Apartment holiday rentals in Winnebago County

A cozy living area is presented, featuring a navy sofa adorned with patterned throw pillows. A wooden coffee table rests atop a patterned area rug. Two barstools are positioned at a sleek counter, while framed artwork and a potted plant are displayed on the walls.

4.95 out of 5 average rating, 61 reviews

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

An industrial living area features exposed brick walls and large windows, allowing natural light to fill the space. A cozy leather armchair sits beside a coffee table on a colorful area rug. Modern seating is arranged around a table in the background.

5 out of 5 average rating, 16 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.

The bedroom features a spacious bed with soft bedding and decorative pillows. A bedside lamp provides warm light, and artwork depicting a serene landscape hangs on the wall. A dresser offers additional storage, while a door leads to an adjoining space.

4.86 out of 5 average rating, 7 reviews

1 BR Condo - Clean and updated! BEST EAA Location

Monthly Stays! This condo is located two blocks from hwy 41 off South Park Ave / hwy 44, so it is easy access to downtown, the west side, restaurants, grocery, Oshkosh Herd Arena, EAA Museum, Wittman Airport, and a short drive south to Fond du Lac and Milwaukee, and north to Appleton and Green Bay. For EAA Adventure, this is 2 blocks (10 minute walk) to the gate 41 entrance where the EAA shuttle bus picks you up and takes you to the 'North 40' entrance. NO PARKING FEES or traffic headaches!

A neatly arranged bedroom features a black metal bed frame with a patterned comforter and decorative pillows. A glass side table sits beside the bed, while natural light filters through large windows adorned with light curtains. A cozy carpet enhances the warm atmosphere of the space.

4.87 out of 5 average rating, 46 reviews

Mini Apt- Safe Walkable- near water + downtown

Enjoy your stay in the heart of the city in an attached Mother in law suite (like a mini apt) w Queen bed, pvt bath, TV/WIFI, pvt entrance w patio & mini kitchen appliances. Jun-Sept: Waterfest is every Thursday Farmers Markets on Wed & Sat (top 10 in US!) Oshkosh is Event City! You will never be bored! EAA, Lifest, XRoads41 & Mile of Music bring ppl worldwide. Best part- located by Downtown Bars, the water - UWO- Everything is walkable 30min drive to ATW and anywhere else in Fox Cities!

A cozy living area is depicted with a soft grey sofa positioned near a small wooden table. A wall-mounted television is visible, and art adorns the walls. A greenery accent adds a touch of nature, creating a relaxed ambiance within the space.

4.92 out of 5 average rating, 79 reviews

Charming Oshkosh - 2 Bedroom, Walk to Downtown

Enjoy a stylish experience at this centrally-located apartment. 2nd Floor with balcony, fully stocked oasis! Walk score A+ to Downtown Oshkosh, UW-Oshkosh Campus, bus routes, library, YMCA, restaurants, Farmers Market, Time Community Theater, Leach Amphitheater, River Walk and shopping! 4 Miles from EAA Grounds, Outlet Shopping and 6 miles to Ford Festival Park. Our cozy 2 Bedroom apartment is the perfect place to rest easy after a busy day out and about! Clean and quiet building.

4.86 out of 5 average rating, 202 reviews

A well-lit hallway features smooth wooden flooring and white walls. Two framed botanical prints are displayed on the left. A small table with a plant is positioned near the doorway, which opens into a bathroom. Light filters in from the bathroom window.

Flat in Neenah

Cozy and Simple Downtown Space

Enjoy this great space in a quiet safe neighborhood. One car allowed at the property! The space has comfortable beds, provided hygiene products, a smart TV and snacks + beverages. Wake up and enjoy coffee provided by us. Shops and restaurants within walking distance! Visit The Plaza downtown with ice skating, fire pits, a coffee shop and more. Great for a couples getaway. Luxury for a great price! A portion of the proceeds from bookings go to housing evacuees, refugees and veterans.

A two-story upper unit residence features a green exterior with white trim. Stairs lead up to a welcoming front door, while a small porch offers outdoor seating. The landscaped yard includes rocks and low-maintenance plants, providing a neat and tidy appearance.

5 out of 5 average rating, 30 reviews

Centrally Located Private Upper Unit

This newly renovated upper unit features 2 bedrooms/1 full bathroom. The unit is across the street from the Paine Art Center, making it an ideal stay for weddings/events held there. It is centrally located with easy access to attractions, restaurants, and parks. Bottom unit is currently being rented as a long term rental. Units are completely separate. Paine Art Center - .1 mi Oshkosh Public Museum - .4 mi Fox River Brewing - .4 mi UWO - .5 mi EAA - 6 mi Lambeau Field - 50 mi

4.98 out of 5 average rating, 64 reviews

A modern living room features a comfortable gray sofa adorned with patterned cushions. A large area rug with a chevron design anchors the space. A wall clock and artwork complement the decor, with a glimpse of the kitchen area visible in the background.

Flat in Winneconne

Boathouse Bungalow

Enjoy a unique getaway in our historic “Boathouse Bungalow” on the Wolf River. The location could not be more perfect when visiting the scenic Fox River Valley; close to walking paths, snowmobile trails and within walking distance to downtown Winneconne. The permanent dock is in a no-wake zone, great for fishing, tying up boats or just relaxing. Located 12 miles to Oshkosh, 23 to Appleton and 48 to Lambeau. A wonderful retreat for making lasting memories.

A charming two-story white house is presented, set against a clear blue sky. Five windows are visible on the front, surrounded by green shrubs. Steps lead up to a porch area, indicating a welcoming entrance.

4.85 out of 5 average rating, 86 reviews

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. 2 blocks from the new Thedacare hospital 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.

A modern living room showcases a large television mounted above an electric fireplace. Built-in shelves are illuminated, displaying decorative items. A cozy atmosphere is created with neutral walls and warm lighting from the fireplace, enhancing the inviting space.

5 out of 5 average rating, 13 reviews

Oshkosh View

Minutes from Downtown, EAA , University - 2 bedroom *Downtown: 6 minutes, Appleton: 20 minutes, Green Bay: 50 minutes, EAA Grounds: 2 minutes Outlet Stores: 3 Minutes This is a recently renovated 2 bedroom, 1 bathroom apartment designed for relaxation, family time, and fun. Up to 6 guests can be accommodated comfortably The living room features a beautiful electric 65” fireplace with a 75” Tv to entertain your family or guests.

The exterior of a two-story house is shown, featuring a porch and a well-maintained lawn. Large windows are visible, offering natural light to the interior. Surrounding trees provide shade, and a pathway leads to the entrance, enhancing accessibility.

4.86 out of 5 average rating, 244 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.

A cozy sleeping area contains two full-size beds adorned with warm-colored bedding. Nightstands with lamps are placed beside each bed. A comfortable chair sits in the corner, and two windows allow natural light to illuminate the room. Decorative rugs cover the laminate flooring.