Vacation rentals in Cooksville

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Cooksville

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

0 of 0 items showing

1 of 3 pages

Top guest favorite

The exterior of a rustic studio is illuminated at night, showcasing wooden siding and a green metal roof. Soft warm light glows from several windows, while a kayak is mounted on the wall. Lush greenery surrounds the entrance, creating a serene outdoor space.

Guesthouse in Mount Horeb

4.96 out of 5 average rating, 607 reviews

Cool, Scenic Country Art Studio

Creative souls love my marvelous studio retreat, a delightful one-room loft-style space featuring tall ceilings, an entire wall of sliding glass doors, kitchenette, piano, and an expansive view of a picturesque barn, pasture, and wooded hills. This amazing, heated, spacious country getaway has no plumbing— it's just a few steps across the yard to the main house guest bathroom. Come create, relax, and renew here! Well-behaved dogs, included in your reservation, must be leashed when outside.

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, 160 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

A compact kitchen area is featured, showcasing a sleek silver refrigerator and a microwave. A coffee maker is positioned nearby on a wooden counter. A whiteboard with a welcoming message is mounted on the wall, alongside a holder with various brochures and a framed decorative sign.

Guest suite in Middleton

4.98 out of 5 average rating, 191 reviews

Quiet sunlit studio near vibrant downtown

This architect-designed studio is bathed in natural light, with skylights and a breakfast nook with a wrap-around window. Featuring an upscale bathroom with a walk-in shower, this comfortable space has all the amenities perfect for a quick weekend getaway or a week-long business trip. The studio adjoins a house and is up a flight of stairs through a separate outdoor entrance. Located just up the hill—a 5-minute walk—to Downtown Middleton and a 15-minute drive to UW and Downtown Madison.

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

A small cottage is illuminated by warm outdoor lighting, creating a welcoming ambiance. A gravel path leads up to the door, surrounded by trees. Two white chairs are positioned nearby, inviting relaxation amid the tranquil woodland setting.

Tiny home in Darlington

4.98 out of 5 average rating, 756 reviews

Arbor Crest Cottage

Thank you for checking out Arbor Crest Cottage! Jeremiah and I would be happy to host you. We are entering our 5th year of hosting and have been enjoying the experience. The farmette is conveniently located 2 miles from town, set off the road, and through the woods. The cottage is located on the edge of our woodland area. We invite you to explore our property and enjoy the animals. The west end of our land over looks town and is a great place to watch the sunset and the goats graze.

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, 188 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, 305 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 modern coffee maker is positioned on a wooden countertop. The machine features a water reservoir on one side and a sleek black design with a single-serve brewing unit at the top. Glassware and kitchen utensils can be seen in the background.

Guest suite in Deerfield

4.95 out of 5 average rating, 130 reviews

Studio on the Prairie Fen

Kick back and relax at the Studio! The Studio is a 400 sq ft unique suite in the lower level of our home. A private locked entrance opens up to a sunny space with great views of a wetland beyond the backyard. Private patio to enjoy morning coffee and the sunrise. A great place to unwind and enjoy nature's beauty! We have binoculars if you love bird watching, and bikes to ride or hike the Glacial Drumlin Trail just 0.1 mile from the front door. Lic LICHMD-2021-00621.

Top guest favorite

A private deck area features wooden lattice gates that open toward the bustling street below. The ground is composed of wooden planks, and two outdoor chairs with patterned cushions offer a cozy spot to relax. A decorative mat lies at the entrance.

Apartment in Stoughton

5 out of 5 average rating, 135 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

A calm lake is depicted, reflecting greenery from surrounding trees under a clear blue sky. The still water creates a mirror-like effect, enhancing the natural beauty of the landscape, while the lush foliage provides a sense of tranquility.

Cabin in Brodhead

4.88 out of 5 average rating, 107 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!

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, 374 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.

Top guest favorite

Cabin in Edgerton

5 out of 5 average rating, 123 reviews

Waterfront modern cabin w/ kayaks

NO CLEANING OR ADD ON FEES! Enjoy your own private dock including 2 kayaks. Beautiful modern riverfront cabin near Lake Koshkonong's eateries and entertainment. Soak in the gorgeous Wisconsin summer with water activities at your fingertips. The rest of the year take in the pristine wonderland views in our enclosed balcony. Only 30 minutes from Madison's world class culinary experiences, performance arts, sports & festivals.

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Cooksville vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Cooksville

Top guest favorite

Cabin in Brodhead

5 out of 5 average rating, 9 reviews

Avail Labor Day-Private Reserve, King Bed, Fishing

RitaRating, 5 stars3 weeks ago

The location and home were great. The view from every corner was scenic. We were able to watch wildlife and take quiet walks around the lake and on the nature trail. There were lots of games to play inside but we enjoyed the beautiful weather and spent our time outside on the lake in the paddle boat and kayaks. The kitchen was plenty big and we were also able to spread out in the other rooms for alone time. We will definitely be back.

Top guest favorite

A spacious bathroom is showcased with light grey walls and a decorative painting featuring figures beside a dog. A white toilet is positioned beside a small table holding toiletries, enhancing the room's functional appeal.

Private room in Whitewater

4.99 out of 5 average rating, 349 reviews

Whitewater Night Lodging

SarahRating, 5 stars2 weeks ago

A nice quiet neighborhood for a quick overnight to the University.

Top guest favorite

A spacious kitchen features modern cabinetry and a central island with seating. Natural light fills the room through windows, with a view of greenery outside. A dining table is set with blue placemats, while appliances and kitchenware are neatly arranged on countertops.

Private room in Madison

4.97 out of 5 average rating, 332 reviews

Mornings with Meg in Madison ZTRHP1-2020-00006

JasmineRating, 5 stars1 week ago

Meg was a very knowledgeable hostess - gave us detial information on places to go and things to do with young kids, shared great details of the history of the area. She was wonderful with kids. She let us use the kitchen to cook meals - which was very helpful to us. She was very kind to do some of our laundry. We would definitely stay here again!

Top guest favorite

An inviting firepit area features two black Adirondack chairs positioned around a circular stone firepit. The A-frame cabin is seen in the background, softly illuminated by decorative lights, surrounded by trees at dusk.

Cabin in Elizabeth

4.95 out of 5 average rating, 22 reviews

Hot Tub+ Firepit+ "Tiny"house+ Views+ Galena Area

JacquelineRating, 5 stars5 days ago

I had a fantastic stay! The accommodations were super comfortable, and the space was decorated so cutely—it had such a welcoming and cozy vibe. Everything I needed for a relaxing weekend was thoughtfully provided. The host was incredibly responsive and made everything so easy with clear instructions for the home, plus helpful recommendations for things to do around town. It really made the whole experience seamless and enjoyable. I would definitely stay here again!

Top guest favorite

A basement arcade area features two vintage arcade machines against a backdrop of artificial greenery. Soft carpeting covers the floor, while modern hexagonal lighting enhances the space. A doorway leads to utility areas, completing the entertainment environment.

Home in Janesville

5 out of 5 average rating, 5 reviews

The Mayfield House

RichardRating, 5 stars4 days ago

What an absolute charming home ! If you’re looking in the Janesville area, you will not be disappointed, BethAnd Eric were great hosts and went above and beyond to exceed our expectations. For the first time we brought one of our dogs with us to an air bnb and even he had the amenities and treats waiting for him ! Absolute awesome experience, thank you .

Guest favorite

A modern kitchen area is shown with white cabinetry and dark appliances. Two stools are positioned at the kitchen island, while a dining setting is visible. Light wood flooring complements the space, and a cozy seating area is framed by a neutral-toned couch and decorative rug.

Home in Cottage Grove

4.85 out of 5 average rating, 13 reviews

The Getaway Loft

KateRating, 5 stars2 weeks ago

Nice, dog-friendly place to stay near Madison. We were in town to visit family so we didn’t spend much time at the Airbnb. The bed was comfortable and the space was clean. It was perfect for our needs for the weekend and we would stay there again. Loved the welcome gifts (waters, snacks, and flowers) that were left for us!

Top guest favorite

The entrance features a pair of glass doors framed by rustic wooden walls. A bench sits beside potted plants, and decorative items adorn the walls. A glimpse of a landscaped outdoor area is visible through the doors.

Private room in Fitchburg

4.92 out of 5 average rating, 156 reviews

Studio with fireplace in private home

RaisaRating, 5 stars1 week ago

Joanne was communicative and made us feel right at home. Check in/out procedures were super easy, the space is kept tidy, and even some snacks. Her home was just a short drive to Madison and nearby areas we were looking to explore while also being a beautiful getaway in a quiet neighborhood. I would highly recommend staying at Joanne’s lovely home if you’re visiting the area!

Top guest favorite

Four wooden chairs are positioned around a circular stone fire pit amidst a grassy area. Natural elements such as trees and shrubs are visible in the background, enhancing the outdoor setting.

Home in Edgerton

5 out of 5 average rating, 10 reviews

Lakeside Retreat

DavidRating, 5 stars1 week ago

Erin is a great host. Very responsive and helpful suggestions. Property is as listed and in a very quiet location. Inside has been redone and is in good shape and clean. Great food at the Lakehouse Inn up the road.

Show all

Vacation rentals in Cooksville

Top-rated vacation rentals in Cooksville

Vacation rentals for every style

Popular amenities for Cooksville vacation rentals

Other great vacation rentals in Cooksville

Destinations to explore