
Holiday houses in Oshkosh
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Top-rated holiday rentals in Oshkosh
Guests agree: these stays are highly rated for location, cleanliness and more.

Linger Longer On The Water
Cozy lake cottage on the west shore of Lake Winnebago featuring 3 bedrooms and 1 bath. Beautiful sunrises over the lake and just minutes from everything in Oshkosh Wisconsin. Large kitchen for preparing meals or just hanging out. 5 minute walk to Menominee Park. 6.5 miles to EAA Grounds. Less than 10 minutes to downtown and the University of Wisconsin, Oshkosh campus, shopping, restaurants and Main Street. Great location for walking, bike riding and just seeing the local sites. Park on site.

Elkhart A-Frame, Wooded Retreat near Road America
The Elkhart A-Frame is an ideal location for the adventure seeker who wants a unique and private experience that is still close to all the action. The home sits on a wooded three-acre private retreat only about a mile from the village of Elkhart Lake, Road America, and Golf Courses. This unique cabin was built in the 1970's but has been recently renovated with a fun Scandinavian modern flair. It has all the amenities for a memorable vacation stay that provides plenty of epic photo opportunities.

Cabin on the Trail
Kick back and relax in this cozy space with up north, cabin vibes. In the summer months enjoy the excellent fishing and boating and in the winter have fun ice fishing on beautiful Fox Lake! *Please read the full description and look at all of the pictures of the property *Not suitable for parties or loud gatherings. Please note, there is a 4 person maximum *All dogs/pets must be pre-approved by the host. There is a $50 pet fee/stay. *Check out our “cottage on the trail”, closer to the lake.

Secluded Cabin with Sauna
Place yourself in nature. Put down your phone and pick up a book. Clear your mind, focus on your breath, connect with your inner self. Sleep like you’ve never slept before accompanied only by the sound of owls and wind in the pines. The Belden Farm offers land that is a true retreat. Enjoy the privacy and quiet of our cabin in the woods. Extensive, well-maintained trails for hiking, skiing or Fattire biking lead you through towering hardwoods, cathedral white pines, and golden meadows.

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.

Leonard Point Birdhouse
Welcome to the Leonards Point Bird House! This newly renovated lake home has all amenities needed for a perfect escape in Oshkosh, WI. You will experience lake views from the south side of Lake Butte Des Morts. For a quieter experience (or louder for the kids) there is a detached bunk house with its own bathroom! The Birdhouse is 10 minutes away from highway 41 and multiple stores for easy access to everything you need. Please feel free to reach out with any questions!

hot tub and sauna on 5 private acres
Looking for a cozy winter retreat? Experience the Bird House, a tranquil Scandinavian-inspired private woodland paradise. Melt away stress in the hot tub and infrared sauna as you take in peaceful views of the meadow. Explore snowshoe and cross-country ski trails nearby in the scenic Kettle Moraine. Stream your favorite movie on the projector near the fireplace or unwind at SoLu winery, just a minute down the road. Near Road America, Kettle Moraine State Forest, and Dundee.

Charming 1870s Downtown Loft
Like your favorite cup of coffee, this sunlit haven energizes and comforts. Just steps from downtown's vibrant pulse, this thoughtfully restored 1870s duplex is crafted for connection, creativity, and relaxation. Work under high ceilings bathed in natural light, or gather with friends in the spacious, open kitchen and dining area. Modern amenities ensure a home-like experience in a space that seamlessly combines the warmth of history with the ease of modern living.

Cozy Relaxing Lake Home with spectacular sunsets!
On the shore of Lake Butte Des Morts Longer stays welcome!!! Awesome Lake view Beautiful Sunsets Gas fireplace Shopping/restaurants/etc… Approx. 40 miles from Lambeau Field pier/summer,sorry nothing can be tied up to pier at any time solo fire pit grill Lake view Bedroom,Living Room,Dining area Near by Wiouwash trail for hiking, biking, etc.. Near EAA Kitchen space for cooking. Washer/dryer Larger 1 bedroom /Queen Sleep Number mattress Off street parking

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.

Beautiful Lake Home.
Our Beautiful two bedroom cottage is located on the shores of Lake Winnebago . Centrally located to many of Wisconsin's best attractions. Less than 1 hour from Milwaukee, Madison, Green Bay, Close to Oshkosh (EAA) and Elkhart Lake. Includes 2 bedrooms, with plush queen beds, 1 full bathroom, Laundry room with washer and dryer. The perfect home for a laid back group of friends, couples or a family to stay with all the comforts of being at home.

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.
Popular amenities for Oshkosh holiday rentals
Other great holiday rentals in Oshkosh

Two Bedroom Craftsman Home

Winnebago Lake View Retreat

Newly remodeled centrally located 2 bedroom home

Woltring Waters Waterfront Home

Appleton's Oldest House Built in 1851

Gorgeous Cabin Vibes Home w/ Pond! Close To Lake!

Our Little Lake House

Cozy fully furnished home
When is the best time to visit Oshkosh?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $315 NZD | $317 NZD | $293 NZD | $464 NZD | $346 NZD | $353 NZD | $836 NZD | $431 NZD | $345 NZD | $334 NZD | $341 NZD | $315 NZD |
| 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 |
Frequently Asked Questions
Are there vacation rentals with a dedicated workspace in Oshkosh?
Yes! Work meets play with ease at over 340 vacation rentals in Oshkosh featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Oshkosh?
Four-legged friends are welcome in Oshkosh. Choose from more than 230 vacation rentals for guests traveling with pets.
Are there Oshkosh vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 40 vacation homes with pools in Oshkosh, available on Airbnb. Make a splash and soak up the sun in style!
Are there family-friendly apartment rentals in Oshkosh?
Oshkosh has more than 40 family-friendly apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in bed and breakfast rentals in Oshkosh?
Experience the best of Oshkosh with our bed and breakfast rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do apartment rentals in Oshkosh have wifi?
Absolutely! We offer over 70 apartment rentals with wifi in Oshkosh. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Oshkosh have a bbq area?
Absolutely! We offer over 210 house rentals with a bbq area in Oshkosh. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Oshkosh have a gym?
Absolutely! We offer over 110 house rentals with a gym in Oshkosh. Enjoy a tailored experience with all the comforts you desire.
Do townhouse rentals in Oshkosh have air conditioning?
Absolutely! We offer over 10 townhouse rentals with air conditioning in Oshkosh. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Condo Rentals in Oshkosh?
Enhance your stay in our Condo Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Quick stats about holiday rentals in Oshkosh

Total holiday rentals
Explore 840 holiday rentals in Oshkosh

Nightly prices starting at
Oshkosh holiday rentals start at $17 NZD per night before taxes and fees

Verified guest reviews
Over 8,530 verified reviews to help you choose

Family-friendly holiday rentals
670 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 230 rentals that welcome pets

Holiday rentals with a pool
40 properties feature pools

Rentals with dedicated workspaces
340 properties have a dedicated workspace

Wi-Fi availability
820 of Oshkosh holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Gym, BBQ grill and Laptop-friendly workspace across Oshkosh rentals

4.9 Average rating
Oshkosh stays are highly rated by guests—averaging 4.9 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
- Trout Springs Winery
- The Bull at Pinehurst Farms Golf Course
- Pine Hills Country Club
- Sunburst
- Oneida Golf Club
- Pollock Community Water Park
- Vines & Rushes Winery
- Little Switzerland Ski Area
- Kerrigan Brothers Winery
- Blackwolf Run Golf Course
- Green Bay Country Club Sports Center




