Entire home

The Tailwind House | Sleeps 6

Photo gallery for The Tailwind House | Sleeps 6

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

Reviews

10 out of 10
Exceptional

Highlights

  • Discover nearby landmarks
    Close to Lake Winnebago
3 bedrooms1+ bathroomSleeps 6

Popular amenities

  • Balcony
  • Air-conditioning
  • Refrigerator
  • Internet
  • Washing machine
  • Onsite parking available

Explore the area

View 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

Rooms & beds

3 bedrooms (sleeps 6)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 Double Bed

1 bathroom, 1 half bathroom

Bathroom 1

Bathtub · Toilet · Shower only

Bathroom 2

Toilet

Spaces

Kitchen
Office
Balcony

About this property

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.

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House Rules

Check in after 4:00 PM
Minimum age to rent: 23
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted
- 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...

Important information

You need to know

Property # 5255487vb
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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that 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 and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

About the area

Oshkosh

Oshkosh is home to this holiday home. Grand Opera House and Paine Art Center and Gardens are cultural highlights, and travellers looking to shop may want to visit Oshkosh Saturday Farmers Market and The Outlet Shoppes at Oshkosh. Looking to enjoy an event or a game while in town? See what's happening at Menominee Nation Arena or Titan Stadium.
Map
Oshkosh, WI

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

Frequently asked questions

Is Charming Updated Home in Oshkosh w/ Free Parking pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at The Tailwind House | Sleeps 6?

As of 10 Oct 2026, prices found for a 1-night stay for 2 adults at The Tailwind House | Sleeps 6 on 9 Mar 2027 start from AU$892, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Charming Updated Home in Oshkosh w/ Free Parking?

On-site parking is available at the property.

What time is check-in at Charming Updated Home in Oshkosh w/ Free Parking?

Check-in begins at 4:00 PM.

What time is check-out at Charming Updated Home in Oshkosh w/ Free Parking?

Checkout is at 10:00 AM.

Where is Charming Updated Home in Oshkosh w/ Free Parking located?

Situated in Oshkosh, this holiday home is within a 15-minute walk of Menominee Park and Lake Winnebago. Oshkosh Saturday Farmers Market and Grand Opera House are also within 1 mile (2 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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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

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

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
Response from VrboOwner on 5 Oct 2026
Hey Abby! Thanks so much for staying with us again. We hope to continue hosting you in the future, and are so thankful for your kind words :)
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
Response from VrboOwner on 28 Sept 2026
Thank you so much for your kind words, Abby! We'd love to have you back in the future :)
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
Response from VrboOwner on 18 July 2026
Thanks for your kind words! Happy to have you back anytime, thanks again for staying with us.

About the host

Hosted by Mark Biesack

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