Holiday rentals with outdoor seating in Sheridan County

Modern 2 Bedroom 6 Blocks to Main St. King & Queen

Check out our discounts for weekly and monthly rentals. This home is strictly a vacation rental property, comparable to a modern Hotel Suite. Easy access entrance has low profile steps and hand bars, suitable for elderly and those with mobility issues. Roku TVs in both bedrooms. The Lamps double as charging stations. One block north is Kendrick Mansion & Park, city pool & Ice Cream stand. Whitney Park is 3 blocks east with a fountain splash pad to beat the heat. Easy access to the bike path

Wright 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, 2 luxurious bathrooms, and a welcome book with all our local favorites!

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.

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!

Cozy Basement w/King Bed |The Rambler

Welcome! We're excited to offer you a charming and inviting 450 sqft basement apartment, located just a block away from downtown. Recently renovated with top-of-the-line features, including a brand new kitchen, remodeled bathroom, and a lavish King size bed - this cozy space offers the perfect place to retreat and relax. If you're traveling with your pet, our small shared backyard offers a great spot to play, and the nearby Whitney Commons offers some of the best walking paths in town.

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 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.

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.

Shire Valley Sanctuary: Equestrian River Cottage

This 2 bd/1 bath cottage by the river is situated on 10 acres of Shire Valley LLC property. Enjoy end-of-the-road privacy, yet within walking distance to Historic downtown Dayton, Wy. The cottage has a covered porch with a beautiful view of the mountains or take a short stroll down to the river. Watch the sunsets in the gazebo with your favorite toddy. Of course, everywhere you look is a pasture full of majestic draft horses.