Sheridan, Wyoming · Personally hosted
A few days
downtown.
Places to stay in and around downtown Sheridan, Wyoming.
Coffee on Main Street. An evening at the WYO. A place of your own to come back to. Explore our homes and plan a little of your time here.
Explore the homes ↓
Your Sheridan address
Stay on Main. Or a short walk away.
Choose a home for your trip. Walking times to Main Street are approximate host estimates.
On Main Street · Sleeps 8
The New York Store
Main Street at your front door
A spacious second-story home with a grand presence and a long history. Across from the WYO Theater, with room for families or couples traveling together.
4 bedrooms · 1 king, 2 queens, twin loft/bunk sleeping
5 bathrooms
A few things to know
- Access
- A large flight of stairs to the second story; no elevator.
- Parking
- One space in a private garage.
- Pets
- No pets.
- Outside
- No outdoor space.
- Also worth knowing
- Allure boutique shares a wall with the TV area; otherwise generally quiet.
The WYO is directly across the street. Frackelton’s is our suggestion for dinner with friends.
Downtown · Sleeps 8
The Pressroom
About 1 minute to Main Street
A carefully considered downtown home with two private patios. A beautiful base for families or two couples, with space for eight guests.
3 bedrooms · 2 kings + 4 Twin XL mattresses in two bunk units
2 bathrooms
A few things to know
- Access
- Approximately 20 steps; no elevator.
- Parking
- One private parking space at the entrance.
- Pets
- Dogs welcome · $250 pet fee per stay.
- Outside
- Two private patios; no yard.
- Also worth knowing
- The Mint can be lively in the evening. The interior is generally very quiet.
Bison Union is a neighbor. The Mint is a favorite place for a beer.
Near downtown · Sleeps 2
The Troubadour
About 5 minutes to Main Street
A small home with thoughtful details, suited to couples, work trips, or a night passing through. Shares a building and yard with the Rambler.
1 bedroom · 1 queen
1 bathroom
A few things to know
- Access
- Four steps at the front or back entrance.
- Parking
- Off-street parking in a long driveway.
- Pets
- Dogs welcome · $75 pet fee per stay.
- Outside
- Shared yard.
- Also worth knowing
- Occasional traffic on the road toward the nearby YMCA. No sofa bed.
Near Whitney Commons and The Hub on Smith. Java Moon is our suggestion for a quick coffee or pastry.
Near downtown · Sleeps 2
The Rambler
About 5 minutes to Main Street
A compact basement home for two, with a king bed and a convenient base near downtown. Shares a building and yard with the Troubadour.
1 bedroom · 1 king
1 bathroom
A few things to know
- Access
- Six steps down into the basement home.
- Parking
- Street parking.
- Pets
- Dogs welcome · $75 pet fee per stay.
- Outside
- Shared yard.
- Also worth knowing
- Occasional traffic on the road toward the nearby YMCA. No sofa bed.
Near Whitney Commons and The Hub on Smith. Real Deals is part of our family’s story here.
Near downtown · Sleeps 4
The Alderman
About 10 minutes to Main Street
A quiet home off the main drag, with a large fenced yard, a generous curved couch, and lovely linens. Well suited to two couples or a smaller family.
2 bedrooms · 2 kings
1 bathroom
A few things to know
- Access
- Four entrance steps; level inside.
- Parking
- Driveway parking plus a private two-car garage.
- Pets
- Dogs welcome · $75 pet fee per stay.
- Outside
- Large private fenced yard.
- Also worth knowing
- Near Coffeen and Wyoming. No sofa bed.
Sackett’s Market is our suggestion for lunch or good groceries to take home.
No homes in this selection fit those needs. Try a smaller group or explore the full Collection.
These filters show which homes suit your group, not live availability. Check dates on the individual home’s page.
The neighborhood, at your pace
A few places to spend your time.
Our picks sit alongside other useful downtown stops. Each place links to its own current information.
Choose a home for a neighborhood note.
Our pick
Java Moon
Coffee and a pastry on Main Street. Choose this location rather than Java Moon Station on Coffeen.
Around town
Bison Union
A coffee stop next to the Pressroom, with coffee roasted on Main Street.
Our pick
Frackelton’s
Our suggestion for dinner with friends. View the current menu and book a table directly.
Our pick
Sackett’s Market
A quick lunch or good ingredients to take back to the house: sandwiches, deli goods and groceries.
Our pick
The Mint Bar
A favorite place for a beer, in a historic Sheridan bar. Evenings can be lively.
Our pick
Verdello
Wine, olive oils, vinegars and provisions for an evening in. Check the shop’s site for tastings and cooking classes.
Our pick
Real Deals
Our family’s home décor and fashion shop. It is part of what brought us to the Troubadour and Rambler property.
Around town
Cowboy Cafe
A café option on Main Street when you want to sit down for a meal.
Around town
Smith Alley Brewing
Food, house-brewed beer, a game room and a dog-friendly outdoor patio. Check patio availability with the restaurant.
Around town
Black Tooth Brewing
A Sheridan brewery stop for locally brewed beer. See the taproom’s current offerings.
Around town
Le Rêve
A more formal dinner option, with French-inspired cooking at Main and Alger. Reservations are available on its website.
Around town
WYO Theater
Plan an evening around a performance, directly across from the New York Store. Check the program before making plans.
Around town
King’s Saddlery & Don King Museum
Western tack, saddles and cowboy history. A downtown stop for browsing and exploring the museum.
Around town
Historic streets & public art
Explore downtown buildings and public art with the Downtown Sheridan Association’s self-guided resources.
Around town
Whitney Commons
Gardens, paths and a playground near Troubadour and Rambler. Dogs must be leashed; spray grounds are seasonal.
Around town
SAGE Community Arts
See an exhibition or browse the art-class schedule. A useful indoor stop downtown.
Around town
Red Bison Studio
Handmade ceramics and wildlife-inspired pieces from a Sheridan studio.
Around town
Sheridan Stationery Books & Gifts
A bookstore stop farther north on Main Street, for a slower afternoon of browsing.
Around town
Kendrick Park
Extend your downtown outing to the park. Check seasonal schedules for Scoops and the pool.
Around town
Trail End
A historic-house visit beyond the Main Street core. Check seasonal opening and access information before setting out.
No places match. Try another category or clear your search.
Walking directions open in Google Maps, where you can choose your starting point. Check each business’s website for current hours, menus and reservations.
No packed itinerary required
A little time out.
A morning downtown
Coffee at Java Moon, a stroll past historic buildings and public art, then King’s Saddlery.
Dinner and a show
Frackelton’s and a performance at the WYO. Choose your show first, then make dinner plans.
An afternoon browsing
Our family’s Real Deals shop, SAGE and a stop at Verdello for something to take home.
Out with the dog
A leashed walk at Whitney Commons, then Smith Alley’s outdoor patio when available.
Suggested combinations, not timed routes. Check opening days, seasonal access and performance schedules.
For later
Your downtown list.
Saved on this browser. Copy the list to send it to someone traveling with you.
Before you settle on a home
Good to know.
Which homes are downtown?
The New York Store has its entrance on Main Street. The Pressroom is about a minute from Main Street. Troubadour and Rambler are about a five-minute walk away; the Alderman is about ten minutes away.
Can I bring a dog?
Troubadour, Rambler and Alderman welcome dogs with a $75 pet fee per stay. The Pressroom’s pet fee is $250 per stay. The New York Store does not allow pets. Confirm any additional requirements before booking.
Do these homes have stairs?
Yes. Troubadour has four entrance steps, Rambler has six steps down into the basement, and Alderman has four entrance steps with a level interior. New York Store and Pressroom have longer flights of stairs and no elevators.
Can two couples stay together?
The Alderman has two king bedrooms and one bathroom. Pressroom sleeps eight across three bedrooms, with two kings and four Twin XL mattresses in two bunk units. New York Store sleeps eight with four bedrooms and five bathrooms.
Are Troubadour and Rambler connected?
They are separate homes in the same structure, with a shared yard. Each sleeps two. Check availability for both separately; booking one does not include the other.
Can we explore without driving?
These homes put Main Street within an approximate ten-minute walk or closer, according to our host estimates. Your comfort walking will depend on weather and mobility. Plan transportation for trips beyond downtown.
Where do we check dates?
Open the individual home using Check In to view its booking information. This guide helps you choose a home and plan downtown stops; it does not display live availability.