Vacation rentals with a kayak in Oshkosh

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Top-rated kayak rentals in Oshkosh

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

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Top guest favorite
A serene view of the water at dusk is framed by trees along the riverbank. The calm surface reflects soft colors of the sunset, enhancing the tranquil natural setting.
Home in Appleton
4.97 out of 5 average rating, 110 reviews

Riverfront log cabin in the heart of the valley

◖30 minutes to Oshkosh(EAA) & Green Bay(Lambeau), 10 minutes to Downtown Appleton ◖10 minutes to Kimberly boat launch; travel the Fox River Locks system You will LOVE this property: ◖Outstanding views from the amazing sunsets to the relaxing water & wildlife ◖Newly renovated with many amenities ◖Enjoy the Northwoods setting in the heart of the valley ◖Relax at end of the day sitting around a campfire or by indoor fireplace ◖Tie your boat to dock in front of property ◖Full kitchen/outdoor grill

Guest favorite
A charming log cabin features rustic wooden architecture, complemented by red window frames. Surrounded by lush greenery, the structure offers a welcoming front porch. Natural light bathes the exterior, enhancing the serene setting among the trees, with a pathway leading to the entrance.
Cabin in Campbellsport
4.94 out of 5 average rating, 104 reviews

Wooded CABIN-Sunset & Lake Views/Kayak to Tiki Bar

Slow down at Fraser Fir log cabin, built in 1958 on Kettle Moraine Lake. In the summer, enjoy quiet moments watching the sun set from the front porch, then relax by the fire pit under a sky full of stars. Fish from the dock, kayak around the lake, or bring your boat to soak up the sun. In the winter, grab your ice-skates or ice-fishing gear and head out on the lake. With countless trails nearby, the hiking options are limitless and beautiful in every season. Your next adventure awaits.

Guest favorite
The living area features a light-colored sofa paired with two armchairs, accompanied by a small table. A decorative rug adds warmth to the hardwood floor. Natural light streams in through large windows, offering views of the surrounding trees.
Cottage in Princeton
4.96 out of 5 average rating, 216 reviews

RiverFront Cottage>Private Pier>Firepit & Wildlife

Cute little cottage located right on the Fox River overlooking the peacefulness nature has to offer. Enjoy your very own private dock as well as 200 feet of river frontage surrounded by tall mature trees. Be submerged by the community of fishermen (& women) located on Puckaway Lake, surround yourself with wildlife, or paddle down the Fox River. Soak up the sun on the dock or learn how to build the best fire in the fire pit! The adventure is all around you! Which one will you be choosing?

Guest favorite
A historic lighthouse stands at the water's edge, illuminated by the vibrant colors of sunset. Smooth stones line the shoreline, reflecting the serene lake. Lush greenery is visible in the background, creating a peaceful coastal setting.
Home in Fond du Lac
4.92 out of 5 average rating, 102 reviews

Woltring Waters Waterfront Home

Wake up to a beautiful view of Lake Winnebago, and enjoy you cup of coffee with the sound of crashing waves off the back porch. You will have breathtaking sunsets with the historical light house backdrop that is in viewing distance from the property. From dining to convenient stores everything you need is in walking distance. Take a peaceful stroll around the marina or take the kids to Lakeside Park, offering a petting zoo, carousel, train, jungle gym & splash pad. Everyone will enjoy!

Guest favorite
The exterior of a renovated Cape Cod house features gray siding and white trim, surrounded by a well-maintained lawn and colorful flower beds. Windows allow natural light to illuminate the interior, while a pathway leads to the entrance. The lake can be seen in the distance.
Home in Fond du Lac
4.96 out of 5 average rating, 114 reviews

Lake Winnebago Cape Cod beautifully remodeled home

Large completely renovated 1500 sf. cape cod with hardwood floors, spacious bedrooms, a den/office with work area. New 16 x 16 deck this year. Completely remodeled kitchen, stainless and quartz counters.  Open floor plan makes cooking and dining a pleasure. 3 seasons room with comfy wicker.  Living room with 58" smart TV and bookcase full of games and books.  Enjoy the lake with the available Kayaks and Canoe.  Laugh the night away with a lakeside fire.  Some of the best walleye fishing.

Top guest favorite
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.
Home in Oshkosh
4.99 out of 5 average rating, 104 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)!

Top guest favorite
The exterior of the cottage features a light gray siding with maroon window trim. A white railing surrounds the entrance, leading up to a set of stairs adorned with a potted plant with red flowers. A small garden with white flowers borders the path.
Cabin in Fox Lake
4.98 out of 5 average rating, 103 reviews

Cottage on the Trail

Welcome to your relaxing retreat on the lake! In the summer months enjoy fishing, swimming and boating right out your back door and in the winter experience ice fishing on beautiful Fox Lake! *Please read the full description and look at all pictures of the property before booking *Not suitable for parties or gatherings. *Due to parking restrictions and the nature of the property, there is a 4 person maximum with room for 2 vehicles or 1 vehicle and 1 boat/trailer. *Sorry, no pets

Guest favorite
A charming lakeside home is nestled among lush greenery. The structure features a wooden deck extending from the front, complemented by a stone chimney. Tall trees surround the property, creating a serene atmosphere, with the outdoor space designed to blend with the natural landscape.
Home in Wautoma
4.88 out of 5 average rating, 131 reviews

Lakefront Home on quiet sandy lake! All seasons

Beautiful lakeside home with wall of windows facing the lake. Giant 2-acre lot feels like you're entering the wilderness, with huge lake frontage. 40-foot deck overlooking Lake Alpine, a sand-bottom lake full of fish. Swim next to the dock (shallow). Gentle sloping path to lake- no steps. Gas fireplace to stay cozy on cool nights. Your own dock, pedalboat, canoe, kayaks, toys and forest to explore. Summer fun and 5 min. to skiing, tubing, snowshoeing, snowmobiling.

Top guest favorite
Chalet in Campbellsport
4.97 out of 5 average rating, 110 reviews

Long Lake Chalet

This recently remodeled and tastefully furnished, PET FRIENDLY, cabin boasts a unique charm. Nestled along the shores of Long Lake in the heart of the Kettle Moraine Forest, this lakefront property offers 45’ of serene, peaceful beauty. This stunning home features a large yard, pier access and year round recreational activities. Disconnect, unwind and take in all that Kettle Moraine has to offer. Whether vacationing with family or friends this retreat is waiting for you.

Top guest favorite
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
4.94 out of 5 average rating, 238 reviews

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.

Top guest favorite
The exterior of a two-story blue lakeside home is displayed, featuring large windows that allow for ample natural light. Adjoining the home, a well-maintained lawn is complemented by a fire pit area with light green Adirondack chairs, creating an inviting outdoor space.
Home in Beaver Dam
4.92 out of 5 average rating, 145 reviews

LakeLife is Dam Good! 4 Bedroom Waterfront Home

Fun for the whole family at this stylish lakeside home in the heart of Beaver Dam. The house as everything a group needs and wants for the perfect weekend, week, or overnight adventure. From the open floor plan living room to the exposed game room basement that leads right out to the lakeside yard. We've filled this home with all the touches needed to guarantee lake life living. The backyard overlooks thousands of acres of lake with endless lake views.

Top guest favorite
A fire pit is surrounded by several woven seating options on a grassy area, overlooking a calm river. Lush greenery lines the background, creating a serene outdoor gathering space. The scene is framed by a black fence, bringing focus to the inviting fire pit.
Home in Sheboygan
4.95 out of 5 average rating, 336 reviews

River Home Getaway with River Access - Sleeps 8

Enjoy your getaway in the comfort of the River Home. With the Sheboygan River flowing through your backyard and living spaces stylishly decorated, the scene is set for a truly remarkable vacation. The eat in kitchen is equipped with all the necessities to whip up a delightful meal. The family room has a variety of board games as well as a smart TV for entertainment. The space is complete with four well-appointed bedrooms.

Popular amenities for Oshkosh kayak rentals

When is the best time to visit Oshkosh?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$38,268 GYDG$37,850 GYDG$37,850 GYDG$51,234 GYDG$51,234 GYDG$53,952 GYDG$87,829 GYDG$53,952 GYDG$46,006 GYDG$40,569 GYDG$41,405 GYDG$41,196 GYD
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Quick stats about vacation rentals with a kayak in Oshkosh

  • Total vacation rentals

    Explore 20 vacation rentals in Oshkosh

  • Nightly prices starting at

    Oshkosh vacation rentals start at G$14,638 GYD per night before taxes and fees

  • Verified guest reviews

    Over 700 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Oshkosh vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Oshkosh rentals

  • 4.9 Average rating

    Oshkosh stays are highly rated by guests—averaging 4.9 out of 5!

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