Vacation rentals with a kayak in Winnebago County

A game room is featured with a sleek rectangular pool table set against a neutral wall. Colorful gaming accessories, including a dartboard and ping pong decor, are displayed. The lighting creates a bright and inviting space for leisure activities.

4.98 out of 5 average rating, 62 reviews

WolfDen Getaway - Winnebago Channel

5/5 (10/10) Rating on another travel site (76 Reviews) - "The Wolf Den is by far the best home our family has rented..." - 6/29/2023 You’re only a 1/4 mile from the boat launch. The channel allows you to dock your boat at the property during your stay. It’s a large home with plenty of space with a newly renovated lower level, including a pool table, ping pong, darts and foosball. Smart TVs in all the right places. 4 bedrooms/3 bathrooms. Plenty of parking. Brand new queen size murphy bed.

Outdoor spacesLocationQuiet

Superhost

Home in Winneconne

4.88 out of 5 average rating, 8 reviews

Lakefront! Private Dock! Water toys! Sleeps 14!

Enjoy Lake Winneconne from this fully furnished lakefront home. Sleeps up to 14 guests, spend your days on the water with paddleboards and kayaks, or fish from the private dock while enjoying sunset views. Unwind by the fire pit or grill lakeside with family and friends. Inside features bright spaces, a fully stocked kitchen, and a coffee bar to start your mornings right. Minutes from downtown Winneconne and local eats, this home is perfect for families and groups to unwind and enjoy the lake!

Outdoor spacesDecorPool

A comfortable living area features leather seating arranged around a coffee table. Large windows allow natural light to fill the space, while decorative lamps add warmth. A flat-screen TV is mounted on the wall, and fishing-themed decor complements the relaxed atmosphere.

4.99 out of 5 average rating, 109 reviews

Oshkosh Escape with Lake Access and Private Dock

We are a year round retreat on beautiful Lake Winnebago. Bring your boat, kayaks, water toys, snow mobile, UTVs and fishing/hunting gear to your own private 18' dock on a channel with complete access to Asylum Bay. We are located in Oshkosh and close to the Fox Valley and GB. Just minutes away are: Outlet Mall, EAA, Lifefest, Sunnyview Expo, fishing tournaments, Sturgeon Spearing, microbreweries, Saturday Farmers Markets, The Herd basketball, Titans/UW-O events, and GB Packers(48min)!

LocationValueSleep quality

A dock extends over calm waters, lined with lush greenery and trees along the shore. The peaceful reflection of the surroundings can be seen on the water's surface. Additional boats and docks are visible in the distance, suggesting a tranquil waterfront atmosphere.

4.96 out of 5 average rating, 55 reviews

Waterfront Retreat*Kayaks*Firepit*Dog Friendly

Waterfront getaway on a peaceful channel with direct access to Asylum Bay and Lake Winnebago Perfect for families, friends, and outdoor enthusiasts. • Easy access to Asylum Bay and Lake Winnebago • Dog‑friendly (additional pet fee applies) • Spacious, fenced‑in backyard (open on the water side for access) • Double dock ideal for boating, fishing, and relaxing by the water • Kayaks available for guest use • Cozy fire pit with firewood provided • Indoor and outdoor games for all‑weather fun

Outdoor spacesValueFamily

Superhost

A person stands on a wooden pier by the lake, holding a large fish. The water reflects the surrounding trees and evening sky. The individual is dressed casually, adding a relaxed element to the scene, which features a serene lake backdrop.

4.8 out of 5 average rating, 5 reviews

Perfect Lake Front Home in a quiet bay!

Relax with the whole family at this peaceful place to stay. This spacious 4 bedroom 2 bathroom lake home is perfect for your get away!! 75 feet of lake frontage with pier. Located in a prime location in a quiet bay. Perfect for water skiing or fishing off the pier. Catch many species of fish, (WALLEYE, CRAPPIE, BLUE GILLS, PERCH, BASS, NORTHERN, WHITEBASS). Visit any time of year. Many fishing tournaments, Ice Fishing, Summer fishing. 15 minutes from EAA. UW-Oshkosh and Fond Du Lac.

LocationHospitalityFamily

4.95 out of 5 average rating, 259 reviews

A cozy firepit area is surrounded by eight Adirondack chairs, set against a backdrop of a vibrant sunset over the lake. The scene is framed by smooth pebbles, while a 60-foot dock extends into the water, creating a serene outdoor atmosphere.

Home in Menasha

Designer Lakefront Home with Views, Firepit, Dock

Relax at Sunset Oasis, where stunning lake views and sunsets set the tone for your stay. Sip coffee in the chef’s kitchen, paddle out in kayaks, grill lunch, and dine lakeside. In the evening, cozy up by the fireplace or gather around the firepit under the stars. Stream your favorite shows on the smart TV or explore nearby downtowns just minutes away. This stylish, updated luxury lake house is the perfect escape to unwind, reconnect, and create unforgettable memories.

Outdoor spacesValuePets

4.87 out of 5 average rating, 15 reviews

A charming outdoor seating area features a round table surrounded by two green metal chairs. A blue bench sits nearby, complementing the inviting entrance of the newly renovated cottage. The building's exterior displays a mix of red and wood tones, with multiple windows ensuring abundant natural light.

Cabin in Larsen

Newly Renovated Waterfront

Take it easy at this unique and tranquil getaway. This newly renovated cottage has a Murphy style Queen bed as well as a pull out couch to sleep four. The quartz counters make a perfect gathering space for friends and family. Plenty of room in the yard for your boat or other toys. Lake access is right around the corner for swimming, boating & kayak rentals. Enjoy a little slice of heaven on Lake Poygan with the Wolf River right around the corner! #fishon #boatlife

LocationFamilyCondition

The exterior of the lakeside home is showcased with a well-maintained lawn and flower beds. Large windows offer expansive views of the surroundings, while a white staircase leads to the inviting entrance. Nearby, comfortable outdoor chairs are positioned for relaxation.

5.0 out of 5 average rating, 42 reviews

Relaxing Lake Winnebago Waterfront Retreat

Experience the simple pleasures of lakeside living in this Oshkosh vacation rental! Featuring 3 bedrooms, 2 full baths, and 2 half baths, this beautifully designed home is the ideal spot to enjoy endless activities on Lake Winnebago. Take the pedal boat out for a spin or cast a line off the private dock! After, relax in the serene living room while admiring panoramic views of the lake through floor-to-ceiling windows, or end the night with stargazing on the patio!

Outdoor spacesLocationHeating

A serene lakeside view is presented, showcasing a lush green lawn leading down to Lake Winnebago. A large tree provides shade as calm water stretches toward the horizon, reflecting soft colors of the sunset in the sky.

4.97 out of 5 average rating, 32 reviews

Lank's Lookout on Lake Winnebago

Lank's Lookout, directly on Lake Winnebago, offers views that don't disappoint. This shallow glacial lake is a peaceful retreat. A short 15 minute drive to the EAA, and 45 minute drive from Lambeau Field. This lakeside home offers a wonderful space for swimming, fishing, birding. The quiet sounds of the waves bring a sense of peace and joy. The wood interior is rustic, yet refined. A perfect getaway for those who love water, nature, and relaxation.

ValueOutdoor spacesAmenities

5.0 out of 5 average rating, 19 reviews

Treehouse in Winneconne

Treehouse with Goats, River, and Hot Tub

The Goat Creek Treehouse is a brand-new build perched 12 feet up in the trees, overlooking the peaceful creek below. Spot deer (including rare albino ones!), watch songbirds from your window, and stargaze from the hot tub at night. Share 5+ private acres with friendly goats, paddle the river by kayak, and gather around the bonfire. A fully stocked kitchen and modern amenities await. Climb up, unplug, and reconnect with nature!

LocationOutdoor spacesBackyard

Superhost

Home in Menasha

New place to stay

Serene Lakefront Retreat

Relax in this beautiful lakefront home. This spacious retreat is perfect for families and large groups, offering 4 comfortable bedrooms and 2.5 bathrooms. Unwind in the outdoor hot tub or enjoy the beautiful lake view from the sunroom. Not ready to relax? Challenge your friends to a game of ping pong or take the kayaks out. Experience lake life at its finest! Forget your worries in this spacious and serene space.

A welcoming living area is highlighted by a brown sofa and an armchair. Light floods in through two windows, casting shadows on the hardwood floor. Notable art pieces are displayed on the wall, and a small side table with a lamp adds to the cozy ambiance.