Vacation Home Rentals By Owner In Oshkosh, WI

Welcome to Oshkosh!brbrOshkosh is Wisconsin's Event City & understands when guests, travelers, & transplants are choosing a location for a stay or event, they want a location that can provide more than a bed to sleep in, which makes my home a solid place to stay while in the area.brbrOshkosh & my home is more than just events & a bed. It's supper clubs, breweries, social clubs, shopping, nightlife, outdoor recreation, + more. Oshkosh is a small city with a big-city feel, so whether you're from Chicago or a small village, you'll find the amenities & attractions you crave combined with genuine Wisconsin hospitality.brbrSeeking a place to stay in a community that has a little bit of everything brbrWe got you! We're a City on the Water. Located in Northeast Wisconsin on the western shore of Lake Winnebago, Oshkosh is banked by the Fox River and Lake Butte des Morts. Both lakes provide the perfect opportunity for water sports, such as boating, sailing, swimming, fishing, ice fishing, & sturgeon spearing. Many of the area’s restaurants offer picturesque outdoor dining along the Riverwalk while numerous events are held outdoors, such as events at the Leach Amphitheater. (My home do NOT include a dock, pier, or boat access - but a public boat launch is 1.5 miles away at Menomoniee Park). brbrOshkosh has it all... https://www.visitoshkosh.com/brbrNATURE brlake life, hiking/bike trails, boating/boat cruises, fishing, ice fishing.brbrLATE-NIGHT ADVENTURE brKeep the candle burning at the Mineshaft, or catch DJ Trivia or Bingo. Embrace the charm of our historic district, where the Fox River meets a vibrant urban center. Explore delightful dining, unique shopping, captivating arts, & a calendar filled with exciting events. Grab a craft beer at a Fox River brewery, sip on Old Fashioned at Sturgeon Spirits, &/or take in a fish fry at a supper club. Dance the night away at a club or karaoke with friends at a local pub. Venture downtown to find live music (The Grand Oshkosh) nearly every night of the week or stop by the comedy club for a good laugh on the weekend. Nightly entertainment is just a short walk or quick Uber ride away in Oshkosh.brbrSPORTS brHome to WI Herd NBA G-league to Milwaukee Bucks and Wisconsin Glo Women's Basketball Team. Multiple local bowling alleys including T & O Bowling Lanes, The Howard (Art Deco), & Revs. Waupaca 'Boatride' grass court Volleyball Tournament = hosted in July - Oshkosh, WI - Brighton Acres. brbrOnly 50 minutes from Lambeau Field - Go Packers!brbrMUSIC brLeach Amphitheater, Waterfest, Oshkosh Arena, XRoads41 Music Festival, Lifefest, Mile of Music.brbrART brPaine Art Center & Veterans Museums. Check out historical Oshkosh through our many museums. The Military Veterans Museum for the Educational Center carries a collection of military artifacts including artwork, books, & photographsbrbrEAA brLet your imagination take flight at the EAA Aviation Museum & Air Show in July. Fly over to the EAA Aviation Museum for aircraft displays & aviation galleries. brbrKID-FRIENDLY brParks, museums, candy stores, & a FREE zoo! Family-friendly activities & events throughout Oshkosh. Paint pottery & other crafts at Fire Escape or race against the clock with puzzles & clues at Escape Oshkosh, EAA Youth Education Center, & Homie Hub Indoor Play Cafe.brbrOUTDOOR FAMILIES brGet on your bikes & ride the Wiouwash Trail, visit the Menominee Park & Zoo (free admission!). Oshkosh Popcorn, Ice Cream, & Frozen Custard taste great all year round. Satisfy that sweet tooth, check out the divine flavors at Leon's Frozen Custard, Caramel Crisp, Rhapsodies, Culver's, Ardy & Ed’s Drive-In, Tamara’s Cupcakes, & Insomnia Cookies (to name a few).brbrFARMERS MARKET brOshkosh Farmer's Market on Saturday mornings during the summer.brbrCOLLEGE LIFE brUW Oshkosh - Go Titans! A public university of 14,000+ students. UWO offers a diverse range of undergraduate & graduate programs with a variety of academic resources, including 200+ student organizations, academic clubs, & service organizations. UWO is home to 3 colleges: College of Business, College of Education & Human Services, and College of Letters & Science + 21 varsity athletic teams (National Collegiate Athletic Association (NCAA) Division III).brbrGOLF brOshkosh Corporate Bank 1st Chamber Golf Invite & future Rider Cup hosting site.brbrSHOPPING brDowntown Antiques, Consignment, Thrift/Vintage Fun, Boutiques, + Outlet Mall. Rain or snow, Oshkosh has indoor activities for you. Head to the Oshkosh Arena for concerts, sports games, shows, & more. Need some retail therapy Stop in Downtown Oshkosh for local boutiques, markets, and thrift stores. We are also home to the Oshkosh Outlet Mall where you will find top brand stores such as Nike, Coach, Gap, and The North Face.brbrWINTER ACTIVITIES brIce fishing, 608 Axe Throwing, Clubhouse Indoor Golf & Bar, Birch Art Studio, Escape Oshkosh, Glow In The Park Indoor Mini Golf & Pinball Arcade, The Morgan House, Oshkosh Community YMCA - 20th Ave, Oshkosh Community YMCA Downtown, Oshkosh Farmers Market (Winter), Sanctuary Aquatics, brbrMy Townhouse is located on Lake Winnebago, 1.5 mile from Menominee Park.brbrAIRPORTSbrOshkosh is served by the Wittman Regional Airport in Oshkosh and the Appleton International Airport, located less than 30 minutes away in Appleton.brbrFUN FACTS ABOUT OSHKOSHbrbrPOPULATION brCity 68,000 | Urban 95,000 within a 1.3 million northeastern population.brMales 52%. Females 48%. Median resident age 34 yearsbrbrAREA & ALTITUDE 24.24 square miles at 767 feetbrbrDRIVE DISTANCE - In Wisconsin:brGreen Bay – 45 milesbrMilwaukee – 80 milesbrMadison – 82 milesbrWisconsin Dells – 82 milesbrDoor County – 93 milesbrbrOut of StatebrChicago – 174 milesbrMinneapolis/St. Paul – 270 milesbrToronto, Ontario – 684 milesbrDetroit – 453 milesbrbrCLIMATEbrAverage Annual Temperature 46 FbrAverage January Temperature 18 FbrAverage July Temperature 72 FbrAverage Annual Precipitation 31.5brAverage Annual Snowfall 36

Lake Channel 'Brewhaus' Townhouse: 2 bedrooms with 6 levels on Lake Winnebago

Oshkosh, Wisconsin, United States

Bed

Bath

Sleeps

$1015.83

Enjoy a peaceful stay at this 3-bedroom, 2.5-bath home in Oshkosh, Wisconsin. The house is situated on a beautifully landscaped wooded lot close to Lake Winnebago with frequent sightings of Bald Eagles, deer, turkeys, ducks, and cranes. The house is within 5 minutes’ drive of Oshkosh's beautiful downtown with easy access to all the shopping and restaurants Oshkosh has to offer. The EAA grounds are only a 15-minute drive away. The kitchen is spacious and updated. There is a family room and a living room on the main level with ample seating for all guests. An open dining room has seating for six. There is also a sunroom off of the kitchen perfect for enjoying your morning coffee. The bedrooms feature a king, queen, and two twin beds, ensuring a comfortable night's sleep for all guests. The master bedroom has it's own private bathroom. With amenities like AC, WiFi, and a fitness room, you'll have everything you need for a relaxing getaway. The large patio is equipped with plenty of seating, a gas fireplace, and a Blackstone grill. In another area outside the main patio area, you can also enjoy the private wood-burning firepit.

3-bedroom, 2.5 bath home in lovely Oshkosh ready to enjoy during EAA AirVenture

Oshkosh, Wisconsin, United States

Bed

Bath

Sleeps

$891.25

Available for 2026 EAA. This family, friendly 3 bedroom rental is minutes away from EAA. Located at the end of a cul-de-sac in a walkable neighborhood. A few minutes away from many restaurants, gas stations, and 1.4 miles from Walmart. If you need additional sleeping, a queen-sized air mattress is available. 4 parking spots.

2026 Oshkosh EAA rental — 4.5 miles from the AirVenture

Oshkosh, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(5)

$267.18

Relax with the whole family at this peaceful place to stay. Spacious house located 3.8 miles from EAA grounds. 1300 sq ft all for use. River views. Boat rental available at marina across the street. Patio, grill(upon request), firepit (upon request). 1 queen, 2 triple bunk beds, 2 sleeper sofas (all brand new.) Air mattresses available upon request. Spacious kitchen. Easy access to area amenities. Extra long driveway can fit multiple boats/trailers if you're in town for fishing, camping, ATVing, etc.br Welcome to The TreeHaus.

Cozy house in northwest Oshkosh

Oshkosh, Wisconsin, United States

Bed

Bath

Sleeps

$896.18

EAA 2026! Stay comfortably in Oshkosh at this 4-bedroom house. The perfect space for families or groups, it features one queen bed and three full beds to ensure a restful night. With three bathrooms, including one with a relaxing bathtub, guests can enjoy plenty of privacy and convenience. The house stays nice and cool with air conditioning, making it a great retreat after a day of exploring. Bright and inviting, this gorgeous home offers a welcoming atmosphere for everyone. You're sure to make fantastic memories with a stay at our place.

EAA-2 miles from grounds. Spacious 4-bedroom house in pleasant Oshkosh

Oshkosh, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(18)

$649.65

Ultimate Lakeside Retreat on Lake Winnebago brbr Lakefront Convenience – Just across the road from Lake Winnebago and Kalbus Country Harbor Campground, with easy boat launch & docking right from your front yard.brbr 4 Queen Bedrooms | 2 Full Baths + 2 Half Baths – Includes a private master ensuite perfect for families, friends, or couples.brFresh & Modern – Newly repainted and furnished, offering a clean, inviting, and stylish lakeside escape.brbr Full House Access – Enjoy privacy, space, and comfort for your stay.brbrLake Life Awaits – Relax, explore, or embark on water adventures. Every detail is designed to make your Lake Winnebago getaway unforgettable! brbrNo parties or large gatheringsbrNo pets allowed on property-$250 FEE- unapproved pets brNo vaping in house, garage or screened in porch area- $250 FEEbrbr`Quiet Hours` after 10:30pm for respect to the campground

Kalbus House- Home on Lakewinnebago

Oshkosh, Wisconsin, United States

Bed

Bath

Sleeps

$123.33

The Brookview cottage penthouse is just that, with great views from your deck of our wooded area and Sawyer Creek that crosses the corner of our lot, you’ll see an abundance of wildlife to include our family of woodchucks, raccoons, squirrels, deer, cranes, ducks and more.brThis is our junior penthouse with a vibrant cottage coastal vibe. The living room has an expansive white leather sectional that can be reconfigured as you desire and a large flatscreen and electric fireplace. Modern black and white canvases of local waterways adorn the walls throughout this entire space, custom created for these properties.brThe master suite is an expansive dreamy home away from home with a specially procured rustic flooring, new king bedroom set and decor to make you feel like you’ve docked your yacht for the night. brSecondary bedroom has a lovely queen bedroom set and a joyful llama inspired design your guests or family members will adore.brbrYes to your own garage, lovely deck, private laundry and all the amenities!

Ritchie’s Oshkosh Chalets: Brookview Penthhouse

Oshkosh, Wisconsin, United States

Bed

Bath

Sleeps

This spacious and beautifully maintained 3-bedroom, 2.5-bath home is ideally located just a short drive from the EAA grounds, making it easy to enjoy all the excitement of the event while having a comfortable retreat to come back to. Step inside and you’ll find a bright, inviting space with plenty of room for families, friends, or small groups. The home features a fully equipped kitchen, cozy living areas, and comfortable bedrooms designed to help you relax and recharge after a full day of activities. brbrEnjoy modern amenities throughout, including high-speed WiFi, a washer and dryer, central air conditioning, and ample parking. Located in a quiet, safe neighborhood, you’ll appreciate the peaceful surroundings while still being conveniently close to local dining, shopping, and all that the area has to offer. Book your stay and make the most of your trip!

Charming 3-bedroom house close to EAA

Oshkosh, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(1)

This is a split rental, House is separated into 2 units, fully closed off. Cozy 2 full size 11x16 w/2 full size closets. + dresser. View of a beautiful backyard trees & bushes, a calm and quit place. There's a patio & BBQ available for your use. Dining room w/ kitchen.brsee map

EAA rental

Oshkosh, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(2)

$888.83

Kick back and relax in this calm, stylish space. You will be surrounded by a variety of well positioned trees on a picturesque country lot, yet you will have a substantial view in both directions. Enjoy the sounds and view of EAA planes overhead. The open night sky will delight you with its brilliance (no city lights). Front and back screened porches. This home is strategically located 1.2 miles from Lake Winnebago, 3.6 miles from EAA Seaplane Base, and 8.5 miles from EAA grounds. Fine dining is just 5.1 miles with lakeside dining even closer.

Secluded Country Home on 6 Acres

Oshkosh, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(2)

Discover the soothing ambiance of Oshkosh from this 3-bedroom house with a view of Lake Winnebago. With 2 king beds, 1 full bed, 1 bunk/twin over full and more, this lovely property offers comfort for all guests. Enjoy the convenience of amenities like AC, WiFi, and a washing machine. Relax in the bathtub or sauna or shower in one of the 2.5 bathrooms. Fully stocked kitchen with bake ware, instantPot, convection oven and microwave. The lower level Family room with an optional extra twin bed provides additional space for your stay. Our outdoor spaces are next level with two fire pits and an propane grill. Our indoor spaces offer Adirondack chairs, cafe table on the indoor porch, a private office nook. We think our home will help you experience everything Oshkosh has to offer.

Cozy Lake view 3-bedroom house WiFi, AC in Oshkosh-Great spaces inside & out EAA

Oshkosh, Wisconsin, United States

Bed

Bath

Sleeps

$208.13

✔Fully Equipped Kitchenbr✔Airconditioningbr✔Pack'n'Playbrbr★Steps to Lake Winnebago Public Pierbr★Downtown Oshkosh – 5 Min Walkbr★Menominee Park & Zoo – 5 Min Drivebr★EAA Aviation Museum – 7 Min Drivebr★Grand Opera House – 7 Min DrivebrbrbrThis freshly remodeled, charming Oshkosh retreat is perfect for families, friends, or anyone visiting for a short getaway or longer visit. Think of it as your own peaceful corner of the city—private enough to recharge, yet close enough to dive into the best of Oshkosh whenever you please.brbrLiving RoombrSpacious and bright, this living area offers plenty of seating for everyone to relax, socialize, or catch a show on the smart TV. Tastefully decorated with character and charm, it’s the perfect spot for family and friends to gather, unwind, and enjoy quality time together.brbrKitchen & DiningbrThe fully remodeled kitchen features new cabinets, countertops, and a complete set of cookware, dishes, and utensils. Whether preparing a quick breakfast or a full dinner, you’ll have everything you need. The dining area provides space for everyone to gather for meals or game nights.brbrBedroom 1brA comfortable double bed awaits in this serene retreat, offering a calm, relaxing space to relax after a day in Oshkosh. Simple, uncluttered décor keeps the atmosphere peaceful, perfect for a restful night or some quiet downtime.brbrBedroom 2brAlso featuring a double bed, this bright, light-filled room offers a fresh and welcoming space. The simple touches create a soothing atmosphere, ensuring guests feel instantly at home.brbrBedroom 3brThis bunk-bed room brings a playful vibe to the house—perfect for relaxing with a book, catching up on sleep, or simply enjoying a cheerful nook during your stay.brbrBathroom brThe full bathroom features a modern shower and bright, clean spaces to refresh and recharge. Thoughtfully maintained and stocked with essentials to get you started, it’s a simple, functional area designed for comfort and convenience during your stay.brbrLaundry Room brEquipped with a washer and dryer, the laundry room makes longer stays simple and convenient. The space is functional, tidy, and easy to use, so you can keep clothes fresh and focus on enjoying your time in Oshkosh without any hassle. brbrYour Oshkosh escape awaits—stroll the waterfront, explore charming streets, or simply savor moments together in comfort.

Central Oshkosh Stay • Walk to Lake and Downtown

Oshkosh, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(2)

$1169.17

Make yourself at home in this warm and inviting modern farmhouse style residence. All the amenities of new construction(central heat/air, hardwood floors, FP, charging station) with a touch of salvaged architecture (8 foot front doors, claw foot tub, and leaded glass windows). Beautiful sunset views of pond and just 10 minutes from EAA grounds, Target, outlet mall, grocery stores, and restaurants!

Industrial chic farmhouse.....

Oshkosh, Wisconsin, United States

Bed

Bath

Sleeps

$1293.75

Within walking distance (or driving/ride-share) to the EAA Airventure grounds. 3 Bed, 1.5 Baths ranch house with deck space in a quiet relaxing neighborhood. brbr1 Queen and 2 Full Beds provided; can make other arrangements upon request. 4 Bars/Restaurants within 20 min. walk, Oshkosh Country Club 1 mile down the road.brbrSpace is clean and only rented for EAA. Bar area is available for use!brbrCan add more guests and sleeping arrangements by request, please reach out! No access to the garage.

3-bedroom house in walking distance to EAA with cool AC and Bar

Oshkosh, Wisconsin, United States

Bed

Bath

Sleeps

Your home away from home in for EAA in Oshkosh with 3 bedrooms. With 1.5 bathrooms, there's plenty of space for everyone to freshen up. Enjoy your time in Oshkosh at our cozy house. Just 10 minutes from EAA grounds

EAA 3 bedroom house in Oshkosh

Oshkosh, Wisconsin, United States

Bed

Bath

Sleeps

$1785.0

Experience Oshkosh like a local in this 5-bedroom house. The space features 2 king beds, 2 queen beds, and 1 full bed, perfect for families or groups. Guests can unwind in the tranquil basement living room, which includes a comfy sofa bed. With 4 bathrooms equipped with showers and hair dryers, everyone enjoys convenience and comfort. The house stays nice and cozy with heating and AC throughout. Whether relaxing indoors or exploring nearby, this enchanting home offers a peaceful retreat. Experience what Oshkosh has to offer with a stay at our house. Perfect for EAA. We are located minutes from the air show entrance. House can comfortably sleep 6-12 people.

Newly renovated spacious 5-bedroom house minutes from Airport for EAA

Oshkosh, Wisconsin, United States

Bed

Bath

Sleeps

Enjoy a peaceful stay at this 4-bedroom rental property in Oshkosh. The fabulous bedrooms include one king bed and three queen beds, offering plenty of space for guests to relax. With 3.5 bathrooms, mornings are easy and convenient for everyone. brbrThe house features air conditioning, Wi-Fi, full fitness room, upscale modern kitchen, 4 streaming TVs, gaming consoles, sauna, jet-stream master bath, a large backyard with a fire pit, barbeque grill, well stocked vegetable garden and patio seating to keep you comfortable throughout your visit. Guests will also enjoy ample parking, along with flexible check-in and check-out times to help make travel easy and stress-free. brbrConveniently located just 5 minutes from the EAA grounds, as well as nearby grocery stores, Target, and restaurants, this home makes it easy to enjoy everything Oshkosh has to offer.brbrFrom mornings in the modern kitchen to evenings around the fire pit, this home is designed for comfort, connection, and relaxation. After an exciting day at AirVenture, unwind in comfort and enjoy everything this welcoming home has to offer.brbrMake EAA one to remember.

Welcome EAA Enthusiasts! New Listing Large 4BR Oshkosh Property, 5 miles to EAA!

Oshkosh, Wisconsin, United States

Bed

Bath

Sleeps

$133.33

Sleeps ~6-8 (five total beds)brbrDubbed “the bait shop house,” this one we had a ton of fun with the design theme, integrating a bait shop theme with a modern edge. White leather furniture contrast a blue background with subtle touches like cattail accents that pull the theme through. This place would be an Air BNB favorite if we weren’t keeping it back for our corporate housing program!brbrHighlights include a large dining area with bench and upholstered chair seating (bench arrived after tour); large multi piece sectional couch that can be reconfigured in a ton of different ways and an electric fireplace media center in living room.

Ritchie’s Oshkosh Chalets: The Baitshop House

Oshkosh, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(1)

$303.58