Experience the refreshing, modern style and genuine service of the DoubleTree by Hilton Deadwood at Cadillac Jack's hotel and casino, located steps away from historic Main Street in the heart of Black Hills' most popular attractions.
We’ll greet you at check-in with a warm DoubleTree chocolate chip cookie. At our tranquil retreat, you’ll feel at home in a stylish guest room with a microwave and mini fridge. Upgrade to a suite for more space and a separate living area. Some suites have wet bars, or sofa beds, ideal for families.
Enjoy a diverse range of appetizers, entrees, and desserts at our restaurant, FLYT Steakhouse, open daily for breakfast, lunch, and dinner. Enjoy Starbuck’s® coffee at the coffee shop, Mexican food at Guadalajara’s restaurant, or deli-style subs, sandwiches, and wraps at Earl of Sandwich. Visit our casino bar for beer, wine, and mixed drinks. Grab a snack, sandwich, and other fresh selections at Made Market.
Many customers praised the hotel for its clean rooms and overall cleanliness, although some noted issues with specific areas.
Customer Service
Feedback on customer service was mixed; while some staff were described as friendly and helpful, others received complaints for rudeness and lack of assistance.
Room Quality
Rooms were generally well-received for their comfort and amenities, but some guests reported issues with noise and views.
Location
The hotel’s location was frequently highlighted as a positive aspect, being conveniently situated near downtown Deadwood and local attractions.
Dining Options
Dining experiences varied; while some guests enjoyed the food, others found it average or had issues with service in the restaurants.
GS
Gabrielle Schneider
Nov 10, 2025
5.0
Awesome experience for first time staying in Deadwood. So much to see and do within walking distance. Hotel located in a gambling resort but rooms are peaceful and clean. Pool and hot tub were amazing! Coffee from Starbucks short walk through casino and lots of on-site dining options. Will be back!
BH
Beth Haynes
Sep 29, 2025
5.0
Loved this place! So clean and so much to offer!
DN
Dani La Noire
Sep 27, 2025
1.0
Horrible! When we booked it said we could cancel if needed prior to our trip. When our route changed, I tried to cancel in the morning as soon as I knew which was 5 days prior to our stay.
I went thru booking.com as required when I made the reservation. I was told the message was sent but never heard back. I followed up for two days with multiple messages and finally just received a one word response: declined. Nothing else. We stay in Double tree hotels all the time and in fact are staying at two during this trip. We’ve never had such bad service and inflexibility. It’s not like it’s high season and we booked for a week. We were staying one night and mid week at that!!!0
Shame on you Deadwood for not being more respectful and courteous. At the very least a more polite response with proper grammar and punctuation.
TJ
Tina Casey Jones
Sep 25, 2025
5.0
Stopped by just for gaming. I wasn't having a good night so went outside to the smoking area (casino is non-smoking). A security guard came outside, asked if I'd been playing a specific machine (I had) and gave me a $20 bill I'd inadvertently left behind. Had tracked me down with security cams! I was so impressed by their diligence that I immediately went inside and spent $100+ in the gift shop (wasn't winning anyway LOL)
Frequently Asked Questions About DoubleTree by Hilton Deadwood at Cadillac Jack's
What are the check-in and check-out times at DoubleTree by Hilton Deadwood at Cadillac Jack's?
Check-in is from 4:00 PM and check-out is at 11:00 AM.
Does DoubleTree by Hilton Deadwood at Cadillac Jack's provide parking facilities?
Yes, both self-parking and valet parking are available for guests.
Are pets allowed at this hotel?
Yes, both cats and dogs are welcome at the hotel.
Is breakfast available at DoubleTree by Hilton Deadwood at Cadillac Jack's?
Yes, breakfast is available at the hotel.
What dining options are available on site?
The hotel features 5 restaurants including FLYT Steakhouse, Guadalajara's Mexican Restaurant, Earl of Sandwich, and a casino bar, plus a coffee shop offering Starbucks®.
Is the hotel accessible for guests with mobility needs?
Yes, the hotel offers accessible parking, an accessible elevator, and is mobility accessible.
Are there any recreational amenities available at the hotel?
Yes, guests can use the fitness center for free and enjoy the on-site casino and bar.
Does the hotel offer free WiFi and digital conveniences for guests?
Yes, free WiFi is available in public areas and there are public internet terminals. Digital guest room keys are also provided.
What nearby attractions can guests visit during their stay?
Guests can explore historic Main Street, visit Deadwood Inn, enjoy Badlands National Park, or experience Custer State Park, all close to the hotel.
Are there convenient dining and beverage options near the hotel?
Yes, nearby dining includes Starbucks for coffee, Guadalajara's Mexican Restaurant, Earl of Sandwich for sandwiches, and bars like Old Style Saloon No. 10 and Springhill Suites Lobby Bar.