Outlaw Homestead-Deadwood, SD vacation rental

05/25/2026

04/15/2026

Great news!! And he’s opening a bar in the new Landmark Casino in Deadwood.

🎶 Headliner Announcement… and it’s time to get 𝙒𝙚𝙨𝙩𝙚𝙧𝙣 🎶

The boots are coming out, the volume’s going UP & we’re going all in on fiddle-fueled fire with Ian Munsick on Friday, September 18th for the 36th Annual Deadwood Jam on the Sue Lundberg Memorial Stage at Outlaw Square!

With over a billion streams, fan-favorite hits like “Long Live Cowgirls” and “Horses Are Faster”, with a sound that hits home out here, and he’s no stranger to HISTORIC DEADWOOD…we already know you’re gonna show up loud!

Best part? It’s a FREE weekend of live music in the Wild West. So mark your calendars for September 18 & 19, grab your crew, and come jam where the cords fly, drinks are cold, and the outlaws, hippies, wanderers, and pickers are in it for the 𝙡𝙤𝙣𝙜 𝙝𝙖𝙪𝙡.

05/20/2025

Another country chart-topping act! We love his rock hits and country hits. Get your tickets and book your stay.

https://www.deadwoodconnections.com/properties/outlaw-homestead/

Concert Announcement 🎸 Aaron Lewis and the Stateliners are bringing their raw and reflective Country sound to the Deadwood Mountain Grand stage in HISTORIC DEADWOOD, SD on Sunday, November 16th at 8:00pm.

With chart-topping albums like Town Line, Sinner, and Frayed at Both Ends, plus his latest release The Hill (2024), Lewis continues to connect through powerful, personal songwriting.

Tickets on sale Friday, May 23 at 10AM! Get yours here → https://bit.ly/DMGALewis25 or by calling The Spotlight Box Office 605.559.1188.

05/19/2025

Exciting couple weeks at Outlaw Homestead. We’ve made some upgrades with new flooring, new shower, fresh paint, all new comforters and bedding, and lots more. We are exciting to welcome our next guests this weekend. Check out the calendar and book your next Black Hills getaway.

https://www.deadwoodconnections.com/properties/outlaw-homestead/

04/29/2025

We know you've been patiently waiting and we're ready to oblige. Festival band announcements start on April 28th at 10:00 am and will continue every Monday, Wednesday and Friday until they've all been announced!

These talented artists hail from all over including Colorado, Minnesota, Oklahoma, California and of course right here in the Black Hills.

Who do you want to see at the inaugural Presents DWD Blues Festival?

Check back here Monday and thereafter for all the details . . . and make sure you share them for us as well.

🎫: https://deadwoodbluesfest.com/get-tickets/

10/16/2024

We have an opening for this weekend!! Book today to enjoy the Wild West Song Writers Festival.

https://www.deadwoodconnections.com/properties/outlaw-homestead/

10/10/2024

⭐️⭐️⭐️⭐️⭐️ click for pictures, video, and this 5-Review.

Book your fall stay today.

★★★★★ "This is such an amazing place to stay. Our family came out to Deadwood, SD and we’re lucky enough to stay here. Location is everything! The house is absolutely beautiful. The neighbors are so welcoming! Sun room in the front and adorable back yard with lights and a hammock! In add...

10/07/2024

🎶⛰️ Wild West Songwriters Festival
📆 October 17-19
🏡 https://www.deadwoodconnections.com/properties/outlaw-homestead

Three cheers for live music, the Black Hills, and our charming little casino town of HISTORIC DEADWOOD! Every year, the Wild West Songwriters Festival takes center stage as a must-see destination event. 🎶

Can you believe it? We’re celebrating 13 fantastic years of WWSF! We’ve grown, adapted, and embraced the ebb and flow of live music, but one thing stays the same: our love for original tunes.

Last year, we added a spark to our already successful event, with the Regional Songwriter’s Competition, bringing in amazing talent from the Black Hills and beyond. The submissions blew us away, and we can’t wait to keep growing this year after year!

No matter where you’re from or what you play, we’re here to celebrate you! Join us to share melodies, sing along, and soak in the soul of every song you create. We will see you this upcoming October 17th - 19th for the 13th Annual Wild West Songwriters Festival.

🤠 We are fine tuning the schedule & will be updating y’all so soon!

09/23/2024

We are fortunate to have you DMG!! Keep the great concerts coming!

09/13/2024

Finally it’s being announced! Book your stay and mark your calendar-oh and call your friends, “we’re going back to Deadwood!!”

https://www.deadwoodconnections.com/properties/outlaw-homestead