Holiday houses in Evansville

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Top-rated holiday rentals in Evansville

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite

A two-story blue house with a covered front porch is framed by a snowy landscape, showcasing a peaceful winter scene. The property is surrounded by a mix of bare trees and evergreens, providing a serene backdrop.

Home in Milton

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.

LocationValueCheck-in

4.97 out of 5 average rating, 104 reviews

Guest favourite

A serene outdoor seating area is highlighted by four wicker chairs arranged around a round table. Lush greenery surrounds the space, and views of the tranquil lake create a peaceful atmosphere. A subtle path leads toward the water's edge, with distant docks visible.

Home in Middleton

Luxury Lakeside Oasis- 4 Bed / 3 Bath Lake Home

Enjoy time with your loved ones at our luxury lake front oasis. Breathtaking views combined with the ideal Middleton location & extensive updating make our home the perfect vacation destination. Huge windows maximize gorgeous views of 60+ feet of lake frontage. A fully updated kitchen boasts custom everything. Our home features: 4 bedrooms, 3 bathrooms, lofted office, open kitchen with an island & dining table. A short drive (5-7 mi) to UW Campus, Camp Randall, Kohl Center & Wi State Capitol

LocationFamilyView

5.0 out of 5 average rating, 20 reviews

Guest favourite

The image displays a serene waterfront view showcasing a private pier extending over calm waters. A stylish three-story house is framed by lush greenery, offering a welcoming outdoor space. The interior features a spacious living room with comfortable seating and a modern kitchen visible in an open layout.

Home in Edgerton

4 Season Fun: Private Fish Pier, Cozy Decks, Grill

4Br/2.5bath, beds for 12 adults+, on water with Private Pier, fire pit, gas grill, covered decks, 2 acre yard + woods. 4 SEASONS OF FUN: Fall Fest Farms, Wineries, Ice Fishing, Snowmobiling & Skiing. Lake Koshkonong is one of WI’s largest, famous for boat-up restaurants/bars, Live Music & fishing. Located on 39/90hwy - 90 mins to Chicago, 30 min to Madison. Perfect for entertaining: fully stocked, professionally cleaned, open floorplan, 3-story outdoor living areas, playroom & more! Pets ok!

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4.92 out of 5 average rating, 155 reviews

Top Guest favourite

Cabin in Brodhead

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.

LocationFamilyHiking

5.0 out of 5 average rating, 43 reviews

Guest favourite

A sandy beach area leads to a two-story house with a spacious deck above. Colorful kayaks are visible beside the house, and an American flag flutters in the breeze. Lush greenery surrounds the setting, providing a serene backdrop to the retreat.

Cottage in Edgerton

Rock River Hideaway - Waterfront w/ Dock

Welcome to the Rock River Hideaway! Located just downriver from Lake Kosh, this house offers a peaceful retreat where you can put your toes in the sand at the private beach, with a natural spring waterfall. Use the kayaks, bring your own boat, fish for walleye and northern, and enjoy some s'mores on an open fire surrounded by scenic views. Watch for a nesting family of bald eagles and eaglets directly across the river from you. Book your stay today and experience the beauty of Rock County.

ValueLocationBarbecue

4.97 out of 5 average rating, 61 reviews

Top Guest favourite

The exterior of a historic one-room schoolhouse is shown, featuring a red front door and a fenced yard. Surrounding trees provide a natural backdrop, and a shed is visible nearby. Soft sunlight enhances the inviting outdoor space, contributing to a peaceful setting.

Place to stay in Brodhead

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.

FamilyLocationAir conditioning

4.98 out of 5 average rating, 243 reviews

Guest favourite

Home in Janesville

Fully Renovated 2BR 1BA Gorgeous Exec Home #8ma-R

Enjoy your stay in Janesville, WI in this fully renovated two-bedroom cozy executive home Professionally Managed by Kevin Bush! The location is central to dining, shopping, and popular Janesville spots like the Rotary Botanical Gardens. This home will truly feel like your home away from home. Located just minutes from I39 giving you easy access for day trips to Madison, Milwaukee, Chicago, and surrounding. Please check out our listing on St. George Lane for more dates. Kevin, Host

ValueLocationSleep quality

4.99 out of 5 average rating, 154 reviews

Top Guest favourite

A scenic view of Historic Downtown Evansville displays tree-lined streets with a mix of storefronts and homes. Cars are parked along the paved road, while street lamps and floral decorations add charm to the urban landscape under a clear blue sky.

Apartment in Evansville

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!

LocationAir conditioningWi-Fi

4.97 out of 5 average rating, 38 reviews

Guest favourite

The living area features a hand-picked stone, free-standing wood stove, providing warmth to the space. An inviting sofa faces the stone feature, complemented by a wooden coffee table. Large sliding doors allow natural light to fill the room, leading to views of the outdoors.

Home in Albany

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.

LocationFamilySleep quality

4.93 out of 5 average rating, 27 reviews

Top Guest favourite

Home in Janesville

Janesville Repose -Hot Tub, Sauna, Gym, and Games

Welcome to your home away from home, where relaxation and fun both get their own wing. Unwind: ○ Private Hot Tub ○ Sauna ○ Private Gym ○ Outdoor fire table ○ Outdoor fire pit Entertain: ○ Surround sound home theater (lower level) ○ Perfect setup for cheering on your team, drink in hand ○ Room to gather, celebrate, and make noise ○ Plenty of outdoor games and activities for the kiddos ○ Self-playing piano Perfect for a private retreat or for larger family gatherings!

LocationFamilyDecor

5.0 out of 5 average rating, 23 reviews

Top Guest favourite

A cozy cabin interior features warm wooden paneling and soft lighting. A brick fireplace adds comfort, while a spacious bed is dressed in a patterned quilt. A inviting sofa and round area rugs enhance the welcoming atmosphere of the living space.

Cabin in Brodhead

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!

ValueLocationCheckout

4.87 out of 5 average rating, 185 reviews

Top Guest favourite

A picturesque view of a dairy goat farm features two red barns with metal roofs, set against a clear blue sky. Goats are seen grazing in a green field, while the surrounding landscape includes trees and open space, contributing to a rural atmosphere.

Farm stay in Orfordville

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.

FamilyLocationCondition

4.97 out of 5 average rating, 136 reviews