Vacation rentals in Oshkosh

A cozy living area is presented, featuring a navy sofa adorned with patterned throw pillows. A wooden coffee table rests atop a patterned area rug. Two barstools are positioned at a sleek counter, while framed artwork and a potted plant are displayed on the walls.

4.96 out of 5 average rating, 23 reviews

Cozy Duplex in Oshkosh

Enjoy this cozy space close to Main St with breweries, restaurants and activities nearby. Within walking distance to the River, Lake Winnebago, Downtown Oshkosh, the Arena and only a 5 minute drive to the EAA Grounds/ Wittman Regional Airport! Less than 2 miles away! In addition to the fantastic location, this single story duplex offers a queen bed and a pull out couch for additional guests. Washer and dryer included in-unit. Street parking available, door code will be provided for self check in

Guest suite in Winneconne

An open-concept living area showcases wooden beams and a warm oak floor. A well-equipped kitchen is visible with bar seating. Comfortable seating is arranged near the staircase, adorned with rustic decor and framed art pieces. Natural light streams through multiple windows.

4.81 out of 5 average rating, 228 reviews

Lake Winneconne Area Cottage "CabinSong" tradition

Northwoods-ish rustic cabin: 750 sq.ft., open-concept, lotsa windows, repurposed oak floor, 3/4 bth, equipped kitchen, dining/fun bar, two decks, E &W. 1 Qn, 1 dbl bed, qn. hide-a-bed, 1 twin. Optional: qn or twin air-bed. Desk, dresser, views , cable TV, wifi, stereo, heat/AC. Access to Lake Winneconne public boat ramp, 200 yrds! On-site & off-st. parking trailers. Quiet neighborhood; 3 mi. from Winneconne; easy access to Oshkosh, Green Bay, Fox Cities. Fun, not fussy seasonal decor.

A wooden deck overlooks Sawyer Creek, featuring two metal chairs with floral cushions positioned around a small fire table. Lush greenery surrounds the area, and a dock extends into the water, providing a serene view of the natural setting.

5 out of 5 average rating, 40 reviews

Fenced Yard; Waterfront; Dock, Cozy & Refreshing

Take it easy at this unique and tranquil getaway. Located on Sawyer Creek; enjoy peaceful views in a quiet neighborhood. Privacy is yours with a fenced in yard & attached 2 car garage. Comfortable 2 bedrooms with Queen beds & a fully stocked kitchen, outdoor grill, 55 in Smart TV and dedicated desk area. Propane firepit, patio table & 2 kayaks, washer & dryer. Close to Wiowash Trail, resturants, UW-Oshkosh and Oshkosh Corp headquarters. EAA grounds is a short 12 minute drive. Dog friendly.

A log home with a wooden exterior is surrounded by lush greenery. The front porch is adorned with a small blue umbrella and features a set of steps leading to the entrance. Gravel driveway and flower beds enhance the welcoming ambiance of the property.

4.88 out of 5 average rating, 189 reviews

Go and Go

Cozy 2 bedroom Log home. Can sleep 4-6. Across the street from Lake Winnebago. Short walk to park, zoo and boat landing. 6.5 miles to EAA grounds. Off street parking. Close to shopping, restaurants and downtown Oshkosh. Great rental for Air Show, Book now and bring your boat, jet ski, trailer, and fishing gear or just go sightseeing, dining and relaxing. Full kitchen, New Bath. Very comfortable with a great location. Perfect place to stay for family with students at UWO. Book now!

A serene bedroom features a spacious bed adorned with a soft, floral-patterned coverlet. Light filters through a window adorned with sheer curtains, while a small nightstand and a chair complete the cozy space. A hanging plant adds a touch of greenery.

4.87 out of 5 average rating, 208 reviews

Quaint 2 bedroom upper apartment in duplex.

This home is located in a safe neighborhood, close to the main highway . Close to UWO, shopping, dining, and a few short blocks from a park, fishing and boating. You have a 2 bedroom, 1 bathroom upper apartment for your use. Queen size beds in bedrooms, futon in the living room. Queen size air bed also available . Full kitchen use and parking for 2 cars, free internet, great backyard, use of grill and fire pit. Owner lives downstairs. Pets may be allowed. Children are always welcome.

4.99 out of 5 average rating, 126 reviews

Cozy Relaxing Lake Home with spectacular sunsets!

Located on the shore of Lake Butte Des Morts Yard,pier, (sorry we do not allow anything to be tied up to our pier)solo fire pit, grill,seating SUNSETS Lake view Bedroom,Living Room,Dining area Close to Wiouwash trail for hiking, biking,snowmobiling Approx. 40 miles to Lambeau Field Close to EAA Restaurants Shopping Gas fireplace in Living / dining room with a desk Kitchen with space for cooking. Washer/dryer Larger 1 bedroom /Queen Sleep Number mattress Off street parking

4.95 out of 5 average rating, 191 reviews

The cottage features a long, metal-roofed exterior with gray siding and contrasting purple shutters. Lush greenery surrounds the home, including decorative flower beds. A paved pathway leads to the entrance, highlighting the spacious yard. Sunlight enhances the bright and welcoming appearance.

Guesthouse in Oshkosh

Cottage on Lake Winnebago

Furnished Cottage on Lake Winnebago with beautiful sunrises. 1 bedroom with queen bed. There is plenty of space for air mattresses in common areas. 1 queen air mattress available. One bath, full kitchen fully stocked with dining area, bring your own food to prepare. Bring your water toys or boat, launch nearby and dock access in warmer months with great fishing. Winter months, bring your snowmobile, trails nearby. Great ice fishing when lake is frozen and ice is safe.

A spacious dining area is illuminated by natural light from large windows. A wooden table with six chairs is centered in the room. Decorative items, including wall art and a wreath, are displayed on the walls, contributing to the charming ambiance.

4.91 out of 5 average rating, 222 reviews

Charming Spacious 2BDR by Downtown/Menominee/Lake

This historic and charming home is located just one block away from Menominee Park and Lake Winnebago. Menominee parks offers amusement rides, the Zoo, asphalt trails, boat tie ups, casting dock, historical interest, fishing, ice rink, picnic areas, large playgrounds, baseball fields, soccer fields, tennis/ pickle ball courts, and volley ball courts. The home boasts a lot of character and has all the amenities to make your stay comfortable and memorable.

4.99 out of 5 average rating, 287 reviews

A relaxing living area features a stone fireplace as its focal point. Comfortable seating options, including a leather chair and a spacious sofa, are arranged around a rustic coffee table. Large windows allow natural light to fill the space, with glimpses of the surrounding scenery.

Cottage in Fond du Lac

Beautiful Lake Home.

Our Beautiful two bedroom cottage is located on the shores of Lake Winnebago . Centrally located to many of Wisconsin's best attractions. Less than 1 hour from Milwaukee, Madison, Green Bay, Close to Oshkosh (EAA) and Elkhart Lake. Includes 2 bedrooms, with plush queen beds, 1 full bathroom, Laundry room with washer and dryer. The perfect home for a laid back group of friends, couples or a family to stay with all the comforts of being at home.

The exterior of a two-story house is shown, featuring a porch and a well-maintained lawn. Large windows are visible, offering natural light to the interior. Surrounding trees provide shade, and a pathway leads to the entrance, enhancing accessibility.

4.86 out of 5 average rating, 217 reviews

No Cleaning Fees! 2 Bedroom Apartment By The Lake

We’re transparent with our pricing, that’s why we don’t have cleaning fees! The price you see is the price you pay (local taxes still apply). Come stay near the heart of Oshkosh - you’ll be on the second floor with views of Lake Winnebago. If you need anything during your stay we live on-site and are only a message away. Don’t worry though, the units are completely separated so you’ll have all the privacy you desire during your stay.

A comfortable living area features a gray sectional sofa and a wooden coffee table. A television is mounted on the wall, and a side cabinet adds storage. Natural light enters through a nearby window, illuminating the space with a warm and inviting feel.

4.87 out of 5 average rating, 242 reviews

EAA-Perfect! 3BR by Lake + Firepit & Parking

☀️ Cozy 3BR across from Menominee Park & Lake Winnebago! Just 10–15 min from EAA with easy shuttle access via nearby UWO. Walk to the beach, zoo, and trail. Sleeps 8 with WiFi, smart TVs, upstairs lounge & basement bar. 🔥 Enjoy summer nights under the gazebo with a gas firepit. Perfect for relaxing after the airshows with driveway parking & self check-in. Now booking EAA week & peak summer!

A cozy sleeping area contains two full-size beds adorned with warm-colored bedding. Nightstands with lamps are placed beside each bed. A comfortable chair sits in the corner, and two windows allow natural light to illuminate the room. Decorative rugs cover the laminate flooring.

4.92 out of 5 average rating, 277 reviews

Rosie's Place A

Hello and Welcome! Rosie's place A features a cozy newly renovated clean furnished upper apartment. Very close to everything in Oshkosh. Great for business travelers, vacationers and visiting University of Oshkosh and Hospital families. Breakfast items, fruit, coffee, tea, soda, water & snacks included. Private parking behind the house. Door code will be provided to enter. No minimum stay!

Vacation rentals for every style

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Quaint homes, peaceful surroundings

Popular amenities for Oshkosh vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Other great vacation rentals in Oshkosh

A single-story house with a white exterior is set against a clear blue sky. A large tree provides shade in the yard, with a shaded patio area visible. The property features a dock along the river, making it accessible for boat parking.

5 out of 5 average rating, 14 reviews

3+ bd 3 bath in Oshkosh on River near EAA

An aerial view of the home reveals a contemporary design with a combination of gray siding and a light wood accent. Lush greenery surrounds the property, complementing the landscaped yard. A spacious upper deck can be seen, along with outdoor seating on the patio.

5 out of 5 average rating, 30 reviews

Menominee House Lake View

Superhost

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.

4.97 out of 5 average rating, 30 reviews

Waterfront Retreat*Kayaks*Firepit*Dog Friendly

4.91 out of 5 average rating, 81 reviews

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

Woltring Waters Waterfront Home

A cozy living area is depicted with a soft grey sofa positioned near a small wooden table. A wall-mounted television is visible, and art adorns the walls. A greenery accent adds a touch of nature, creating a relaxed ambiance within the space.

4.91 out of 5 average rating, 67 reviews

Charming Oshkosh - 2 Bedroom, Walk to Downtown

A living area features two cozy gray sofas positioned around a textured area rug. Two circular coffee tables sit in the center, complemented by decorative cushions on the sofas. Natural light enters through a window, which is framed by light curtains, while a floor lamp provides additional illumination.

4.88 out of 5 average rating, 64 reviews

Cozy fully furnished home

A modern living room showcases a large television mounted above an electric fireplace. Built-in shelves are illuminated, displaying decorative items. A cozy atmosphere is created with neutral walls and warm lighting from the fireplace, enhancing the inviting space.

5 out of 5 average rating, 9 reviews

Oshkosh View

A dining area features a wooden table surrounded by white chairs, with a framed artwork displayed on the wall. Double glass doors lead to a screened porch overlooking the backyard, which is illuminated by soft string lights.