Vacation rentals in Oshkosh

Guest suite in Winneconne

An aerial view captures the open-concept living space of the rustic cabin, featuring wooden beams and repurposed oak flooring. Bright light streams in from numerous windows, highlighting decorative rugs and cozy furnishings. A ceiling fan and antler accents complement the inviting atmosphere.

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 dock area is set against a backdrop of lush green grass and a wooden fence. The dock features multiple platforms extending into the water, surrounded by natural vegetation, creating a serene outdoor space ideal for relaxation or water activities.

5 out of 5 average rating, 38 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.

The staircase is showcased from an upper perspective, featuring wooden treads and a carpet runner along the bottom. White banisters frame the stairs, leading down to a landing that connects to a well-lit area. Natural light filters in from nearby doors.

4.83 out of 5 average rating, 101 reviews

Jackson Farmhouse

PERFECT FOR ANY FAMILY, CONFERENCE / EVENT ATTENDEE AND YOUR 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!

A modern shower space features a sleek design with grey tiled walls and a distinctive centerpiece of smooth pebbles. An adjustable showerhead is positioned overhead, and built-in shelves are available for convenient storage of toiletries.

4.88 out of 5 average rating, 188 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!

Apartment in Downtown Neenah

A modern coffee maker is positioned on a white marble surface, alongside a wooden tray. The tray holds assorted coffee and tea packets, sugar, and creamers, along with a bottle of water, providing convenient beverage options for guests.

4.84 out of 5 average rating, 160 reviews

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.

Two wooden chairs are positioned near a stone fire pit, facing the serene lake. A wooden pier extends into the calm water, with an additional chair situated on it. The scene is complemented by a clear blue sky and fluffy white clouds.

4.99 out of 5 average rating, 124 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, 190 reviews

A wooden dock extends into the calm waters of Lake Winnebago, surrounded by a clear blue sky. The water reflects the light, creating a serene atmosphere. A small boat can be seen in the distance, with gentle ripples radiating from its path.

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 historic home features a light-colored exterior with large windows, allowing ample natural light. The entrance is framed by steps leading up to a porch, complemented by a well-maintained garden. The sky above is bright blue with scattered clouds.

4.91 out of 5 average rating, 218 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 view of a fire pit featuring a gentle flame against a serene lake backdrop at dusk. The horizon displays soft gradients of orange and blue. Silhouettes of adirondack chairs and a boat dock can be seen in the distance, enhancing the tranquil atmosphere.

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.

4.9 out of 5 average rating, 79 reviews

Two horses are seen grazing in a grassy field at sunset. A white horse is positioned in the foreground, while a smaller brown horse grazes nearby. The sun is setting behind trees in the background, casting a warm glow over the landscape.

Farm stay in Omro

Comfy Cabin on 170 Beautiful Acres - Come Explore!

The cabin rests on 180 acres of scenic farm wildlife habitat. The property includes an 1800s-era barn & blacksmith shop, a host of wild & domestic animals, miles of private canal with access to the Wolf & Fox Rivers, a hiking trail, garden, orchard, and much more! The farm has been the pride of our family for 6 generations. A converted grainary, the cabin features a queen bed, full kitchen, full bathroom, high-speed satellite Wifi and smart-TV.

4.87 out of 5 average rating, 215 reviews

A light-filled kitchen is visible through a doorway, featuring white cabinetry and a wooden countertop. A window allows natural light to illuminate the space. Decorative shelves on one side display colorful glass items and personal touches, enhancing the room's character.

Apartment in Oshkosh

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.

4.92 out of 5 average rating, 276 reviews

A private bathroom is shown, featuring a white pedestal sink and a toilet. A small window allows natural light to enter, and a hand towel is hung on a rack. A bath mat lies on the floor, enhancing comfort and accessibility.

Apartment in Oshkosh

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

A space thats all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Oshkosh vacation rentals

Vacation rentals with pools in Oshkosh

4.96 out of 5 average rating, 25 reviews

The outdoor area features a spacious pool surrounded by multiple lounge chairs and umbrellas. Lush greenery and landscaped gardens enhance the inviting atmosphere. The house in the background complements the serene setting, providing a relaxed environment for gatherings and leisure activities.

Home in Wisconsin

Sunny Days Await | Private Pool & Hot Tub Retreat

5 out of 5 average rating, 22 reviews

Home in Green Bay

Next Level~100K Game Room~ Sleeps 20~ Pool~Spa

4.95 out of 5 average rating, 19 reviews

A heated pool area features numerous guests enjoying the water, with colorful floats and toys scattered throughout. Surrounding the pool, white lounge chairs are arranged on the concrete deck. A fence encloses the area, with lush greenery visible in the background.

Cabin in Montello

The Rabbit Retreat #1

4.86 out of 5 average rating, 232 reviews

An indoor pool with clear blue water is featured, surrounded by smooth concrete flooring. Bright overhead lights illuminate the space, while large glass doors offer views of the outdoor landscape. Greenery decorates the walls, adding a touch of nature to the area.

Home in Allouez

Amazing Six Bedroom Green Bay Vacation Home!!

4.81 out of 5 average rating, 37 reviews

A circular, above-ground swimming pool with clear, inviting water is visible, surrounded by lush greenery. The pool deck features wooden planks, and a set of steps leads into the water, creating easy access. The tranquil lake can be seen in the background.

Home in Montello

3bed lake house, private heated pool near WI Dells

4.97 out of 5 average rating, 35 reviews

The exterior of a two-story home is portrayed, featuring a welcoming front porch with potted plants. Lush green grass lines the pathway leading to the stairs. The facade combines traditional elements with modern updates, reflecting a craftsman style. A clear sky with scattered clouds adds to the scene.

Home in Plymouth

Private Home 4 BR+2Ba, Heated Pool by Road America

4.88 out of 5 average rating, 24 reviews

An indoor heated pool is framed by light-colored walls adorned with subtle marine-themed decor. Smooth tiles line the edge of the pool, while several white chairs are arranged nearby. Natural light filters through windows, reflecting on the calm water.

Home in Two Rivers

Cool City, Warm Pool

4.97 out of 5 average rating, 104 reviews

A spacious kitchen and dining area is visible, featuring modern white cabinetry and a large island with a stone surface. A wooden dining table is surrounded by four chairs, and sunlight is let in through multiple windows that offer a bright atmosphere.

Home in Ashwaubenon

Indoor Pool, 5 Bedrooms, 10 Min Walk to Lambeau

Show all

Other great vacation rentals in Oshkosh

A charming craftsman home is presented, featuring a welcoming front porch with three steps leading to the entrance. A well-maintained lawn surrounds the house, complemented by shrubs and trees. Large windows provide ample natural light, enhancing the exterior's inviting appearance.

5 out of 5 average rating, 34 reviews

Two Bedroom Craftsman Home

5 out of 5 average rating, 13 reviews

3+ bd 3 bath in Oshkosh on River near EAA

The exterior of the home displays a spacious patio area with comfortable seating arranged on a concrete surface. A second-floor balcony, adorned with orange chairs, overlooks the backyard, which features manicured landscaping and a mix of trees and shrubs.

5 out of 5 average rating, 28 reviews

Menominee House Lake View

A spacious patio area is visible, featuring a comfortable seating arrangement with navy blue cushions and a glass-top table. The home is designed with large floor-to-ceiling windows that offer expansive views of the surrounding greenery and landscaping. Steps lead up to the entryway from the patio.

5 out of 5 average rating, 24 reviews

Relaxing Lake Winnebago Waterfront Retreat

A corner seating area is featured, furnished with a comfortable brown couch adorned with blue and purple accent pillows. A round glass coffee table sits atop a decorative rug, while natural light streams through multiple windows, creating a bright and welcoming space.

4.96 out of 5 average rating, 84 reviews

Newly remodeled centrally located 2 bedroom home

A coffee station is positioned on a marble countertop, featuring a Keurig machine alongside a decorative carousel displaying various coffee pods. A glass jar containing creamers and sugar packets adds convenience to the setup, with sunlight streaming in from a nearby window.

4.91 out of 5 average rating, 23 reviews

The Dreamliner-0.6 mi to airport

4.96 out of 5 average rating, 24 reviews

An outdoor view of the barn studio suite is shown, featuring a covered porch with several colorful chairs arranged for relaxation. The building showcases a metal roof and large windows, surrounded by landscaped gravel and local greenery.

Barn in New London

Irish Acres Farm Glamping: Hayloft Hideaway Suite

A doorway opens to a patio area facing the water, featuring a round table and four chairs. The reflection of greenery is visible in the calm water, with a grill stationed nearby and recreational vessels seen along the shore.