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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
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Guesthouse in Rapid City
4.94 out of 5 average rating, 78 reviewsBlack Hills Cabin - Aspen Room
![](https://a0.muscache.com/im/pictures/dee272ff-25a6-42b1-82ee-95731d6ec42d.jpg?im_w=720)
Guesthouse in Rapid City
4.83 out of 5 average rating, 125 reviewsBlack Hills Loft in the Black Hills Pines
![](https://a0.muscache.com/im/pictures/miso/Hosting-5306656/original/a1b7ec13-513e-4eb5-8eef-891b53cde0e3.jpeg?im_w=720)
Guesthouse in Rapid City
4.91 out of 5 average rating, 623 reviewsPriceless Black Hills View!
![](https://a0.muscache.com/im/pictures/4903af31-945c-4bd8-bcae-f2f7462dacf2.jpg?im_w=720)
Guesthouse in Rapid City
4.9 out of 5 average rating, 182 reviewsGayle's Cottage
Guest house rentals with a patio
![](https://a0.muscache.com/im/pictures/7eb0f868-a172-4787-bf20-7dd5617b32f2.jpg?im_w=720)
Guesthouse in Deadwood
4.95 out of 5 average rating, 65 reviewsBackyard Cottage - Historic Deadwood
![](https://a0.muscache.com/im/pictures/miso/Hosting-1196388862443995931/original/211c3396-5578-4950-84f1-eb5666397b7d.jpeg?im_w=720)
Guesthouse in Lead
New place to stayAspen View Guest House
![](https://a0.muscache.com/im/pictures/miso/Hosting-922373070859885148/original/d0593b0e-8e82-476e-81ec-0a130f5409e6.jpeg?im_w=720)
Guesthouse in Spearfish
4.86 out of 5 average rating, 7 reviewsBuena Vista Retreat
![](https://a0.muscache.com/im/pictures/miso/Hosting-617341813481921392/original/243a9524-c958-4fba-940e-990be18e89eb.jpeg?im_w=720)
Guesthouse in Spearfish
4.89 out of 5 average rating, 108 reviewsAdorable loft carriage house with hot tub
![](https://a0.muscache.com/im/pictures/miso/Hosting-900780243567345367/original/dfbada50-1e09-4fd8-bb85-8857110543e3.jpeg?im_w=720)
Guesthouse in Rapid City
4.75 out of 5 average rating, 56 reviewsGuest Suite-Hot Tub-Close to Town
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Guesthouse in Sturgis
5 out of 5 average rating, 27 reviewsSturgis 1-Bedroom Guesthouse! Beautiful Location!
![](https://a0.muscache.com/im/pictures/hosting/Hosting-U3RheVN1cHBseUxpc3Rpbmc6MTA1ODI0MjgyODQ0NzYwNTI2NQ%3D%3D/original/8be4845e-21a4-484f-bdc9-fba2e057a947.jpeg?im_w=720)
Guesthouse in Custer
4.8 out of 5 average rating, 10 reviewsCuster Cozy Guest House
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Guesthouse in Custer
4.96 out of 5 average rating, 54 reviewsPerfect 2 BR Guesthouse in the heart of Custer!
Guest house rentals with a washer and dryer
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Guesthouse in Custer
4.96 out of 5 average rating, 54 reviewsPerfect 2 BR Guesthouse in the heart of Custer!
![](https://a0.muscache.com/im/pictures/miso/Hosting-813706304849168488/original/af4ca85a-2dff-4d52-9a2c-8b980259a52d.jpeg?im_w=720)
Guesthouse in Whitewood
4.83 out of 5 average rating, 23 reviewsHideaway Guesthouse - Hot Tub, workplace & Deck!
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Guesthouse in Hermosa
5 out of 5 average rating, 5 reviewsDry Creek Living
![](https://a0.muscache.com/im/pictures/miso/Hosting-676684314896830364/original/622c39dd-4a98-4b84-9cb9-67093b1a2e3d.jpeg?im_w=720)
Guesthouse in Rapid City
4.94 out of 5 average rating, 31 reviewsCozy Carriage House
![](https://a0.muscache.com/im/pictures/miso/Hosting-1008935790467601655/original/07b80ddb-697e-45ad-8ed0-d9971d380e5d.jpeg?im_w=720)
Guesthouse in Lead
4.33 out of 5 average rating, 3 reviewsEsther's Apartment-Amazing Mtn Views Over Lead!
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Guesthouse in Custer
New place to stayCuster's Rendezvous
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