Incredible Downtown 6 bedroom with Pool, Hot Tub, Waterfall, Arcades & Speakeasy
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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The host requires you to complete the following before checking out:
Load and start the dishwasher
Remove personal items, remove leftover food and drinks and take out the rubbish
Turn off the lights and lock the doors
Ensure hot tub cover is on
Failure to complete these may result in a negative review from the host.
Guests must have a guest rating of 4.5 or higher to use the instant book feature. Otherwise, reach out first.
Rental agreement, liability waiver and security deposit required to receive check in details.
Important information
You need to know
Property # 4977157vb
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
About the area
Cadillac
Located in Cadillac, this holiday home is in the city centre and on a lake. McGuire's Resort and Adventure Island Family Fun Park are worth checking out if an activity is on the agenda, while those looking for area attractions can visit Jennings Community Playground and Little Creek Park. Take in the nearby slopes with cross-country skiing and snowboarding, or try out other outdoor activities such as ice skating and snowmobiling.
Wexford County Historical Museum - 3 min walk - 0.3 km
Lake Cadillac - 5 min walk - 0.5 km
Cadillac Lake Park and Boat Dock - 6 min walk - 0.6 km
Diggins Park - 6 min walk - 0.6 km
Cadillac Sound Garden - 11 min walk - 1.0 km
Restaurants
McDonald's - 5 min drive
The Truck Stop - 4 min drive
Culver's - 5 min drive
Cadillac Java - 9 min walk
Taco Bell - 4 min drive
Frequently asked questions
Does Incredible Downtown 6 bedroom with Pool, Hot Tub, Waterfall, Arcades & Speakeasy have a pool?
Yes, this property has an outdoor pool. Pool types include heated pools.
How much does it cost to stay at Incredible Downtown 6 bedroom with Pool, Hot Tub, Waterfall, Arcades & Speakeasy?
As of 9 May, 2026, prices found for a 1-night stay for 2 adults at Incredible Downtown 6 bedroom with Pool, Hot Tub, Waterfall, Arcades & Speakeasy on 28 May, 2026 start from S$1,286, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
Is Incredible Downtown 6 bedroom with Pool, Hot Tub, Waterfall, Arcades & Speakeasy pet-friendly?
No, pets are not allowed at this property.
How much is parking at Incredible Downtown 6 bedroom with Pool, Hot Tub, Waterfall, Arcades & Speakeasy?
On-site parking is available at the property.
What time is check-in at Incredible Downtown 6 bedroom with Pool, Hot Tub, Waterfall, Arcades & Speakeasy?
Check-in begins at 4:00 PM.
What time is check-out at Incredible Downtown 6 bedroom with Pool, Hot Tub, Waterfall, Arcades & Speakeasy?
Checkout is at 10:00 AM.
Where is Incredible Downtown 6 bedroom with Pool, Hot Tub, Waterfall, Arcades & Speakeasy located?
This family-friendly Cadillac holiday home is located on a lake, within a 10-minute walk of Wexford County Historical Museum, Cadillac Lake Park and Boat Dock and Lake Cadillac. Diggins Park and Cadillac Sound Garden are also within 15 minutes.
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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.
Barb H.
Stayed 3 nights in Feb 2026
About the host
Hosted by Sam and Jesse
Languages:
English
Premier Host
They consistently provide great experiences for their guests