Family-friendly holiday rentals in Sheridan

Stylish 1BR Near Main St |The Troubadour Suite

Experience historic charm in our cozy cottage, nestled in a vibrant, picturesque town. This house is bright and airy with access to everything Sheridan has to offer. With a large living area, full kitchen with local coffee and a queen bed and radiant heat this space is perfect for all your needs. You will be close to great restaurants, shopping and all the area attractions. Enjoy the beautiful outdoors with nearby trails and parks just a few minutes away along with a short walk to downtown!

WYOHANA Studio

Studio apartment at the edge of town not far from interstate. Full kitchen and tankless hot water. 2 memory foam beds, one is a trundle twin so please let me know if you’re going to need it set up. Large outdoor space for truck and trailer parking, let us know if you’ll need the larger parking area. Beautiful views! Less than a mile to bar and grill, gas station, bakery, coffee kiosk and just a few miles from the Big Horn Mountains. No TV, but there is WiFi! Everything is as seen in photos.

Our Little Slice of Heaven 🐶 Pet Friendly

Quiet and Relaxing 1,000 sq ft Cabin with gorgeous view will make you feel like you're in Heaven. 10 miles (16km) outside of Sheridan Wy on Hwy 14, easy access off I-90, with a beautiful drive. This is the perfect get away for you to unplug. Those crisp Wyoming winter days, relax by the stove with a cup of hot coco . Cabin stays cool in summer if you open windows at night and close up in the morning. Pets welcome after approval & $20 pet fee. Must be pet & child friendly. Starlink WIFI

Cozy and Charming Bungalow

We welcome you to come experience a convenient and charming 2-bedroom home, pleasantly located in the heart of Sheridan, WY. A short 5-minute drive to downtown shops and wonderful restaurants. This home has a warm and modern design with newly remodeled kitchen, 2 bedrooms (queen beds), quaint office, newly renovated bathroom, and room for the portable crib (provided). Our favorite spot to hang out is on the patio; fenced, covered, grill, and ample space to lounge and relax.

Holloway Hideaway Tiny Home

Welcome to your cozy tiny home retreat minutes from downtown Sheridan, WY. This charming tiny home is the perfect blend of rustic comfort and style. Visit historic downtown Sheridan and enjoy a day of shopping or visit one of the many local western museums. Spend an evening out to one of our local breweries and enjoy some local talent. Take a day rip enjoying the mountains only 20 minutes from the Holloway Hideaway front door.

Big Horn Getaway

The bedroom is in the loft above a working ceramics studio. The bathroom is on the main floor with one flight of stairs. We are located about two miles from the base of the Bighorn Mountains with a beautiful view and lots of privacy. It is a perfect getaway for two people who can handle the stairs. The space is not suitable for children under 18 or pets. We are unable to accommodate service dogs due to host's allergies.

Cozy 2BR Getaway | Sleeps 6 | Pets Allowed

Just minutes from downtown Sheridan and historic Main Street, this cozy 2-bed, 1-bath retreat is your perfect home base. Explore shops, breweries, and the stunning Bighorn National Forest by day—then relax in comfort with a fully equipped kitchen, two queen beds, a sleeper sofa, and a small enclosed yard perfect for your pup. Thoughtfully designed for rest and recharge, it’s everything you need for a memorable stay

The Hideaway

Hidden away a short 5 block walk from Sheridan's downtown, The Hideaway is in the perfect location for your stay. This stand alone cozy structure (728 sq ft) is fully furnished and prepared to be your home away from home. Kendrick Park is a 1.5 block walk when looking for a cool treat or something fun for the kids to do. All new furnishing and a fresh concept are ready for your arrival

The Loft on Main in Sheridan, WY

Historic building, fully renovated, open floor plan & exposed brick walls, gorgeous hardwood floors & fireplace, huge granite island w/ comfortable seating plus an expansive dining table for 8. Balcony view over Main Street for the rodeo parade & street dance, 3rd Thursday Street Fest. Downtown Loft Eateries Shopping Nightlife Central