Holiday 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.

Lindbergh Cabin at Ever Sky Ranch - VIEWS! NEW!

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.

Cozy Master suite

Master suite conveniently located in town on a quiet street. Located in a private, tucked-away location, you enjoy wide-open Wyoming skies while having the benefit of in-town access. A luxurious queen bed and a spacious ensuite bath will help you unwind after a day of adventuring. Natural light washes in through big windows unless you pull the black-out curtains tight for some extra zzzs in the morning! Having rocking chairs and solar cafe lights outside is a must, and we've got you. Enjoy!

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!

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.

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.

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.