Holiday houses in Cooksville

YurtSimple

YurtSimple is where life slows down and people unplug. It’s forest bathing in nature. It’s getting away from it all to spend time with a partner, by oneself, and sometimes with pets. You’ll be driving past YurtCation (about 300 feet past YurtCation) to get to YurtSimple. YurtCation is 20’ in diameter and YurtSimple is 16’ in diameter. Wood and charcoal are provided. You may cook on the indoor wood stove top, or visit any number of great restaurants 2 miles away. You can even order pizza delivery

Stay With Horses Equestrian Escape Near Madison

Get ready for a quiet and peaceful stay. Take your pick: - 1King+1Queen Bed & 1 bath for 4 people - 1King+2Queen Beds & 2 baths for 6. (+$125 per night, contact host for payment) This home is attached to a barn with 6 Icelandic horses! Wake up to Icelandic horses just outside your window. A scenic escape with quiet mornings, fuzzy horses, and a one-of-a-kind IamGlytja experience - only 25 minutes from Madison - No horse riding allowed, owners to supervise all horse visits - No smoking / parties

Lake House Summer Getaway

Welcome to the historic Bingham House! Enjoy everything beautiful Lake Koshkonong has to offer at this stylishly updated home. Amazing lake views throughout the inside and on the large patio. Situated on a calm canal with direct access to the lake. Expansive backyard with 150’ of canal shoreline and large hot tub. Enjoy the water on our kayaks, standup paddle-board or fishing off our dock. Prep a meal in our beautifully remodeled kitchen, on our large gas grill or by the shore on our fire pit.

HotTub/Kayaks/Arcade Your Dream Vacay Starts Here

🔥NO AIRBNB FEES🔥 Plan an unforgettable stay for a group of up to 8—and a dog or 2—at Harbor House, a spacious waterfront home with a hot tub & private dock where the Rock River emerges from 10,000-acre Lake Koshkonong offers a world of water sports—boating, kayaking, paddleboarding & more. Battle on 3 classic arcade games or ping pong table in the heated game room, gather at the firepit 12 steps from the water, and grill & dine on the deck overlooking the water. Close to Madison & Janesville.

Spacious Executive 2BR Home Near Shopping & Dining

Professionally Managed by Kevin Bush, this rental is nestled in a safe and quiet neighborhood in a desired location that is convenient to Woodman’s Center, Janesville shopping and dining destinations. Enjoy the city’s hundreds of acres of tranquil parkland, miles of peaceful trails, and beautiful downtown riverwalk. Bonus: This location is an easy drive for day trips to Madison, Milwaukee, Chicago, and surrounding. Please check out our listing on Margate Drive for more dates. Kevin, Host

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

Gather at the White House: a 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 & much more!

Waterfront modern cabin w/ kayaks

VERY romantic getaway for 2! Enjoy your own private dock, welcome to tie off your own boat or rent locally. Complimentary use of 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.

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.

Quiet Waterfront 2BR w/Dock & Huge Patio

Escape to a charming cottage on the tranquil Rock River in Edgerton, WI, where each season offers unique beauty. In summer, enjoy kayaking, fishing, and boating. Fall brings vibrant foliage and crisp air, perfect for outdoor walks. Winter transforms the landscape into a serene, snow-covered wonderland. With picturesque views, modern amenities, and nature at your doorstep, this cozy retreat invites relaxation and adventure year-round. Watch the stars light up the night sky in any season.

Rustic Lake Home Retreat

Our home is located just across the street from the lake. We have lake access via a private beach everyone in the area uses. We do not have a dock for your use. Make left out of the house to Lake Shore Dr. Then left to walking path located 100 feet up on the right side. When using the beach please be mindful of others who may be using it as well. Use proper etiquette, respect others, leash your dogs, and ensure you clean up the area when you leave. PETS NEGOTIABLE, BY INQUIRY ONLY

Buoys UP! Lake Life & Sunsets

Looking to unwind & enjoy Lake Life-where weekends begin any day of the week-any season you choose? Here at Buoys UP! you will be able to do just that. Enjoy private access to our newly remodeled 2 bedroom lake house at Lake Koshkonong, WI. Overlook the private road this little gem is located on and enjoy the wonderful lake views and the beautiful sunsets. Stroll down the road for apx. a 2 minute walk to take advantage of your personal lake access Buoys UP! offers just for you.

Main St 2 Bdrm - Walk to coffee & sushi!

* Be sure to check out our winter extended stay discounts for 3+ nights! * Welcome to historic downtown Oregon! Nestled in a picturesque setting, this elegant retreat combines modern comfort with historic charm. You'll be steps away from locally owned coffee and gift shops, a wine reserve & restaurants! With convenient access to Madison (14 mi), experience the best of both worlds – small-town tranquility and urban excitement. Whether for work or leisure, welcome home!