Entire home
Rolling Pines Overlook – Cozy Comfort Meets Breathtaking Views!
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Reviews
9.4 out of 10
Exceptional
4 bedrooms2 bathroomsSleeps 11161.1 sq m
Popular amenities
Rooms & beds
4 bedrooms (sleeps 11)
Bedroom 1
1 Queen Bed
Bedroom 2
1 Double Bed and 1 Single Bed
Bedroom 3
1 Queen Bed
Bedroom 4
1 Queen Bed
2 bathrooms
Bathroom 1
Bathtub · Toilet · Shower only
Bathroom 2
Bathtub · Toilet · Shower only
Spaces
Kitchen
Balcony
Dining area
About this property
Rolling Pines Overlook – Cozy Comfort Meets Breathtaking Views!
Summary:
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.
The Space:
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
Guest Access:
Guests have access to the entire property.
The Neighborhood:
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.
Getting Around:
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*
Other Things to Note:
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**
Interaction with Guests:
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!
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.
The Space:
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
Guest Access:
Guests have access to the entire property.
The Neighborhood:
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.
Getting Around:
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*
Other Things to Note:
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**
Interaction with Guests:
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!
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9.4 out of 10, Exceptional, (91 reviews)
House Rules
Check in after 4:00 PM
Minimum age to rent: 24
Check out before 10:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
No pets allowed
Smoking
Smoking is not permitted
Important information
You need to know
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
About the area
Lead
Located in Lead, this holiday home is near a water park. The area's natural beauty can be seen at Black Hills National Forest and George S. Mickelson Trail, while Living Map Theater and Historic Homestake Opera House are cultural highlights. Homestake Gold Mine and Matthews Opera House & Arts Center are also worth visiting. Discover the area's water adventures with nearby fishing, or enjoy the great outdoors with cycling and horse riding.

Lead, SD
What's nearby
- Terry Peak Ski Area - 6 min drive - 2.8 km
- Living Map Theater - 10 min drive - 10.8 km
- Historic Homestake Opera House - 10 min drive - 11.5 km
- Homestake Gold Mine - 10 min drive - 11.9 km
- George S. Mickelson Trail - 15 min drive - 12.2 km
Restaurants
- Latchstring Restaurant - 26 min drive
- Lewies Saloon & Eatery - 9 min drive
- Cheyenne Crossing - 18 min drive
- Dakota Shivers Brewery - 10 min drive
- Boars Nest - 9 min drive
Frequently asked questions
Reviews
9.4
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window8.6/10
Cleanliness
10/10
Check-in
10/10
Communication
9.6/10
Location
9.8/10
Listing accuracy
Reviews
Verified
14 October 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 4 nights in Oct 2025
Verified
8/10 Good
jerry s.
14 August 2025
Liked: Check-in, communication, location, listing accuracy
jerry s.
Stayed 6 nights in Aug 2025
Verified
10/10 Excellent
Eric E.
24 July 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Eric E.
Stayed 3 nights in Jul 2025
Verified
10/10 Excellent
David W.
22 March 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent views near Terry Peak.
David W.
Stayed 3 nights in Mar 2025
Verified
10/10 Excellent
Marques A.
26 June 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing location close to terry peak
Marques A.
Stayed 4 nights in Jun 2024
Verified
10/10 Excellent
Krista B.
1 July 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Spectacular view and cozy lodging
Krista B.
Stayed 4 nights in Jun 2024
Verified
8/10 Good
Jennifer R.
26 June 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful views, cozy cabin
Jennifer R.
Stayed 2 nights in Jun 2024
Verified
10/10 Excellent
Brenda J.
29 August 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Relaxing Vaca
Brenda J.
Stayed 3 nights in Aug 2023
Verified
10/10 Excellent
Janet R.
9 April 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful
Janet R.
Stayed 3 nights in Apr 2023
Verified
8/10 Good
Erin F.
4 July 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful Property!
Erin F.
Stayed 4 nights in Jun 2023
Verified
10/10 Excellent
Chris J.
30 September 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay and great views
Chris J.
Stayed 4 nights in Sep 2024
Verified
10/10 Excellent
Alison D.
1 August 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful location
Alison D.
Stayed 6 nights in Jul 2024
Verified
10/10 Excellent
Brandi R.
12 April 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful views!
Brandi R.
Stayed 7 nights in Mar 2023
Verified
10/10 Excellent
Jayne K.
24 June 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great Stay in the Black Hills
Jayne K.
Stayed 4 nights in Jun 2023
Verified
10/10 Excellent
Carla W.
20 July 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful Inside and Out
Carla W.
Stayed 3 nights in Jul 2023
Verified
10/10 Excellent
Wade R.
1 February 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent location & views!
Wade R.
Stayed 4 nights in Jan 2023
Verified
8/10 Good
Mindy R.
19 July 2024
Liked: Check-in, communication, location, listing accuracy
Vacation
Mindy R.
Stayed 4 nights in Jul 2024
Verified
8/10 Good
Katy K.
24 July 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Fantastic View!
Katy K.
Stayed 4 nights in Jul 2023
Verified
6/10 Okay
Sandra Y.
4 September 2024
Liked: Check-in, communication, location, listing accuracy
Disliked: Cleanliness
A Mouse With No Name
Sandra Y.
Stayed 4 nights in Aug 2024
About the host
Hosted by Jonna Kandolin
Languages:
English
Premier Host
They consistently provide great experiences for their guests
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