Downtown~Historic~HotTub~Fireplace~Speakeasy
About
🧖♀️Hot Tub 🍻Downtown ⛱️Pool 🐟2 Blocks to Lake 🥃Speakeasy 🛌 6 Bedrooms - Sleeps 16 🔥Fireplace ⛷️19 miles to Caberfae Peaks 🌽Cornhole 🕹️Arcade Games 🍿Theater Room 🍕Wood Fire Pizza Oven 🎱Pool Table ☕Coffee & Cereal Bar ♟️Board Games 🎵Alexa Speakers 🔥Fire-pit 🍳Chef’s Kitchen 🍔Propane Grill 🚴2 Blocks to White Pine Trail
Good to know
✨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 the area. 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 * 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 & 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 Perfect for gatherings, movie nights, or just unwinding after exploring Cadillac. 🍳 Chef’s Kitchen & 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. ⚠️ 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 Escape 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!
Other Details to Note
Some very basic rules for the home and grounds: - Must be 25 years or older to book - Max occupancy is 16 (plus infants or toddlers) - NO smoking - NO drugs - NO pets - NO parties - Don't take or break items - Be respectful of our property - we love it dearly and want you, other guests, and our family to continue to make wonderful memories in the home. - Check in is at 4:00 PM - Check out is at 10:00 AM Please note, a rental agreement, refundable security deposit, and liability waiver are required. The security deposit is collected via an online guest portal and is deducted from your card 2 days before check-in. It is refunded 2-days after check out, provided there is no damage to the property. It is our goal NOT to keep any of your deposit, and we will not nickel and dime you - it's really there just for significant damage.
Availability
What this place offers
Amenities
Common
- Air conditioning
- Cooking basics Pots and pans, oil, salt and pepper
- Dishes and silverware
- Dryer In the building, free or for a fee
- Essentials Towels, bed sheets, soap, toilet paper, and pillows
- Hair dryer
- Heating Central heating or a heater in the listing
- Hot tub
- Kitchen Space where guests can cook their own meals
- Dedicated workspace
- Pool
- TV
- Washing Machine
- Wifi
Outdoors
- Alfresco dining
- BBQ
- Fire pit
- Garden or backyard
- Outdoor seating
- Patio
- Sun loungers
Kitchen and dining
- Baking sheet
- Barbecue utensils
- Blender
- Coffee
- Coffee maker
- Dining table
- Dishwasher
- Freezer
- Microwave
- Oven
- Refrigerator
- Stove
- Toaster
- Wine glasses
Common
- Air conditioning
- Cooking basics Pots and pans, oil, salt and pepper
- Dishes and silverware
- Dryer In the building, free or for a fee
- Essentials Towels, bed sheets, soap, toilet paper, and pillows
- Hair dryer
- Heating Central heating or a heater in the listing
- Hot tub
- Kitchen Space where guests can cook their own meals
- Dedicated workspace
- Pool
- TV
- Washing Machine
- Wifi
Outdoors
- Alfresco dining
- BBQ
- Fire pit
- Garden or backyard
- Outdoor seating
- Patio
- Sun loungers
Kitchen and dining
- Baking sheet
- Barbecue utensils
- Blender
- Coffee
- Coffee maker
- Dining table
- Dishwasher
- Freezer
- Microwave
- Oven
- Refrigerator
- Stove
- Toaster
- Wine glasses
Bedroom and laundry
- Bed linens
- Iron
- Room-darkening shades
- Clothing storage
Family
- Board games
- Children's tableware
- High chair
Bathroom
- Body soap
- Conditioner
- Shampoo
- Shower gel
Entertainment
- Books
- Pool table
- Sound system
- Theme room
Services
- Breakfast Breakfast is provided
Home safety
- Carbon monoxide detector
- Fire extinguisher
- First aid kit
- Smoke detector
Heating and cooling
- Ceiling fan
- Indoor fireplace
- Portable fans
Parking and facilities
- Free parking on premises
Location features
- Private entrance Separate street or building entrance
House Rules
Accessibility
Neighborhood
Guest Access
Find us
Sorry we're unable to show you the location for this property
Approximate location. Full address will be provided on booking.