Holiday 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

Exceptional Apartment in Historic Downtown Oshkosh

This 2nd floor apartment (all guests must be able to climb stairs) is located in the heart of downtown Oshkosh. Guests are welcomed by natural light streaming through the skylights in nearly every room of this serene space. The interior is a thoughtful blend of modern furnishings & historic accents, paying homage to the history of the building and city. The Harmony Wellness Center operates on the 1st floor & the Farmer’s Market is right outside from June through Oct. Includes driveway parking.

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.

Two bedrooms with attached garage

Easy access from Hwy 41, located in a quiet neighborhood. A private condo w/attached garage, allowing you to enter directly into the will equipped kitchen without exposure to the elements. High-speed internet, complete furnishings, perfect for a comfortable stay. Private laundry room in the basement. - Lambeau Filed 27 miles - EAA Oshkosh 28 miles - Appleton Medical Center 3 miles - Downtown Appleton 3 miles - St Elizabeth Hospital 5 miles - Appleton Airport 7 miles - Theda Clark 14 miles

Waterfront Retreat*Kayaks*Firepit*Dog Friendly

Waterfront getaway on a peaceful channel with direct access to Asylum Bay and Lake Winnebago Perfect for families, friends, and outdoor enthusiasts. • Easy access to Asylum Bay and Lake Winnebago • Dog‑friendly (additional pet fee applies) • Spacious, fenced‑in backyard (open on the water side for access) • Double dock ideal for boating, fishing, and relaxing by the water • Kayaks available for guest use • Cozy fire pit with firewood provided • Indoor and outdoor games for all‑weather fun

Secluded Cabin with Sauna

Place yourself in nature. Put down your phone and pick up a book. Clear your mind, focus on your breath, connect with your inner self. Sleep like you’ve never slept before accompanied only by the sound of owls and wind in the pines. The Belden Farm offers land that is a true retreat. Enjoy the privacy and quiet of our cabin in the woods. Extensive, well-maintained trails for hiking, skiing or Fattire biking lead you through towering hardwoods, cathedral white pines, and golden meadows.

hot tub and sauna on 5 private acres

Looking for a peaceful retreat? Experience 5 acres of tranquil, private woodland paradise. Cool nights are perfect for warming up in the hot tub or infrared sauna which overlook the meadow. Explore hiking trails and lakes that the scenic Kettle Moraine has to offer. Grill a delicious meal and later craft perfect s’mores by campfire as the crickets sing. Unwind at SoLu winery, just a minute down the road. Near Road America, Kettle Moraine State Forest, and Dundee. Your getaway awaits!

Sky & Stream Escape

Welcome to your cozy, newly renovated retreat in Oshkosh, WI! Ideally located, it provides easy access to leisure and essentials. For water enthusiasts, boat ramps for the Fox River and Lakes Winnebago and Butte des Morts are within 5 miles. For aviation fans, the EAA Museum is also 5 miles away. Aurora Medical and the University of Wisconsin Oshkosh are within 2.5 mi, and the Outlet Shoppes are 4.5 mi away. The vibrant downtown dining scene is also readily accessible.

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.

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.

Winnebago Lake View Retreat

Newly constructed duplex Lake view retreat nestled on South Main St in Oshkosh, comfortable and coveniently located retreat is perfect for famillies, couples, business travellers and EAA visitors, walkable to Oshkosh Arena, Oshkosh University, Golf course. Escape to modern luxury and endless recreation at our newly constructed duplex lakeview. Step in side to discover a professionally designed interior where sophiscated style meets lakeside comfort