Cottage vacation rentals in Pennington County

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Top-rated cottage rentals in Pennington County

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Guest favorite
A single-story green house sits nestled among greenery, featuring a welcoming front porch with three light-colored chairs and a small table. Two windows allow natural light, and a stone wall leads to a gently sloped yard.
Cottage in Rapid City
4.95 out of 5 average rating, 22 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.

Cottage in Spearfish
4.92 out of 5 average rating, 53 reviews

Cozy Spearfish Cottage < 1 Mi to Hiking Trail

Plan the perfect Black Hills escape at this updated cottage in Spearfish. Whether you are in search of adventure or reprieve from city life, you will find it amongst the natural beauty surrounding this 2-bedroom, 1-bathroom vacation rental. Watch the sunrise from Lookout Mountain Trail — less than a mile away! Take scenic Spearfish Canyon to Bridal Veil Falls for breathtaking views or get a taste of the Wild West in Historic Deadwood. Dine al fresco on the patio to end your unforgettable day.

Guest favorite
Cottage in Custer
4.86 out of 5 average rating, 42 reviews

Red Roof*Sauna*HotTub*Pet Friendly

Hot tub and Sauna and Pet friendly in Custer, SD! Custom wood cottage with 2 bathrooms, set up for families. Only 8 min to Custer State Park, 20 min to Mount Rushmore, 16 min to Jewel Cave, 15 min to Crazy Horse Memorial, and 21 min to Wind Cave! Full kitchen, BBQ grill, air conditioning, bunk room, and a fully fenced yard for privacy. Walking distance to downtown restaurants, shops, and museums. Free off-street parking and additional parking are available for large vehicles and trailers.

Guest favorite
A leather couch is positioned in front of two windows, allowing natural light to fill the room. Soft grey curtains frame the windows, while a patterned area rug adds color to the floor. A floor lamp stands nearby, providing additional lighting.
Cottage in Spearfish
4.93 out of 5 average rating, 219 reviews

Cottage #1 - Spearfish Orchard Creek Cottages

Welcome to Spearfish Cottages - we are happy to host you! Cottage #1 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. THERE IS A ONE-TIME PET FEE OF $30. NO CATS. PLEASE MESSAGE ME FOR DETAILS.* *No smoking allowed on property*

Guest favorite
A living area is presented with a comfortable sectional sofa and a sleek ceiling fan. A wall-mounted television is positioned opposite a dining set for two. Natural light filters through sheer curtains, enhancing the relaxed atmosphere of the space.
Cottage in Spearfish
4.94 out of 5 average rating, 180 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 TVs with HULU LIVE, Disney+, and ESPN+. Free WIFI. *WE ALLOW UP TO TWO DOGS ONLY. WITH A ONE TIME PET FEE OF $30. NO CATS. PLEASE MESSAGE ME FOR DETAILS.* *No smoking allowed on property*

Guest favorite
A charming vacation home is set within a spacious green lawn, surrounded by trees. The exterior features a mix of warm wood tones and a dark shingled roof. A picnic table and chairs are placed nearby, creating an inviting outdoor gathering space.
Cottage in Rapid City
4.93 out of 5 average rating, 45 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.

Top guest favorite
A charming house exterior features a welcoming front porch with two sets of comfortable seating. Potted plants adorn the porch, and large windows allow natural light to fill the interior. A well-maintained lawn complements the inviting facade.
Cottage in Sturgis
4.97 out of 5 average rating, 64 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.

The exterior of the cottage is characterized by rustic wooden siding and a distinct peaked roof. A welcoming entrance features a glass door flanked by two small metal chairs on a wooden deck that overlooks the expansive grassy landscape.
Cottage in Sturgis
4.79 out of 5 average rating, 29 reviews

The Farmhouse Cottage (studio home)

If you are looking for a unique country setting with peace and quiet, look no further than The Farmhouse Barn Cottage! We are only 10 miles outside of Sturgis. The Farmhouse Barn Cottage is settled on 14 acres next to The Farmhouse Barn Event Venue, the Cottage's big sister. Rest assured, when you stay in the cottage, there will not be events taking place at the same time so you will get the full relaxation experience our property offers.

Guest favorite
A charming cottage is set against a backdrop of lush greenery and tall trees under a partly cloudy sky. The paved lane leads to the cottage, surrounded by open fields that invite a sense of tranquility and space.
Cottage in Nemo
4.93 out of 5 average rating, 14 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 (12 miles north) thru this spectacular canyon road should not be missed! A small creek meanders thru the 5 acres of land where our cottage sits--book now!

Top guest favorite
Cottage in Spearfish
4.96 out of 5 average rating, 269 reviews

Off-Grid Cottage at Granny Flats

Welcome! Cappie, Star of Building Outside the Lines on Magnolia Network, built this adorable off-grid cottage as his own, but now you have the opportunity to stay! This beautiful 3-acre property, once the Swisher Farm, is today a working homestead, dozens of chickens, and a large garden. This cottage is handmade, from the bespoke front door to the custom 2-headed shower. We know you'll appreciate the details!

Guest favorite
A charming cottage with a red exterior is surrounded by tall pine trees. A spacious deck features a table with chairs and a grill, providing a relaxing outdoor space. Lush green grass and a pathway lead up to the entrance, emphasizing the peaceful setting.
Cottage in Custer
4.91 out of 5 average rating, 122 reviews

Cozy Creekside Cottage

This Creekside cottage located just slightly off the beaten path, only a block of the main street in downtown Custer. With a large partially fenced yard and French Creek Park next door, this makes it the perfect stay for a family, or secluded enough for “just the two of us”. With access to free WiFi, TV, and fully furnished including a stove, refrigerator, kitchen utensils/silverware and washer/dryer.

Top guest favorite
A single-story house is depicted with a wooden exterior in a soft grey shade. Large glass sliding doors offer views of the interior, framed by two side windows. A small seating area with two chairs is visible on the porch, surrounded by grassy grounds and pine trees.
Cottage in Hill City
4.99 out of 5 average rating, 231 reviews

Mystic Road Cottage… -Peaceful -Private -Hot tub

Kick back and relax in this calm, stylish space. Conveniently located adjacent to the Mickelson Trail and UTV Trails. If you enjoy water adventures, Deerfield Lake, Sheridan Lake and Pactola Lake are only a short drive away. Come enjoy nature and explore the Black Hills. End your day relaxing in the hot tub gazing at the stars.

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