Shady Grove Cottage | Poolside Stay in Madison

Step into Shady Grove Cottage, a charming retro-inspired retreat where vintage character meets modern comfort in the heart of Madison. This thoughtfully renovated 5-bedroom, 2-bath split-level home comfortably sleeps up to 12 guests, making it the perfect gathering space for families, groups, or weekend getaways.

Inside, you’ll find a welcoming main level designed for connection and ease. The cozy living room offers plenty of seating for relaxing conversations, movie nights, or catching the big game, while a dedicated workspace provides a quiet spot to check in on emails if needed. The fully equipped kitchen has everything you need to prepare meals at home, featuring a full-size fridge, stove, coffee maker, and all the essentials. Enjoy meals together at the sleek dining table or keep things casual with additional seating nearby.

The home’s split-level layout offers both privacy and personality. Downstairs, you’ll find two bedrooms and a beautifully updated full bathroom with a walk-in shower and marble finishes. One bedroom features two full beds and fun extras like chess and darts for a little friendly competition, while the second offers a cozy queen bed retreat.

Upstairs on the third level are three additional bedrooms—two with queen beds and one with a king—along with a shared full bath that showcases charming powder blue retro tile and a tub/shower combo, adding to the home’s nostalgic appeal.

Step outside to enjoy the spacious yard, shaded by mature trees, or unwind on the patio with comfortable seating and a charcoal grill—perfect for laid-back evenings. During warmer months, guests can take advantage of the seasonal above-ground pool (open through October 1st, weather permitting), offering a refreshing way to relax and enjoy the outdoors.

Additional amenities include a washer and dryer, driveway parking for up to four vehicles, and convenient self check-in with a digital keypad. Please note that due to the split-level design, stairs are required to access both sleeping areas, as there are no bedrooms or bathrooms on the main floor.

Located in a quiet residential neighborhood just over a mile from grocery stores, dining, and everyday essentials, Shady Grove Cottage offers both comfort and convenience—making it an ideal home base for your stay in Madison.