
Holiday rentals in Lake Winnebago
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Top-rated holiday rentals in Lake Winnebago
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Soaking Pool • Hot Tub • 27 min to Arrowhead
Escape to KCcabin — a modern, secluded retreat in the Lake Lotawana area (no lake access). This new-build hideaway offers 2 bedrooms plus bunk beds, NEWLY ADDED soaking pool and hot tub with wooded views, spacious deck & grill, 65" smart TV, WiFi, washer/dryer, and a workspace with standing desk. Just minutes to dining, marinas, and only 30 min to downtown KC. Perfect for families, couples, or remote work getaways. If you'd like to view a walkthrough video, message me and I can send you a link.

The Cottage
The Cottage, with a studio style layout, is a bright and clean space just one mile from historic downtown lees summit with local shops, bars and restaurants. The cottage is ~20 min from downtown Kansas City and 15 min from Kaufman and Arrowhead Stadium. This newly renovated 1900s milk barn is unique and special with a lot of charm, with a few of the modern conveniences. Guests are welcome to take advantage of the two acre landscaped yard and enjoy a delicious s’more at the outdoor fire pit!

Cozy Private Barndominium/studio
Private studio on the second level of our detached garage behind our main house. Located in a resort-like property. Quiet and safe neighborhood. Minutes from downtown Lee's Summit. Coffee shop/bakery within walking distance. Several restaurants close by, 1 mile to iconic antique malls. Perfect place for traveling professionals. Close to Hwy 291. We use the garage for storage and to work on our vehicles occasionally, you might hear us working. *There is no smoking/vaping in the apartment*

Meadow Brooke Lane
Nested on 3 beautiful acres of fenced land. 4 bedrooms (3 with ensuite), fully equipped kitchen, projector, fire, bbq, plus more! This property is located near multiple event spaces making it ideal for small gatherings or enjoying the countryside. Kids and pets alike with love the vast outdoor space to roam and play. There is a charming train that runs the backside of the property making for a unique and fun backdrop. A fantastic dog friendly brewery is within walking distance.

The Cabin at Big Creek
Ultimate Seclusion Nestled away on 120 acres this fully updated log cabin sets on a 5 acre private lake loaded with fish with a rolling creek. Approximately 20 miles from Kansas City. We get several inquires about small weddings, events, parties, etc. Owner has strict no more than 10 guests spending the night. However for micro weddings and events- as long as it stays under 50 people- the flat rate is 1950 plus fees. Can send special quote if wanting to book event

Lone Jack Cabin - Studio Suite
Beautiful private log cabin suite, conveniently located just east of the Kansas City Metro with great highway access. Close to wedding venues: Lone Summit Ranch, Powell Gardens and Stonehaus Winery. All the comforts of home! The suite features a king bed, sitting area with gas fireplace, private bath with shower, whirlpool jetted tub and kitchenette. The kitchenette includes a full-size refrigerator, small stove/oven, microwave and sink. Electric grill on private deck.

Nick's Place
*This is a smoke-FREE property* Need a home away from home? Come stay in our beautiful, fully renovated A-frame home on 3 secluded acres. Whether you are coming to visit the KC area or looking to get away from the city, we have you covered. Located just off 150 Hwy with quick easy access to I-49 Hwy, and 291 Hwy we are 30 minutes from the Country Club Plaza, Kauffman and Arrowhead Stadiums, and Downtown Kansas City. 50 minutes from Kansas City International Airport.

OneNinth-Luxury Downtown Retreat
Experience comfort & style in this spacious 4-bedroom, 6-bed retreat near Downtown Lee’s Summit. Perfect for families or professionals, it boasts 2 living spaces, 5 Roku TVs, a fully stocked kitchen, & a pet-friendly upstairs. Enjoy the private yard, outdoor lounge, front porch swing, & basement games. Located in a quiet cul-de-sac, it’s close to shops, bars, & restaurants. Ideal for getaways, holidays, work trips, or stay-cations!

The Landing at The Roost
Welcome to The Landing at The Roost! Located in historic downtown Pleasant Hill, this beautifully restored 100+ year-old Craftsman Victorian blends timeless charm with modern comfort. The Landing is a private lower-level unit featuring 2 bedrooms and 1 bathroom, offering a comfortable and thoughtfully updated space to unwind. Step outside and enjoy walkable access to local shops, dining, and community events in the heart of town.

Cozy cottage, perfect for traveling families.
There is a cozy gas fireplace that always sets the right mood. The open kitchen is fully equipped for cooking & baking. The back yard is fenced-in, perfect for kids & pets. There is a pond and lovely nature trail just outside the back gate and a children's park across the street in the front of the house. Walkable to nearby grocery, wine/spirits, gym, & restaurants. Available for 27 day rentals or more.

Cozy New Build near Harrisonville Square
Unwind in this newly built 3-bed, 2-bath home away from home just 45 minutes from Kansas City. Designed and built by our family, this home blends modern comfort with a peaceful, welcoming feel. Enjoy two queen bedrooms, a versatile twin trundle that converts to a king, a fully stocked kitchen, cozy living space, and fast Wi-Fi—just minutes from downtown Harrisonville.

Pilot's Pad Studio on 75 Acres + Fishing Pond
✈️ 1 Bedroom + Living Space • 1 Bath • Sleeps 3 ✈️ Breathtaking countryside views ✈️ King Bed + Futon Couch ✈️ Smart TV & High-Speed Wi-Fi ✈️ Fully Equipped Kitchen + Coffee Bar ✈️ Bar Height Dining for 2 ✈️ Luxury Tommy Bahama Bath Products ✈️ Private Patio with Fire Pit ✈️ Stocked Fishing Pond & Private Runway ✈️ Mini Split HVAC ✈️ Private Parking
Popular amenities for Lake Winnebago holiday rentals
Other great holiday rentals in Lake Winnebago

Serene Countryside Glamping

The Jefferson Loft

Exquisite Family Haven On 11 Acres

LS Bungalow in downtown Lee's Summit

New Conestoga 1843 Wagon

South KC/ Lee's Summit spacious charmer!

The Summers Silo

Rooftop Hot Tub Lake Getaway, Golf Cart & Fire Pit
Destinations to explore
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- GEHA Field at Arrowhead Stadium
- Oceans of Fun
- Kauffman Stadium
- Kansas City Zoo
- LEGOLAND Discovery Center Kansas City
- The Nelson-Atkins Museum of Art
- Legends Outlets Kansas City
- Kansas City Convention Center
- Jacob L. Loose Park
- T-Mobile Center
- Union Station
- University of Kansas - Lawrence Campus
- Overland Park Convention Center
- Negro Leagues Baseball Museum
- Midland Theatre
- Children's Mercy Park
- Overland Park Arboretum & Botanical Gardens
- Kansas Speedway
- Hyde Park
- Uptown Theater
- Kauffman Center for the Performing Arts
- Kansas City Power & Light District
- National World War I Museum and Memorial
- Crown Center





