Vacation rentals with outdoor seating in Sheridan County

Goose Valley Farm, Alpaca Farm under the Big Horns

Idyllic farm setting located below the Big Horn Mountains. Enjoy laying in hammock alley while watching Alpacas graze in the pasture w/ the Mountains as your back drop or read a book and listen to the symphony of birds & the clucks of happy chickens. You’ll feel enveloped by nature & the slow relaxing pace of the farm w/ open access to the farm animals. Enjoy the wide open spaces w/ abundant wildlife, & unobstructed views of the Big Horn Mountains w/ a vast country night sky filled with stars.

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.

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.

The Magpie Cabin · Big Horn Views & Ranch Stay

Located just 13 miles from Sheridan right off a paved highway, the Magpie Cabin is a cozy, modern getaway on a horse ranch. Enjoy breathtaking sunsets and the authentic feel of ranch life. The cabin includes all of the modern amenities needed to make your stay comfortable (minus a dishwasher). Step onto the porch to possibly see wildlife and horses graze nearby; you might even spot a cowboy training horses right outside! It's the perfect location to stay while you visit the Sheridan area!

Tongue Canyon River Retreat with Hot Tub & AC

Located on the Tongue River at the base of Tongue Canyon. Our property offers AC, hottub & private fishing along 5.5 acres & many public fishing access areas as you venture up the canyon. The trailhead is about 1.5 miles past the cabin offering easy hiking, biking, walking or atv'ing to the trail. There is also an atv trail nearby off Smith Creek Rd. Dayton has wonderful amenities including a wine/tapas bar, a mercantile with yummy sandwiches and homemade ice cream and a few bars.

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.

Rustic 3 BR/2 Bath on Wyoming Ranch

Host pays service fees! This spacious home on a working ranch is perfect, whether just traveling through (Yellowstone,Mt Rushmore) or wanting to stay longer. We recommend 2 nights based on conversations with past guests! Get away from city life & escape the 9-5, have coffee on the deck with view of the Big Horn Mtns and wildlife sightings. Can work remotely with Great WIFI/cell service, enjoying a quiet respite. 3 BR sleeps 8. Located 30-45 minutes from 3 historical towns.

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.

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.

Stylish 1BR Near Main St |The Troubadour Suite

Five minutes from Main Street. Five decades of considered choices inside. The Troubadour Suite occupies the entire upper level of a 1950s cottage — 500 sq ft of recently refurbished space with corduroy cherry wood paneling, Restoration Hardware leather chairs, radiant heat, and a queen bed that earns its reputation. Walk to Java Moon, Frackelton’s, Le Rêve, Whitney Commons, and Kendrick Park. Midway between Yellowstone and Mount Rushmore.

Luxe Main St Loft with Rooftop Lounge and Balcony

Experience historic downtown Sheridan from our luxurious 2-bed, 2-bath loft in an 1892 building. Comfortably sleeps 6 with two king suites & a cozy alcove. Features a gourmet kitchen, fireplace, and a private balcony overlooking Main Street, perfect for watching parades! Enjoy the best of Sheridan's dining, shopping, and culture, all just steps away from your front door. Walkable with free dedicated parking included.

Cozy 2BR Getaway | Sleeps 6 | Pets Allowed

Just minutes from downtown Sheridan and historic Main Street, this cozy 2-bed, 1-bath retreat offers an affordable, high-quality stay for up to six guests. Enjoy two queen bedrooms, a sleeper sofa, a fully equipped kitchen, fast WiFi, and a small enclosed yard ideal for your pup. Close to shops, breweries, and the Bighorns, it’s the perfect home base to relax, recharge, and explore everything Sheridan has to offer.