Holiday rentals with breakfast in Sheridan County

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

Gone Fishin' – Hot Tub & BBQ | Mountain Retreat

Discover the charm of Story, Wyoming in this inviting 3-bedroom mountain retreat, located just 20 minutes from downtown Sheridan. You’ll have plenty of space to relax, thanks to an open-concept living and dining area, a well-equipped kitchen, and cozy sleeping options: two queen beds and one bunk bed. A single bathroom ensures everyone’s comfort, while the attached garage lounge area and private hot tub offer the perfect spots to unwind after a day of adventure. Whether you’re exploring local

"Slice of Paradise" Tranquil Rural Escape + Spaceo

Immerse yourself in some of the best of Sheridan Wyoming with our cozy 3-bedroom getaway, 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 in this amazing guest house. Just a short drive away from bustling eateries, vibrant bars, boutique shopping, museums and galleries - a perfect spot for relaxation and experiencing rural Sheridan,

Western Elegance: Downtown Sheridan Base

Discover "Western Elegance" at our downtown Sheridan base, where historic charm meets modern comfort. Managed by Wyo Stays, this exclusive retreat is designed for those who seek a unique Wyoming experience. Located in the heart of historic downtown Sheridan Wyoming, our property offers easy access to local culture, dining, and the serene beauty of the West. Perfect for adventure seekers and relaxation enthusiasts alike, enjoy a stay that’s as captivating as the landscape that surrounds it.

Impression - A Cozy Vintage Quirky Home

Welcome! Come experience a Sheridan local home! This 3 bedroom home is only 3 minutes from downtown. Peacefully tucked away from downtown in one of Sheridan's most peaceful neighborhoods, this family home is a fully furnished stay! You will have a wonderful kitchen, Vintage layouts to the dining and living room area, 2 comfy queen beds, 1 comfy queen/twin bunk bed, and 2 awesome bathrooms! Keep reading to learn more about the unbeatable location and features!

Frackleton Charming Escape

Welcome! Come experience a Sheridan local home! This 2 bedroom home is only 3 minutes from downtown. Peacefully tucked slightly away 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, 1 full bed, and an awesome bathroom! Fully fenced yard for the pet! Keep reading to learn more about the unbeatable location and features!

Zen Den | Sauna + King Bed, Health Oasis - 15+

Welcome to The Zen Den — Sheridan’s premier wellness stay. Enjoy a private electric sauna, red light therapy, filtered water systems, grounding sheets, baby gear, and more. Sleep 8–10+ comfortably with flexible beds and cozy touches throughout. Whether you're here to relax or recharge, this pet-friendly home is stocked for health, rest, and good vibes. Ask about e-bike rentals and special wellness perks!

The Vaquero: King Bed + Downtown View Charm

Experience the best of Sheridan from this beautifully connected dual-suite retreat, located right on iconic Main Street. With a luxurious king bed and a comfy queen, tasteful Western-chic interiors, and a front-row seat to downtown charm, The Vaquero Suite is where flexibility meets style. Whether you’re here for a restful escape or a weekend of exploration, you’ve found your perfect base.