Sleeps 6
2 Baths
4 Hot Tubs
Fireplace
Pool
Next to Lifts
4 Beds
2 Baths
Sleeps 6
Hot Tub
Indoor Fireplace
Pool
Mins to Lifts
Where Downtown Meets Down Time
Welcome to our historic downtown Oregon vacation rental! Experience small-town charm and modern comfort in the heart of Oregon, Wisconsin, just 15 minutes from downtown Madison. This beautifully restored retreat blends elegant design with cozy amenities, offering the perfect escape for couples, families, or business travelers. Step outside to explore locally owned coffee shops, boutique stores, the Oregon Wine Reserve, and delicious restaurants all within walking distance. Whether you’re visiting for work, a weekend getaway, or a relaxing stay near Madison, this is your ideal home away from home.
Front Row Seat to Downtown Oregon
Step into a space where history and comfort meet at our beautifully restored downtown Oregon apartment, once home to the town’s first library. Picture yourself soaking in a relaxing bathtub, curling up by the cozy indoor fireplace, or sipping fresh coffee as morning light fills the room. This historic Oregon WI vacation rental offers the best of both worlds, timeless character and modern comfort with features like air conditioning, a fully equipped kitchen, and high-speed WiFi for a seamless stay.
Nestled in the heart of downtown Oregon, you’re just steps from charming local cafés, boutique shops, the Oregon Wine Reserve, and neighborhood restaurants, with Madison only 15 minutes away. Whether you’re visiting for work, a weekend getaway, or a peaceful escape, this elegant retreat invites you to relax, recharge, and experience small-town charm at its finest.
Key Amenities
🏙️ Historic Downtown Oregon Location
☕ Across from Coffee Shops & Cafés
🍽️ Walk to Local Restaurants & Wine Reserve
🛏️ Cozy Bedrooms with Cotton Linens
🛁 Bathtub & Public Goods Toiletries
💇♀️ Hair Dryer & Cleaning Essentials
🧺 Washer + Paid Dryer (in Building)
❄️ Air Conditioning & Heating
🌬️ Ceiling Fan for Comfort
📺 Smart TV & Board Games
👶 Pack ’n Play Available on Request
💻 High-Speed WiFi
🍳 Fully Equipped Kitchen
☕ Keurig & French Press + Free Coffee
🍷 Wine Glasses & Dining Table
🚗 Free Parking On-Site & Street Parking
🚪 Private Entrance + Smart Lock Check-In
🧯 Smoke & CO Detectors + First Aid Kit
📹 Exterior & Doorbell Cameras
🪟 Room-Darkening Shades for Restful Sleep
📍 Just 15 Minutes to Downtown Madison
Book Your Stay at
Downtown Den
2 Beds
1 Bath
Sleeps 4
1 Bedroom
Frequently Asked Questions
Full refund for cancellations made within 48 hours of booking. Partial refund of 50% up to 7 days before check-in. No refund after that.
Check-in is at 3 pm and check-out is 10 am.
No smoking
Use of fire pit is prohibited during the burn ban
No parties or Events ($500 fine). 6 guests maximum strictly enforced. If you are looking for a party house, this is not for you. Although we are on a wooded lot, we have neighbors to be considerate of.
We will send you our full list of favorite restaurants and attractions when you book :)