Incredible Downtown 6 bedroom with Pool, Hot Tub, Waterfall, Arcades & Speakeasy

Cadillac, Michigan
$1230 avg/night
Bed 6

Bed

Bath 3

Bath

Home Private Vacation Home

Property Type

Sleep 16

Max Sleeps

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!

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • SKI

    Cross-country Skiing And Snowboarding Nearby
  • PETS

    No Pets Allowed
  • BEACH

    Beach Sun Loungers Beach Towels
  • DINING

    Dining Table Free Breakfast Available
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Deadbolt Lock Fire Extinguisher First Aid Kit Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    6 Bedrooms Bed Sheets Provided
  • GENERAL

    Unit Size: 4000 Sq Ft (372 Sq M)
  • KITCHEN

    Dishwasher Electric Kettle Lobster/crab Pot Microwave Oven Paper Towels Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking Onsite Parking Options Include A Garage
  • INTERNET

    Free WiFi, With Speed Of 500+ Mbps (good For 6+ People Or 10+ Devices)
  • OUTDOORS

    Balcony Barbecue Grill Firepit Garden Outdoor Furniture
  • POOL/SPA

    Heated Pool Hot Tub Outdoor Pool
  • BATHROOMS

    3 Bathrooms Hair Dryer Shampoo Shower Soap Toilet Paper Towels Provided
  • WORKSPACES

    Desk Desk Chair
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Ecotours Nearby Golf Nearby Hiking Nearby Hunting Nearby Jet Skiing Nearby Power Boating Nearby Swimming Nearby Theme Parks Nearby Wildlife And Game Walks Nearby
  • ENTERTAINMENT

    Arcade/game Room Books Games Pool Or Billiards Table Stereo Smart TV
  • LIVING SPACES

    Dining Room Fireplace Living Room Wood Stove
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Children's Dinnerware Children's Games Highchair
  • LOCATION HIGHLIGHTS

    In The City Center Near A Health Or Beauty Spa Near A Hospital On The Lake
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Area Rugs In Public Areas Hardwood Flooring In Public Areas If You Have Requests For Specific Accessibility Needs, Please Contact The Property Using The Information On The Reservation Confirmation Received After Booking. No Elevators Smoke-free Property Tile Flooring In Public Areas Well-lit Path To Entrance

CheckIn Check-in : 04:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 16

Map Map

School District Rates & Availability

Review Review

  • Barb H.

    Submitted Feb 16, 2026

    Stayed Feb 13, 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.

Your dates are Available!

Total

Includes taxes and fees
$1,230+
View details