Holiday rentals with outdoor seating in Sheridan

The Pearl - Luxe Gem | Fire Pit, King & Walkable

Immerse yourself in the heart of Sheridan Wyoming with our cozy 3-bedroom retreat, designed for memorable stays. Offering seamless self check-in, complimentary Wi-Fi, and coffee & tea, your comfort is our priority. Experience the ease of a private kitchen, bathroom, and a welcoming living space. Steps away from bustling eateries, vibrant bars, boutique shopping, museums and galleries - a perfect spot for exploring. Message us to unlock the secrets of Sheridan from your own serene haven and hom

"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.

Pet friendly home with yard. The Wyoming Gem

Cozy & Quiet & Close to Everything Your whole family (Dogs who are well behaved are welcome too at no extra charge) will be close to everything when you stay at this centrally-located, newly renovated, historic home with a fully fenced back yard, deck with outdoor seating, a fire pit area, dining area, and a covered swing. A park with entrance to one of the many walking trails is just down the street & getting to downtown is just a stroll away while shopping centers are within a 5 min car ride.

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!

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.

Walk to historic downtown, backyard, pets welcome!

Experience the vintage charm and cozy atmosphere of the Burkitt Bungalow, a beautifully renovated 100-year-old downtown family-style home in the heart of Sheridan, Wyoming. This vacation house offers the perfect blend of history and modern comforts, with 3 1/2 bedrooms, 2 bathrooms, 2 living rooms, and a fully stocked kitchen. Located just 3 blocks from downtown, you'll be within walking distance of all the best restaurants, shops, and nightlife that Sheridan has to offer.

Holly Ponds Getaway

Kick back and relax in this calm, stylish space. Enjoy a great walk along the ponds with lots of wildlife on Sheridan’s greenway which is located right behind the house. The neighborhood is quiet and friendly, so it is a wonderful place to sit outside and enjoy a wonderful view of the Big Horn Mountains. We hope you enjoy our home, we do when we visit. The furniture is all new and very comfortable and there is a desk for those of you who choose to try and work while here.

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.

Buffalo Hideout

Enjoy your stay at this newly remodeled quiet condo along Goose Creek in a private neighborhood. The Buffalo Hideout features a fenced in backyard with a patio, front patio over looking the creek and bike path, full kitchen, private laundry, and two queen beds. Sheridan is a western town, and we strive to create a unique western experience for you with authentic decorations. Minutes away from downtown and conveniently off I-90.

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.