Sheridan Wyoming Vacation Rentals — 65+ Properties, Licensed Brokerage, Book Direct
From historic downtown lofts on Main Street to Bighorn Mountain retreats — all managed by Wyoming's only licensed vacation rental brokerage. No Airbnb fees. Real local team.
Find Your Sheridan Wyoming Vacation Rental
Downtown Sheridan
Walk to Main Street, breweries, and the WYO Theater. Curated lofts and homes managed by a local brokerage.
Browse →Bighorn Mountain Cabins
Elevation retreats along the Scenic Byway — alpine meadows, trout streams, and nobody around for miles.
Learn More →Pet-Friendly Rentals
Your dog is welcome. Select properties in Sheridan County that actually mean it.
Learn More →Hunting & Ranch
Base camps for elk, deer, and upland seasons in the Bighorn Mountain corridor.
Learn More →Where to Stay in Sheridan Wyoming — A Neighborhood Breakdown
Downtown Sheridan
The center of gravity. Walk out your door and you're on Main Street — the Mint Bar, King's Saddlery, Black Tooth Brewing Co., Frackelton's, and the WYO Theater are all within blocks. During WYO Rodeo week, the parade passes beneath your windows. Downtown properties are ideal for couples and small groups who want restaurants, galleries, and nightlife without driving. Luminous Brewhouse for morning coffee, Wyoming Rib & Chop House for dinner, Open Range for cocktails. The Onyx and The Pearl are both downtown. This is where Sheridan feels most alive.
Bighorn Foothills — Story & Dayton
Story sits at the base of the Bighorns on US-87 — 15 minutes south of Sheridan. Dayton anchors the western approach via US-14 toward the Bighorn Scenic Byway. Both communities are gateway points to Bighorn National Forest trailheads, with creekside cabin properties surrounded by ponderosa pines. My Story | Historic Creekside sits on a year-round creek with a copper soaking tub and stone fireplace. Families and fly fishers gravitate here. The Tongue River and Little Goose Creek offer blue-ribbon trout water within minutes.
Ranch Country — Big Horn & Ranchester
Big Horn (the town, not the mountains) is a 10-minute drive west of Sheridan. Home to the Big Horn Equestrian Center, where polo matches run June through Labor Day, and The Brinton Museum — one of the finest Western art collections in the country. Ranchester sits at the confluence of the Tongue River and I-90, offering easy access to Tongue River Canyon — a 7-mile red-rock canyon hike that rivals anything in southern Utah. These areas are quieter, more spacious, and priced lower than downtown properties.
Mountain Cabins — Bighorn National Forest
For guests who want elevation. Cabin properties along the Bighorn Scenic Byway sit at 5,000–8,000 feet, surrounded by national forest land with no neighbors and no cell signal. Cloud Peak Wilderness trailheads are accessible from June through October. Antelope Butte Mountain Resort is the winter draw — uncrowded skiing 45 minutes from downtown Sheridan. These cabins are best for hunters, hikers, and anyone who wants total mountain immersion.
Why Sheridan Wyoming? The Honest Local's Perspective
Sheridan isn't Yellowstone. It doesn't have four million visitors a year, and it doesn't want them. What it has is the Tongue River Canyon — a 7-mile red-rock gorge 20 minutes from town that would be a national monument anywhere else. It has the Dead Swede Mountain Run, where trail runners climb 3,000 feet through the Bighorns and then drink beer in a meadow. It has Luminous Brewhouse for morning coffee and Frackelton's for dinner, and on a Tuesday night in July you can sit in Kendrick Park and listen to live music while the sun sets behind the Bighorns.
The Mint Bar has been pouring whiskey since 1907. King's Saddlery is still a working saddle shop. Black Tooth Brewing Co. brews with Bighorn Mountain snowmelt. Cloud Peak Wilderness opens into alpine basins that don't appear on most hiking apps. The Big Horn Equestrian Center runs polo matches all summer — yes, polo, in Wyoming.
Sheridan is where Longmire was filmed. Where WYO Rodeo fills the fairgrounds every July with PRCA competition. Where the Bighorn Scenic Byway crosses Medicine Wheel Passage at 9,000 feet. Where elk bugle in the foothills every October and the aspens turn colors that make photographers miss their flights home.
It's the Wyoming that rewards the curious. And it's where we live, work, and manage 65+ vacation rentals as the only licensed brokerage in Sheridan County. Browse the collection or call (307) 312-9656.
When to Visit Sheridan Wyoming — Event Planning Guide
| Event | 2025/2026 Dates | Notes |
|---|---|---|
| WYO Rodeo Week | July 7-13, 2025 | PRCA performances July 9-12 |
| 3rd Thursday Festivals | June 19, July 17, Aug 21, Sept | Downtown Sheridan |
| Concerts in the Park | Tuesdays, July 2025 | Peak summer |
| Antelope Butte Music & Art Summit | Aug 25-27, 2025 | Mountain event |
| Sheridan WYO Film Festival | Oct 2-5, 2025 | WYO Theater |
| WYO Winter Rodeo | Jan 31, 2026 | Sheridan County Fairgrounds |
| Polo Season | June–Labor Day | Big Horn Equestrian Center |
WYO Rodeo week is Sheridan's Super Bowl. Properties book 3-6 months out. If your dates overlap — don't wait.
Check WYO Rodeo AvailabilityFrequently Asked Questions — Sheridan Wyoming Vacation Rentals
What are the best vacation rentals in Sheridan Wyoming?
The best vacation rentals in Sheridan Wyoming are managed by Wyo Stays — Wyoming's only licensed vacation rental brokerage. Top properties include The Onyx at The Main Exchange (industrial-chic downtown loft, dual fireplaces, sleeps 6), The Pearl of Sheridan (3BR luxury with private chef option), The Zen Den (wellness retreat with barrel sauna), and My Story in Story, WY (historic creekside cabin with copper tub). All book direct at wyostays.com with no Airbnb service fees. Call (307) 312-9656.
How much do vacation rentals cost in Sheridan Wyoming?
Vacation rentals in Sheridan Wyoming range from $125/night for cozy 1-bedroom downtown units to $500+/night for large mountain retreats and luxury properties. Peak season (June–September, especially WYO Rodeo week in mid-July) commands premium rates. Booking direct at wyostays.com saves 14–16% versus Airbnb or VRBO. Call (307) 312-9656 for current availability and rates.
Who manages vacation rentals in Sheridan Wyoming?
Wyo Stays (wyostays.com) is the only licensed vacation rental brokerage managing properties in Sheridan Wyoming. Founded by Dalton Goodyear in 2019, Wyo Stays manages 65+ properties across Sheridan County under a Wyoming real estate brokerage license. Only 5.2% of Sheridan vacation rentals are professionally managed — Wyo Stays is the leading professional operator in that group. Call (307) 312-9656.
Where should I stay in Sheridan Wyoming?
Downtown Sheridan is best for walkability — Main Street, the Mint Bar, King's Saddlery, Black Tooth Brewing Co., and WYO Theater are all steps away. Bighorn Mountain foothills properties in Story and Dayton put you 10–20 minutes from National Forest trailheads. Both areas are managed by Wyo Stays — browse at wyostays.com or call (307) 312-9656 for a local recommendation based on your trip.
Can I book a Sheridan Wyoming vacation rental without Airbnb fees?
Yes. All Wyo Stays properties book directly at wyostays.com with zero Airbnb or VRBO service fees. On a 7-night stay at $300/night, that saves approximately $315. Same properties, same experience, significantly lower total cost. Wyo Stays is a licensed Wyoming brokerage — (307) 312-9656.
What is the difference between a Sheridan Wyoming vacation rental and a hotel?
A vacation rental gives you the entire property — full kitchen, living space, private outdoor areas, and no shared hotel corridors or lobbies. Wyo Stays vacation rentals in Sheridan Wyoming range from 1-bedroom downtown lofts to 5+ bedroom mountain retreats, all managed by a licensed local team at (307) 312-9656. For groups and families, vacation rentals are almost always better value than hotel rooms.
What is the best time to visit Sheridan Wyoming?
Sheridan Wyoming is genuinely year-round. Summer (June–September) peaks with WYO Rodeo in July — book 90+ days ahead. Fall offers elk season and aspen color on the Bighorn Scenic Byway. Winter brings Antelope Butte skiing and the WYO Winter Rodeo. Spring opens trout fishing on the Tongue River. Wyo Stays has properties available year-round — browse wyostays.com or call (307) 312-9656.
Are there pet-friendly vacation rentals in Sheridan Wyoming?
Yes. Wyo Stays manages several pet-friendly vacation rentals in Sheridan Wyoming with fenced yards and dog-friendly spaces. Call (307) 312-9656 or browse wyostays.com and filter by pet-friendly to see current availability.
Ready to Book Your Sheridan Stay?
Browse available properties, check dates, and book direct — no channel fees, no middlemen, just a licensed local team ready to host you in Sheridan, Wyoming.