Vacation rentals in Oshkosh

A bright sunroom features large windows offering views of the lake. Two chairs and a small table are arranged on a patterned rug, inviting relaxation. Natural light fills the space, highlighting the serene atmosphere and the vibrant colors of the surrounding nature.

4.84 out of 5 average rating, 128 reviews

Linger Longer On The Water

Cozy lake cottage on the west shore of Lake Winnebago featuring 3 bedrooms and 1 bath. Beautiful sunrises over the lake and just minutes from everything in Oshkosh Wisconsin. Large kitchen for preparing meals or just hanging out. 5 minute walk to Menominee Park. 6.5 miles to EAA Grounds. Less than 10 minutes to downtown and the University of Wisconsin, Oshkosh campus, shopping, restaurants and Main Street. Great location for walking, bike riding and just seeing the local sites. Park on site.

A lush green lawn extends towards the lake, flanked by two large trees. Two wooden Adirondack chairs provide a comfortable seating area, facing the water. The serene lake view stretches into the distance, with a small boathouse visible nearby.

4.99 out of 5 average rating, 128 reviews

Cozy Relaxing Lake Home with spectacular sunsets!

Located on the shore of Lake Butte Des Morts Yard,pier(summer months), (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

A neatly arranged bedroom features a black metal bed frame with a patterned comforter and decorative pillows. A glass side table sits beside the bed, while natural light filters through large windows adorned with light curtains. A cozy carpet enhances the warm atmosphere of the space.

4.88 out of 5 average rating, 26 reviews

Studio Apt near Downtown, River + Lake Winnebago

Enjoy your stay in the heart of the city in an attached Mother in law suite (like a mini apt) w Queen bed, pvt bath, TV/WIFI, pvt entrance w patio & mini kitchen appliances. Jun-Sept: Waterfest is every Thursday Farmers Markets on Wed & Sat (top 10 in US!) Oshkosh is Event City! You will never be bored! EAA, Lifest, XRoads41 & Mile of Music bring ppl worldwide. Best part- located by Downtown Bars, the water - UWO- Everything is walkable 30min drive to ATW and anywhere else in Fox Cities!

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, 211 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.

4.85 out of 5 average rating, 171 reviews

A well-lit hallway features smooth wooden flooring and white walls. Two framed botanical prints are displayed on the left. A small table with a plant is positioned near the doorway, which opens into a bathroom. Light filters in from the bathroom window.

Apartment in Neenah

Cozy and Simple Downtown Space

Enjoy this great space in a quiet safe neighborhood. One car allowed at the property! The space has comfortable beds, provided hygiene products, a smart TV and snacks + beverages. Wake up and enjoy coffee provided by us. Shops and restaurants within walking distance! Visit The Plaza downtown with ice skating, fire pits, a coffee shop and more. Great for a couples getaway. Luxury for a great price! A portion of the proceeds from bookings go to housing evacuees, refugees and veterans.

4.95 out of 5 average rating, 194 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.

4.96 out of 5 average rating, 202 reviews

A red door with a decorative wreath opens to a outdoor patio area, featuring a comfortable seating arrangement and potted flowers. Lush greenery surrounds the space, enhancing the connection to nature, with a glimpse of the lake in the background.

Cabin in Fox Lake

Cabin on the Trail

Kick back and relax in this cozy space with up north, cabin vibes. In the summer months enjoy the excellent fishing, swimming and boating and in the winter have fun ice fishing on beautiful Fox Lake! *Please read the full description and look at all of the pictures of the property *Not suitable for parties or loud gatherings. Please note, there is a 4 person maximum, including children. *All dogs/pets must be pre-approved by the host. There is a $50 pet fee/stay.

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, 226 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.

The dining area features a long wooden table surrounded by metal stools. Natural light enters through multiple windows with classic blinds, highlighting the rich wood accents and flooring. A modern light fixture hangs above the table, enhancing the room's inviting character.

4.84 out of 5 average rating, 107 reviews

Jackson Farmhouse

Perfect for a big group! Our beautifully restored 100 YEARD OLD farm house is located on Jackson St in Oshkosh giving you quick and easy access to highway 41! **Please note this home is old and has sloping floors and a few drafts** The easy in and out driveway can hold at lease 8 cars if needed during your stay at our comfortable property. After a long day of whatever you may be in town for you'll be able to relax in your own piece of country!

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, 223 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 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, 285 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

Get the amount of space that is right for you

Houses

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Apartments

Convenient locations with everyday essentials

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Oshkosh vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Pet-friendly vacation rentals in Oshkosh

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.

4.86 out of 5 average rating, 249 reviews

Late Summer Retreat • Firepit • Lake • Downtown!

4.79 out of 5 average rating, 289 reviews

The two-story home features a charming yellow exterior with white trim and a red metal roof. Flower baskets hang from the porch, which is framed by neatly manicured bushes and vibrant landscaping. A sidewalk leads to the entrance, enhancing accessibility.

Home in Sheboygan

Home Away From Home-One Block From Lake Michigan!

4.98 out of 5 average rating, 198 reviews

The cabin exterior is surrounded by a serene pine forest. A spacious porch features a dining table and seating areas, while a fire pit is situated nearby. A hot tub rests on the patio, inviting relaxation amidst nature.

Cabin in Montello

The Loch at WhiskyWood, secluded cabin + hot-tub

Place to stay in Elkhart Lake

A tree-lined pathway leads to a cozy cottage, framed by colorful fall foliage. Orange pumpkins are placed near vibrant purple flowers, enhancing the seasonal charm. The yard is spacious, surrounded by mature trees, providing a serene and inviting atmosphere.

4.97 out of 5 average rating, 244 reviews

Cottage @ Schoolhouse*Firepit*Petfriendly

4.95 out of 5 average rating, 188 reviews

An open concept living area features a modern kitchen with stainless steel appliances and a marble countertop. A round dining table with upholstered chairs complements the sleek bar stools at the kitchen island. Light wood flooring enhances the spacious feel of the room.

Home in Appleton

Modern, Freshly Renovated House - Great Location

4.95 out of 5 average rating, 143 reviews

Cottage in Neshkoro

Pet Friendly Antique Schoolhouse with Fenced Yard

4.96 out of 5 average rating, 222 reviews

The cabin features a welcoming front porch with a swing and a picnic table. A charcoal grill is positioned nearby, set against a backdrop of lush greenery. The exterior is adorned with wood siding and large windows, creating a pleasant connection with the surrounding nature.

Cabin in Hancock

Peaceful Cabin in the Woods

4.96 out of 5 average rating, 163 reviews

A spacious studio apartment is highlighted by a large, unique chandelier above the bed. Natural light floods the area through multiple windows, illuminating the polished wooden floors and cozy seating arrangement. The open layout includes a kitchenette visible in the background, enhancing the inviting atmosphere.

Loft in Amherst

Tiny Town Bakery Flatlet

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Other great vacation rentals in Oshkosh

4.69 out of 5 average rating, 85 reviews

The exterior of the cottage features string lights above a patio area with a glass-top table and four chairs. A barbecue grill is positioned nearby. The cottage is surrounded by lush green grass, and a soft sunset hue provides a warm backdrop.

Cottage in Oshkosh

Kalbus Cottage Lake Winnebago

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, 18 reviews

3+ bd 3 bath in Oshkosh on River near EAA

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, 32 reviews

Waterfront Retreat*Kayaks*Firepit*Dog Friendly

A spacious primary bedroom features a large king bed with crisp white linens and multiple pillows. Two windows allow natural light to fill the room, and a ceiling fan provides added comfort. Light grey curtains frame the windows, and a small bedside lamp sits on each side of the bed.

4.92 out of 5 average rating, 12 reviews

Charming 2 bedroom with king bed and pet friendly!

4.92 out of 5 average rating, 88 reviews

A charming dining area features a large round table surrounded by wooden chairs, set against a backdrop of eclectic mirrors and wall decor. Natural light streams through the windows, illuminating the rustic elements and adjoining open kitchen area.

Home in Green Bay

Charming 1870s Downtown Loft

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.

4.92 out of 5 average rating, 38 reviews

Ranch Duplex on Golf Course - Location! 2BR 1BA

A spacious living room is highlighted by a large, comfortable couch while a TV is mounted on the wall. Natural light enters through two windows, and a colorful triangular wall design adds interest. A side table and an accent chair complement the seating area.

5 out of 5 average rating, 8 reviews

Home Away from Home - 2 BD Mid-Century Ranch

A peaceful lakeside setting is shown, featuring a circular fire pit surrounded by four wooden chairs on lush green grass. The calm waters of Lake Winnebago can be seen in the background, with trees framing the scene and a distant dock visible along the shore.