Fitness-friendly holiday rentals in Sheridan

A Reimagined 1908 Historic Building

This special place is close to everything, making it easy to plan your visit. Renovation of this historic Main Street property will have you staying in a modern 2-bedroom, one-bath condo. Located minutes from downtown. Guests can utilize the on-site 10,000sqft gym. Walk across the street to nearby eateries and entertainment. El Tapitio Mexican, Thai take out, Rib and Chop Steak House, Silver Spur Cafee, and the No Name Bar. Check out our welcome packet upon arrival for guest discounts and perks.

Roosevelt Suite

This spacious mountain retreat blends rustic charm with modern comfort. The lofted master bedroom boasts a king bed, and you'll find 3 full-size sofa sleepers in the living room. Enjoy a fully equipped kitchen with essentials, a dishwasher, and a dining table. Relax in the soaking tub or enjoy the fire pit by the stream. Shared amenities include a sauna, laundry, weight room, and common area. Walk to trails, fishing, and the Wagon Box Restaurant. Come soak up the fresh air here in the Bighorns!

The Yukon

Welcome to The Yukon! This cozy apartment attached to the Wagon Box Lodge offers a comfortable and private retreat with modern amenities. Inside, you'll find a spacious bedroom, a bathroom with a shower, and a well-equipped kitchenette. Guests can also enjoy the lodge's shared facilities, including a sauna, gym, common area, and covered porch. The Wagon Box Restaurant is only a short walk away. Whether you're here for adventure or tranquility, The Yukon provides a welcoming base for your stay.

Elegant Creekside Golf Retreat Clubhouse and Pool

Elegant 2-bed, 2-bath creekside retreat in the Powderhorn Golf Community. This private guest suite comfortably fits 4 and features a cozy fireplace, beautiful kitchen and an expansive patio with a BBQ overlooking Goose Creek. Perfect for a quiet getaway with easy access to Sheridan's attractions and the Bighorn Mountains. Guests have access to premium amenities including pool, clubhouse and restaurant, fitness center, tennis courts, and more. PLEASE NOTE: OFFSITE pool, tennis courts, and gym

Mountain side Barndominium

Escape to a quiet country space nestled near the beautiful Bighorn Mtns. This cozy two-story apartment is located inside a barn and offers a unique and peaceful place to stay surrounded by wide-open spaces and scenic views. The space includes a comfortable living area, a kitchenette with a kitchen sink for meal prep, and a private bathroom with a shower and toilet. Upstairs you’ll find a queen bed in the loft along with extra sleeping space if need available with a futon couch downstairs.

Harbour Hideout & Event Space| 3 Kings | MMA-Perk

Drop your bags in the heart of downtown Sheridan. Harbour Hideout is a 3-bedroom basement apartment with 3 king beds, a full kitchen, and fast WiFi—across from Blacktooth Brewing and blocks from Main Street. Guests get a FREE first BJJ/MMA class at Grindhouse upstairs. Sleeps up to 8 with two sofas and optional air mattress. Provided by Wyo Stays with concierge service, private chef, and airport transfers on request. Your Wyoming basecamp starts here—message us with questions.

Parkside Gardens "Dahlia Suite" Kendrick City Park

Our 1905 Victorian Apartment feels like you stepped back to the 40's & 50's. Completely remodeled with vintage, yet modern amenities. Enjoy the serenity and peacefulness of Sheridan's Beautiful City Park right next door. We provide equipment for tennis courts, pool & basket ball courts. We also have bicycles for our guests to enjoy a ride through the park or venture further via the bike trails. Also, the YMCA , the Public Library and down town are within walking distance.

Historic Apartment by Park

1905 Victorian, completely remodeled with vintage, yet modern amenities. Enjoy the serenity and peacefulness of Sheridan's Beautiful City Park right next door. Your own Apartment, with your private entrance and parking. We provide equipment for tennis courts, pool & basket ball courts. We also have bicycles for our guests to enjoy a ride through the park or venture further via the bike trails. Also, the YMCA , the Public Library and down town are within walking distance.

7 Mi to Bighorn Nat’l Forest: Dog-Friendly Home

Quiet Setting | Newly Remodeled | Large Fenced Backyard | RV Parking On-Site Year-round adventure abounds at this Dayton vacation rental! With 3 bedrooms and 2 bathrooms, ‘Whispering Pines’ has space for family, friends, and even furry travelers, too. Head to Bighorn National Forest to fish along the Tongue River or ride over 300 miles of groomed snowmobiling trails, then come home to light the pellet stove and bust out the board games. Book your Bighorn getaway today!

Parkside Gardens "The Daisy" Private Room & Bath

Welcome to Parkside Gardens! The “Daisy" is upstairs, in a 1905 Victorian located by Sheridan's Kendrick City Park. This private, Touchpad Keyless Entry, room includes a private bathroom, a mini fridge, microwave & coffee maker. Host supplies coffee, creamer and sugar. Just steps from walking path, tennis courts and the city pool, buffalo and elk pasture. We supply bicycles, pool towels, totes and Park toys. You may relax on the Patio within the Rose Garden.

Your Bighorn Mountain Getaway!

Find your peace in our rustic mountain cabin! Located at the foot of the Bighorn Mountains, this cabin home welcomes you to beautiful Story, Wyoming. Two bedrooms offer queen size beds for a restful night as well as a full sized couch for any additional guests. A cozy kitchen awaits for home cooked meals and gathering around the table. Spacious living room area ready for laughter and memories to be made here at The Lazy JJ Homestead. We welcome you!

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.