Cottage vacation rentals in Pennington County

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Top-rated cottage rentals in Pennington County

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Guest favorite

Cottage in Rapid City

4.92 out of 5 average rating, 13 reviews

Remodeled Home In The Woods, Just Past City Limits

Come enjoy the peace and quiet of this remodeled home in a canyon neighborhood setting conveniently located minutes from various trailheads, multiple lakes, and endless scenic roadways. Or just enjoy a peaceful walk or bike ride from your front door down the scenic Cleghorn Canyon. This location is also just a couple of miles from Rapid City's downtown including parks, restaurants, breweries, and shopping. This home is fully furnished with everything you should need including A/C and free Wi-Fi.

Jul 21 – 28

G$65,840 GYD per night

Guest favorite

Cottage in Deadwood

4.99 out of 5 average rating, 154 reviews

Best little house in Deadwood

Welcome to Dogwood! This great in-town cottage offers one bedroom with king bed, an extra large living-dining area and well stocked kitchen, but no dishwasher. The bathroom has a large tile shower with glass doors. You can relax with a movie on our 50" TV with cable and Netflix. A washer and dryer are provided. We have private off street parking for two vehicles directly in front of the house. The large covered front porch is great for sitting outside in the shade on a summer day.

Apr 2 – 9

G$33,074 GYD per night

Guest favorite

Cottage in Custer

4.93 out of 5 average rating, 44 reviews

Cozy Retreat Steps from Downtown Custer

Experience a rejuvenating retreat to the captivating Black Hills. Our place is conveniently located a short walk from the lively downtown main street. Indulge in the remarkable shops and eateries that Custer has to offer. After a long day of exploring the picturesque Black Hills, unwind and recharge in the comfort of our cozy memory foam queen beds, ensuring a peaceful night's sleep. Start your day off right with a freshly brewed cup of coffee to energize you for your next adventure.

Sep 9 – 16

G$55,414 GYD per night

Guest favorite

Cottage in Hermosa

4.85 out of 5 average rating, 26 reviews

Black Hills Guest Ranch With View of Mt Rushmore

Experience SD country in a new 3,000 square foot home on 22 acres close to Mt Rushmore & Custer State Park. Enjoy a quiet get away with your family/friends in a peaceful setting with amazing views of the black hills including Mount Rushmore lit up in the distance at night. Watch horses, deer, and even fox roam the countryside. Step out onto the deck at dusk and watch the sunset light up the Rushmore Mountain Range. 15 mins south of Rapid City. Amenities of a smaller town 5 mins away.

Apr 8 – 15

G$64,503 GYD per night

Guest favorite

Cottage in Wasta

4.9 out of 5 average rating, 437 reviews

The Rock and Block house

This is a Great Little House with Rustic yet Modern Charm, Beautiful View of the Cheyenne River Breaks. Two very comfy king sized beds. Wasta is a "very" small town, a gas station, a fabulous military museum and a bar. You can take in the Badlands on your way, you might drop down through Interior, S.D. and drive through the Badlands then come out just south of Wall. We are about 20 miles from the Badlands, 40 miles from Rapid City, and Beautiful Black Hills. Thank You, Billie

Oct 11 – 18

G$21,564 GYD per night

Superhost

Cottage in Custer

4.5 out of 5 average rating, 6 reviews

2 Benches Cottage in Custer by Mount Rushmore

Relax with the family at this peaceful place to stay near downtown Custer, SD. Just minutes to Custer State Park, Mount Rushmore, Crazy Horse, Wind Cave, Jewel Cave, Mickelson Trail. This updated, fresh and clean vacation home sleeps 8 with 3 bedrooms and a sofa bed, 2.5 bathrooms. Propane BBQ grill and outdoor seating on the home's large deck allows you to rest and relax with the peaceful pines of the Black Hills National Forest. Air conditioning makes the home cool.

Apr 1 – 8

G$106,093 GYD per night

Cottage in Nemo

4.83 out of 5 average rating, 6 reviews

Little Elk Cottage in Beautiful Vanocker Canyon

At Little Elk Cottage, we offer you a memorable place to stay during your visit to the Black Hills! We are conveniently located in Vanocker Canyon--30 minutes from Rapid City or Deadwood. We are approximately 3 miles north of Nemo. The drive from our cottage to Sturgis thru this spectacular canyon road should not be missed! We still have availability after the Sturgis Rally. A small creek meanders thru the 5 acres of land where our cottage sits--book now!

Jul 16 – 23

G$58,617 GYD per night

Guest favorite

Cottage in Spearfish

4.95 out of 5 average rating, 132 reviews

Cottage #3 - Spearfish Orchard Creek Cottages

Welcome to Spearfish Cottages - we are happy to host you! Cottage #3 is a 1 bedroom, 1 bath cozy cabin. We have a shared hot tub close by and is walking distance to the creek and walking paths. One hour from Mt Rushmore and Rapid City Airport. Three blocks from BHSU! Flat screen Tv's with HULU LIVE, Disney+, and ESPN+. Free WIFI. *WE ALLOW UP TO TWO DOGS ONLY. PET FEE APPLICABLE. NO CATS. PLEASE MESSAGE ME FOR DETAILS.* *No smoking allowed on property*

Dec 11 – 18

G$14,448 GYD per night

Guest favorite

Cottage in Rapid City

4.92 out of 5 average rating, 36 reviews

Cottages on Canyon Lake 30 Minutes to Mt Rushmore

Fully Equipped Two Bedroom Vacation home located by beautiful Canyon Lake in Rapid City just thirty minutes from Mt Rushmore. Perfectly located for access to all the Black Hills area attractions. Terrific paved bike and walk path winding around Canyon Lake and down Rapid Creek. Great fishing in Canyon Lake and Rapid Creek. Highly Rated Lake Park Campground and Cottages has been supplying vacation lodges to Black Hills visitors for 29 years.

Nov 15 – 22

G$42,886 GYD per night

Guest favorite

Cottage in Sturgis

5.0 out of 5 average rating, 38 reviews

Level 3Br 2Ba Home 2 Blk from Sturgis Main St Cute

Your family will be close to everything when you stay at this centrally-located place. Minutes from the Interstate 90 and 2 blocks from Historic Sturgis Main St. It is 20 minutes to the mouth of Spearfish Canyon and 15 minutes from Deadwood. Relax on the back patio with firepit and large grill. This home is small but very comfy and has a welcoming outdoor space and a perfect front porch for sitting. One level with all the amenities you need.

Aug 17 – 24

G$41,109 GYD per night

Guest favorite

Cottage in Rapid City

5.0 out of 5 average rating, 106 reviews

The Cottage on Saint Cloud

This fully renovated 1917 Cottage is nestled in the quaint Historic District of Rapid City, SD. If hiking/biking is on your vacation agenda, you're in luck. Just 0.5 miles from the front door you will find the Skyline Wilderness Area with a network of trails spanning 150 acres in the heart of the city. The Cottage is also an easy walk to downtown shops, restaurants, pubs and delicious coffee. Welcome to the memories!

Dec 3 – 10

G$78,012 GYD per night

Guest favorite

Cottage in Rapid City

4.9 out of 5 average rating, 30 reviews

Flyfisher’s Oasis on Rapid Creek

Come enjoy a perfect getaway in the heart of the Black Hills. Located minutes from Rapid City, Mount Rushmore, Custer State Park, Sturgis & OHV/snow mobile trails. This property sits on a prime stretch of Rapid Creek. Enjoy amazing trout fishing opportunities and abundant wildlife watching. Whether you’re looking for relaxation, adventure, hunting/fishing, motorcycle riding, or sightseeing, this is the place for you!

Oct 7 – 14

G$84,024 GYD per night