House in Cadillac, MI
16 guests · 6 bedrooms · 3 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Top-tier experienceA high end property in this area
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About this house rental
Pool~~~~~~~~~~Downtown
Hot Tub~~~~~~~~~~2 Blocks to Lake
Speakeasy~~~~~~~~6 Bedrooms
Arcades~~~~~~~~~~Waterfall Pond
Fireplace~~~~~~~~~19 miles to Caberfae Peaks
Cornhole~~~~~~~~~Propane Grill
Theater Room~~~~~Wood Fire Pizza Oven
Pool Table~~~~~~~~Coffee & Cereal Bar
Board Games~~~~~Alexa Speakers
Fire-pit~~~~~~~~~~~Chef’s Kitchen
WELCOME TO THE ROOSEVELT: Cadillac's Most Luxurious & Historic Downtown Retreat
Step into a one-of-a-kind Northern Michigan escape combining restored historic charm with modern luxury. Located just one block off Main Street, The Roosevelt puts you steps from Cadillac’s best restaurants, breweries, boutiques, and lakefront attractions — all while offering your own private pool, year-round hot tub, brick oven pizza maker, and a hidden speakeasy unlike anything else in town.
Whether you’re planning a family vacation, a friends’ weekend, a golf or ski trip, or a relaxing retreat, this home delivers unforgettable comfort and entertainment in every season.
PROPERTY HIGHLIGHTS
RESORT-LEVEL OUTDOOR LIVING
* Private Pool (open 5/8–Labor Day)
* Year-Round Hot Tub for stargazing and snowy-night soaks
* Wood-Fired Brick Pizza Oven — create your own gourmet pies
* Fully Fenced Backyard - high privacy walls
* Outdoor Dining & Lounging with string lights and gas tiki torches
* 3-Stall Heated Garage for cars, gear, and winter convenience
Two blocks from Lake Cadillac — perfect for boating, beach days, and waterfront sunsets.
HIDDEN SPEAKEASY AND GAME LOUNGE
Welcome to your private underground hangout:
* 85” Theater TV for movies & game days
* Pool Table for late-night competitions
* Cozy bar-style seating and moody speakeasy lighting
* Your own “secret” entrance vibe — a true guest-favorite experience
* Arcade Machines - NBA Jam and Ms.Pac Man/Galaga
Perfect for gatherings, movie nights, or just unwinding after exploring Cadillac.
CHEF'S KITCHEN AND ENTERTAINING SPACES
Create, cook, and connect in a kitchen built for hosting:
* Professional Cooktop & Premium Appliances
* Coffee & Wine Bar (complimentary coffee included!)
* Large island perfect for groups
* Beautiful dining area for shared meals
Ideal for holidays, celebrations, or weekend feasts with friends and family.
6 BEDROOMS — SLEEPS LARGE GROUPS COMFORTABLY
Room for everyone, thoughtfully designed for comfort:
* Primary Suite — King bed, patio access
* Bedroom 2 — Two Queen beds
* Bedroom 3 — Queen bed
* Bedroom 4 — Two Bunk Beds (kid-approved!)
* Bedroom 5 — Two Twin beds
* Bedroom 6 — King bed with lake view
Perfect for multi-family trips, retreats, or larger gatherings.
LOCATION PERKS — WALK TO EVERYTHING
* 1 block – Downtown Cadillac (restaurants, shops, breweries, coffee, nightlife)
* 2 blocks – Lake Cadillac (beach, marina, park, lakefront path, White Pine trail)
* 5 min – Kenwood Beach & Boat Launch
* 8 min – Adventure Island Theme Park
* 9 min – Mitchell State Park
* 10 min – Mountain Biking at Cadillac Pathway
* 25 min – Caberfae Peaks Ski Resort
* 50 min – Crystal Mountain Ski Resort
* 1 hour – Traverse City (wineries, dining, festivals, airport)
A perfect base for skiing, boating, hiking, biking, fishing, snowmobiling, golfing, or relaxing by the pool.
FOUR-SEASON ADVENTURE HUB
Summer: boating & jet skiing (rentals available nearby), swimming, hiking, beaches
Fall: color tours, local breweries, golf, scenic drives, biking the 92 mile White Pine Trail
Winter: Caberfae Peaks skiing, x-country skiing, snowmobiling (rentals available nearby), ice fishing Spring: trails, fishing, brewery hopping, quiet getaways, biking the 92 mile White Pine Trail
Your garage offers easy storage for boats, bikes, trailers, snowmobiles, and adventure gear.
PARKING MADE EASY
* Heated 3-stall garage
* Spacious driveway Total room for 6+ vehicles, trailers, or adventure gear.
*Additional parking available on the public lot across the street
GOOD TO KNOW
* No smoking ($750+ extra cleaning fee if violated)
* No parties (immediate eviction)
* No pets
* Pool cleaned weekly (Fridays)
* Rental Agreement and liability waiver required upon booking
* Late checkout without approval = $150+
Safety first: children must be supervised at all times
YOUR LUXURY DOWNTOWN CADILLAC RETREAT AWAITS
Relax by the pool, walk to dinner, unwind in the speakeasy, or soak under the stars — The Roosevelt offers a truly unique blend of history, luxury, and unbeatable location.
Book your stay now and experience Cadillac’s most iconic, amenity-packed retreat!
Hot Tub~~~~~~~~~~2 Blocks to Lake
Speakeasy~~~~~~~~6 Bedrooms
Arcades~~~~~~~~~~Waterfall Pond
Fireplace~~~~~~~~~19 miles to Caberfae Peaks
Cornhole~~~~~~~~~Propane Grill
Theater Room~~~~~Wood Fire Pizza Oven
Pool Table~~~~~~~~Coffee & Cereal Bar
Board Games~~~~~Alexa Speakers
Fire-pit~~~~~~~~~~~Chef’s Kitchen
WELCOME TO THE ROOSEVELT: Cadillac's Most Luxurious & Historic Downtown Retreat
Step into a one-of-a-kind Northern Michigan escape combining restored historic charm with modern luxury. Located just one block off Main Street, The Roosevelt puts you steps from Cadillac’s best restaurants, breweries, boutiques, and lakefront attractions — all while offering your own private pool, year-round hot tub, brick oven pizza maker, and a hidden speakeasy unlike anything else in town.
Whether you’re planning a family vacation, a friends’ weekend, a golf or ski trip, or a relaxing retreat, this home delivers unforgettable comfort and entertainment in every season.
PROPERTY HIGHLIGHTS
RESORT-LEVEL OUTDOOR LIVING
* Private Pool (open 5/8–Labor Day)
* Year-Round Hot Tub for stargazing and snowy-night soaks
* Wood-Fired Brick Pizza Oven — create your own gourmet pies
* Fully Fenced Backyard - high privacy walls
* Outdoor Dining & Lounging with string lights and gas tiki torches
* 3-Stall Heated Garage for cars, gear, and winter convenience
Two blocks from Lake Cadillac — perfect for boating, beach days, and waterfront sunsets.
HIDDEN SPEAKEASY AND GAME LOUNGE
Welcome to your private underground hangout:
* 85” Theater TV for movies & game days
* Pool Table for late-night competitions
* Cozy bar-style seating and moody speakeasy lighting
* Your own “secret” entrance vibe — a true guest-favorite experience
* Arcade Machines - NBA Jam and Ms.Pac Man/Galaga
Perfect for gatherings, movie nights, or just unwinding after exploring Cadillac.
CHEF'S KITCHEN AND ENTERTAINING SPACES
Create, cook, and connect in a kitchen built for hosting:
* Professional Cooktop & Premium Appliances
* Coffee & Wine Bar (complimentary coffee included!)
* Large island perfect for groups
* Beautiful dining area for shared meals
Ideal for holidays, celebrations, or weekend feasts with friends and family.
6 BEDROOMS — SLEEPS LARGE GROUPS COMFORTABLY
Room for everyone, thoughtfully designed for comfort:
* Primary Suite — King bed, patio access
* Bedroom 2 — Two Queen beds
* Bedroom 3 — Queen bed
* Bedroom 4 — Two Bunk Beds (kid-approved!)
* Bedroom 5 — Two Twin beds
* Bedroom 6 — King bed with lake view
Perfect for multi-family trips, retreats, or larger gatherings.
LOCATION PERKS — WALK TO EVERYTHING
* 1 block – Downtown Cadillac (restaurants, shops, breweries, coffee, nightlife)
* 2 blocks – Lake Cadillac (beach, marina, park, lakefront path, White Pine trail)
* 5 min – Kenwood Beach & Boat Launch
* 8 min – Adventure Island Theme Park
* 9 min – Mitchell State Park
* 10 min – Mountain Biking at Cadillac Pathway
* 25 min – Caberfae Peaks Ski Resort
* 50 min – Crystal Mountain Ski Resort
* 1 hour – Traverse City (wineries, dining, festivals, airport)
A perfect base for skiing, boating, hiking, biking, fishing, snowmobiling, golfing, or relaxing by the pool.
FOUR-SEASON ADVENTURE HUB
Summer: boating & jet skiing (rentals available nearby), swimming, hiking, beaches
Fall: color tours, local breweries, golf, scenic drives, biking the 92 mile White Pine Trail
Winter: Caberfae Peaks skiing, x-country skiing, snowmobiling (rentals available nearby), ice fishing Spring: trails, fishing, brewery hopping, quiet getaways, biking the 92 mile White Pine Trail
Your garage offers easy storage for boats, bikes, trailers, snowmobiles, and adventure gear.
PARKING MADE EASY
* Heated 3-stall garage
* Spacious driveway Total room for 6+ vehicles, trailers, or adventure gear.
*Additional parking available on the public lot across the street
GOOD TO KNOW
* No smoking ($750+ extra cleaning fee if violated)
* No parties (immediate eviction)
* No pets
* Pool cleaned weekly (Fridays)
* Rental Agreement and liability waiver required upon booking
* Late checkout without approval = $150+
Safety first: children must be supervised at all times
YOUR LUXURY DOWNTOWN CADILLAC RETREAT AWAITS
Relax by the pool, walk to dinner, unwind in the speakeasy, or soak under the stars — The Roosevelt offers a truly unique blend of history, luxury, and unbeatable location.
Book your stay now and experience Cadillac’s most iconic, amenity-packed retreat!
Amenities at Incredible Downtown 6 bedroom with Pool, Hot Tub, Waterfall, Arcades & Speakeasy
Non-smoking
No pets allowed
Family friendly
Map of Cadillac, MI
Ratings and reviews
10 / 10Outstanding·Feb 2026
The cabin provided nicely for our family. We were there for a ski weekend at Cabaret. We enjoyed the hot tub and fire pit in the evening. We could walk downtown Cadillac. Also the game room in the basement was a hit with my grandkids.Sam and Jesse, our hosts were very responsive to any questions we had. They were great hosts.
$$$$
Top rated by guests
10Outstanding
(2 Ratings)
"The cabin provided nicely for our family. We were there for a ski weekend at Cabaret. We enjoyed the hot tub and fire pit in the evening. We could walk downtown Cadillac. Also the game room in the bas..."
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