Availability details can be found on the Deadwood Connections website.

Book Direct through Deadwood Connections for maximum savings and service!

Property Description

Escape to Rolling Pines Overlook, a cozy and beautifully designed 3-bedroom + loft cabin tucked in the Terry Peak Subdivision near Deadwood, South Dakota. With room for up to 11 guests, double back decks overlooking the pines, a private hot tub, and a warm open-concept living area with gas fireplace, this mountain retreat is perfect for families, couples, and groups seeking peace and adventure in the Black Hills.

Your Perfect Black Hills Adventure Starts at Rolling Pines Overlook!

Nestled in the sought-after Terry Peak area, Rolling Pines Overlook blends modern comfort with rustic charm, offering guests the perfect balance of relaxation and outdoor adventure. Just minutes from skiing, hiking, and historic attractions, this 3-bedroom + loft home features an inviting open floor plan, stunning wood finishes, and breathtaking mountain views from every level.

Main Level Highlights:
■ Open-Concept Living Space: A bright and spacious main area featuring a fully equipped kitchen with microwave, dishwasher, and breakfast bar seating for 3. The dining table seats 4, and the living room boasts a cozy gas fireplace, vaulted wood ceilings, large picture windows, and plenty of comfortable seating with two couches and a recliner—perfect for relaxing after a day of exploring.
■ Entertainment & Relaxation: A large TV by the fireplace makes this the ultimate gathering space for movie nights or casual lounging.
■ Outdoor Living Space: Step through the glass doors off the dining area to a beautiful deck offering panoramic mountain views, a BBQ grill, and outdoor seating—ideal for morning coffee or evening dinners under the stars.

Bedrooms & Bathrooms on This Level
■ Bedroom 1- Queen bedroom
■ Full Bathroom with shower and tub
■ Washer & Dryer conveniently located near the entrance

Upper Level Highlights:
■ Open Loft Area: A cozy and airy space connecting the upper bedrooms, ideal for reading or relaxing in a quiet nook.

Bedrooms & Bathrooms on This Level:
■ Bedroom 2- Queen bedroom

Lower Level Fun & Relaxation:
■ Spacious Family Room: Features a comfortable sofa area, game table for four, wall-mounted TV, and a foosball table for friendly competition.
■ Outdoor Living Space: Glass doors open to a lower deck with a private hot tub—perfect for soaking under the stars and taking in the peaceful Black Hills views.

Bedrooms & Bathrooms on This Level:
■ Bedroom 3– Bunk bed (twin/full)
■ Bedroom 4 – Queen bed
■ Full bathroom with walk-in shower


Additional Features:
■ Central Air Conditioning
■ Private Hot tub on patio
■ Wi-Fi
■ Smart TV
■ Washer/Dryer
■ Gas BBQ Grill
■ Gas Fireplace

Guests have access to the entire property.

This is a beautiful area of the Black Hills. It is on the Terry Peak Ski Area - over 6000 ft elevation. The scenery is beautiful.
Nearby Attractions:
■ Snowmobile and ATV right from the cabin. Trail access at Recreational Springs Resort.
■ Terry Peak Ski Area: just a 1.0 miles from the cabin to the main ski lodge
■ Mickelson Trailhead, fishing, golfing, scenic Spearfish Canyon: 15 minutes away.
■ Lead: 10 minutes. Deadwood: 15 minutes. Sturgis: 25 minutes.
■ Mount Rushmore and Custer State Park: Just an hour’s drive.

There are taxis you can take to get around. If you drive, there is a large driveway that can accommodate 2-3 vehicles. *4-wheel drive is required for winter driving conditions*

Additional Information:
**This home does NOT allow pets
Access and Parking:  Driveway accommodates 3-4 vehicles.  1.0 miles of unpaved, hard-packed road.
**4-WHEEL DRIVE IS REQUIRED IN THE WINTER**

Deadwood Connections is a locally owned and managed vacation rental management company that puts the guest first. Our team is available to assist you at any point during your stay—from arrival to departure. You can reach out if you need local recommendations or have any issues during your visit to the Black Hills. We aim to make your stay with us comfortable and peaceful so you can spend your vacation making memories! While we won't meet you upon arrival, we're just a phone call away should you need anything!

Activities and Special Interests

This property provides access to the following activities and special interests:

Other Activities and Interests:
Rock Climbing, Snowboarding