Holiday rentals 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.

Chic 3BR Industrial Loft: Main St. w/ Garage

Stay in a gorgeous modern three bedroom condo right on Main Street Sheridan! You’ll be in the heart of downtown with walking accessibility to restaurants, shops, breweries, & historic sites. Sheridan sits at the base of the Big Horn Mountains that offer the best hiking, fly fishing and exploring around. Sheridan/Big Horn is also home to world class polo matches and renowned art museum a short drive away. Skiing within driving distance and events year-round make Sheridan a wonderful destination!

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.

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.

Western Elegance: Downtown Sheridan Base

Discover "Western Elegance" at our downtown Sheridan base, where historic charm meets modern comfort. Managed by Wyo Stays, this exclusive retreat is designed for those who seek a unique Wyoming experience. Located in the heart of historic downtown Sheridan Wyoming, our property offers easy access to local culture, dining, and the serene beauty of the West. Perfect for adventure seekers and relaxation enthusiasts alike, enjoy a stay that’s as captivating as the landscape that surrounds it.

Our Little Slice of Heaven 🐶 Pet Friendly

Quiet and Relaxing 1,000 sq ft Cabin with gorgeous view will make you feel like you're in Heaven. 10 miles (16km) outside of Sheridan Wy on Hwy 14, easy access off I-90, with a beautiful drive. This is the perfect get away for you to unplug. Those crisp Wyoming winter days, relax by the stove with a cup of hot coco . Cabin stays cool in summer if you open windows at night and close up in the morning. Pets welcome after approval & $20 pet fee. Must be pet & child friendly. Starlink WIFI

Holloway Hideaway Tiny Home

Welcome to your cozy tiny home retreat minutes from downtown Sheridan, WY. This charming tiny home is the perfect blend of rustic comfort and style. This tiny home will feel spacious with its vaulted ceilings and extra loft space. The tiny home has a queen bed downstairs in a closed off bedroom. Enjoy the loft with one queen bed and a fold out futon, a great place for kids to enjoy the tiny home as the ceiling clearance is very low. A fully equipped kitchenette, and fast Wifi await.

Creekside Cabin at 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.

Charming Cabin for Two Nestled Along Piney Creek

Come stay in gorgeous Story, Wyoming. This little cabin for two is at the end of a private lane. The property is shared with a larger, private family cabin. The guest cabin is perfect for those who love the outdoors. Nearby activities include fishing, hiking, horseback riding, four-wheeling, golf and sightseeing. Located in the Bighorn Mountains between Sheridan and Buffalo, where there is access to dining, shopping and year-round local activities and events.

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.

Cedar & Sage House | A Calm & Charming Retreat

The Cedar & Sage House — a cozy cottage tucked in a quiet neighborhood, just 1 mile from downtown & the airport. Filled with natural light, this charming 2BR offers modern comfort, fast fiber internet, Smart TV, and a full kitchen. Enjoy the fenced backyard with patio, grill & fire pit. Perfect for families, couples, or travelers with a furry friend. Modern amenities & personalized services make this the perfect spot in Sheridan.

Big Horn Getaway

The bedroom is in the loft above a working ceramics studio. The bathroom is on the main floor with one flight of stairs. We are located about two miles from the base of the Bighorn Mountains with a beautiful view and lots of privacy. It is a perfect getaway for two people who can handle the stairs. The space is not suitable for children under 18 or pets. We are unable to accommodate service dogs due to host's allergies.