
Apartment holiday rentals in Oshkosh
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Top-rated apartment rentals in Oshkosh
Guests agree: these apartments are highly rated for location, cleanliness and more.

Charming 1BR Apartment - 25 Mins to Lambeau Field
The Artist’s Perch - a private 2nd floor walk-up on dead-end overlooking a wooded ravine features modern, updated decor in a beautiful old house. Hardwood floors, screened porch, entry/workspace, kitchen/dinette, living room, bathroom w/clawfoot tub/shower, and bedroom with a cozy loft. Close to downtown, library, nature center & recreational trail system. Situated 8.5 mi E of Appleton, 30 mi NE of Oshkosh, 30 mi SW of Green Bay (only 20 mi to Lambeau Field!), and 60 mi NW of Sheboygan/Kohler

Historical Haven Downtown Appleton
History meets style in this perfectly located downtown spacious 2 bdrm 2 story (2nd n 3rd story) apartment with a full kitchen. The 2nd floor bdrm has a queen bed with a BIFOLD BARN door, the 3rd floor bdrm is its own private oasis boasting a queen bed, a desk, closet and futon. Cozy, updated, historical and has beautiful surroundings. A few blocks to amazing restaurants, Mile of Music venues, Performing Arts Center, The Expo Center, Lawrence University, parks, river trails, and shopping.

The Hemingway on Church - It Tolls For Thee
"Kristine's property has all the charm of a modern day Mayberry" -Michael This 1906 historic home is nestled in the heart of the equally historic "Village of Kohler." Completely remodeled in 2019 adding Kohler spa amenities and modern touches to its original charm. Mixing modern & antique furniture finds like the Hemingway Sideboard (which inspired the literary theme) make this historic hideaway a true Kohler destination. "You cannot get a better location in Kohler than this house!" -Dennis

Homey lower level apartment with private entrance
This living space is in the lower level of our ranch home, which is located in a lovely and safe neighborhood. The furnishings in this area are mostly antique pieces that came from special family members. You may also use the screen porch and patio for relaxing in the spring/summer. You will have a private entrance through the garage so you can come and go as you like. The kitchen is furnished so you may cook. There are also many restaurants close by. Ask us if you need anything!

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.

Cozy Sheboygan Upper
We began caring for this home and property in 2018, and this 1870's home needed some love. We have been steadily remodeling since we moved in and it's starting to feel pretty great. We're excited to share it and the neighborhood with you. We are two blocks west of North Beach/Deland Park, 4 blocks to the river front boardwalk, home to many restaurants, cafe's, and shops. We are also four quick blocks to downtown which hosts many more restaurants, shops, museums and parks.

Lakeshore Bungalow Boutique
Newly remodeled upstairs 2 bedroom, very spacious apartment. Shaby sheek style downtown very cute home away from home. Just minutes from beautiful biking and walking trails and beaches along the beautiful shores of Lake Michigan. Walking distance to restaurants, pubs, wine bar, museums, beaches, shopping, grocery store, bakerie, zoo, car ferry, gym's, coffee shops, library. Beautiful lake Michigan Marina and Light House, Manitowoc is a very cute and quaint small town.

The Hideaway Ripon WI -just 12 min to Green Lake
APARTMENT: This welcoming walk up flat is located on historic downtown Watson Street where you will find boutique shopping, and your choice of restaurants steps away! It’s walking distance to Knuth Brewery. a short 10 minute drive to Vines and Rushes winery. 12 minute drive to Green Lake. 30 minute drive to Oshkosh and Fond Du Lac. 50 minute drive to Lambeau Field in Green Bay. This renovated space will have you wanting to stay again and again.

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.

The Blue Cobb House
My place is close to 20 minutes south of Elkhart Lake and Road America. You’ll love my place because of the outdoors space, the comfy bed, and the kitchen. My place is good for couples, solo adventurers, and business travelers. The Blue Cobb House is about 15 minutes from Kohler-Andrae State Park and 30 minutes from Harrington Beach State Park. The Kettle Moraine area is just to our west and it is filled with hiking trails.

GGG Spacious Log Cabin apartment on the IAT
With 10-11’ ceilings and 1000 sf, this sunny apartment is the second floor of an 1860’s log cabin. Completely updated with new floors, paint, fixtures and more, it’s a perfect retreat from the city. Explore the adjoining 500 acres of state forest, with public lake and boat launch across the street for fishing and paddling. The adjacent trail leads right the Parnell Segment of the Ice Age trail and Mauthe Lake State Park.

Sheboygan Surf House - The Elbow
Located just 24 steps above Wisconsin's first Surf Shop, EOS Surf. Our Urban living oasis is a studio and a half that is conveniently located in the heart of downtown, just steps from renown bars and restaurants and only blocks to Lake Michigan, The Sheboygan River, South Pier and Blue Harbor. Whether you are here for adventure sports like Surfing on the Great Lake or leisure time SSH is perfect for you.
Popular amenities for Oshkosh apartment rentals
Weekly apartment rentals

Charming Historic Lower Unit King/Queen Sleeps 6

Twilight Suite with fenced in dog yard

Contemporary Two-Bd Upper Suite

Furnished 2 bedroom with attached garage

NEW Riverfront Loft - Fantastic location

Boathouse Bungalow

Charming Oshkosh - 2 Bedroom, Walk to Downtown

Parkside Studio Apartment
Private apartment rentals

Loft Unit Historic Kiel 8 miles to Road America

Recombobulation Station-Locally Owned Surf Escape

Home Away on Holmgren II

Local Landmark CF / Coffeehouse / Kettle Moraine

Michiels Lodge

Porlier Place - 1 Block Hospital

Watson St. View Apartment

Quiet 2BR stay near downtown w/ fireplace
Apartment rentals with a hot tub

Fox Hills '25 Draft Rental - Willing to Accept OBO

Siebkens Lockout Unit

Helene's room

Resort Condo on Elkhart Lake

Vintage chic+EAA+Horicon Marsh

Pink Door Loft
When is the best time to visit Oshkosh?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $116 SGD | $136 SGD | $120 SGD | $129 SGD | $136 SGD | $135 SGD | $289 SGD | $143 SGD | $136 SGD | $141 SGD | $140 SGD | $127 SGD |
| Avg. temp | -8°C | -6°C | 0°C | 7°C | 14°C | 19°C | 21°C | 20°C | 16°C | 9°C | 2°C | -4°C |
Quick stats about flat rentals in Oshkosh

Total holiday rentals
Explore 70 holiday rentals in Oshkosh

Nightly prices starting at
Oshkosh holiday rentals start at $13 SGD per night before taxes and fees

Verified guest reviews
Over 1,860 verified reviews to help you choose

Family-friendly holiday rentals
40 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
70 of Oshkosh holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Oshkosh rentals

4.8 Average rating
Oshkosh stays are highly rated by guests – averaging 4.8 out of 5!
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- Lambeau Field
- Kohler-Andrae State Park
- Whistling Straits Golf Course
- Bay Beach Amusement Park
- West Bend Country Club
- The Bull at Pinehurst Farms Golf Course
- Trout Springs Winery
- Sunburst
- Pine Hills Country Club
- Oneida Golf Club
- Pollock Community Water Park
- Little Switzerland Ski Area
- Kerrigan Brothers Winery
- Vines & Rushes Winery
- Blackwolf Run Golf Course
- New Zoo & Adventure Park




