Sheridan, Wyoming · Tyler & Kayla Hert
Downtown Sheridan
vacation rentals.
A few days downtown. A place of your own.
Stay on Main Street or a short walk away in downtown Sheridan, Wyoming. Our six vacation rentals sleep two to eight guests, with kitchens, living space, and Tyler and Kayla as your local hosts.
Morning coffee, dinner with friends, a show at the WYO. Choose the beds, parking, and setting that suit your trip, then check your dates with us.
Six downtown homes
Compare six downtown Sheridan stays.
Space for the family, a king bed for each couple, or a small place for two. Every home below is personally hosted by Tyler and Kayla Hert of Late Checkout.
| Home | Guests | Bedrooms / baths | Main Street* | Dogs | Parking |
|---|---|---|---|---|---|
| New York Store Suite | 8 | 4 / 5 | At your door | No pets | One garage space |
| Pressroom Atelier | 8 | 3 / 2 | About 1 minute | $250/stay | One private space |
| Troubadour Suite | 2 | 1 / 1 | About 5 minutes | $75/stay | Off-street driveway |
| The Rambler | 2 | 1 / 1 | About 5 minutes | $75/stay | Street parking |
| The Alderman | 4 | 2 / 1 | About 10 minutes | $75/stay | Driveway + two-car garage |
| The Van Winkle House | 4 | 2 / 1 | One block away | $75/stay · Up to 2 pets | Two-car driveway |
*Walking times are approximate host estimates to Main Street. Times to individual businesses vary. All six homes have stairs. Pet fees are per stay; confirm dog limits and other requirements before booking.
Choose your part of downtown
On Main Street, or a little removed.
The right downtown address depends on how you want to spend your days. Here is how we would narrow down these six homes.
Main Street at your door.
The New York Store Suite is on Main Street, across from the WYO Theater. The Pressroom Atelier is about a minute from Main, beside Bison Union and near the Mint Bar. Both sleep eight; compare bedrooms, bathrooms, and stairs before choosing.
A smaller place for two.
The Troubadour Suite and The Rambler are separate homes in the same building, about five minutes from Main Street. Choose a queen bedroom and driveway parking at Troubadour, or a king bed and basement setting at Rambler.
A yard and two king beds.
The Alderman is about a ten-minute walk from Main Street, with two king bedrooms, a private fenced yard, and a two-car garage. It is a comfortable option for two couples who want a quieter base.
The Van Winkle House is another option for up to four, one block off Main Street. It has a queen bedroom and a full-size Murphy bed in the second bedroom, so it works particularly well for a couple with children.
Walking times are approximate host estimates to Main Street, not to every downtown business. Check your route and allow for weather, stairs, and your group’s mobility.
Your Sheridan address
Six homes on and near Main Street.
Take a closer look at the beds, outdoor space, parking, and little things worth knowing before you arrive.
On Main Street · Sleeps 8
The New York Store Suite
A grand second-story home directly across from the WYO Theater. Four bedrooms and five bathrooms give families and friends room to settle in, with Main Street at the front door.
1 king · 2 queens · twin loft/bunk sleeping
One private garage space · No pets
Access, parking & things to know
- Access
- A large flight of stairs to the second story; no elevator.
- Parking
- One space in a private garage.
- Outside
- No outdoor space.
- Setting
- Allure boutique shares a wall with the TV area; otherwise generally quiet.
About 1 minute to Main Street · Sleeps 8
The Pressroom Atelier
A downtown home with two private patios, two king beds, and room for the family. Bison Union is a neighbor, and the Mint Bar is nearby for an evening out.
2 kings · 4 Twin XL mattresses in two bunk units
One private parking space · Dogs: $250/stay
Access, parking & things to know
- Access
- Approximately 20 steps; no elevator.
- Parking
- One private space at the entrance.
- Outside
- Two private patios; no yard.
- Setting
- The Mint can be lively in the evening. The interior is generally very quiet.
About 5 minutes to Main Street · Sleeps 2
The Troubadour Suite
A small home with thoughtful details for a couple, a work trip, or a night passing through. Near Whitney Commons and The Hub on Smith, with off-street parking.
1 queen · No sofa bed
Shared yard · Dogs: $75/stay
Access, parking & things to know
- Access
- Four steps at the front or back entrance.
- Parking
- Off-street parking in a long driveway.
- Outside
- Yard shared with The Rambler, in the same building.
- Setting
- Occasional traffic on the road toward the nearby YMCA.
About 5 minutes to Main Street · Sleeps 2
The Rambler
A compact basement home with a king bed and a convenient base near downtown. Shares a building and yard with The Troubadour Suite.
1 king · No sofa bed
Street parking · Dogs: $75/stay
Access, parking & things to know
- Access
- Six steps down into the basement home.
- Parking
- Street parking.
- Outside
- Yard shared with The Troubadour Suite.
- Setting
- Near Whitney Commons and The Hub on Smith. Occasional traffic toward the YMCA.
About 10 minutes to Main Street · Sleeps 4
The Alderman
A quiet home off the main drag, with two king bedrooms, a generous curved couch, and a large private fenced yard. A comfortable choice for two couples or a smaller family.
2 kings · No sofa bed
Two-car garage + driveway · Dogs: $75/stay
Access, parking & things to know
- Access
- Four entrance steps; level inside.
- Parking
- Driveway parking and a private two-car garage.
- Outside
- Large private fenced yard.
- Setting
- Near Coffeen and Wyoming. Sackett’s Market is our suggestion for lunch or groceries.
One block off Main Street · Sleeps 4
The Van Winkle House
Original wood trim, pressed-tin-style ceilings, and a gas fireplace give this house its character. There’s a full kitchen, a washer/dryer, and a deck with a grill. Kendrick Park and Whitney Commons are an easy walk.
1 queen · 1 full-size Murphy bed
Two-car driveway · Up to 2 pets: $75/stay
Access, parking & things to know
- Beds & bath
- The full-size Murphy bed suits kids or one adult best; four adults should expect cozy sleeping. Both bedrooms connect to the shared bathroom, which has a walk-in shower.
- Access
- Four entrance steps; not step-free. The basement and garage are owner storage and off-limits.
- Parking
- Private driveway for two cars.
- Outside
- Deck with a grill. The private fenced yard is about 20 feet from the house, not attached; the walk is flat and lit by a street light at night.
- Pets
- Up to two pets welcome for a one-time $75 fee. Dogs may stay inside and must be crated if left unattended indoors.
- Cooling
- Mini split A/C in the queen bedroom only; ceiling fans in the other rooms.
- Setting
- Older windows can let in road noise. A sound machine is provided in the queen bedroom.
- Cleaning
- $125 per stay. Check the full total and booking terms on the property page.
No homes here fit that combination. Change your filters or explore the full Collection.
Filters match your group to the homes; they do not show live availability. Open a home to check your dates.
A different way to stay
Considering a hotel near downtown Sheridan?
A hotel may suit a trip when you want a staffed front desk or particular on-site services. A vacation rental gives you a kitchen and living space of your own, with separate bedrooms in the larger homes.
Our downtown collection ranges from one-bedroom places for two to homes that sleep eight. Compare the sleeping arrangements, stairs, and parking alongside the total for your dates. That is more useful than comparing nightly rates alone.
An evening on Main Street
Stay near the Mint Bar.
Looking for a vacation rental near the Mint Bar in downtown Sheridan? Start with The Pressroom Atelier, beside Bison Union and near the Mint, or The New York Store Suite, on Main Street across from the WYO Theater.
Both sleep eight and are personally hosted by Late Checkout. For a smaller stay, Troubadour and Rambler each sleep two, about a five-minute walk from Main Street.
Bring the family. Make a week of it.
A downtown base for WYO Rodeo.
For a family of eight attending Sheridan WYO Rodeo, The New York Store Suite and The Pressroom Atelier each offer room for everyone under one roof. Choose the sleeping arrangement that fits your group, then check your dates.
4 bedrooms · 5 bathrooms · Sleeps 8
The New York Store Suite
One king, two queens, and twin loft/bunk sleeping. Main Street at your door, one private garage space, and room to gather between outings. No pets; access is by a large flight of stairs.
View New York Store Suite & dates →3 bedrooms · 2 bathrooms · Sleeps 8
The Pressroom Atelier
Two kings and four Twin XL mattresses in two bunk units. Two private patios and one private parking space. Dogs welcome with a $250 fee per stay; access includes approximately 20 steps.
View Pressroom Atelier & dates →The neighborhood, at your pace
Things to do in downtown Sheridan.
Coffee, restaurants, shops, and a few places for a slower afternoon. These are our personal picks and downtown essentials, with links to each business for current hours and plans. For outings farther afield, explore our Sheridan map and local guide.
Choose a home for a neighborhood note.
Our pick · Coffee
Java Moon
Coffee and a pastry on Main Street. Choose this location rather than Java Moon Station on Coffeen.
Coffee
Bison Union
A coffee stop next to the Pressroom, with coffee roasted on Main Street.
Our pick · Dinner
Frackelton’s
Our suggestion for dinner with friends. View the menu and book a table directly.
Our pick · Lunch & groceries
Sackett’s Market
A quick lunch or good ingredients to take home: sandwiches, deli goods, and groceries.
Our pick · Drinks
The Mint Bar
A favorite place for a beer in a historic Sheridan bar. Evenings can be lively.
Our pick · Wine & provisions
Verdello
Wine, olive oils, vinegars, and provisions for an evening in. Check for tastings and cooking classes.
Our pick · Our family’s shop
Real Deals
Our home décor and fashion shop, and part of what brought us to the Troubadour and Rambler property.
Breakfast & lunch
Cowboy Cafe
A Main Street café for a sit-down meal during your downtown outing.
Food & beer
Smith Alley Brewing
Food, house-brewed beer, and a game room. Ask about current access to the dog-friendly outdoor patio.
Drinks
Black Tooth Brewing
A Sheridan brewery stop for locally brewed beer. See the taproom’s current offerings.
Dinner
Le Rêve
French-inspired cooking at Main and Alger for an evening out. Visit the website for reservations.
Performing arts
WYO Theater
A performance directly across from the New York Store Suite. Choose your show, then make dinner plans.
Western history & shops
King’s Saddlery
Western tack, saddles, and cowboy history. Leave time to explore the Don King Museum.
Walks & history
Historic streets & public art
Explore the buildings and public art using the Downtown Sheridan Association’s self-guided resources.
Parks
Whitney Commons
Gardens, paths, and a playground near Troubadour and Rambler. Keep dogs leashed; spray grounds are seasonal.
Arts
SAGE Community Arts
See an exhibition or browse the art-class schedule. A good indoor stop downtown.
Arts & shops
Red Bison Studio
Handmade ceramics and wildlife-inspired pieces from a Sheridan studio.
Books & gifts
Sheridan Stationery
Books and gifts farther north on Main Street, for a slower afternoon of browsing.
Parks
Kendrick Park
Extend your downtown outing to the park. Check seasonal schedules for Scoops and the pool.
History
Trail End
A historic-house visit beyond the Main Street core. Check seasonal opening and access information.
No places match. Clear your search or choose another category.
Walking directions open Google Maps so you can choose your starting point. Selecting a home above provides a neighborhood note, not a calculated route.
A little time out.
A morning downtown
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 the show first, then book dinner.
An afternoon browsing
Our family’s Real Deals shop, SAGE, and 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.
Your hosts in Sheridan
We live here. We’ll help you choose.
We’re Tyler and Kayla Hert. Tell us who is coming and what matters—a king bed for each couple, a place for the dog, or Main Street at your door. We will point you toward the home that fits.
Before you settle on a home
Good to know.
Are these hotels or vacation rentals?
These are six individually hosted vacation rentals on or near Main Street in Sheridan, Wyoming. Each has a kitchen and living space. Choose a one-bedroom home for two, a two-bedroom home for four, or a larger home for up to eight guests. Open the property page for dates and booking terms.
Where can we stay near the WYO Theater and downtown restaurants?
The New York Store Suite is on Main Street directly across from the WYO Theater. The Pressroom Atelier is about a minute from Main Street, beside Bison Union and near the Mint Bar. Both sleep eight. Our downtown guide includes Frackelton’s, Java Moon, and other places to eat and explore.
Which Late Checkout homes are closest to Main Street?
The New York Store Suite is on Main Street. The Pressroom Atelier is about a one-minute walk away. The Van Winkle House is one block off Main Street. Troubadour and Rambler are about five minutes away; The Alderman is about ten minutes away. These are approximate host estimates to Main Street.
Which vacation rentals are near the Mint Bar?
The Pressroom Atelier is beside Bison Union and near the Mint. The New York Store Suite is on Main Street across from the WYO Theater. Both sleep eight. Check the route to 151 N Main Street from your chosen home; our Main Street estimates are not exact Mint Bar walking times.
Where can a family of eight stay for Sheridan WYO Rodeo?
The New York Store Suite has four bedrooms and five bathrooms. The Pressroom Atelier has three bedrooms and two bathrooms, with two kings and four Twin XL bunk mattresses. Each sleeps eight and has stairs. Check date availability on the property pages and arrange transportation to performances at the Sheridan County Fairgrounds.
Which home has two king bedrooms and a fenced yard?
The Alderman sleeps four, with two king bedrooms, one bathroom, a large private fenced yard, driveway parking, and a private two-car garage. Dogs are welcome with a $75 fee per stay.
Can I bring a dog?
Troubadour, Rambler, Alderman, and Van Winkle welcome dogs with a $75 pet fee per stay. Van Winkle allows up to two pets; dogs left unattended indoors must be crated. The Pressroom’s pet fee is $250 per stay. The New York Store Suite does not allow pets. Confirm any dog limits and additional requirements before booking.
Do these homes have stairs?
Yes. Van Winkle and Troubadour each have four entrance steps; Rambler has six steps down into the basement; Alderman has four entrance steps and 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. The Pressroom has two king beds plus four Twin XL bunk mattresses, across three bedrooms with two bathrooms. The New York Store Suite has four bedrooms and five bathrooms, with one king, two queens, and twin loft/bunk sleeping.
Are Troubadour and Rambler connected?
They are separate homes in the same building, with a shared yard. Each sleeps two. Check and book both separately if you want both homes; one reservation does not include the other.
Can we explore downtown without driving?
All six homes put Main Street within an approximate ten-minute walk or closer. Weather and mobility will affect what feels comfortable. Plan transportation for outings beyond downtown, including the fairgrounds, Big Horn, and the mountains.
Who hosts these rentals, and how do we book directly?
Tyler and Kayla Hert of Late Checkout personally host all six homes. Use the “View home & dates” links to explore each property and check booking information, or call us at 307.217.6516.
Find your kind of Sheridan.
Tell us who’s coming and what matters. We’ll help you choose.