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 cleanliness of the hotel and rooms, although some noted issues with specific areas.
Customer Service
Feedback on customer service was mixed; while some guests highlighted friendly and helpful staff, others reported poor service and unhelpful responses to issues.
Location
The hotel is well-located, with easy access to downtown Deadwood and various amenities, making it convenient for guests.
Amenities
Guests appreciated the variety of amenities, including the casino, pool, and on-site dining options, although some found the food quality inconsistent.
Reservation Issues
Several customers experienced problems with reservations and cancellations, leading to dissatisfaction with the hotel's policies.
KT
Kayla Tucker
4 days ago
5.0
Love to stay at double tree! Beds are comfortable and rooms are clean! So many things right onsite so you don't have to even leave if you don't want to. There is a parking fee but they give you free play to offset.
DM
Dillon Mckean
Jan 1, 2026
5.0
This place was great. Everything we needed was here. Of course we left but didn't need to. Excellent restaurants and bars. Staff was extremely friendly. Definitely going to stay here anytime we come to Deadwood.
SH
Shaun Hess
Dec 21, 2025
5.0
Great place for a Christmas party
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!
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.
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.