ago
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!
Superhost
Cottage in Deadwood
4.78 out of 5 average rating, 32 reviews

Bullock Cottage at First Deadwood Cottages

AlyssaRating, 5 stars9 months ago
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!!
Guest favorite
Cottage in Wasta
4.9 out of 5 average rating, 500 reviews

The Rock and Block house

SarahRating, 5 stars3 weeks ago
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

Guest favorite
Cottage in Spearfish
4.94 out of 5 average rating, 157 reviews

Cottage #7 - Spearfish Orchard Creek Cottages

ShealynRating, 5 stars8 months ago
The personalized text message if any help was necessary sets this place and owner apart!
Guest favorite
Cottage in Custer
4.91 out of 5 average rating, 108 reviews

Cozy Creekside Cottage

MaggieRating, 5 stars5 days ago
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!!
Guest favorite
Cottage in Spearfish
4.94 out of 5 average rating, 186 reviews

Cottage #9 Spearfish Orchard Creek Cottages

KaeleighRating, 5 stars1 month ago
We really enjoyed our stay! It was super cozy
Guest favorite
Cottage in Spearfish
4.95 out of 5 average rating, 165 reviews

Cottage #3 - Spearfish Orchard Creek Cottages

CraigRating, 5 stars2 weeks ago
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.
Guest favorite
Cottage in Spearfish
4.93 out of 5 average rating, 213 reviews

Cottage #4 - Spearfish Orchard Creek Cottages

KallieRating, 5 stars3 weeks ago
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!
Top guest favorite
Cottage in Hill City
4.99 out of 5 average rating, 184 reviews

Mystic Road Cottage… -Peaceful -Private -Hot tub

TysonRating, 5 stars3 days ago
(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!
Top guest favorite
Cottage in Deadwood
4.99 out of 5 average rating, 179 reviews

Best little house in Deadwood

AprilRating, 5 stars2 days ago
Perfect place for our small group. Clean and exactly as described. It is an easy walk to downtown Deadwood.
Guest favorite
Cottage in Wasta
4.9 out of 5 average rating, 500 reviews

The Rock and Block house

SarahRating, 5 stars3 weeks ago
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!

Destinations to explore