Best Cottages in Deadwood in 2026

A town nestled in a valley with a river running through it, surrounded by hills.

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Our top choices for Deadwood cottages

A two-story log cabin with a front porch and a covered walkway connecting the two units.

1. Spearfish Cottages

Spearfish

Melinda

includes taxes & fees

3 Nov - 4 Nov

A wooden cabin with a pergola, a stone wall, and a fire pit.

2. Off-Grid Cottage at Granny Flats

Spearfish

Andrea

includes taxes & fees

2 Nov - 3 Nov

A row of white cabins with a grassy yard and trees, under a sunset sky.

3. Cottage #3 - Spearfish Orchard Creek Cottages

Spearfish

Chuck T.

includes taxes & fees

3 Nov - 4 Nov

A single-story mobile home with a small porch and a covered outdoor area, surrounded by trees and grass.

4. 2 Mi to Sturgis Motorcycle Rally: Peaceful Home

Sturgis

Toni

includes taxes & fees

20 Oct - 21 Oct

A white single-story building with a small window and a door, surrounded by snow-covered trees.

5. Cottage #9 Walk-in Shower Hot Tub Poster Bed

Spearfish

Leslie M.

includes taxes & fees

3 Nov - 4 Nov

A single-story mobile home with a white exterior, a small porch, and a backyard with snow on the ground.

6. Cottage#6 - Spearfish Orchard Creek Cottages

Spearfish

Lin V.

includes taxes & fees

2 Nov - 3 Nov

A backyard with a wooden fence, two chairs, a small table, a potted plant, and a hot tub.

7. Cottage #7- Spearfish Orchard Creek Cottages

Spearfish

Karridy W.

includes taxes & fees

3 Nov - 4 Nov

A narrow pathway leading to a house with a covered porch, surrounded by trees.

8. Cottage #5 - Spearfish Orchard Creek Cottages

Spearfish

Brian G.

includes taxes & fees

3 Nov - 4 Nov

9. Cottage #2 - Spearfish Orchard Creek Cottages

Spearfish

Kevin H.

includes taxes & fees

3 Nov - 4 Nov

A single-story house with a dark front door, three windows, and a white picket fence.

10. Cottage #4 - Spearfish Orchard Creek Cottages

Spearfish

brock w.

includes taxes & fees

2 Nov - 3 Nov

A single-story house with a white exterior, a front porch, and a small front yard.

11. Cottage #1 - Spearfish Orchard Creek Cottages

Spearfish

Mike M.

includes taxes & fees

2 Nov - 3 Nov

A single-story house with a covered porch, a wooden fence, and a dirt driveway.

12. Downtown Carriage House

Rapid City

Joan C.

includes taxes & fees

12 Oct - 13 Oct

A single-story house with a covered garage and a front porch.

13. NEW - Pickle Cottage with Hot Tub + Pickleball Court

Rapid City

"Property was located in a much lower income and sketchy neighborhood. No broom closet with mop and broom to clean cooking spills. Therefore we did not cook not to mention there is no dishwasher. Deal breaker in my opinion. I’m staying in an home environment instead of a hotel and wanted to cook. But wanted to be able to load dishes in a dishwasher and go on about our vacation. Also, when people are staying a week in a property need to be able to clean their toilet more than once during that...

Donna W.

includes taxes & fees

2 Nov - 3 Nov