Vacation rentals in Oshkosh

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

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!

Downtown Loft with historic charm

Stay in historic downtown Ripon, less than a block away from it all! It has large beautiful windows to watch the downtown bustle, as well as see the magical night-time lights. The moment your leave the front door you'll have famous shops, on point drinks, amazing food, Wisconsin ice cream, retro candy, coffee shop, and much more! 10 minutes from Green Lake! 30 minutes from Oshkosh and Fond du Lac. Less than 90 minutes away from Appleton, Green Bay, Madison, Milwaukee, etc.

Charming 1870s Downtown Loft

Like your favorite cup of coffee, this sunlit haven energizes and comforts. Just steps from downtown's vibrant pulse, this thoughtfully restored 1870s duplex is crafted for connection, creativity, and relaxation. Work under high ceilings bathed in natural light, or gather with friends in the spacious, open kitchen and dining area. Modern amenities ensure a home-like experience in a space that seamlessly combines the warmth of history with the ease of modern living.

Two Bedroom Craftsman Home

Enjoy a short getaway in this beautiful two bedroom craftsman home, situated in the heart of Oshkosh, Wisconsin. The home is located less than 15 minutes drive from Wittman Regional Airport, and 5 minutes drive from Lake Winnebago. The Paine Art Center, University of Wisconsin-Oshkosh, Downtown Oshkosh, Wiouwash Trail, Fox River and Congress Field/Playground are all within walking distance. Grocery stores, restaurants, and other essentials are also close by.

Shorehaven Lakehouse

Welcome to the Shorehaven Lake House! Perfect for a couples retreat, an outing for the entire family, or those in town for any of Oshkosh and the surrounding cities many events! Have the ultimate Wisconsin getaway by escaping to this beautifully renovated Lake Butte des Morts home that comfortably sleeps 6. This home provides beautiful sunsets and sunrises over the lake and a quiet neighborhood for your escape! Please let us know if you have any questions!

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.

Sunset Point Lake House

Super cute, old, little lake house located on Lake Butte Des Mortes in Oshkosh, WI. It definitely lives up to its name— with breathtaking sunsets. Perfect spot for biking, hiking, bonfires, and relaxing. Walking distance to Wiouwash Trail. Ideal location for couples, but sleeps 4 (1 king bed & 2 twin beds). 1 little bathroom (Please note: I do not supply firewood, there is not a grill on the deck, or a dock for boats) insta: @yellowdoorsunsetpoint

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.

Comfortable 2 bedroom upper unit #1

Be Advised Neighborhood construction possible starting Spring 2026. The whole group will enjoy easy access to everything from this centrally located place. 4 miles from Wittman Regional Airport 4 blocks from the Oshkosh Arena 5 blocks from the Oshkosh Convention Center. Walking distance to restaurants and local bars. Live music Thursdays in summer at Fox on the river, you can hear the music outside the unit.

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!

Cozy getaway 1 mile from downtown and UWO campus!

2 bedroom home with a living room and dining room, kitchen with appliances, laundry room and Big backyard. (Kid friendly) Grocery store, gas station, and restaurants are less than a mile away. (Within walking distance) Great, clean neighborhood. Only a mile from Menominee park, arena, and other destinations you may want to explore.