30 Best Deadwood Cabins on Holiday Lettings - Vacation rentals

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34 Vacation rentals

24

Vacation home in Deadwood

South Dakota / Deadwood

7 15 2 nights min

  • 7 bedrooms
  • Sleeps 15
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
The home is uniquely situated blocks from the casinos, restaurants and entertainment downtown in one direction; while in the other direction, it's only half that distance to the forest line. The neighborhood gives you all of the charm, warm reception and slower pace of …see more

from $425 / night

$2975 / week

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from $425 / night

(1) Excellent 

26

Vacation home in Deadwood

South Dakota / Deadwood

7 28 Min stay varies

  • 7 bedrooms
  • Sleeps 28
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Ask about pets
This is the perfect Lodging for large and small groups. You can rent the whole vacation home, which will sleep 26 people. Or if you have a smaller group, you can rent the lower "Bunk Suite" with 1 large bunk room that has 3 queen beds and a sofa sleeper, 1 bedroom with …see more

from $300 / night

$2100 / week

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from $300 / night

(9) Excellent 

22

Deadwood Vacation log cabin rental

South Dakota / Deadwood

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Suitable for children age 5+
  • Pet friendly
(Note: Recently re-listed with Flip Key. Usually use one of the other vacation rental sites. Have many reviews listed on these.) 'Mountain Crest' is a beautifully hand-hewn, non-smoking, authentic log cabin occupying five acres on a mountain top. It offers a large par …see more

from $175 / night

$1225 - $1470 / week

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from $175 / night

(5) Very Good 

26

Home rental in Deadwood

South Dakota / Deadwood

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Ask about children
  • Ask about pets
This country home has lots of charm and a private, central location in the Hills! Located South of Deadwood on Highway 385, it`s just minutes from Deadwood, the Mickelson Trail, snowmobile trails and the ski areas and only 35 miles to Mt. Rushmore & Crazy Horse. This 2- …see more

from $300 / night

$2100 / week

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from $300 / night

(4) Excellent 

34

Vacation b&b in Deadwood

South Dakota / Deadwood

6 21 2 nights min

  • 6 bedrooms
  • Sleeps 21
  • 2 nights min
  • Child friendly
  • Air conditioning
This historic Queen Anne house is one of the largest built by Deadwood's merchant class during the gold boom between 1876 and 1930. The home kept much of its original woodwork, light fixtures and stained glass. Over the past five years, it's been gradually updated with …see more

from $900 / night

$6000 - $7050 / week

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from $900 / night

(1) Excellent 

13

Vacation log cabin in Deadwood

South Dakota / Deadwood

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Suitable for children age 5+
  • Car not necessary
  • Ask about pets
Experience this brand new construction, conveniently located near the Highway 385/Highway 14 Junction. Enjoy our home away from home as you explore the South Dakota Mickelson trail or the beautiful Black Hills. Deadwood offers a Vegas style gambling experience with mi …see more

from $300 / night

$1800 / week

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from $300 / night

(6) Very Good 

22

Vacation home in Deadwood

South Dakota / Deadwood

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Ask about pets
A three bedroom, three bathroom cottage located on Main Street Deadwood within walking distance of all the downtown action yet far enough to get away from it all. With Plenty of on-site private parking. This cottage includes central heating and cooling with washer and …see more

from $250 / night

$2800 - $3500 / week

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from $250 / night

(5) Excellent 

24

Deadwood Vacation home rental

South Dakota / Deadwood

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Ask about children
  • Ask about pets
This amazing new Construction is just south of Deadwood, with the Creek running right off the back deck - for beautiful views and scenery! Built in the summer of 2015, beautiful home has many custom features, large wood beam accents throughout, and rustic decor. Upon en …see more

from $195 / night

$1365 / week

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from $195 / night

(1) Excellent 

19

Deadwood Vacation home rental

South Dakota / Deadwood

1 6 Min stay varies

  • 1 bedroom
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
This charming cottage is conveniently located in town near major Deadwood attractions. Inside was freshly updated last year with new laminate floors, carpet, extra large shower, fresh paint, new queen-size sofa beds and 50" TV, plus a new front porch outside. The larg …see more

from $135 / night

$895 - $2500 / week

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from $135 / night

14

Vacation home in Deadwood

South Dakota / Deadwood

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Ask about pets
This beautifully decorated, newer home on the north end of Deadwood is the perfect home to enjoy the Sturgis Rally! Paved roads, single garage for parking bikes, beautiful scenery and a quiet location to get away after riding all day. 3 Bedrooms with queen size beds and …see more

from $625 / night

$4375 / week

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from $625 / night

(4) Very Good 

14

Vacation home in Deadwood

South Dakota / Deadwood

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
  • Ask about pets
Enjoy Deadwood and the Black Hills in the newly built, custom home on the east side of Deadwood! The location is only 1 mile from downtown but still in a secluded, very scenic area in the Black Hills - you'll see lots of Wildlife and enjoy quiet evenings. The Deadwood L …see more

from $185 / night

$1295 / week

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from $185 / night

(4) Excellent 

15

Vacation home rental

South Dakota / Deadwood

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Ask about pets
This beautifully decorated home was recently, completely remodeled inside! Located on Williams Street, right behind Deadwood Main Street - you can easily walk to downtown or enjoy the sounds from your front deck! Spacious, open living, kitchen and dining area with an up …see more

from $175 / night

$1225 / week

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from $175 / night

9

Vacation home in Deadwood

South Dakota / Deadwood

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Ask about pets
You can`t beat the location and layout of this great home in Deadwood! Just a few blocks from downtown Deadwood and close to a Trolley Stop, you can relax at the house or head downtown and enjoy the Night Life! This home has plenty of space and everything you need! It f …see more

from $400 / night

$2800 / week

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from $400 / night

10

Vacation home in Deadwood

South Dakota / Deadwood

8 18 Min stay varies

  • 8 bedrooms
  • Sleeps 18
  • Min stay varies
  • Child friendly
Vacation home in the Black Hills of South Dakota a quater mile from Trailshead lodge. Next to 350 miles of groomed snowmobile trails. This house has a full kitchen, dining room, 8 bedrooms, 3 that have king size beds, 4 Queen beds and one room with 4 Twin Beds, a 6 pers …see more

from $450 / night

$3150 / week

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from $450 / night

(22) Excellent 

56

Deadwood ski apartment to rent.

South Dakota / Deadwood

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ski
  • Ask about children
  • Car not necessary
This Home was built in 1954. A Frank Lloyd Wright ranch inspired home. Located in the Historical Presidential district of Deadwood. The house sets on the side of the cliff over looking Deadwood, Among the 1800's old Victorians in the Mount Moriah "Boot Hill' Histor …see more

from $109 / night

$763 / week

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from $109 / night

18

Vacation home in Deadwood

South Dakota / Deadwood

4 14 Min stay varies

  • 4 bedrooms
  • Sleeps 14
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
At Gold Dust Manor you'll stay in a 4 bedroom/3 bath private home located one mile to Deadwood, 8 miles to Sturgis, 6 miles to Terry Peak Skiing, and 45 miles to Mt. Rushmore. Attached garage space available and all paved roads. Six person hot tub, 106" theater room wi …see more

from $450 / night

$3150 / week

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from $450 / night

9

Vacation apartment in Deadwood

South Dakota / Deadwood

1 6 Min stay varies

  • 1 bedroom
  • Sleeps 6
  • Min stay varies
  • Child friendly
Stay in the Old Deadwood Jail! This property was where Butch Cassidy and The Sundance Kid were brought to after robbing a bank in Bell Fourche. It has been recently renovated and comfortably sleeps 6. This 1 bedroom vacation rental is walking distance to beautiful downt …see more

from $125 / night

$875 / week

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from $125 / night

(6) Very Good 

26

Vacation home in Deadwood

South Dakota / Deadwood

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Ask about pets
You`ll love the location of this cozy cabin in the hills. You can ride your snowmobile`s and ATV`s right to the miles of trails or walk/ride your bicycle to the Mickelson trail head. Enjoy the breathtaking views of the surrounding mountains while nestled in the pines, o …see more

from $150 / night

$1050 / week

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from $150 / night

(3) Excellent 

17

Vacation home in Deadwood

South Dakota / Deadwood

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
  • Ask about pets
Enjoy this wonderful home located in the heart of the Northern Black Hills! Just ten minutes to the ski areas, minutes from the Sugarloaf Trail head for snowmobiling, biking and hiking and 10 minutes from Deadwood. The 2 level cabin has 4 bedrooms (4 queen beds and 1 se …see more

from $200 / night

$1400 / week

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from $200 / night

(3) Good 

15

Deadwood Vacation log cabin rental

South Dakota / Deadwood

1 4 5 nights min

  • 1 bedroom
  • Sleeps 4
  • 5 nights min
  • Suitable for children age 5+
In the heart of the Black Hills of South Dakota this is a get away that will take you back in time... A modern hotel, with the look and feel of the last century. You can have all the privacy and beauty along with luxury. At Hotel Roy and the adjoining Mercantile y …see more

from $100 / night

$650 / week

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from $100 / night

(3) Excellent 

25

Vacation home in Deadwood

South Dakota / Deadwood

5 14 Min stay varies

  • 5 bedrooms
  • Sleeps 14
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Ask about pets
Relax and enjoy the quiet scenery and splendor of this beautiful home east of Deadwood! Main level has a large Living/Dining/Kitchen area, large family room on the lower level, 3 decks, patio, fire pit, hot tub and is fully equipped with washer/dryer, dishwasher, centra …see more

from $375 / night

$2625 / week

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from $375 / night

9

Vacation home in Deadwood

South Dakota / Deadwood

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
A quaint two bedroom duplex decorated in true Victorian style with a large living area, private bath and entrance. The central yard offers a hot tub and bbq kitchen area for relaxing below the red rock cliffs. Off-street parking is available near the door. The convenien …see more

from $100 / night

$700 / week

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from $100 / night

23

Deadwood Vacation home rental

South Dakota / Deadwood

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Ask about pets
Cozy home close to a trolley stop, across the street from the Mickelson Trail Head and within walking distance to downtown Deadwood! Enjoy all the comforts of home in this 1,200 sq ft ranch style home right in Deadwood. Great for all ages as this house is on a level str …see more

from $139 / night

$973 / week

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from $139 / night

13

Vacation home in Deadwood

South Dakota / Deadwood

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Ask about pets
If you are looking for a house in Deadwood - minutes from the casinos, with spacious living areas and great amenities, this is it! This home is right in Deadwood with 4 bedrooms (3 Queen beds and 1 Full-size bed), 2 full bathrooms, 2 large living areas with big screen T …see more

from $395 / night

$2765 / week

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from $395 / night

22

Deadwood Vacation home rental

South Dakota / Deadwood

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Private garden
Looking for an exceptional rental? Our home is 9 miles from Sturgis, 15 from Deadwood, with 5 miles of gravel road. It has 3 bedrooms,1 king bed,1 queen bed, & 2 twins, 1 bathroom and an outside shower, only in the summer.. Covered deck and large deck in front, relax …see more

from $245 / night

$1715 / week

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from $245 / night

(18) Excellent 

16

Vacation home in Deadwood

South Dakota / Deadwood

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Ask about pets
This newly remodeled cottage is in walking distance to Deadwood Main street. Perfect for 2 people, the cottage is laid out like a studio apartment with an oversized queen sofa sleeper and single sleeper, full bathroom, washer and dryer, and full kitchen. With a new, ext …see more

from $95 / night

$665 / week

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from $95 / night

10

Vacation home in Deadwood

South Dakota / Deadwood

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
If you want a home with a great location, paved roads and wonderful amenities - this is it!! This 3 bedroom home is just on the outskirts of Deadwood - 1 block from the Trolley stop and 2 miles from downtown. The home has wonderful amenities with a full kitchen, washer …see more

from $500 / night

$3500 / week

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from $500 / night

7

Deadwood Vacation home rental

South Dakota / Deadwood

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Air conditioning
While this two-bedroom cottage is located at a Main Street address, the entrance is located facing a quiet “off Main Street” residential area. A convenient parking area next to the front door provides a private entrance and the small patio directly below the cliffs of r …see more

from $150 / night

$1050 / week

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from $150 / night

24

Vacation home in Deadwood

South Dakota / Deadwood

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Ask about pets
This beautiful Victorian home is truly one of a kind, built in 1878, with updated amenities and restored architecture. The great location allows you to walk to downtown Deadwood or jump on the trolley. The main level has a remodeled kitchen with updated appliances and p …see more

from $800 / night

$5600 / week

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from $800 / night

9

Vacation home in Deadwood

South Dakota / Deadwood

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
The Poker Alice is a home away from home. This cottage sleeps 8 people and if rented with the Wild Bill can sleep up to 12 people with 3 bathrooms. It has a full kitchen so you can prepare your favorite meals. A living room and dinning area. An upstairs sleeping loft wi …see more

from $250 / night

$1750 / week

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from $250 / night

12

Deadwood ski log cabin to rent.

South Dakota / Deadwood

5 10 3 nights min

  • 5 bedrooms
  • Sleeps 10
  • 3 nights min
  • Ski
  • Child friendly
5 Bedroom Log Cabin. Beautiful log home nestled in the gorgeous Black Hills of South Dakota. Enjoy all the area has to offer- Terry Peak Ski Resort, Mickelson Bike Trail, Sturgis Motorcycle Rally- Mt. Rushmore, Legendary Deadwood- then come home and relax. Crafted of D …see more

from $375 / night

$2625 / week

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from $375 / night

13

Vacation home in Deadwood

South Dakota / Deadwood

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Ask about pets
This is a newly built home just north of Deadwood in a beautiful location with paved roads! Just 2 miles from Downtown Deadwood and 12 miles from Sturgis, with paved roads and easy access, this is a great Rally choice! 3 Bedrooms and 2.5 baths on the main level - 1 King …see more

from $650 / night

$4550 / week

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from $650 / night

13

Deadwood Vacation farmhouse rental

South Dakota / Deadwood

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Private garden
This beautiful family ranch house, sits on over 80 acers in a pristine valley surrounded by national forest. It is located 9 miles from Sturgis and 15 miles from Deadwood. The secluded nature of the property involves 5 miles of gravel road. It has gravity flow spring …see more

from $275 / night

$2900 / week

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from $275 / night

15

Vacation condo in Deadwood

South Dakota / Deadwood

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
2 bed/1 bath Walking distance to downtown Deadwood, w/ off street parking. One queen bed, one full bed, one blow up bed. Fully furnished with washer/dryer, cable TV, charcoal grills, AC, outdoor fire pit/seating area, large fireproof safe for valuables. …see more

from $429 / night

$3000 / week

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from $429 / night

1