Vacation rentals in Oshkosh

5 out of 5 average rating, 7 reviews

A modern kitchen features sleek cabinetry and a spacious island with seating. Large windows allow natural light to illuminate the space, highlighting the exposed brick walls and vintage accents. Two pendant lights hang over the counter, creating a warm and inviting ambiance during evening hours.

Apartment in Oshkosh

Downtown Loft Third Floor

Situated in a prime location, this stunning 2-bedroom industrial loft condo has an expansive rooftop deck that overlooks the beautiful Fox River. With it's specatacular views, luxury amenities and spacious living area it is perfect for a romantic getaway or special celebration. Within blocks of the Leach Amplitheater, farmers market and bike trail, it is the perfect destination. The private rooftop deck is the perfect setting to capture all the excitement of Oshkosh, including the EAA flyovers.

A wooden dock area is set against a backdrop of lush green grass and a wooden fence. The dock features multiple platforms extending into the water, surrounded by natural vegetation, creating a serene outdoor space ideal for relaxation or water activities.

5 out of 5 average rating, 38 reviews

Fenced Yard; Waterfront; Dock, Cozy & Refreshing

Take it easy at this unique and tranquil getaway. Located on Sawyer Creek; enjoy peaceful views in a quiet neighborhood. Privacy is yours with a fenced in yard & attached 2 car garage. Comfortable 2 bedrooms with Queen beds & a fully stocked kitchen, outdoor grill, 55 in Smart TV and dedicated desk area. Propane firepit, patio table & 2 kayaks, washer & dryer. Close to Wiowash Trail, resturants, UW-Oshkosh and Oshkosh Corp headquarters. EAA grounds is a short 12 minute drive. Dog friendly.

A modern shower space features a sleek design with grey tiled walls and a distinctive centerpiece of smooth pebbles. An adjustable showerhead is positioned overhead, and built-in shelves are available for convenient storage of toiletries.

4.88 out of 5 average rating, 187 reviews

Go and Go

Cozy 2 bedroom Log home. Can sleep 4-6. Across the street from Lake Winnebago. Short walk to park, zoo and boat landing. 6.5 miles to EAA grounds. Off street parking. Close to shopping, restaurants and downtown Oshkosh. Great rental for Air Show, Book now and bring your boat, jet ski, trailer, and fishing gear or just go sightseeing, dining and relaxing. Full kitchen, New Bath. Very comfortable with a great location. Perfect place to stay for family with students at UWO. Book now!

4.95 out of 5 average rating, 189 reviews

A wooden dock extends into the calm waters of Lake Winnebago, surrounded by a clear blue sky. The water reflects the light, creating a serene atmosphere. A small boat can be seen in the distance, with gentle ripples radiating from its path.

Guesthouse in Oshkosh

Cottage on Lake Winnebago

Furnished Cottage on Lake Winnebago with beautiful sunrises. 1 bedroom with queen bed. There is plenty of space for air mattresses in common areas. 1 queen air mattress available. One bath, full kitchen fully stocked with dining area, bring your own food to prepare. Bring your water toys or boat, launch nearby and dock access in warmer months with great fishing. Winter months, bring your snowmobile, trails nearby. Great ice fishing when lake is frozen and ice is safe.

4.96 out of 5 average rating, 191 reviews

A cozy outdoor fire pit area is illuminated by soft twinkling string lights. An Adirondack chair is positioned nearby, facing the glowing fire, surrounded by landscaped stones and plants, creating an inviting atmosphere for evening gatherings.

Cabin in Fox Lake

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, swimming 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, including children. *All dogs/pets must be pre-approved by the host. There is a $50 pet fee/stay.

A spacious patio area is visible, featuring a comfortable seating arrangement with navy blue cushions and a glass-top table. The home is designed with large floor-to-ceiling windows that offer expansive views of the surrounding greenery and landscaping. Steps lead up to the entryway from the patio.

5 out of 5 average rating, 23 reviews

Relaxing Lake Winnebago Waterfront Retreat

Experience the simple pleasures of lakeside living in this Oshkosh vacation rental! Featuring 3 bedrooms, 2 full baths, and 2 half baths, this beautifully designed home is the ideal spot to enjoy endless activities on Lake Winnebago. Take the pedal boat out for a spin or cast a line off the private dock! After, relax in the serene living room while admiring panoramic views of the lake through floor-to-ceiling windows, or end the night with stargazing on the patio!

A historic home features a light-colored exterior with large windows, allowing ample natural light. The entrance is framed by steps leading up to a porch, complemented by a well-maintained garden. The sky above is bright blue with scattered clouds.

4.92 out of 5 average rating, 216 reviews

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.

4.99 out of 5 average rating, 287 reviews

A view of a fire pit featuring a gentle flame against a serene lake backdrop at dusk. The horizon displays soft gradients of orange and blue. Silhouettes of adirondack chairs and a boat dock can be seen in the distance, enhancing the tranquil atmosphere.

Cottage in Fond du Lac

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.

A comfortable living area features a gray sectional sofa and a wooden coffee table. A television is mounted on the wall, and a side cabinet adds storage. Natural light enters through a nearby window, illuminating the space with a warm and inviting feel.

4.87 out of 5 average rating, 238 reviews

3BR Across from Park • Watch Fireworks from Porch!

Unbeatable Fourth of July Location! 🎆 Watch Menominee Park’s spectacular fireworks burst directly overhead from the front yard or porch — one of the best views in Oshkosh, just steps from the park! This cozy, modern getaway is perfect for families, groups, or peaceful retreats. Enjoy a stylish interior, gazebo with firepit table, and unbeatable access to the lake, zoo, walking trails, and downtown Oshkosh — all just a short stroll away.

4.99 out of 5 average rating, 82 reviews

A hammock is positioned between two trees, surrounded by lush green grass. Soft reeds line the edge of a calm waterway, with distant views of the lake visible beyond. A small fire pit and a few stones are placed nearby, creating a relaxing outdoor space.

Farm stay in Omro

Private Island Cabin + 170 Scenic Acres to Explore

Abundant wildlife, calming lake views, and quiet, starry nights. Accessible only by boat, this beautiful but bare-bones cabin is for the real adventurers. The main property (which includes 160 acres of protected wildlife habitat) is a short paddle away, giving the perfect balance of convenience and seclusion. Although rough around the edges, the cabin's natural privacy and minimalist style are perfect for anyone who enjoys the outdoors.

4.86 out of 5 average rating, 214 reviews

A light-filled kitchen is visible through a doorway, featuring white cabinetry and a wooden countertop. A window allows natural light to illuminate the space. Decorative shelves on one side display colorful glass items and personal touches, enhancing the room's character.

Apartment in Oshkosh

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.

4.93 out of 5 average rating, 134 reviews

Cottage in Fond du Lac

The Beach House

Cute year round home with fantastic evening sunsets on the East shore of Lake Winnebago. Enjoy the lake life with this 3 bedroom, 1.5 bath, private beach and pier, located on a private beach road and a close drive to restaurants in the surrounding area. Ideal for Walleye Weekend, EAA Convention, Road America, Green Bay Packer games, Wisconsin Badger games, Milwaukee Brewer games, Ryder Cup and more

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

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Houses

A space thats all yours, with room for everyone

Popular amenities for Oshkosh vacation rentals

Vacation rentals with pools in Oshkosh

4.96 out of 5 average rating, 24 reviews

The outdoor area features a spacious pool surrounded by multiple lounge chairs and umbrellas. Lush greenery and landscaped gardens enhance the inviting atmosphere. The house in the background complements the serene setting, providing a relaxed environment for gatherings and leisure activities.

Home in Wisconsin

Sunny Days Await | Private Pool & Hot Tub Retreat

ShannonRating, 5 stars1 week ago

Thanks so much for a great stay!!! Beautiful house and fantastic property!! Our family of 19 had an amazing stay! Thanks so much for an incredible stay!!

5 out of 5 average rating, 20 reviews

Home in Green Bay

Next Level~100K Game Room~ Sleeps 20~ Pool~Spa

DianeRating, 5 stars3 days ago

We chose this home for our family vacation, and couldn’t be happier. The pool, hot tubs, and game room were thoroughly enjoyed by my four grandsons. Actually, they were a big hit for all of the adults also! The home is absolutely beautiful and very thought through. The one small problem was the lack of window coverings in the master. Other than that, our stay was amazing!!! Richard was very responsive.

4.95 out of 5 average rating, 19 reviews

A heated pool area features numerous guests enjoying the water, with colorful floats and toys scattered throughout. Surrounding the pool, white lounge chairs are arranged on the concrete deck. A fence encloses the area, with lush greenery visible in the background.

Cabin in Montello

The Rabbit Retreat #1

KevinRating, 5 stars2 weeks ago

Very nice place, friendly campers as well

Superhost

An indoor pool with clear blue water is featured, surrounded by smooth concrete flooring. Bright overhead lights illuminate the space, while large glass doors offer views of the outdoor landscape. Greenery decorates the walls, adding a touch of nature to the area.

Home in Allouez

4.86 out of 5 average rating, 231 reviews

Amazing Six Bedroom Green Bay Vacation Home!!

SandraRating, 5 stars2 weeks ago

Beautiful home felt like home!! Very roomy and cozy. Thanks Thomas for being responsive and answering my questions. Me and my family had a great time!!! Will definitely book again at this location or other locations you have.

Superhost

A circular, above-ground swimming pool with clear, inviting water is visible, surrounded by lush greenery. The pool deck features wooden planks, and a set of steps leads into the water, creating easy access. The tranquil lake can be seen in the background.

Home in Montello

4.79 out of 5 average rating, 34 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.

4.97 out of 5 average rating, 33 reviews

The exterior of a two-story home is portrayed, featuring a welcoming front porch with potted plants. Lush green grass lines the pathway leading to the stairs. The facade combines traditional elements with modern updates, reflecting a craftsman style. A clear sky with scattered clouds adds to the scene.

Home in Plymouth

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.

4.97 out of 5 average rating, 102 reviews

A spacious kitchen and dining area is visible, featuring modern white cabinetry and a large island with a stone surface. A wooden dining table is surrounded by four chairs, and sunlight is let in through multiple windows that offer a bright atmosphere.

Home in Ashwaubenon

Indoor Pool, 5 Bedrooms, 10 Min Walk to Lambeau

RachelRating, 5 stars3 weeks ago

This place is absolutely beautiful! Beds were comfy and had everything we needed. Pool was warm and had floats and towels right there. The porch was great and the massage chair even better. The host responded fast to any questions we had. Was close to so much as well. Would stay here again for sure.

5 out of 5 average rating, 50 reviews

A serene outdoor pool area is enclosed by a fence, featuring a uniquely shaped pool with clear water. Surrounding greenery includes trees and flowers, with a pathway leading to the poolside. A small shed is visible in the background, enhancing the tranquil atmosphere.

Home in Green Bay

4 BR home w/pool (lg groups) kid friendly

Stephanie NicholeRating, 5 stars3 weeks ago

The place is very relaxing, it’s really nice. We really enjoyed the place. There’s a lot of things to do. Our whole family enjoyed it! Will definitely booked it again next time. Thank you so much!!!

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Other great vacation rentals in Oshkosh

A charming craftsman home is presented, featuring a welcoming front porch with three steps leading to the entrance. A well-maintained lawn surrounds the house, complemented by shrubs and trees. Large windows provide ample natural light, enhancing the exterior's inviting appearance.

5 out of 5 average rating, 34 reviews

Two Bedroom Craftsman Home

JenniferRating, 5 stars2 days ago

Amazing hosts! Jennifer and Jeremiah were fantastic hosts ! Their house was pristine. It’s perfect for small gatherings. The beds are comfortable. The bathrooms are squeaky clean with great water pressure. Absolutely love the fenced in backyard.. I highly highly recommend this place! Beautiful and centrally located next to shopping and coffee shops. Very private back yard for a town of Oshkosh’s size!

5 out of 5 average rating, 13 reviews

3+ bd 3 bath in Oshkosh on River near EAA

MikiRating, 5 stars2 weeks 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!

A corner seating area is featured, furnished with a comfortable brown couch adorned with blue and purple accent pillows. A round glass coffee table sits atop a decorative rug, while natural light streams through multiple windows, creating a bright and welcoming space.

4.96 out of 5 average rating, 83 reviews

Newly remodeled centrally located 2 bedroom home

ThurstonRating, 5 stars1 week ago

Loved this newly renovated house. It was very conveniently located and felt like home. A great place to relax.

Superhost

A well-lit office space features a wooden desk with a rolling chair and decorative plant. A modern lamp sits on the desk, providing additional light. A small side table with a plant is positioned nearby. Natural light enters through the window, enhancing the airy atmosphere.

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.

4.9 out of 5 average rating, 63 reviews

A small balcony is showcased, featuring a round, green table and a bright yellow chair. A vase of vibrant flowers adds color to the scene. The view includes trees and a well-maintained street, providing a sense of openness and connection to the neighborhood.

Apartment in Oshkosh

Charming Oshkosh - 2 Bedroom, Walk to Downtown

Kevin And Jenny-MeadeRating, 5 stars2 weeks ago

Clean, quiet, cozy, close to soccer fields. A peaceful respite between games. Kyla was responsive and gracious. We will be back!

4.97 out of 5 average rating, 32 reviews

Hot tub - 4 Bedroom 3.5 Bath

TracyRating, 5 stars6 days ago

First time staying at air bnb, was an amazing experience, great home and host, looking forward to more visits in the future, perfect location and lots to do if you don’t want to go out!

4.99 out of 5 average rating, 90 reviews

A secluded cabin is surrounded by snow-covered trees, with large windows reflecting the winter scene. A bright red fat tire bike rests in the foreground, contrasting against the white snow. The structure's wooden exterior shows signs of weathering, blending into the serene natural setting.

Cabin in New London

Secluded Cabin with Sauna

AlexRating, 5 stars6 days ago

Staying at the Belden Farm was an absolute dream. Sasha and I came here for a weekend away but it felt like stepping into a different world. It was a very peaceful and serene experience, tapping into nature and one another. We were very grateful to be able to be detached from our usual lives. We had endless fireside chats and marshmallow roasts by the meadow. Nature was plentiful, and the cabin was amazing. The sauna is a game changer. Tighe was an incredibly accommodating and friendly host. Would highly recommend this experience.

A spacious bedroom is highlighted by a comfortable bed featuring soft bedding. Large sliding glass doors provide a view of Lake Winnebago, while a wooden dresser and a lamp with a warm glow are positioned nearby. Natural light fills the room, creating a relaxing ambiance.