Holiday rentals with outdoor seating in Sheridan

Big Horn Hideaway: 4 bedroom cabin, 100-mile view

Mountains higher than Yellowstone, wildlife that's really wild, exciting history, and no crowds! The Bighorn region is a vacation destination for the discriminating visitor, and this rustic cabin with a huge new deck and a treehouse view on the eastern face of the mountains is filled with charm and located near Sheridan, Wyoming. Owners occupy a separate basement apartment. Single group rental includes shared deck space and laundry access and by request at extra charge additional sleeping space.

"Circle Bar Manor" Central Main Stay

Welcome! Come experience a Sheridan local home! This 4 bedroom home is only 1 minute from downtown. Peacefully tucked away just 2 blocks from downtown, this family home is a fully furnished stay! You will have a wonderful kitchen, open layouts to the dining and living room area, 1 comfy king bed, 3 Queen beds, 1 Bedroom on main floor with 2 single beds and a great sunroom/patio turned into additional sleeping! 3 Bathrooms and a fully fenced yard that has been newly updated, keep reading to learn

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.

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!

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 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.

Vaulted Den|Chic 1BR w/Fireplace|Downtown Sheridan

Step into The Vaulted Den — a thoughtfully designed 1-bedroom retreat just off North Gould Street in downtown Sheridan. Enjoy vaulted ceilings, in-floor heat, and a modern electric fireplace that creates an instant sense of calm. Work comfortably at the standing desk with a balance board, recharge with wellness gear, or unwind by the fire. Walk to coffee, dining, and breweries, then return to a quiet, private space that feels effortlessly elevated.

Main St Retreat | 2BR, 3BA +Near Downtown, On Main

Your Sheridan escape starts here. This stylish 2-bedroom, 3-bath retreat sits on Main Street, steps from downtown dining, shopping, and nightlife. Sink into queen beds, cook in a fully equipped kitchen, and unwind on your private deck. Keyless entry, blazing Wi-Fi, endless hot water, and free parking make everything effortless. Guests call it "a hotel with the comforts of home." Message us to plan your perfect Wyoming stay.

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.