Holiday rentals in Sheridan County

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Top-rated holiday rentals in Sheridan County

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Home

5 out of 5 average rating, 18 reviews

Deer Run, mountain home getaway

Bring everyone to this house in the beautiful Bighorn Mountains. The house was built in the 1940s, expanded in the 70's, and remodeled in 2023. The home features 3 bedrooms, 2 bathrooms, full kitchen, seating area by a fire, living room, two car indoor garage, dining room, and over an acre of outdoor space. The house is built next to a seasonal creek and is regularly visited by white tail deer and turkeys. This house is perfect for people who want to get away from it all. Snowmobile trailers OK

Guest favourite

Loft

4.98 out of 5 average rating, 42 reviews

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!

Guest favourite

Home

4.98 out of 5 average rating, 163 reviews

Sadie's Place, Two Bedroom tucked into paradise.

Sadie's Place is a cozy, comfortable two bedroom home located in the heart of Story on a secluded corner of paradise. The house is well equipped to provide a worry free stay. It is a short walk to the local store, library and post office. On the property there is a private walking trail (walking, snow shoeing or cross country skiing), three holes of rustic golf, a beautiful mountain stream and an abundance of opportunities for wild life watching. For relaxation, there is no place better.

Superhost

Cabin

4.86 out of 5 average rating, 7 reviews

Shire Valley Cabins, Charming Dayton Retreat (3 O

Only minutes from the top of the Bighorn mountains, our cabins offer great access to snowmobiling, hunting, fishing and mountain trails, and much more. We are located 20 minutes from Sheridan WY, and 45 minutes from Bear Lodge Resort. Guests will be amazed at the fine craftsmanship and attention to detail in all cabins. Each cabin has it's own washer and dryer, a full bath, a separate bedroom, a microwave, refrigerator, living area with a pull-out sofa, and covered porch. Come and enjoy!

Guest favourite

Cabin

4.95 out of 5 average rating, 445 reviews

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 & $15 pet fee. Must be pet & child friendly. Starlink WIFI

Guest favourite

Bungalow

5 out of 5 average rating, 25 reviews

Amenities Galore Sweet Li’l Bungalow in Sheridan

Beautiful front porch invites you into the living room of this freshly renovated craftsman w/ fireplace, built-in bookcases & glass cupboards in sunlight filled dining rm, charming kitchen w/ bar seating, main floor en suite, and laundry upstairs in mudroom. Additional bedroom, bathroom & cozy den located downstairs (steep stairs). Large screened back porch overlooking lovely fenced back yard. Street parking (or garage available w/ advance notice for longer term stays & addtl fee).

Guest favourite

Home

4.95 out of 5 average rating, 109 reviews

Cozy 3BR Sheridan Home Close to Walking Paths

Located 5 minutes from Downtown Sheridan, this cozy home is the perfect place for travelers headed to the Big Horn Mountains or just passing through on the way to Yellowstone or Tetons National Park. And since this home is so close to Downtown, visitors can enjoy weekly local events and the Fair Grounds. Take time to meander or run on the jogging path with a stocked pond just minutes from the house as well. This home is ideal for a family or small group wanting to enjoy Wyoming.

Guest favourite

Cabin

5 out of 5 average rating, 52 reviews

Cabin by the River

The Cabin has end-of-the-road privacy, beautifully detailed craftsmanship throughout the cabin along with tons of luxury and rustic charm. It is situated on a 10-acre Equine property with a peaceful walking trail along the river. Early mornings and sunset are magical times to sit in the gazebo along the river. Historic Downtown Dayton with all of its Hallmark charm, is within walking distance from the Cabin. Shire horse wagon rides can be booked in advance.

Guest favourite

Flat

4.98 out of 5 average rating, 44 reviews

Cozy guest suite Near Golf Course

Indulge in the ultimate mountain getaway at this stunning 1-bedroom private guest suite nestled just moments from breathtaking peaks and a premier golf course. Offering a seamless blend of comfort and adventure, this private oasis is the perfect destination for your next vacation. Hike scenic trails, tee off on championship fairways, then return to your private sanctuary to unwind in pure bliss. Elevate your getaway and book your stay today.

Guest favourite

Cabin

4.92 out of 5 average rating, 87 reviews

Charming Cabin for Two Nestled Along Piney Creek

Come stay in gorgeous Story, Wyoming. This little cabin for two at the end of a private lane 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.

Guest favourite

Cottage

4.95 out of 5 average rating, 144 reviews

Darlene's Cottage

Beautiful 2 Bedroom 2 Bath Cottage full of charm with all that you will need for your short stays. This Home is wheelchair and walker accessible with a roll in shower. Walking distance to downtown Sheridan, the city walking paths and Kendrick Park. Close to the County Fairgrounds and Sheridan Memorial Hospital.