Entire home

The Tailwind House | Sleeps 6

Oshkosh vacation home with kitchen

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Photo gallery for The Tailwind House | Sleeps 6

A living room with a sofa, coffee table, and lamps.
A kitchen with wooden cabinets, a marble countertop, a black refrigerator, a sink, and a stove.
A bedroom with a bed, bedside tables, a window, and a view of the outdoors.
A two-story house with a front porch, a visible front door, and a small front yard.
A dining area with a wooden table, black chairs, a woven centerpiece, and a hanging light fixture.

Reviews

10 out of 10
Exceptional

Entire home

3 bedrooms2 bathrooms118 sq m

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Air conditioning
  • Parking available

Explore the area

View in a map
Oshkosh, WI
  • Place, Menominee Park
    ‪8 min walk‬
  • Place, Lake Winnebago
    ‪11 min walk‬
  • Place, Oshkosh Convention Center
    ‪16 min walk‬
  • Airport, Appleton, WI (ATW-Appleton Intl.)
    ‪26 min drive‬

Room options

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About the area

Oshkosh

In Oshkosh .You'll find Menominee Park and Lake Winnebago within a 15-minute walk of this Oshkosh vacation home. Oshkosh Saturday Farmers Market and Grand Opera House are also within 2 miles (3 km).

What's nearby

  • Menominee Park - 8 min walk - 0.7 km
  • Lake Winnebago - 11 min walk - 1.0 km
  • Oshkosh Convention Center - 16 min walk - 1.4 km
  • Grand Opera House - 16 min walk - 1.4 km
  • University of Wisconsin-Oshkosh - 2 min drive - 1.9 km

Getting around

  • Appleton, WI (ATW-Appleton Intl.) - 31 min drive

Restaurants

  • ‪Elsewhere Market and Coffee House - ‬16 min walk
  • ‪Kowboi Kitchen - Chicago Style food - ‬10 min walk
  • ‪Roxy Supper Club - ‬15 min walk
  • ‪Ruby Owl Tap Room - ‬15 min walk
  • ‪Varsity Club - ‬14 min walk

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

The Tailwind House | Sleeps 6

Summary:

Welcome to Oshkosh. This charming, fully updated home makes a comfortable, welcoming place to stay. It has a spacious layout, thoughtful updates throughout and great curb appeal, plus easy access to local dining, parks and attractions.



Whether you're in town for work, family, a getaway or EAA AirVenture, this home gives you a relaxing and convenient base for exploring Oshkosh and Northeast Wisconsin.



The Space:

This updated three-bedroom home has plenty of room to relax, gather and spread out.

-Bright, spacious living room for relaxing and spending time together

-Updated kitchen with a snack bar

-Dining area next to the kitchen for meals and conversation

-Half bathroom on the main floor

-Three large bedrooms upstairs

-Full bathroom upstairs

-Charming front porch for morning coffee or quiet evenings

-Free parking

The bedrooms and full bathroom are upstairs, so guests should be comfortable using stairs.



Guest Access:

The entire home is yours during your stay, including the living room, kitchen, dining area, all three bedrooms, both bathrooms and the front porch.

You'll have your own private entrance with keypad entry. Your check-in instructions and personal entry code will come through Breezeway before you arrive.

Please make yourself at home, and respect any locked doors, storage areas or spaces marked private.



The Neighborhood:

The home sits in a quiet residential area of Oshkosh. It's a peaceful place to stay, and restaurants, shopping, parks and everyday conveniences are still close by.

It's especially handy for visitors to the EAA Aviation Museum and the AirVenture grounds, which are about 2 to 5 miles away (a 5 to 10 minute drive).

The home also makes a great central base for exploring Northeast Wisconsin:

Appleton: about 20 to 25 miles (25 to 30 minutes)

Green Bay: about 35 to 40 miles (40 to 50 minutes)



Getting Around:

Uber and Lyft are available for trips around Oshkosh and nearby communities. It can take longer to get a ride late at night, during big events like AirVenture, or in winter weather, so we suggest booking a little early.

Driving is the easiest way to explore the area, and Oshkosh is easy to get around by car. Free parking is included with your stay.



Other Things to Note:

The home is in a residential neighborhood, so please be considerate of the neighbors, especially when you're outside or on the front porch.

The bedrooms and full bathroom are upstairs, and the main floor has a half bath.

Smoking and vaping are not allowed inside the home. If we find signs of smoking or vaping, a $250 fine will be charged. Parties and events are also not allowed. Please keep noise down, especially after 10:00 PM.

If you notice any damage or maintenance problems, please message us through Breezeway right away so we can fix them.



Interaction with Guests:

We want you to feel welcome and well taken care of during your stay. With self check-in and your own private entrance, you can come and go as you please and enjoy Oshkosh at your own pace.

Guesty handles reservation communication, including booking details and important stay information.

Breezeway is our main platform for guest communication before and during your visit. Your check-in instructions, keypad code and property updates will all come through Breezeway.

If you have a question, need help or want a local recommendation, just message us through Breezeway. We're happy to help.

Similar properties

Property amenities

Internet

  • Available in the house: WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Microwave
  • Oven
  • Refrigerator
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 3 bedrooms
  • Bedsheets provided

Bathroom

  • 1.5 bathrooms
  • Hair dryer
  • Shampoo
  • Shower
  • Towels provided

Living spaces

  • Dining table

Entertainment

  • TV

Outdoor areas

  • Balcony

Laundry

  • Washing machine

Work spaces

  • Office

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher
  • First aid kit

General

  • Unit size: 1,272 square feet

Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age: 23

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Rules

- We want you to enjoy everything our house has to offer. All we ask is that you treat It with respect and leave it in the same good, working cond...

Pets

  • No pets allowed

Children and extra beds

  • Children are welcome.

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector, and a first aid kit in each accommodation.

Property is also known as

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Frequently asked questions

How close is The Tailwind House | Sleeps 6 to the airport?

This vacation home is 21.1 mi (31-min drive) away from the Appleton, WI (ATW-Appleton Intl.) airport, the closest popular airport to the property.

Does The Tailwind House | Sleeps 6 have an airport shuttle?

Airport shuttle services are not available at this vacation home.

Does The Tailwind House | Sleeps 6 offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at The Tailwind House | Sleeps 6?

No, there is no casino at this vacation home.

What time is check-in at The Tailwind House | Sleeps 6?

Check-in begins at 4:00 PM.

Is there free parking at The Tailwind House | Sleeps 6?

Free parking is not available at this vacation home.

Does The Tailwind House | Sleeps 6 have a pool?

This vacation home does not have a pool.

Does The Tailwind House | Sleeps 6 have a spa?

There are no spa services available at this vacation home.

How close is The Tailwind House | Sleeps 6 to downtown Oshkosh?

This vacation home is 0.5 mi away from Oshkosh.

The Tailwind House | Sleeps 6 Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 3 out of 3 reviews
Rating 8 - Good. 0 out of 3 reviews
Rating 6 - Okay. 0 out of 3 reviews
Rating 4 - Poor. 0 out of 3 reviews
Rating 2 - Terrible. 0 out of 3 reviews

10/10

Cleanliness

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This is our second stay at this property! It’s a great place!
Stayed 2 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We loved staying at this property. It was clean and comfortable. We enjoyed sitting on the front porch in the evenings. We actually booked it for another weekend before we left!
Stayed 3 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Cozy little house, perfect for my family on our week. Long stay in oshkosh. What definitely stay again.
Stayed 6 nights in Jun 2026