Vacation rentals in Evansville

Fun Lake Kosh Private Pier, Decks, Fire Pit, Grill

Gather at the White House: stylish lake house with private pier, 4Br/2.5bath/beds for 15 people, fire pit, gas grill, huge yard, 2 wooded acres. Lake Koshkonong is one of WI’s largest, famous for its boat-up restaurants/bars, fishing, and water sports all accessible from our private pier. Located along 39/90hwy - 90 mins to Chicago/30 min to Madison. Perfect for entertaining: fully stocked, professionally cleaned, open floorplan, 3-story outdoor living, dining & patio, playroom & more! Pets ok!

Peaceful Pines on 59~Welcome! 5 bdrm river front!

Relax, unwind and play on 4+ acres of beautiful nature: green space, woods, the Rock River, gardens and fresh clean air! Enjoy life from the back deck or rocking on the front porch. Stroll down the tree covered lane to fish from our shoreline, watch river traffic, picnic in the cabin, untie your watercraft from our pier and go travel the river and Lake Koshkonong, play a variety of outdoor games, grill dinner outside and end the day around the firepit. Hosts live in the lower level apartment.

Secluded Log Cabin w/ Private Lake & Hiking Trails

Escape to a secluded 50-acre nature retreat featuring a private 3-acre lake, a winding creek, and miles of peaceful forest, prairie, and wetland trails. This cozy log cabin offers comfort, privacy, and space for up to six guests—perfect for families, couples, and nature-lovers alike. Each stay includes full access to our HappyGuest digital guide, featuring aerial maps, trail routes, local highlights, and everything you need to make the most of the house, property, and surrounding community.

Historic Randall Schoolhouse

You'll love this beautifully redone Historic One-room Schoolhouse. Situated on the edge of the Driftless area 5 miles from the Sugar River Trailhead. An easy 30 minutes to Monroe, Beloit & Janesville and just an hour outside Madison. Relax in comfort with all new appliances including a full kitchen, washer/dryer, dishwasher and fireplace. Fenced yard. Just a mile down the road from a working homestead where you can milk a cow, pet a goat, harvest fresh produce and eggs and so much more.

The Allen Creek Apt. Historic Downtown Evansville

Experience stylish comfort in this centrally located apartment in Historic Downtown Evansville! Situated above a trendy coffeehouse with a welcoming atmosphere! This upper-unit apartment sits next to Allen Creek, making it easy to explore the outdoors—bring your bike and ride the Ice Age Trail, which runs through town! You’ll be within walking distance of charming shops and restaurants, and just a 25-minute drive to downtown Madison, or Alliant Energy Center, hope you enjoy your stay!

Downtown Lake Monona Haven | SUPs, Hot Tub & Sauna

Stay in your private 3BR, 2BA section of our lakefront home. Paddle from the dock, relax in the hot tub or sauna and enjoy mornings on the balcony with coffee. You’re moments from Willy Street restaurants and right on the bike path. Inside, find a full kitchen, comfy living spaces. Two parking spots included. Spend days on the water or exploring the city and evenings grilling or roasting marshmallows by the fire. Paddleboards included. Pontoon rental available in warmer months.

25min to Capitol - KING Suite - Game Room - Groups

🔸Large groups & families - 1 King, 2 Queen, 2 twin beds, and 2 queen floor mattresses 🔹Game room w/ 85" TV, ping pong, foosball, stick hockey, arcade game & board games 🔸Private yard w/ concrete patio, lounge furniture, gas fire pit & corn hole 🔹Highchair & pack n’ play - free to use 🔸Fully stocked kitchen w/ island seating 🔹You'll find "The Kohl Center, UW-Madison, Camp Randall Stadium, State Street, The Capitol, & The Alliant Energy Center" within a 25 minute drive

Firefly Wood Lodge

Welcome to our hidden gem – a charming log home nestled on 15 acres of wooded land. Located just 30 minutes south of Madison, perfect for larger groups looking for winter or summer retreat and secluded location. The hosue can accommodate up to 13 guests with 3 bedrooms on the first floor and 5 additional beds in the loft area, has a wood burning fire place and bon fire outside. This serene retreat is surrounded by lush trees and the scenic rural landscape of Green County.

Bees on Main: sweeter than ever

Located in the heart of Stoughton's Downtown Historic District, "Bees on Main" is a lovingly renovated upstairs apartment. You'll find the Opera House, Chorus, and Stoughton's wonderful shops, restaurants, pubs, and galleries only steps away. The Yahara River and Fairgrounds are within a few blocks, and there's space on the private deck to safely store your bikes or kayaks if you want to enjoy the great outdoor activities and nature surrounding Stoughton.

Cozy Cabin on Decatur Lake

Relax in this cozy cabin on the lake. Fish, hike or even swim (after a short canoe/kayak paddle); just like being Up-North without the drive! Use our canoe or kayaks or bring your own. Cook indoors or out. Near Sugar River Trailhead, Headgates Park and Three Waters Reserve. A few miles away from tubing on the Sugar River. An hour from Madison and 30 minutes from Beloit, Monroe or Janesville. Previously listed by Betty and under her same great management!

Guest House

Take a step away from the everyday hustle and bustle and surround yourself with the sights, sounds, and smells of the country. Our guest house sits amid our family dairy goat farm and will offer you the opportunity to visit animals from goats and horses to chickens, dogs, and cats. We milk around 100 goats with baby goats born February through June. In the summer months you'll find homegrown, fresh produce on our roadside stand.

The Dairy at the Wegmueller Farm

Welcome! You are about to experience life on an active 4th-generation farm nestled in the rolling hills of Green County. Meet the cows, feed the pigs, befriend a horse, or just enjoy the relaxing and peaceful serenity of rural Wisconsin farm life. Located less than five miles from Monroe, this home away from home is close enough to all that Monroe & the surrounding community has to offer, but still has room to stretch your legs.