Entire home

Rolling Pines Overlook – Cozy Comfort Meets Breathtaking Views!

Vacation home in Lead with a water park and a hot tub

Photo gallery for Rolling Pines Overlook – Cozy Comfort Meets Breathtaking Views!

Interior
Outdoor spa tub
Interior
Fridge, microwave, oven, stovetop
Fridge, microwave, oven, stovetop
Escape to the Terry Peak development in the Black Hills and unwind at this cabin, where modern comfort meets natural beauty. Enjoy a gas fireplace, flat-screen TVs, and large windows that fill the space with light. Take advantage of central A/C, internet access, a washer & dryer for convenience.

Reviews

9.4 out of 10
Exceptional

Entire home

4 bedrooms2 bathroomsSleeps 111734 sq ft

Popular amenities

  • Dryer
  • Washer
  • Barbecue grill
  • Fireplace
  • Outdoor Space

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About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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!

Property amenities

Pool/Spa

  • Hot tub

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Microwave
  • Oven
  • Refrigerator
  • Stovetop
  • Toaster

Bedrooms

  • 4 bedrooms
  • Bedsheets provided

Bathroom

  • 2 bathrooms
  • Bathtub
  • Hair dryer
  • Shower
  • Towels provided

Living spaces

  • Fireplace

Entertainment

  • TV with cable/satellite channels

Outdoor areas

  • Balcony
  • Gas grill

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoking not allowed

Things to do

  • Optional golf privileges
  • Water park
  • Casino nearby
  • Cycling nearby
  • Fishing nearby
  • Hiking/biking trails nearby
  • Horseback riding nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher

General

  • Unit size: 1,734 square feet

Similar properties

Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age: 24

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Rules

1. By signing this License Agreement, I certify that I have read, understand, and abide by all rules, policies, regulations of Deadwood Connections...

Pets

Pets not allowed

Children and extra beds

Children are welcome

Events

No events 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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated 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, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

Property is also known as

056ed068-eecd-4720-88d6-4619d7c3db04

About the neighborhood

Map
Lead, South Dakota

What's nearby

  • Terry Peak Ski Area - 6 min drive - 1.8 miles
  • Homestake Gold Mine - 13 min drive - 7.4 miles
  • Deer Mountain Ski Area - 17 min drive - 7.8 miles
  • George S. Mickelson Trail - 18 min drive - 7.6 miles
  • Spearfish Canyon Nature Area - 29 min drive - 13.1 miles

Restaurants

  • ‪Boars Nest - ‬9 min drive
  • ‪Latchstring Restaurant - ‬26 min drive
  • ‪Cheyenne Crossing - ‬18 min drive
  • ‪Dakota Shivers Brewery - ‬10 min drive
  • ‪Lewies Saloon & Eatery - ‬9 min drive

Frequently asked questions

Is Rolling Pines Overlook – Cozy Comfort Meets Breathtaking Views! pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Rolling Pines Overlook – Cozy Comfort Meets Breathtaking Views!?

Check-in begins at 4:00 PM.

What time is check-out at Rolling Pines Overlook – Cozy Comfort Meets Breathtaking Views!?

Check-out is at 10:00 AM.

Where is Rolling Pines Overlook – Cozy Comfort Meets Breathtaking Views! located?

Situated in Lead, this vacation home is 2.5 mi (3.9 km) from Terry Peak Ski Area and within 6 mi (10 km) of Living Map Theater and Historic Homestake Opera House. Black Hills Mining Museum and Homestake Gold Mine are also within 6 mi (10 km).

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Rolling Pines Overlook – Cozy Comfort Meets Breathtaking Views! Reviews

Reviews

9.4

Exceptional

Rating 10 - Excellent. 12 out of 18 reviews
Rating 8 - Good. 5 out of 18 reviews
Rating 6 - Okay. 1 out of 18 reviews
Rating 4 - Poor. 0 out of 18 reviews
Rating 2 - Terrible. 0 out of 18 reviews

8.4/10

Cleanliness

Reviews

10/10 Excellent

David W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent views near Terry Peak.

The cabin was great for our group. We enjoyed the close proximity to Lead, Deadwood, and Terry Peak. No issues, would definitely stay there again.
Stayed 3 nights in Mar 2025

10/10 Excellent

Marques A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing location close to terry peak

Very nice place to stay. Great view!
Stayed 4 nights in Jun 2024

10/10 Excellent

Krista B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Spectacular view and cozy lodging

We loved the view out the giant back windows as well as from the deck and hot tub. It was extremely relaxing and supplied everything we needed to have a great family vacation. We would happily stay again.
Stayed 4 nights in Jun 2024

10/10 Excellent

Chris J.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay and great views

We had a wonderful 4 days in the Black Hills. This property was clean, had great views, peace and quiet, beautiful starry nights and was close to town. It was also very spacious and would accommodate a large family. Hot tub was awesome after a long day of hiking. Thanks for the memories!
Stayed 4 nights in Sep 2024

10/10 Excellent

Brenda J.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Relaxing Vaca

Beautiful views, very quiet & relaxing. Communication with owners was easy & they had everything we needed.
Stayed 3 nights in Aug 2023

10/10 Excellent

Janet R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful

Would stay agian for sure
Stayed 3 nights in Apr 2023

8/10 Good

Erin F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful Property!

Very nice property! The view is absolutely stunning! Worked perfect for our family of 6 and could have fit even more people!
Stayed 4 nights in Jun 2023

10/10 Excellent

Brandi R., United States

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful views!

The cabin had beautiful views from the large windows. The kitchen had everything we needed, bedrooms had extra blankets, and the property was clean. The hot tub was also well maintained and a nice extra. Check-in and check-out was easy and the property manager responded quickly during our stay. We would bring our family back!
Stayed 7 nights in Mar 2023

10/10 Excellent

Jayne K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Stay in the Black Hills

Wonderful view of the hills and a fun location. House was great for our family with lots of space for everyone. The only thing I would suggest is having a place to put your clothes. There were no dressers or luggage holders in the bedrooms. Overall, wonderful stay in a great vacation area!
Stayed 4 nights in Jun 2023

10/10 Excellent

Carla W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful Inside and Out

Beautiful cabin!! Very clean, comfortable and amazing view. Easy, convenient check in and out. Loved the keyless entry and not having to worry about keeping track of a key!! Had everything we needed to cook meals - well stocked with Cookware and utensils. Any questions were answered quickly. Enjoyed our stay!!
Stayed 3 nights in Jul 2023

10/10 Excellent

Wade R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent location & views!

Excellent location, you could ski home if you need to 😉 The views were fantastic! It wasn’t the best sleeping, pillows and comforters were thin. The kitchen wasn’t as well stocked as others we’ve stayed in in this neighborhood. The hot tub is smaller but ok for 3 kids. If you are sensitive to overwhelming laundry detergent, bring your own sheets and blankets. But overall a great home for a family of 5.
Stayed 4 nights in Jan 2023

8/10 Good

Katy K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fantastic View!

PROS: This cabin was a good fit for our group and offered enough privacy with sleeping on 3 levels. Loved the exterior and the rustic charm of this cabin. The view was FABULOUS (pictures don't do it justice) from the deck and patio where the hot tub is. CONS: The cabin's kitchen had all the items we needed, but are lower quality items. The beds were okay, but Id recommend bringing your own sheets if you don't like polyester sheets/bedding. The parking here is somewhat limited if you're bringing multiple trucks and trailers for side-by-side riding, but we made it work with 3 trucks and 2 trailers. Some maintenance needed on the cabin, but we notified the property management company and I'm sure they will get them fixed as they were very communicative.
Stayed 4 nights in Jul 2023

6/10 Okay

Sandra Y.

Liked: Check-in, communication, location, listing accuracy
Disliked: Cleanliness

A Mouse With No Name

We stayed 8/28-9/1/24. We were concerned about parking, as we had 2 trucks with 25' trailers, but found we could park both vehicles there. The lodge was nice & had a beautiful view towards Wyoming/West. Sunsets were absolutely stunning. Once settled, we were going to throw some pizzas in the oven and quickly discovered the dishes weren't very clean and the oven had not been cleaned. We opened windows to let the smoke out from previous burnt items on the bottom (also no pizza cutter). We sat on the deck, however there was no table to set anything on (we used our coolers as a substitute). A couch cushion was slipping out/off and when we went to put it back, we found a pacifier, several goldfish crackers, candy wrappers, popcorn, etc. Ironically, as we were talking about the "grossness under the cushions", we saw a mouse scurry into the kitchen. We looked for traps under the kitchen sink (and found mouse droppings). I wrote to the owner; she responded very quickly that she would get maintenance up there immediately to set traps. The following evening, we saw another mouse in the kitchen and one in the basement bedroom. Vents going downstairs were filthy dirty (and going down the steps, you could see under the couches had not been cleaned for a while). This is a cute place, but the cleanliness left us disappointed and frankly, grossed out. I did advise the owner directly and she apologized for the mice. Needs a DEEP CLEANING!!!
Stayed 4 nights in Aug 2024

10/10 Excellent

Alison D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful location

Cabin was very cute and the views are amazing! Kids watched a deer and her fawn wander through the trees while they were in the hot tub. Space was great for our family of 5 and my in-laws. Very convenient to Deadwood and Leeds and Spearfish Canyon.
Stayed 6 nights in Jul 2024

8/10 Good

Mindy R.

Liked: Check-in, communication, location, listing accuracy

Vacation

Pots and pans still dirty in cupboard when we went to use them to cook. Hot tub had err code and would go past a certain degree. Dining room chair broken/wouldn’t lock,couldn’t use. Dirty towels in drawer to wipe off counters
Stayed 4 nights in Jul 2024

8/10 Good

Jennifer R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful views, cozy cabin

We stayed here the first week in June. The views are amazing, the cabin is cozy. The location was perfect for us to explore Deadwood and Spearfish Canyon.
Stayed 2 nights in Jun 2024