Rolling Pines Overlook – Cozy Comfort Meets Breathtaking Views! Vacation Rental With Hot Tub

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!

Additional house rules
1. By signing this License Agreement, I certify that I have read, understand, and abide by all rules, policies, regulations of Deadwood Connections and the property referenced in this agreement. I agree to vacate Property upon demand for any violation of any of these rules, policies and regulations. 2. The guests security deposit would cover but not limited to the following: broken or stolen items, unnecessary cleaning, excessive or unbagged garbage, damage to hot tub, visible stains or damages to carpet and furniture. In addition, Agent may deduct from the security deposit the amount of any unpaid long distance or per call telephone charges (this includes 411 calls) and cable or satellite television charges that are not included with the property. No charges will be run through as long as no problems are found. 3. Guest agrees to indemnify and hold harmless Agent and the owner from and against any liability for personal injury or property damage sustained by any person (including Renter`s guests or visitors) as a result of any cause, unless caused by the negligent or willful act of Agent or owner. Renter agrees that Agent, the owner, or their representative may enter the Property during reasonable hours to inspect the Property, to make such repairs, alterations or improvements thereto as agent or owner may deem appropriate, or to show the Property to prospective purchasers or Renters. Furthermore, Agent reserves the right to enter the Property at any time to inspect for suspected Unlawful Parties or pets, which are strictly prohibited. Renter shall not assign this agreement or sublet the Property in whole or part without written permission of Agent. 4. Please note the Maximum Occupancy of the property. Occupancy cannot exceed the Maximum. 5. Deadwood Connections will only rent to persons 25 years of age or older. Deadwood Connections reserves the right to check ID`s to verify age. 6. Check-in time will be 4:00pm. Check-out time for all units is 10:00am. Renters that have not checked out by 10:00am will be charged $50.00 and will still be expected to vacate the property immediately. Renter agrees not to park on the Property or occupy any portion of the property prior to their check-in time or after the check-out time. Deadwood Connections reserves the right to delay check-in time for cleaning & repair services. 7. Some vacation units will be provided with a set of keys. Renter agrees to pay $5.00 for each lost key. Lockout service is available for a fee of $25.00 until 10:00pm and $40.00 after 10:00pm. Fee is payable directly to Agent upon service. 8. Deadwood Connections will make every effort to ensure that Renter`s stay is safe, comfortable, and enjoyable. No refunds or discounts will be made for inclement weather, mechanical breakdowns, or other nuisances beyond our control. Examples of these which DO NOT warrant any refund, discount, or another property, etc. include but are not limited to: breakdown of air conditioners, TV`s, VCR`s, Hot Tubs, electronics or appliances, construction in the area, disruption of utility services, problems which have not yet been reported to agent, bad weather, or noisy neighbors. Renter agrees to report any and all problems to Deadwood Connections immediately. Deadwood Connections agrees to make every effort to resolve the problem as quickly as possible. 9. Renter agrees to: (i)leave the Property in the same condition as it was at check in, (ii) be financially responsible for unwarranted or unneeded service calls and service calls caused by Renters misuse of the property, (iii)report any and all problems to Deadwood Connections immediately, (iv)not to enter owner`s private storage spaces, (v) to abide by occupancy limits of the Property at all times, (vi) not move furniture in the cabin. Upon Departure, Renter agrees to (i)wash and put away dishes, (ii)strip sheets off beds, (iii)remove garbage to garbage receptacles outside. Renter agrees to pay any charges associated with failure to complete the above. The Renter, being the person whose name the contract is in, will be the sole contact person in regards to this agreement and the tenancy. Such Renter is responsible for all guests/visitors` adherence to this Agreement. 10. Renter agrees to abide by all other ordinances, rules, and regulations that may be imposed by parties other than Deadwood Connections, such as local governments, homeowner association, etc. 11. Most properties do not allow pets on the premises. Violation of a no pet property will result in immediate eviction without refund, will result in a $500.00 no pet fee and will be subject to all cleaning costs, any losses incurred by Property Owner and/or Agent due to this violation. There is a non-refundable pet fee of $75.00 per pet in the homes that allow them. It is Renters responsibility to let AGENT aware of the number of pets they will be bringing. 12. NO SMOKING. There is no smoking in any of the homes. When in violation of the smoking policy, Renter agrees to pay all costs associated with cleaning to remove smoke odors, any losses incurred by Property Owner and/or Agent, and a $500.00 handling fee. Please dispose of cigarette butts properly outside or a $50.00 fee will be charged