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House vacation rentals in Oshkosh

Find and book unique houses on Airbnb

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Popular amenities for Oshkosh house rentals

House rentals with a pool

Guest favorite
Home in Wisconsin
4.96 out of 5 average rating, 23 reviews

Sunny Days Await | Private Pool & Hot Tub Retreat

AdolfoRating, 5 stars2 months ago
House was amazing! Host was great! Will be back soon! everything is accurate as shown and in top condition looking forward to come back when the weather is nicer!
Superhost
Home in Newton
4.88 out of 5 average rating, 8 reviews

Country Cottage Indoor Pool HOT TUB NFL Draft ava

CassandraRating, 5 stars10 months ago
Great stay! My group loved it and had a blast. House was Beautiful & Host was GREAT, was very understanding and helpful. DEFINITELY recommend and would love another stay sometime.
Guest favorite
Home in Mequon
5 out of 5 average rating, 10 reviews

Vacation home: heated inground pool on 4+ acres

AvremiRating, 5 stars1 month ago
Was a wonderful stay at the home, will definitely go back again in the summer for a nice swim in the beautiful pool! If you are looking for a little getaway in a quiet area with a home that's both comfortable and modern I highly recommend this stay!
Superhost
Home in Montello
4.82 out of 5 average rating, 33 reviews

3bed lake house, private heated pool near WI Dells

MariaRating, 5 stars9 months ago
Has a great experience. Was a quite and private stay. Beautiful lake view so peaceful.
Guest favorite
Home in Plymouth
4.97 out of 5 average rating, 33 reviews

Private Home 4 BR+2Ba, Heated Pool by Road America

FrancoisRating, 5 stars4 months ago
Very nice house, ideal for us coming to town. We were 2 families with 4 kids and the place was the perfect size and convenient for all. The hot tub is a great addition, right next to the backdoor deck, very close actually from the house. Very clean and very flexible hosts, kitchen was great and the large dining table is perfect for 8 guests.
Superhost
Home in Portage
5 out of 5 average rating, 4 reviews

Exec Retreat Heated Pool 7 Beds; 2.5 Bath 6000 sf

AnthonyRating, 5 stars4 months ago
This house was incredible! There was tons of space, and the kitchen had everything we needed. We brought 4 children, and the layout of the house was perfect for naptimes. We were a 20 to 30-minute drive from skiing, restaurants, and other outings. We were there during an incredibly cold weekend, but we could imagine how fun it would be to stay there in the warmer months with the pool and outdoor area!
Guest favorite
Home in Two Rivers
4.88 out of 5 average rating, 24 reviews

Cool City, Warm Pool

KRating, 5 stars2 months ago
Our family had a lovely stay at this Airbnb. The pool was the highlight (especially during a cold and rainy spring break week) but the whole house was cozy and extremely well stocked for cooking and entertainment. Jill was a great communicator and offered us early check in and late check out. Lake Michigan is minutes away. Highly recommend this Airbnb!
Guest favorite
Home in Kewaunee
4.93 out of 5 average rating, 29 reviews

Freshly Updated Lake Michigan Home, Heated Pool!

EliseRating, 5 stars6 months ago
Awesome place! The layout of this place worked so good for our family with all our grandkids. The place was so clean and well equip with everything you need! We have stayed at quite a few AIRBNB properties and this one ranks up there with the best. We were not there during weather where we used the pool, but the pool area looks great and well taken care of by the owner's crew. So happy we found this gem!

Weekly house rentals

Guest favorite
Home in Oshkosh
5 out of 5 average rating, 13 reviews

3+ bd 3 bath in Oshkosh on River near EAA

MikiRating, 5 stars1 week ago
I was in town for my dad’s memorial and Shawn worked with me to ensure that I was able to focus on my family during that time. We needed a peaceful location where I could bring my mom and her houseguests for meals and relaxation while we prepared her house for the gathering. Shawn’s house was perfect with plenty of indoor and outdoor seating, including a lovely fire pit with wood for evening fires. The deck was a lovely place for morning coffee. A bonus for the kids were all the “hidey holes” throughout the that made the house seem almost magical. Watching the lift bridge go up and down, the bank anglers, princess parties at the lovely park across the canal all added to the charm while still feeling very private. Highly recommend!
Top guest favorite
Home in Oshkosh
5 out of 5 average rating, 6 reviews

The Lakehouse at Winnebago

DaxRating, 5 stars2 weeks ago
We had a dad and kids memorial day weekend fishing trip at Lake Winnebago. This was the perfect base camp. Our boys ages 6-16 enjoyed fishing in the back dock every day and hanging out in the very cozy living room. The beds were very comfortable and the kitchen had everything you needed!
Guest favorite
Home in Oshkosh
4.96 out of 5 average rating, 28 reviews

Waterfront Retreat*Kayaks*Firepit*Dog Friendly

BridgetRating, 5 stars1 month ago
This was our first experience using AirBnb versus hotel rooms. It was much more costly than we anticipated. We didn't have much time to research and compare against other similar properties due to the nature of our trip. However, in the end and having 6 people and a dog, this turned out to be ideal all things considered. We all agree, it turned out to be one of our best visits. It provided the space we needed for our family as well as accommodate for our friends and family to visit us in a much more relaxed and spacious environment. We enjoyed kayaking, cooking on the grill, relaxing in front of the firepit making and eating smores, and resting in the hammock. Everything was labeled, clean, and organized. Francois responded quickly to any questions/concerns I had. The only drawback was one bathroom for 6 people, but we managed to make it work.
Guest favorite
Home in Neenah
5 out of 5 average rating, 16 reviews

Rickers Bay Lake house

NikkiRating, 5 stars1 week ago
The location is great! Right on the lake and beautiful views. The house is small, but was perfect the me and my 4 friends l. It didn't feel like we were on top of each other. It was a great place and we went and explored a bit of Neenah/Menasha as well. It's somewhere we would stay again!
Superhost
Home in Oshkosh
4.73 out of 5 average rating, 30 reviews

Destination Downtown

BrittanyRating, 5 stars1 month ago
The bedrooms were cute and tidy. There was a walkable marina and the neighborhood was quite. It was exactly what I needed for the week at the draft. There were places to go around town and the stores were conveniently less than 10minutes if I needed anything.
Top guest favorite
Home in Oshkosh
5 out of 5 average rating, 5 reviews

Waterfront Cottage with Full Recreational Room

JodiRating, 5 stars10 months ago
Nick was amazing. The place was great! Great host!
Top guest favorite
Home in Oshkosh
4.97 out of 5 average rating, 31 reviews

Hot tub - 4 Bedroom 3.5 Bath

JosephRating, 5 stars3 weeks ago
My family, our dog and I had a great time. The house was beautiful and wonderfully decorated with so many games and activities available in the basement. Thank you. Joe
Guest favorite
Home in Oshkosh
4.83 out of 5 average rating, 58 reviews

Shorelane Sunrise Waterfront Lake House

SovanoraRating, 5 stars2 weeks ago
Our first time there at the lake house and We really like the location. The bedrooms, beds were great condition. Very comfy. Kitchen, dining room and living room were huge and nice wood floors. Backyard room, garage, fire pit and dock were nice. Huge basement with washer machines there. We didn’t have a chance to enjoy the fire pit at all because it was kind of windy, chilly at the evening. One power outlet that runs the kitchen sink light was not working correctly. We didn’t use that all Over all, we really enjoyed the place 👍😊 Sovanora & Somaly

Private house rentals

Guest favorite
Home in Oshkosh
4.86 out of 5 average rating, 28 reviews

Newly remodeled lower unit #2

ChadRating, 5 stars1 month ago
The place was pristine clean and was remodeled! The beds were comfortable! The host was very accommodating with early check-in. Easy to get in and out. Conveniently located close to Green Bay.
Top guest favorite
Home in Appleton
5 out of 5 average rating, 87 reviews

SevenTwenty-an unforgettable stay in any season

J BlairRating, 5 stars1 week ago
I love this home. My family loves this home. Everything is labeled and instructions for the home are clear. The decor is thoughtful, functional and lovely to be around. So many properties these days look like someone got a gift card to TJ Maxx. That is not this. The kitchen is fully stocked with useful items. The beds are comfortable with televisions in each bedroom. If you arrive late, don’t worry. The owners leave enough items to relax in the evening or get you started in the morning. It’s a nice, quiet neighborhood, close to everything, with off street parking. It’s hard to get a reservation because this is such a great place. It is my first choice when I stay in Appleton. Unfortunately, this was the first Air B n B I ever stayed in. I thought they were all like this. They are not. The small, personal touches really set this property apart.
Superhost
Home in Oshkosh
4.9 out of 5 average rating, 20 reviews

Lakeside Lux of Oshkosh- Lake/Games/10beds/Luxury

DevlinRating, 5 stars2 weeks ago
Hi my name is devlin! I’ve recently stayed at Tyler’s Airbnb in Oshkosh and it was a dream! I thought the photos looked to way to go! (Some I even thought were photoshopped) but no everything I saw on the photos for this place was real! Gorgeous rooms and living rooms! The game room was mind blowing! Plus they got a pool table! (Who doesn’t love that) but this was able to fit me and my 7 other friends no problem! And we all had our own Rooms! This was my first ever Airbnb I bought and I’m so glad it went so well! Fully worth the prices for such an amazing experience! Thank you again Tyler!!!
Guest favorite
Home in Fond du Lac
4.91 out of 5 average rating, 76 reviews

Woltring Waters Waterfront Home

BarbRating, 5 stars1 month ago
We had a great stay at this cozy house on Lake Winnebago with a nautical theme. You’ll have everything you need with a large TV, comfortable furniture, washer and dryer, and the best selection of Kreurig coffees. Danielle is very helpful and quick to answer any questions.
Superhost
Home in Oshkosh
4.94 out of 5 average rating, 88 reviews

Home Overlooking Lake Winnebago on EAA flight path

AnjaRating, 5 stars2 months ago
Everything was great.
Guest favorite
Home in Oshkosh
4.88 out of 5 average rating, 17 reviews

Lakefront Cottage Escape | Fire pit | Kayaks

EmmaRating, 5 stars8 months ago
Super cool property and cute little home. Quiet and cozy for our fam of three including infant, as well as our dog. Loved visiting the Oshkosh farmer’s market and enjoying the sunrises and sunsets at the house. We hope to return sometime, thanks!
Guest favorite
Home in Oshkosh
4.95 out of 5 average rating, 20 reviews

Lank's Lookout on Lake Winnebago

MiguelRating, 5 stars6 months ago
This place is just something else. It’s more than perfect actually! 🙏🏼🫶🏻
Guest favorite
Home in Neenah
4.98 out of 5 average rating, 40 reviews

Whole House on Reed Street

ValerieRating, 5 stars1 month ago
We had a cozy relaxing stay. This home exceeded our expectations. We enjoyed the big backyard, nature, comfortable bed, kitchen utensils and yummy snacks. Very clean and the most of all, a comfortable safe environment. Our family really had fun with all the activities. I hope we can stay again soon..& Such a wonderful host.Thanks so much!

Quick stats about house rentals in Oshkosh

  • Total rentals

    710 properties

  • Nightly prices starting at

    G$4,183 GYD before taxes and fees

  • Total number of reviews

    5.5K reviews

  • Family-friendly rentals

    600 properties are a good fit for families

  • Pet-friendly rentals

    180 properties allow pets

  • Rentals with a pool

    30 properties have a pool

Destinations to explore

  1. Airbnb
  2. United States
  3. Wisconsin
  4. Winnebago County
  5. Oshkosh
  6. House rentals