Guesthouse vacation rentals in Pennington County
Find and book unique guesthouse rentals on Airbnb
Top-rated guesthouse rentals in Pennington County
Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Pennington County guesthouse rentals
Family-friendly guest house rentals
Guesthouse in Rapid City
4.92 out of 5 average rating, 638 reviewsPriceless Black Hills View!
Guesthouse in Rapid City
4.9 out of 5 average rating, 191 reviewsGayle's Cottage
Guesthouse in Rapid City
4.82 out of 5 average rating, 134 reviewsBlack Hills Loft in the Black Hills Pines
Guesthouse in Rapid City
4.94 out of 5 average rating, 80 reviewsBlack Hills Cabin - Aspen Room
Guest house rentals with a patio
Guesthouse in Lead
5 out of 5 average rating, 18 reviewsAspen View Guest House
Guesthouse in Rapid City
4.92 out of 5 average rating, 52 reviewsModern Smart House In The Woods W/ 2 King BDS 2 BA
Guesthouse in Deadwood
4.96 out of 5 average rating, 77 reviewsBackyard Cottage - Historic Deadwood
Guesthouse in Spearfish
4.73 out of 5 average rating, 11 reviewsBuena Vista Retreat
Guesthouse in Rapid City
4.76 out of 5 average rating, 80 reviewsGuest Suite-Hot Tub-Close to Town
Guesthouse in Lead
4.56 out of 5 average rating, 9 reviewsEsther's Apartment-Amazing Mtn Views Over Lead!
Guesthouse in Sturgis
5 out of 5 average rating, 35 reviewsSturgis 1-Bedroom Guesthouse! Beautiful Location!
Guesthouse in Spearfish
4.91 out of 5 average rating, 133 reviewsAdorable loft carriage house with hot tub
Guest house rentals with a washer and dryer
Guesthouse in Black Hawk
New place to stayRidgeview Guesthouse
Guesthouse in Custer
4.97 out of 5 average rating, 66 reviewsPerfect 2 BR Guesthouse in the heart of Custer!
Guesthouse in Rapid City
4.92 out of 5 average rating, 36 reviewsCozy Carriage House
Guesthouse in Whitewood
4.89 out of 5 average rating, 37 reviewsHideaway Guesthouse - Hot Tub, workplace & Deck!
Guesthouse in Custer
4.9 out of 5 average rating, 21 reviewsCuster Cozy Guest House
Guesthouse in Lead
4.56 out of 5 average rating, 9 reviewsEsther's Apartment-Amazing Mtn Views Over Lead!
Guesthouse in Custer
4.8 out of 5 average rating, 5 reviewsCuster's Rendezvous
Destinations to explore
- Guesthouse rentals United States
- House rentals United States
- House rentals Rapid City
- Guesthouse rentals South Dakota
- House rentals South Dakota
- House rentals Deadwood
- Guesthouse rentals Black Hills
- House rentals Black Hills
- Rentals with a kayak Pennington County
- Cabin rentals Pennington County
- Rentals with a fireplace Pennington County
- Bed and breakfasts Pennington County
- Rentals with a patio Pennington County
- Family-friendly rentals Pennington County
- Farmstay rentals Pennington County
- Tiny house rentals Pennington County
- Rentals with a hot tub Pennington County
- Rentals with lake access Pennington County
- Private suite rentals Pennington County
- Monthly Rentals Pennington County
- Rentals with pools Pennington County
- House rentals Pennington County
- Rentals with an accessible height toilet Pennington County
- Fitness-friendly rentals Pennington County
- Kid-friendly rentals Pennington County
- Waterfront rentals Pennington County
- Apartment rentals Pennington County
- Rentals with a fire pit Pennington County
- Rentals with a sauna Pennington County
- Cottage rentals Pennington County
- Rentals with breakfast Pennington County
- Rentals with outdoor seating Pennington County
- Chalet rentals Pennington County
- Pet-friendly rentals Pennington County
- Condo rentals Pennington County
- Rentals with a washer and dryer Pennington County
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes