Vacation Rentals By Owner In Oshkosh, WI

Showing 100 Of 175 Vacation Rentals

$1979.64

Minutes from EAA! Spacious 4BR home in a quiet neighborhood.

Oshkosh, Wisconsin, United States

Large open concept home with 4 bedrooms (one king bed and 3 queen beds), 3.5 bathrooms, 3000 square feet in quiet Oshkosh neighborhood only 10 minutes from EAA grounds!brbrPrimary bedroom is large with a king size Select Comfort bed and flat screen TV. Attached bathroom with double vanities and jetted tub. Second and third bedrooms each have high quality and comfortable queen size beds and are attached through a Jack and Jill bathroom. Each bedroom has it's own vanity area! Fourth bedroom is on the lower level and also has a comfortable queen size bed and a bathroom steps away. Quality linens and towels provided!brbrFull kitchen with modern appliances and all the amenities. Large outdoor patio with gas grill, furniture and great views! Bright and sunny sunroom for morning coffee. 2 fireplaces. Large family room, big screen TV, ping pong table, dart board and bar in beautifully finished basement. Open concept kitchen/dining/living area on first floor. Screened in 3-season room for evening cocktails with no bugs! Den/office with height adjustable desk and monitor. Workout space with treadmill, rower and Peloton bike available for use. Washer and dryer available for use.brbrQuality linens, towels and bedding provided. Strong wi-fi access included. Smart TV's.

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Exceptional(4)

$225.19

/ Nightly

Private Vacation Home

Charming Family Home Near University of Oshkosh

Oshkosh, Wisconsin, United States

Summary:brbr●Downtown: 4 minutes. Appleton: 27 minutes Green Bay: 60 minutes. EAA Grounds: 12 minutesbrbr●Flexible self check-in/outbrbr●Exquisitely maintained character homebrbr●Beautifully updated home with many upgradesbrbr●Yard with gas grillbrbr●Driveway with plenty of parking spacebrbr●Safe residential neighborhood brbr●Brand new super comfortable bedsbrbrbrbrThe Space:brbrYou will absolutely love this house. Here's why...brbr●Centrally located and close to EVERYTHINGbrbr●High speed WIFIbrbr●Fully equipped kitchen with a crockpot and instapot brbr●Updated kitchen with new cabinets brbr●Dining room opens to spacious living roombrbr●Fabulous original hardwood floors brbr●Amazing decor brbr●Generous sized bedrooms w/walk in closets. brbr●Updated bathroom adds to this great home.brbrbrbrThe Neighborhood:brbrQuiet, safe residential neighborhood. Great for walking around and a short drive to Downtown Oshkosh.brbrbrbrGetting Around:brbrUber and Lyft are always available and abundant.brbrbrbrInteraction with Guests:brbrWe give you your space while you enjoy our space. You will have the house completely to yourself, and we are just a text or phone call away if something should come up.

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Exceptional(2)

$756.0

/ Nightly

Private Vacation Home

Four bedroom home great for EAA, Lifest, XRoads41 and other Oshkosh events!

Oshkosh, Wisconsin, United States

This 4 bedroom 2 bath home sits just north of Oshkosh on 2.5 acres away from it all but close enough for EAA Air Venture (15 minute drive away), Lifest 2024 (1 mile down the street on the same road!) or Xroads41 (across from the EAA grounds). Spend all day with the crowds and spend every night in peace and quiet. Four bedrooms sleeps 8 comfortably or up to 12 with two queen air mattresses.

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$1218.95

/ Nightly

Private Vacation Home

House for EAA Week 2 minutes from Airport!

Oshkosh, Wisconsin, United States

You will love to stay at this lovingly cared for house for EAA week as it's walking distance (8-minutes) to Oshkosh Wittman Airport. You can catch a shuttle bus from the airport terminal to get to the EAA grounds. 2 queen beds and a finished basement with sofa bed. The basement can also be used as a sleeping area with air mattresses. Lots of space for you and your guests! Quiet street and community and very close to grocery stores and gas stations.

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Exceptional(21)

$713.08

/ Nightly

Private Vacation Home

Hickory on the Lake - Home directly on Lake Winnebago

Oshkosh, Wisconsin, United States

3 Bedrooms | 3 Bathrooms – Stylish, comfortable, and perfect for friends, couples, or small familiesbr Four-Seasons Room – Sip your morning coffee or evening cocktail while soaking in stunning sunrises & sunsets br Quiet, Private Neighborhood – Relax and recharge while staying close to Oshkosh attractions, dining, and outdoor adventures brbrLakeside Living at Its Best – Reconnect, unwind, and create unforgettable memories in a space designed for both relaxation and inspiration brbrNo parties or large gatheringsbrNo pets allowed on the property-$250 FEE - unapproved petsbrNo vaping in house or garage- $250 FEE

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Exceptional(24)

$138.0

/ Nightly

Private Vacation Home

Downtown Tiny Home - Oshkosh

Oshkosh, Wisconsin, United States

Charming 1920's House located in downtown Oshkosh.brbrWelcome to our efficiency style, tiny home located withing walking distance of Lake Winnebago and the grocery store.brbrThis is a perfect place for up to 2 people to stay while visiting!brbrThis tiny home was built in the 1920's and has been completely renovated in a 50's retro theme.brbrIt is an efficiency style house with one bathroom and a queen murphy bed with a very comfortable bed. It has a full kitchen and sitting area outside.

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$1643.95

/ Nightly

Private Vacation Home

Lovely 5-bedroom house in Oshkosh with AC, WiFi 8 miles from EAA Grounds

Oshkosh, Wisconsin, United States

Stay in our 5-bedroom ranch home located 8 miles (11 minutes) from EAA grounds. Nestled in a tranquil neighborhood, our property offers a pond with a gorgeous beach to watch the sunset, and a back patio to watch the sunrise, a soothing retreat for guests. The spacious bedrooms feature a king bed, 2 queen beds, 1 crib, and 1 twin bed, ensuring a comfortable stay for everyone. Indulge in the jetted bathtub or take a refreshing shower in one of the 3 bathrooms. With amenities like AC, a washing machine, iron, heating, hair dryer, and WiFi, kid toys and babyproofed home, your needs are well taken care of. Enjoy all that Oshkosh has to offer when you stay at our place.

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Exceptional(12)

$322.77

/ Nightly

Private Vacation Home

Hickory Hideaway-2 Bedroom with Dock

Oshkosh, Wisconsin, United States

br Lake Winnebago Cottage – Comfort & Family-Friendly Charm!brbr 2 Bedrooms | 1 Bathroom – Newly renovated and perfect for couples or small families.br Peaceful Neighborhood – Nestled in a family-oriented, tranquil setting.brCentral Location – Ideal base to explore Oshkosh and create lasting memories.brbr Exclusive Use – Entire cottage with two-car detached garage and private on-site dock .brBoating Adventures – Let us know in advance for trailer storage and launch/docking info.brOutdoor Fun – Bring your bikes for a ride to Menominee Park or kayaks to explore the calm waters of Lake Winnebago .brbrWhether it’s a couples’ getaway or a small family retreat, enjoy lake views, private dock access, and an unforgettable lakeside escapebrNo parties allowed.brNo pets allowed-$250 FEE - unapproved petsbrNo vaping in the home or garage-$250 FEE

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Exceptional(10)

$258.3

/ Nightly

Private Vacation Home

Lake House on Libby Point, Oshkosh

Oshkosh, Wisconsin, United States

Newly remodeled house on the shore of Lake Winnebago. Nice lot with large shade trees. The house is located in a safe place to walk, jog or bike with very few cars. Close to the events and stores yet far from the chaos.

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Exceptional(1)

Select Dates for Price

Private Vacation Home

EAA AirVenture Whole Home Rental

Oshkosh, Wisconsin, United States

Great location for EAA AirVenture guests. Located in a west side subdivision, 5 min off Hwy 41 and 10 minutes from the EAA AirVenture grounds. Ranch home layout with 4 Bedrooms, 3 full bathrooms, 1 half bath, and kitchen areas on both main & basement floors. We look forward to having private or corporate guests stay with us!

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Exceptional(3)

$293.25

/ Nightly

Private Vacation Home

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

Oshkosh, Wisconsin, United States

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

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$1015.83

/ Nightly

Private Vacation Home

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

Oshkosh, Wisconsin, United States

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.

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$891.25

/ Nightly

Private Vacation Home

2026 Oshkosh EAA rental — 4.5 miles from the AirVenture

Oshkosh, Wisconsin, United States

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.

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Exceptional(5)

$267.18

/ Nightly

Private Vacation Home

Cozy house in northwest Oshkosh

Oshkosh, Wisconsin, United States

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.

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$149.09

/ Nightly

Caravan Park/Campsite

Hidden Haven Camper Beach, Pond, Firepit

Oshkosh, Wisconsin, United States

Escape to Hidden Haven cozy, fully equipped, and perfect for a weekend getaway. Great value for couples or small families seeking a relaxing escape!brbrWhy Book This Camper:br• Firepit & outdoor space for relaxing eveningsbr• Pond, beach & playground nearbybr• Ideal for couples or small familiesbr• Looking for more space Our sister camper Private Paradise is near by! Book your private escape today!brbrBook your stay at Hidden Haven today and enjoy your perfect weekend escape!

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$896.18

/ Nightly

Private Vacation Home

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

Oshkosh, Wisconsin, United States

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.

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Exceptional(18)

$649.65

/ Nightly

Private Vacation Home

Kalbus House- Home on Lakewinnebago

Oshkosh, Wisconsin, United States

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

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$123.33

/ Nightly

Private Vacation Home

Ritchie’s Oshkosh Chalets: Brookview Penthhouse

Oshkosh, Wisconsin, United States

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!

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Select Dates for Price

Private Vacation Home

Charming 3-bedroom house close to EAA

Oshkosh, Wisconsin, United States

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!

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Exceptional(1)

Select Dates for Price

Private Vacation Home

EAA rental

Oshkosh, Wisconsin, United States

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

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Rent a place that suits your needs

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View 216 Private vacation home

Most popular vacation rentals in Oshkosh

Exceptional(1)

$393.75

/ Nightly

Private vacation home

Sky & Stream Escape, EAA AirVenture Oasis

Oshkosh, Wisconsin, United States

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Exceptional(1)

$303.58

/ Nightly

Private vacation home

Lakeside- peekaboo views, dock access: ensuite baths, professionally furnished.

Oshkosh, Wisconsin, United States

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Exceptional(1)

$312.89

/ Nightly

Cabin

Cabin Oasis on Lake Winnebago \"Minutes from EAA\"

Oshkosh, Wisconsin, United States

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Exceptional(1)

$320.35

/ Nightly

Private vacation home

Cozy & Quiet in Oshkosh!

Oshkosh, Wisconsin, United States

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Exceptional(1)

$324.69

/ Nightly

Private vacation home

Waterfront Lake House, Kayaks and Large Yard

Oshkosh, Wisconsin, United States

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Exceptional(1)

$328.65

/ Nightly

Private vacation home

Beautiful, relaxing lake home.

Oshkosh, Wisconsin, United States

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Exceptional(1)

$331.78

/ Nightly

Private vacation home

Welcome to Our Home in Oshkosh – “Close to Everything, Cozy and Full of Heart”

Oshkosh, Wisconsin, United States

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Exceptional(1)

$355.69

/ Nightly

Private vacation home

Cozy year round Lake Front Vacation Home

Oshkosh, Wisconsin, United States

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Exceptional(1)

$356.82

/ Nightly

Private vacation home

Perfect Waterfront Retreat Destination on Lake Winnebago

Oshkosh, Wisconsin, United States

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Exceptional(1)

$483.66

/ Nightly

Private vacation home

Lilly Lakeside Retreat Near Lake Winnebago – Cozy Fireplaces & Family Fun

Oshkosh, Wisconsin, United States

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Vacation Rentals By Owner In Oshkosh, WI

$1979.64

$225.19

$756.0

$1218.95

$713.08

$138.0

$1643.95

$322.77

$258.3

$293.25

$1015.83

$891.25

$267.18

$149.09

$896.18

$649.65

$123.33

Rent a place that suits your needs

Most popular vacation rentals in Oshkosh

$393.75

$303.58

$312.89

$320.35

$324.69

$328.65

$331.78

$355.69

$356.82

$483.66

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