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. - The Tailwind House | Sleeps 6 (Oshkosh)
A two-story house with a front porch, a visible front door, and a small front yard. - The Tailwind House | Sleeps 6 (Oshkosh)
A bedroom with a bed, bedside tables, a window, and a view of the outdoors. - The Tailwind House | Sleeps 6 (Oshkosh)
A kitchen with wooden cabinets, a marble countertop, a black refrigerator, a sink, and a stove. - The Tailwind House | Sleeps 6 (Oshkosh)
A dining area with a wooden table, black chairs, a woven centerpiece, and a hanging light fixture. - The Tailwind House | Sleeps 6 (Oshkosh)
Charming Updated Home in Oshkosh w/ Free Parking provides everything that you need. Guests can connect to in-room WiFi.

Reviews

10 out of 10
Exceptional

Entire home

3 bedrooms2 bathrooms1272 sq ft

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Air-conditioning
  • Parking available

Add dates for prices

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.

Property amenities

Internet

  • Available in the house: WiFi

Parking and transport

  • Parking on site

Kitchen

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

  • Smoke-free property

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)
  • First aid kit
  • Fire extinguisher

General

  • Unit size: 1,272 square feet

Similar properties

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

Pets not allowed

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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
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
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.

About the area

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. Visit our Oshkosh travel guide
View more Holiday homes in Oshkosh
Map
Oshkosh, WI

What's nearby

  • A sunset over a calm lake with a sandy shore.
    Lake Winnebago
    11 min walk - 0.6 miles
  • A historic opera house with ornate architecture and large windows.
    Grand Opera House
    16 min walk - 0.9 miles
  • Menominee Park
    8 min walk - 0.5 miles
  • Oshkosh Convention Center
    16 min walk - 0.9 miles
  • University of Wisconsin-Oshkosh
    2 min drive - 1.2 miles

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 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).

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Reviews

The Tailwind House | Sleeps 6 Reviews

10

Exceptional

10

Cleanliness

10

Location
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

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