Vacation rentals in Cooksville

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Top-rated vacation rentals in Cooksville

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Guest favorite

A coffee station features a Keurig machine and a variety of coffee pods in an organized drawer. Blue ceramic mugs and decorative tea sets, including a black teapot and a floral sugar bowl, are displayed on a stainless steel countertop.

Home in Janesville

4.95 out of 5 average rating, 106 reviews

Renovated Restful 1 BR Brick Cottage with Deck

Newly renovated very clean one bedroom house. All new bathroom and redone kitchen. Bright and cheery interior with high end comfortable furnishings perfect for reading and relaxing. Pillow-top queen bed with quality linens. Large backyard with furniture and deck. Quiet residential area walking distance to Palmer Park, Ice Age Trail and Rotary Gardens as well as historic Court House Hill and Downtown Janesville. Casual neighborhood eateries within walking distance, fine dining nearby.

Top guest favorite

A vibrant streetscape features a charming mix of historic buildings, with a focus on the storefronts below. The ground floor includes a cozy café adorned with bright flowers and outdoor seating, while the upper levels showcase colorful facades and decorative window details.

Loft in Monroe

4.99 out of 5 average rating, 175 reviews

Loft 3 - On The Historic Monroe Square

Loft 3 is 40 steps (2 flights of stairs) above the Monroe Square. It's a climb, but the view is totally worth it! Newly remodeled in 2021, and reminiscent of the 1859 character of the building, this space is cute, cozy, and truly one of a kind. Literally a couple steps away from your entryway is Sunrise Donut Cafe, featuring customized donuts and a full menu of excellent coffee items. From there, explore the rest of the Square for food, drinks, and shopping in a quaint Main Street atmosphere.

Top guest favorite

An exterior view of an old schoolhouse is captured, showcasing its classic architecture. A group of children stands in front, dressed in period attire. The surrounding trees add a natural backdrop, enhancing the historic character of the building.

Place to stay in Brodhead

4.98 out of 5 average rating, 163 reviews

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.

Top guest favorite

The exterior of the home features a grey facade with two garage doors and a paved driveway. Soft landscaping is visible, with patches of grass and remnants of snow in the yard, contributing to a neat and welcoming appearance.

Home in Janesville

5 out of 5 average rating, 134 reviews

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

Top guest favorite

The image shows a serene creek bordered by lush greenery. The water is clear and gently flowing, with scattered vegetation alongside the banks. Sunlight reflects off the surface of the water, enhancing the natural beauty of the surroundings.

Apartment in Evansville

5 out of 5 average rating, 20 reviews

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!

Top guest favorite

The bathroom features a colorful shower curtain depicting a sea turtle swimming among coral and marine life. A gray towel is hung on a rack, and modern lighting fixtures highlight the bright hues of the artwork. Clean white paneling complements the overall design.

Apartment in Janesville

4.97 out of 5 average rating, 189 reviews

Cozy Apartment Close to Downtown Janesville

This welcoming 1 bedroom apartment is located close to downtown Janesville, the city of parks. It has been updated throughout and has all the amenities necessary for a very comfortable stay, including a gas grill in the wooded back yard. It even has off street parking. You can easily walk to the Janesville Performing Arts Center and continue downtown and enjoy the Saturday morning Farmer's Market, shopping, restaurants and bars. Access to the Bike Trail is only a few minutes away.

Guest favorite

The entryway features a wall adorned with a decorative life preserver and a sleek flat-screen television mounted above a cozy fireplace. Pendant lights hang from the ceiling, providing warm illumination. A dining area with a wooden table and white chairs is visible, complemented by natural light from large windows.

Home in Edgerton

4.94 out of 5 average rating, 307 reviews

Vast Lake Koshkonong Views from Pier, Deck, & Home

Our 2 Bedroom, 1 Bathroom House is located directly on the shores of Lake Koshkongong. The back deck overlooks thousands of acres of lake with endless lake views. Just steps off the deck, one can enjoy the grassy landscape leading to the lakeside fire-pit. Then continue out onto the end of the 140 foot top notch pier. The pier (seasonally of course) includes a bench on the end and stairs into the water so that you can take a refreshing swim on our sandy bottom shoreline.

Top guest favorite

A welcoming front porch is featured, showcasing a comfortable seating area with a large chess table at the center. Two rocking chairs are positioned along the side, while a potted plant adds a touch of greenery. Natural light filters through the space, enhancing the calm ambiance.

Farm stay in Stoughton

5 out of 5 average rating, 68 reviews

Peaceful farmstay, 20 min to Madison, 3 King beds

Escape to a winter wonderland at our cozy farmstay! Enjoy your morning coffee with peaceful views, then explore winter activities like sledding or hiking scenic trails. Visit local shops, indulge in nearby dining, or relax indoors with a book, puzzle, or creative project. Perfect for family getaways, reunions, or a peaceful work-from-home retreat, our farm blends tranquility and seasonal charm. Book your stay today and experience winter’s magic in the countryside!

Top guest favorite

Apartment in Stoughton

5 out of 5 average rating, 137 reviews

Bees on Main: a Honey of a Place

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.

Guest favorite

The cabin is nestled among tall trees along the water's edge, reflecting beautifully in the calm lake. A paddleboat and canoe are visible tied to the dock, with lush greenery framing the scene.

Cabin in Brodhead

4.88 out of 5 average rating, 108 reviews

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!

Superhost

A modern wood-burning fireplace stands at the center of the living area, offering warmth with a visible flame. Large glass doors flank the fireplace, extending views of the natural landscape outside, enhancing the connection between indoor comfort and outdoor scenery.

Home in Stoughton

4.93 out of 5 average rating, 15 reviews

The Orchard House

In a complex world that makes so many demands your time and attention, the Orchard House is a simple, Nordic-inspired refuge where you can be restored, reconnected, and refreshed. The Orchard House is a private retreat set on 30 acres in the Wisconsin countryside, just 20 minutes from Madison. A wood -fired hot tub set in a secluded forest clearing is available year round for outdoor soaking unless overnight low drops below 10 degrees.

Guest favorite

A tranquil outdoor seating area features two green chairs positioned around a small fire pit. Surrounding trees and foliage provide a natural backdrop, while the ground is paved with gray stones, contributing to a cozy gathering space suitable for relaxation.

Guesthouse in Stoughton

4.94 out of 5 average rating, 376 reviews

Country cabin, birders paradise.

Country cabin with small kitchen, SMALL BATHROOM, large porch, gardens and birds galore. Located in the country just south of Madison WI. Enjoy the country life, quiet yet close enough to the city to enjoy Madison's activities or Stoughton's Opera House. Sauna, Fire pit, hiking, ask about pets. WiFi is available but not reliable, this is a country setting with slow connections. Please communicate with me regarding pets before booking.