Holiday rentals with a patio in Sheridan County

Cozy and Charming Bungalow

We welcome you to our charming 2-bedroom home, pleasantly located in the heart of Sheridan, WY. A short 5-minute drive to downtown, M & M Ice Rink, Fairgrounds, and less than 20 minutes to the Equestrian Center. This home has a warm and modern design with newly remodeled kitchen, 2 bedrooms (queen beds), quaint office, newly renovated bathroom, and room for the portable crib (provided). Our favorite spot to hang out is on the patio; fenced, covered, grill, and ample space to lounge and relax.

Dark Horse Casita

The Dark Horse Casita has spectacular views of the Big Horn Mountains. Close to Big Horn, Wyoming and 15 minutes from downtown Sheridan, Wyoming. The DHC is equipped with A/C, Wi-Fi, DISH Network, well-equipped kitchen, full size washer & dryer, patio and parking. The Dark Horse Casita is on the owner's property with horses and steers in close proximity. If livestock is not your jam, then the Dark Horse Casita may not be your best choice. No guests animals allowed. No smoking on property.

The Historic Benham-Johnston Bungalow

As seen in the "Old House Journal". Welcome to the Benham-Johnston Bungalow, an exquisitely restored 1915 Craftsman home just a few blocks from Main Street in the heart of Sheridan. This fully furnished, 1,900-square-foot retreat is brimming with historical charm, art, and creature comforts. Enjoy ample private parking, a blend of modern and historic amenities, and a truly timeless stay. I’m Joe, your host, and I’m just a message away if you need anything, please feel free to reach out anytime.

Earhart Cabin at Ever Sky Ranch - NEW! THE VIEWS!

Amazing views in every direction, this Wyoming cabin sits on the 300 acre Ever Sky Ranch at the base of the Bighorn Mountains. Peaceful and serene ~ enjoy the sunrise over the mountains and sunset into the valley, watch cattle and horses graze as well as plenty wildlife, experience incredible birdwatching and spectacular starry night skies. Inside the cabin, enjoy comfy bedding, modern western decor, a well stocked kitchen, a luxurious bathroom, and a welcome book with all our local favorites!

Blue Line Condo, at the Ice Haus, downtown luxury

Welcome to the Blue Line Condo, your ideal home base in downtown Sheridan. Located in the Ice Haus, est. 2024, we are 1 of 8 multi-level condos. On the main floor is the Ice Haus Eatery which includes coffee, ice cream, sandwiches, liquor sales and the Penalty Box Bar. While the vibe downstairs is fun, they close at 9 pm and the condo offers a peaceful retreat. Just a few blocks away, you'll find the historic charm of downtown, we are next to the M&M Center ice rink and city trail system.

Luxurious, downtown loft with a warm, family feel

Enhance your dream vacation, by booking this luxurious 1700 sq. ft. loft in the heart of Historical Downtown Sheridan, WY. Experience a bit of the wild west, while soaking in all the local amenities: with 3 craft breweries (within walking distance), numerous restaurants, local coffee houses, street art & live music; fabulous specialty shops, beautiful parks, family friendly activities, outdoor pools/splash parks, fitness facilities, and miles of walking/bike paths. This is the place to stay!

Spacious & Sunny Retreat | Quiet Walkable Location

Charming 3-bdrm ranch home perfect for 6 guests. Enjoy a cozy living space, vaulted ceilings, & a large fenced backyard. This mid-century retreat is just blocks from downtown & Kendrick City Park, & offers a perfect blend of comfort & convenience. Features a fully equipped kitchen, spacious lvg areas, a dedicated workspace, BBQ grill, board games & cards, a large outdoor patio & easy access to city paths. Ideal for families & friends seeking a quiet, residential getaway with modern amenities.

Cozy Suite

Tucked away on a quiet street in Sheridan, the Cozy Suite offers a peaceful and comfortable place to land while still being close to everything in town. A plush queen bed and spacious ensuite bathroom make it effortless to unwind after a day of exploring. Natural light pours in through large windows, or pull the blackout curtains for a slower morning and a few extra zzz’s. Step outside to enjoy the patio, a perfect spot for a quiet morning coffee or a relaxed evening under the café lights.

Creekside Cabin and Story Brooke Lodge

Come relax at a cozy cabin along Piney Creek with a large wrap around porch. Open your windows to listen to the water running by all night with fresh cool air. The cabin features a queen size bed and a pull out couch. Kitchenette includes a sink, Keurig, toaster oven, microwave, hot plate, and mini fridge. The cabin features a gas fireplace, a covered porch with skylights and also has a glass dining table with four chairs. This cabin has cable TV that is also a smart TV and wifi.

Outstanding mtn view, 5 bdr sleeps 11, 4400sqft

This is one of the largest if not the largest guest home in the area. Located just outside Dayton WY city limits and ready for any traveler/family/friend groups. Welcome to bring horses, utv and snowmachines but of course they are not required. This is a quiet, safe, place to relax with views of wildlife (on property deer, turkeys, pheasants), camp fire, hot tub, pond (with fish) and garden. Nicely stocked 4400 sq. ft. 5 bdr (sleeps 11), 2 ½ bath, with city water and amenities.

Ranchester Rail Retreat

Step into a fully remodeled 1972 train caboose in the quiet town of Ranchester, WY (10 minutes to Sheridan, WY) - where rustic charm meets modern comfort. This unique stay offers cozy, train-era nostalgia with updated amenities. Nestled near the Bighorn Mountains, Ranchester is a peaceful, friendly town perfect for relaxing or exploring. Whether you’re road-tripping, seeking solitude, or chasing adventure, this one-of-a-kind caboose promises a stay to remember.

Fire Pit Under the Stars |The Wayfarer Bungalow

Centrally located and newly built, this stylish two-bedroom home is perfect for couples, families, or friends. Each bedroom has a queen bed and its own climate control for a personalized stay. Enjoy a cozy night in with a home-cooked meal and movie, or head outside to roast s’mores by the gas fire pit. Luxury linens, heated bathroom floors, and plush towels add a touch of indulgence, while two cruiser bikes are available for exploring town at your own pace.