Holiday rentals in Oshkosh

5 out of 5 average rating, 7 reviews

Downtown Loft Third Floor

Situated in a prime location, this stunning 2-bedroom industrial loft condo has an expansive rooftop deck that overlooks the beautiful Fox River. With it's specatacular views, luxury amenities and spacious living area it is perfect for a romantic getaway or special celebration. Within blocks of the Leach Amplitheater, farmers market and bike trail, it is the perfect destination. The private rooftop deck is the perfect setting to capture all the excitement of Oshkosh, including the EAA flyovers.

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.

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!

4.86 out of 5 average rating, 59 reviews

Cozy fully furnished home

Are you a traveling professional looking for a cozy and fully furnished home in Oshkosh, Wisconsin? Look no further than this lovely 2-bedroom property! With newer updates, fresh paint throughout, and central air conditioning. Located just a short distance from the lake, trails, and parks, this home is perfect for outdoor enthusiasts who love to explore the great outdoors. And with its convenient location you'll find shopping, dining, entertainment, and medical facilities near by.

5 out of 5 average rating, 16 reviews

Cozy 2 Bedroom Home in Oshkosh

We are located about 10 minute drive from EAA AirVenture. We are only 1 mile from the Downtown Oshkosh, which hosts a great farmers' market on Saturdays and many small businesses. There are various grocery stores and restaurants within walking distance of our house. Prepare delicious meals in our fully equipped kitchen. Bedrooms are furnished with comfortable beds, and soft linens. The bathrooms are clean and stocked with fresh towels and toiletries. Family and pet friendly.

Superhost

4.79 out of 5 average rating, 38 reviews

The Manor on Church

Welcome to The Manor on Church! This newly renovated first floor apartment has all amenities needed for a perfect escape in Oshkosh, WI. Located in central Oshkosh, you’ll be just minutes away from downtown Oshkosh, and steps away from University of Oshkosh - Wisconsin! The Manor is just 10 minutes away from highway 41 and multiple stores for easy access to everything you need. For some reason I can't add towels as an amenity but we do provide all of those as well!

4.95 out of 5 average rating, 189 reviews

Guest house 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.

4.92 out of 5 average rating, 216 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.

4.9 out of 5 average rating, 79 reviews

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, 239 reviews

3BR Across from Park • Watch Fireworks from Porch!

Unbeatable Fourth of July Location! 🎆 Watch Menominee Park’s spectacular fireworks burst directly overhead from the front yard or porch — one of the best views in Oshkosh, just steps from the park! This cozy, modern getaway is perfect for families, groups, or peaceful retreats. Enjoy a stylish interior, gazebo with firepit table, and unbeatable access to the lake, zoo, walking trails, and downtown Oshkosh — all just a short stroll away.

4.84 out of 5 average rating, 76 reviews

Comfortable 2 bedroom upper unit #1

Relax in this 2 bedroom upper unit. The whole group will enjoy easy access to everything from this centrally located place. Reconnect with loved ones in this family-friendly 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.

4.86 out of 5 average rating, 214 reviews

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.

Holiday rentals for every style

Get the amount of space that is right for you

Flats

Convenient locations with everyday essentials

Cottages

Quaint homes, peaceful surroundings

Houses

A space that's all yours, with room for everyone

Popular amenities for Oshkosh holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Oshkosh

4.86 out of 5 average rating, 7 reviews

Month to Month Furnished Oasis: Budget Friendly! 1

StephenRating, 5 stars7 months ago

Nice place and fit my area stay for the time I was here, close to downtown and the lake side shore for a gorgeous and refreshing walk.

5 out of 5 average rating, 5 reviews

Newly Renovated Upper Unit

DanRating, 5 stars1 week ago

Nice 2 bedroom apartment & very nice kitchen. Much better than a hotel room.

5 out of 5 average rating, 23 reviews

Relaxing Lake Winnebago Waterfront Retreat

ColeRating, 5 stars1 month ago

Great place to stay. House is very large and has plenty of room for a lot of guests. Kitchen and bathrooms are all well stocked and there are a lot of extras that you won’t get at most units. It was also nice to have so many beds on each floor and the availability of the air mattress. Would highly recommend if staying in this area.

4.88 out of 5 average rating, 17 reviews

Beautiful home right on the lake - outdoors dream!

StewartRating, 5 stars11 months ago

Beautiful location. Great place to come with a small boat!

5 out of 5 average rating, 3 reviews

Cozy, updated, 2-Bedroom Condo, blocks from EAA.

DebraRating, 5 stars11 months ago

We loved staying at Kari ‘s place. Will be contacting her in the future! Such a great stay!!!

Guest house in Oshkosh

4.52 out of 5 average rating, 23 reviews

Luxury In A Quaint Lil' Package

BonitaRating, 5 stars3 weeks ago

It was a cute little place. The outside is deceiving to what is provided inside. It was the perfect place we were needing for the night.

4.86 out of 5 average rating, 206 reviews

Quaint 2 bedroom upper apartment in duplex.

Er-JinRating, 5 stars1 month ago

A friend and I stayed here for about a week to attend an event in town. Steve, our host, was super flexible with our arrival time and very accommodating. He even went out of his way to supply us with an iron and board last minute, and we really appreciated that! Thank you Steve for having us!