Name: DoubleTree by Hilton Deadwood at Cadillac Jack's
Address: 360 Main St, Downtown Deadwood, Deadwood, South Dakota, United States of America, Deadwood, Lawrence County, US
Price range: US$72–US$503 per night
Rating: 8.93

What guests think

Across many reviews, DoubleTree by Hilton Deadwood at Cadillac Jack's earns praise for clean, comfortable rooms, friendly staff, and a lively attached casino complex with multiple dining options, offering a walkable base near downtown and the trolley.

Common frustrations include paid, limited, and sometimes inconvenient parking, plus a confusing layout shared by three hotels that requires walking through the casino and separate access for the pool. Several guests reported unreliable Wi-Fi, occasional low water pressure or temperature control issues, and intermittent housekeeping lapses. While most staff interactions are welcoming, a few guests encountered slow or unfriendly service, and some experienced late-night fire alarms or noise. Expect a clean, activity-filled stay with casino energy and some logistical trade-offs.

Facilities

Cleanliness

Rooms

Service

Location

Dining

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AI-generated summary based on recent guest reviews

Facilities

Large casino complex with three hotels offers plenty on site, but many guests report paid, limited parking and a confusing layout, with the pool located in an adjacent property requiring separate access. Wi-Fi is often unreliable, and some amenities like laundry service or elevators were unavailable at times.

Related guest reviews

10

Jeffrey

19 Feb 2023

·

Stayed 1 night

Internet is awful other than that everything was awesome!!

8

Lisa

16 Jun 2025

·

Stayed 3 nights

Great stay, only concern is that they advertise laundry service and there is not laundry service. We wanted to do laundry halfway and was really disappointed about this. When talking to front desk their response was “we can have someone come in from Spearfish” ??? Just fyi for others staying who may be planning this. Also only laundry mat in area was dirty and not maintained.

6

Marie

29 May 2023

·

Stayed 2 nights

You have 3 hotels under one roof- but only one pool area. If you are not staying in the hotel that has the pool - your room key will not work to get into the pool area. You have to get a separate key from the hotel that it is in to obtain access to it. $15.00 extra a day to park in the underground parking garage. There is parking outside the casino for free but pretty crowded when you have 3 motels. Probably would stay somewhere else if we come back to Deadwood.

8

mark

12 May 2025

·

Stayed 1 night

Parking in front of the building under repair. 3 hotels under 1 roof.. confusing. From parking garage take elevator to casino level to check-in, walk through casino to a 2nd elevator to go to room. Property is at far end of town so either a long walk or drive to downtown.

6

Brett

12 May 2024

·

Stayed 2 nights

Hidden cost that was not requested till checkout. I paid the cost of two night stay thru Expedia. Upon checkout I was informed that the hotel was charging my account an additional $31 for parking! I assumed parking at motel was included in charge per night. Not the case here at the Hilton / Cadillac jack casino in deadwood SD. Thanks for letting me know I was being charged $15 plus tax to park at hotel!

6

Mary

17 Oct 2025

·

Stayed 1 night

Hotel and room were satisfactory. However, pet owners beware! A $50 fee per night per pet. Also, the wifi did not work.

8

Robert

16 Aug 2024

·

Stayed 1 night

The room was nice and clean. Front desk was very responsive. The hotel itself has a very confusing setup. It’s one long building with 3 separate hotel brands within. The front desk does not align under the proper hotel, instead it’s flipped with a different one. You need to go into the casino to check in. The parking garage is shared but you need to go up to the casino get off then walk through the casino to the appropriate elevator. To use the indoor pool you need to go outside through the casino, walk to the end of the property and go back into the far north hotel. There you get a different card for the pool access. Just very unnecessary confusing setup!

10

Sarah

23 Oct 2024

·

Stayed 2 nights

Parking was inconvenient because the parking lot was torn up. One of the elevators was down. But the area was clean and good options for food away from the strip!

6

Taylor

9 Feb 2024

·

Stayed 2 nights

Everything was pretty decent except the internet didnt work for the duration of our stay. The first night they said they had a tech coming to fix it. The next they they said they didnt know anything about. They also charged $47.64 for parking without advertising it or letting us know at check in which was pretty shady. Keep that in mind when comparing rates. There are also many free options had we known.

8

jodi

14 Jul 2025

·

Stayed 4 nights

Very friendly staff, the room was quiet and clean! Our only issue is parking is very LIMITED and when we checked out we found out we had to pay $15 per night for parking which came as quite a surprise considering one night we had to park down the road in a public lot since there was no parking spots available.

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AI-generated summary based on recent guest reviews

Cleanliness

Many reviews praise very clean rooms and common areas, but there are recurring reports of housekeeping lapses, odors, and occasional pests or missed bathroom details. Overall standards appear inconsistent across stays.

Related guest reviews

4

megan

24 Feb 2025

·

Stayed 2 nights

Finding the entrance wasn’t exactly easy. Once inside you have to walk thru the casino to get to the elevators to get to the hotel. Didn’t like having to do that. There were additional fees that I wasn’t aware of. Valet parking was nice. The room wasn’t clean. There were large black ants. They did move us to another room after I showed pictures of the ants. The room has hair in the shower that wasn’t ours. The shampoo in the shower was empty. It was like the room hasn’t been cleaned before checking in. Won’t stay here again.

6

Ronald

3 Jul 2023

·

Stayed 4 nights

Our room bedding was dirty from previous person and the next day they thru the bed together and did nothing else. When we told front desk they did come and redo it.

4

Jennifer

16 Sept 2024

·

Stayed 5 nights

The hotel in general was fine, staff was friendly. Room was ok. My problem is with housekeeping. Our room was never cleaned properly. I had to continually call the front desk. We were running out of things like towels, coffee, cups. They did not vacuum our room, when I asked the front desk they said they were supposed to do that daily but they did not. We did not have a proper clean in our room until the day before we left and we stayed an entire week. That was very disappointing.

10

Heather

4 Nov 2025

·

Stayed 1 night

Clean room, polite staff.

6

Hillary

14 Jan 2024

·

Stayed 1 night

The rooms are nice and the beds are cozy but for some reason our room smelled like sewage or a backed up toilet. The hallways were very dirty, didn't look like they had vacuumed the carpet in weeks. Our car was also hit in the parking lot, hit and run, we came out to find it, and asked for them to review the cameras to see if the accident was caught. We live out of state and all that was done was they took my name and info and said "uhhh probably won't be able to see anything." We were parked right in front of the hotel, next to the Vallet. There were about 8 cameras there, there is no way something wouldn't have been seen. The food court there is handy but the employees in the food court were incredibly rude and awful to customers. We ordered chicken wraps, 4 of them, not a single one came with chicken. When we let them know the worker about lost his cool and tried to refuse to give us the correct meals. He then huffed and puffed and tossed some cold chicken into a bowl and grunting tossed it our way. That meal was over 60 bucks. None of us could eat it. The lettuce and ingredients were spoiled. DoubleTree advertises the food court as a perk or amenity for the hotel guest, if I were Hilton I think I'd have some quality control with their "amenities". Also the TV was unusable. It lagged and would shut off or log you out in the middle of a movie. The closed captions didn't work. You would literally scroll down 8 shows and maybe 5 minutes later it would select

10

Janet

25 Feb 2025

·

Stayed 1 night

Very clean modern room. Comfy beds, quiet.

10

Casey

7 Jun 2024

·

Stayed 1 night

Very clean, wonderful shower. Hotel is mixed with a few restaurants and a casino which was cool. Also walking distance from Main Street in Deadwood

4

Philippe

6 Jul 2024

·

Stayed 1 night

Filthy, dark rooms, blood stains on beds, sticky floor, dirty bathrooms

10

Tracy

10 Oct 2024

·

Stayed 1 night

Excellent place to stay! Super clean and comfortable!

10

Katie

14 Aug 2024

·

Stayed 1 night

Amazing staff & one of the cleanest hotels i’ve been to

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Rooms

Rooms are modern, spacious, and generally comfortable and quiet, with good beds and showers. Downsides noted include hard mattresses, low water pressure or temperature control, some poor views or noise near the lobby/casino, and unreliable Wi-Fi or TV.

Related guest reviews

10

Jeffrey

19 Feb 2023

·

Stayed 1 night

Internet is awful other than that everything was awesome!!

8

Gary

24 Jun 2025

·

Stayed 2 nights

It's a great place to stay with an nicely updated room and walk out shower but the cell phone reception in our room was very poor. We were in a back room on a lower floor with a steep rock face very close outside our window. Stay in a front facing room and it might be better.

10

Jeff

18 Jul 2023

·

Stayed 1 night

The staff were all extremely friendly. The room was HUGE and very clean. The bed was fantastic!

6

Jeffery

6 Jun 2024

·

Stayed 1 night

Tv did not work properly

8

Kayla

4 May 2025

·

Stayed 2 nights

We stayed here for a weekend trip in Deadwood. Room was clean and overall no complaints. Pillows and bed were extremely hard. Only major complaint is that we could hear the music from either outside or from front lobby area and it was really loud about 4/5 am. We stayed on level 4 but our room we right over the lobby so very loud.

10

Janelle

23 Oct 2024

·

Stayed 1 night

Great room, very comfortable bed. Dining attached.

10

Pamala

26 May 2024

·

Stayed 1 night

I love that we were able to take the elevator downstairs and enjoy food and drink and gaming. The room was large. The bed was comfortable.

10

Janet

25 Feb 2025

·

Stayed 1 night

Very clean modern room. Comfy beds, quiet.

6

CINDEE

23 Jun 2025

·

Stayed 1 night

The room was good. Water pressure is extremely low. Hazel was awesome! 😁

8

Jeremy

4 Jul 2025

·

Stayed 1 night

The bed looked very comfortable but wound up being hard. Shower was small and the water pressure was awful. Our mini fridge didnt get cold. Every time we stay here, our room faces the wall. We rented a junior suite and expected more then just a basic room.

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Service

Staff are often described as friendly and helpful, with several standout front-desk experiences. However, some guests encountered rude or unaccommodating service, booking or check-in mishaps, and slow responses from housekeeping or the robot delivery.

Related guest reviews

10

Karen

10 May 2024

·

Stayed 3 nights

Extremely friendly staff

6

Heather

3 Sept 2024

·

Stayed 3 nights

The bartenders were rude about finding a station. It was either “ I don’t know how to change the channel or I’m too busy “ but had no problem flirting with patrons. Our AC unit broke in our room and maintenance was quick and efficient with replacing it. Staff made us feel unwelcome due to being out of towners mostly. Didn’t matter if it was getting food, buying toiletries at the shop inside the hotel or bar, no one was friendly.

10

Cristian

11 Jun 2024

·

Stayed 2 nights

Everything was great! Good experience. Front desk personnel were very friendly and nice, particularly Jessie

10

Rebecca

15 Jul 2024

·

Stayed 3 nights

Overall, it was a great experience! Nikki, the front desk clerk was super sweet and helpful. The property was well maintained and clean. The room was spacious, very clean, and comfortable. The only down side was the paid parking. .

6

Sandra

9 May 2025

·

Stayed 2 nights

Front desk people were rude like they didn’t want to be there. Couldn’t answer the simplest question.

2

Joel

5 Jan 2024

·

Stayed 1 night

We tried to use the robot butler and no one opened the app to see there was even an order not once but twice. We won’t be using this hotel anytime soon

2

Monty

4 Jun 2023

·

Stayed 4 nights

Spent 4 nights here. Had to go to Wal Mart to buy trash bags to but trash in call front desk 4 times to get towels and trash removed. Finaly got towels last night. We had 4 kitchen trash still in room when we left. We drove from Denver all night after missing our connecting flight. The front desk clerk was extremely rude. Would never recommend !!!!

2

Barth

6 Jul 2025

·

Stayed 1 night

Did not get the room I was promised to check in. I’m traveling with my 90-year-old mother. We need an accessible room with a rolling in shower. I was told that room would be available tonight without doubt I got here and they said they sorry they overbooked and they would give me a regular queen room and then switch it to the next day and I am staying three nights here. I was so mad I got your weight. It was a long 10 1/2 hour drive to get here and then they spoke with someone named Zoe night before last to make sure everything was available in and right and when I get here it wasn’t yeah I’m not happy at all

10

Craig

25 Jul 2025

·

Stayed 1 night

Front desk agent was great, friendly. The hotel was in great condition, the room was the best we stayed in on our 8 day road trip. We liked the convenience of a really good restaurant in the hotel.

10

Daniel

29 Sept 2024

·

Stayed 3 nights

Nikki at the front desk was cheerful, knowlegeable and very helpful. The cleaning staff went out of their way to be helpful. The entire stay was very enjoyable.

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Location

Walkable to Main Street and close to a trolley stop, making it convenient for exploring Deadwood. A few note it sits at the far end of downtown but still manageable on foot.

Related guest reviews

10

Elizabeth

17 Mar 2025

·

Stayed 4 nights

Great hotel! Big rooms! Little bit of a walk to downtown but very doable when it’s nice out! Trolley is also an option. Lots of food and drink options!

10

Carrie

31 Aug 2025

·

Stayed 2 nights

Awesome trip. Walking distance to Main St. Deadwood.

10

Diana

26 Sept 2024

·

Stayed 1 night

Great location for sights ,shopping and restaurants

10

Alexis

22 Jul 2025

·

Stayed 2 nights

Absolutely beautiful view and great walking distance from downtown. Would stay there again.

8

Christopher

15 Aug 2025

·

Stayed 5 nights

Was nice to walk to places for the most part in deadwood

10

Steven

10 Sept 2025

·

Stayed 2 nights

Location was perfect. Parking on site. Several food choices. Staff amazing. Easy walk into town

10

Peter

22 Sept 2024

·

Stayed 1 night

Gamblers paradise. Not suitable for non-gamblers. No real services like morning coffee. Actually it is three hotels in one. Not what I expected and a real disappointment. It’s on Main Street but way out of the historic center of Deadwood. Parking was great for handicap people

8

Jason

23 May 2025

·

Stayed 1 night

Clean room, comfortable beds, and a nice casino downstairs all make for a pretty pleasant stay. It’s a short walk to the edge of downtown deadwood and plenty to do there

10

Robyn

1 May 2023

·

Stayed 2 nights

It had everything we wanted. Food options and amenities were great. And a nice stroll into the main street of Deadwood. The way some people had described it, I thought it was further our than it was. But then again, a 10-15 minute walk doesn't bother us.

10

Christina

22 Jul 2023

·

Stayed 3 nights

Great location

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Dining

Multiple on-site options, with many compliments for FLYT Steakhouse and the overall variety. Some guests found certain outlets overpriced or sub-par and missed having complimentary breakfast or quick morning choices.

Related guest reviews

10

Leslie

19 Sept 2023

·

Stayed 1 night

Room was very nice and clean. Great amenities. Wish there was quick breakfast options on-site besides Starbucks frozen burritos.

10

Bruce

29 Jul 2025

·

Stayed 1 night

Our hotel room was very nice and the food options are great here. We had all our meals {late lunch, evening appetizers and drinks at the bar, and breakfast) at the FLYT Steakhouse and nothing disappointed.

10

Roger

19 May 2025

·

Stayed 1 night

Great place to stay. Flyt restaurant was excellent too!

10

Jay

30 Sept 2024

·

Stayed 1 night

Is an amazing place to stay with super good restaurants inside!!

8

Joel

9 Apr 2025

·

Stayed 1 night

The room was nice. I was just disappointed when I found out there was no complementary breakfast.

6

Hillary

14 Jan 2024

·

Stayed 1 night

The rooms are nice and the beds are cozy but for some reason our room smelled like sewage or a backed up toilet. The hallways were very dirty, didn't look like they had vacuumed the carpet in weeks. Our car was also hit in the parking lot, hit and run, we came out to find it, and asked for them to review the cameras to see if the accident was caught. We live out of state and all that was done was they took my name and info and said "uhhh probably won't be able to see anything." We were parked right in front of the hotel, next to the Vallet. There were about 8 cameras there, there is no way something wouldn't have been seen. The food court there is handy but the employees in the food court were incredibly rude and awful to customers. We ordered chicken wraps, 4 of them, not a single one came with chicken. When we let them know the worker about lost his cool and tried to refuse to give us the correct meals. He then huffed and puffed and tossed some cold chicken into a bowl and grunting tossed it our way. That meal was over 60 bucks. None of us could eat it. The lettuce and ingredients were spoiled. DoubleTree advertises the food court as a perk or amenity for the hotel guest, if I were Hilton I think I'd have some quality control with their "amenities". Also the TV was unusable. It lagged and would shut off or log you out in the middle of a movie. The closed captions didn't work. You would literally scroll down 8 shows and maybe 5 minutes later it would select

6

David

6 Jul 2025

·

Stayed 5 nights

Outside patio area for smokers cushions full of ashes. Flyt restaurant food way overrated, tenderloin rubbery potato rubbery pasta rubbery….pool in other hotel have to walk through casino in bathing attire and wet.

10

Megan

4 Sept 2023

·

Stayed 1 night

We love Deadwood! The restaurant in the hotel was great!

10

Craig

25 Jul 2025

·

Stayed 1 night

Front desk agent was great, friendly. The hotel was in great condition, the room was the best we stayed in on our 8 day road trip. We liked the convenience of a really good restaurant in the hotel.

8

Jeffrey

21 May 2025

·

Stayed 7 nights

Casino and Hotel were nice. Dining I would rate as sub-par!

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AI-generated summary based on recent guest reviews

Month	Average price
January	US$96
February	US$91
March	US$104
April	US$89
May	US$116
June	US$213
July	US$207
August	US$261
September	US$209
October	US$187
November	US$107
December	US$94

Su	Mo	Tu	We	Th	Fr	Sa
				1 $134	2 $243	3 $299
4 $94	5 $129	6 $212	7	8 $274	9 $298	10 $192
11 $120	12 $129	13 $129	14 $129	15 $147	16 $232	17 $264
18 $94	19 $103	20 $112	21 $112	22 $120	23 $265	24 $294
25 $72	26 $72	27 $76	28 $76	29 $94	30	31 $362

DoubleTree by Hilton Deadwood at Cadillac Jack's

Prices for DoubleTree by Hilton Deadwood at Cadillac Jack's

Monthly average prices

About this property

Location

Room options

Room, 2 Queen Beds, Accessible (Roll-In Shower, Mobility & Hearing)

Junior Suite, 1 King Bed, Accessible (3X3 Shower, Mobility & Hearing)

Suite, 1 King Bed, Accessible (Roll-In Shower, Mobility & Hearing)

Room, 2 Queen Beds

Room, 1 King Bed

Junior Suite, 1 King Bed

Room, 1 King Bed, Accessible (3X3 Shower, Mobility & Hearing)

Suite, 1 King Bed

Room, 2 Queen Beds, Accessible (3X3 Shower, Mobility & Hearing)

Guest reviews of DoubleTree by Hilton Deadwood at Cadillac Jack's

Who stays here?

What guests think

Property policies

Check-in instructions

Good to know

Optional extras

FAQs about DoubleTree by Hilton Deadwood at Cadillac Jack's

Prices for upcoming dates

Su	Mo	Tu	We	Th	Fr	Sa
		1	2	3	4	5
6	7	8	9	10	11	12
13	14	15	16	17	18	19 $503
20 $184	21 $202	22 $239	23 $242	24 $230	25 $456	26 $486
27 $120	28 $129	29 $129	30 $129