Best Vacation Homes in Oshkosh
New
House
4 Bedrooms
1 Bath
9 Guests
Fireplace/Heating
Air Conditioner
Internet
Child Friendly
CA $1,032/Night
7 Nights - CA $7,222
House
10.0(8 Reviews)
3 Bedrooms
3 Baths
6 Guests
240.39 ft²
- Fireplace/Heating
Balcony/Terrace
View
Kitchen
CA $205/Night
7 Nights - CA $1,437
Bed & Breakfast
9.4(29 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Balcony/Terrace
Breakfast- Kitchen
CA $208/Night
7 Nights - CA $1,454
New
House
3 Bedrooms
1 Bath
10 Guests
- Fireplace/Heating
Pet Friendly- Air Conditioner
- Internet
CA $476/Night
7 Nights - CA $3,330
House
10.0(3 Reviews)
3 Bedrooms
2 Baths
7 Guests
1356.25 ft²
Parking- Air Conditioner
- Internet
- Child Friendly
CA $252/Night
7 Nights - CA $1,760
House
10.0(90 Reviews)
4 Bedrooms
3 Baths
12 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
CA $683/Night
7 Nights - CA $4,779
House
10.0(53 Reviews)
3 Bedrooms
4 Baths
10 Guests
2594 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
CA $637/Night
7 Nights - CA $4,461
House
10.0(52 Reviews)
4 Bedrooms
3 Baths
10 Guests
2196 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
CA $605/Night
7 Nights - CA $4,236
Oshkosh Luxury Rentals
House
3 Bedrooms
4 Baths
12 Guests
5000 ft²
Hot Tub- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $10,260/Night
7 Nights - CA $71,821
House
10.0(3 Reviews)
4 Bedrooms
4 Baths
10 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $2,923/Night
7 Nights - CA $20,464
House
4 Bedrooms
4 Baths
10 Guests
Private Pool- Hot Tub
Pool- Air Conditioner
CA $2,905/Night
7 Nights - CA $20,338
House
6 Bedrooms
4 Baths
10 Guests
- Hot Tub
- Fireplace/Heating
- Kitchen
- Parking
CA $2,532/Night
7 Nights - CA $17,725
House
3 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
CA $2,484/Night
7 Nights - CA $17,385
House
5 Bedrooms
3 Baths
10 Guests
- Hot Tub
- Fireplace/Heating
Ocean View- Balcony/Terrace
CA $2,250/Night
7 Nights - CA $15,752
House
3 Bedrooms
4 Baths
4 Guests
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
CA $2,101/Night
7 Nights - CA $14,709
House
10.0(2 Reviews)
5 Bedrooms
3 Baths
10 Guests
3500 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
CA $1,910/Night
7 Nights - CA $13,367
Oshkosh Pet Friendly Vacation Rentals
House
10.0(33 Reviews)
4 Bedrooms
3 Baths
10 Guests
2400 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $708/Night
7 Nights - CA $4,959
House
9.5(2 Reviews)
3 Bedrooms
3 Baths
8 Guests
2174.31 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Internet
CA $748/Night
7 Nights - CA $5,234
Cottage
1 Bedroom
1 Bath
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
CA $721/Night
7 Nights - CA $5,047
House
10.0(28 Reviews)
3 Bedrooms
2 Baths
6 Guests
2100 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
CA $385/Night
7 Nights - CA $2,698
House
1 Bedroom
2 Baths
8 Guests
2002.09 ft²
- Fireplace/Heating
- View
- Pet Friendly
- Parking
CA $660/Night
7 Nights - CA $4,617
House
10.0(24 Reviews)
2 Bedrooms
1 Bath
4 Guests
980 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $494/Night
7 Nights - CA $3,460
House
10.0(14 Reviews)
3 Bedrooms
3 Baths
10 Guests
3200 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
CA $356/Night
7 Nights - CA $2,493
Cottage
10.0(13 Reviews)
3 Bedrooms
1 Bath
7 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
CA $692/Night
7 Nights - CA $4,842
Oshkosh Large Vacation Homes
House
10.0(37 Reviews)
5 Bedrooms
3 Baths
12 Guests
4700 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
CA $971/Night
7 Nights - CA $6,799
House
10.0(2 Reviews)
4 Bedrooms
3 Baths
10 Guests
2002.09 ft²
- Fireplace/Heating
- Balcony/Terrace
- Parking
- Air Conditioner
CA $931/Night
7 Nights - CA $6,516
House
10.0(18 Reviews)
3 Bedrooms
3 Baths
10 Guests
3089 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
CA $707/Night
7 Nights - CA $4,947
House
10.0(1 Review)
4 Bedrooms
4 Baths
10 Guests
1603.82 ft²
- Fireplace/Heating
- Balcony/Terrace
- Parking
- Air Conditioner
CA $873/Night
7 Nights - CA $6,113
House
10.0(15 Reviews)
5 Bedrooms
3 Baths
10 Guests
3000 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $1,157/Night
7 Nights - CA $8,099
House
10.0(4 Reviews)
4 Bedrooms
2 Baths
10 Guests
2900 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
CA $1,479/Night
7 Nights - CA $10,350
House
10.0(4 Reviews)
5 Bedrooms
2 Baths
7 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
CA $1,063/Night
7 Nights - CA $7,438
House
10.0(4 Reviews)
3 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
CA $1,030/Night
7 Nights - CA $7,211
Why Choose Rent By Owner for your Oshkosh Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Oshkosh
When should you plan your Vacation Rentals stay?
To make the most of your stay, consider visiting during the region's peak seasons when local events and weather conditions align to enhance your experience in this destination.
Peak Season Highlights
Summer (June to August)
During the summer months, this destination experiences warm and inviting weather, making it ideal for outdoor activities and exploring the region.
Average Temperature Daytime: around 80°F to 85°F - Nighttime: approximately 60°F to 65°F
Fall (September to November)
In early fall, the area boasts beautiful foliage and pleasant temperatures, attracting visitors seeking scenic views and outdoor adventures.
Average Temperature Daytime: about 70°F to 75°F - Nighttime: roughly 45°F to 50°F
Off-Season Highlights
Winter (December to February)
During the winter months, colder temperatures and potential snow create a quieter atmosphere for those looking to enjoy cozy getaways and indoor comforts.
Average Temperature Daytime: around 30°F to 35°F - Nighttime: close to 15°F to 20°F
Spring (March to May)
In early spring, the region begins to thaw, offering mild weather and fewer crowds for travelers seeking peaceful escapes and nature’s rebirth.
Average Temperature Daytime: approximately 50°F to 60°F - Nighttime: roughly 30°F to 40°F
Weekly Weather Forecast for Oshkosh
How to Book Your Oshkosh Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Oshkosh
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor dining with a spacious patio or picnic area
- Relax in a private hot tub to unwind after exploring the region
- Take advantage of a large backyard for outdoor activities and games
- Benefit from direct access to walking trails or nature paths nearby
- Utilize a barbecue grill for family cookouts during your stay
- Experience shaded lounging areas perfect for sunny days
- Spend time by a fire pit for cozy evenings under the stars
Top Attractions Around Oshkosh
What attractions are nearby?
Nearby, you can explore a variety of outdoor activities and cultural attractions that showcase the best of this destination’s vibrant community and natural beauty.
Family Activities
- EAA Aviation Museum: Discover the fascinating history of flight and explore aircraft exhibits that will captivate both kids and adults alike, making it a perfect family outing in town.
- Menominee Park and Zoo: Enjoy a day outdoors at this scenic park featuring a small zoo, playgrounds, and picnic areas, ideal for memorable family fun here.
- Oshkosh Public Museum: Engage with interactive exhibits and local history displays that offer an educational experience tailored for families eager to learn about the region's heritage.
- Lake Winnebago: Take advantage of the area's largest lake with activities like boating, fishing, or relaxing by the shore, providing countless ways for your family to unwind together.
Adult Activities
- Visit the EAA Aviation Museum: Discover interactive exhibits and historic aircraft that highlight this area's rich aviation history, making it a must-see attraction for enthusiasts staying in Oshkosh.
- Explore Lake Winnebago: Engage in water-based activities such as boating, fishing, or simply relaxing by the shore, offering a quintessential experience when visiting the region.
- Enjoy the Oshkosh Public Museum: Dive into local history through engaging exhibits and collections that showcase the area's cultural heritage and community stories.
- Stroll through Menominee Park: Take a leisurely walk or have a picnic in this scenic park with beautiful views of the encompassing lake, ideal for unwinding after your journey.
Other Places to Stay in Oshkosh, WI
Winnebago County
Titan Stadium
Pollock Community Water Park
Oshkosh Public Museum
Paine Art Center and Arboretum
Paine Art Center and Gardens
University of Wisconsin-Oshkosh
Grand Opera House
Aurora Medical Center Oshkosh
Oshkosh Saturday Farmers Market
Menominee Nation Arena
Black Wolf
Oshkosh Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Events: Check the area’s event calendar to discover local festivals, markets, and cultural activities that can enrich your stay in Oshkosh.
- Plan Outdoor Adventures: Take advantage of the region’s natural beauty by scheduling outdoor activities like kayaking or biking around here’s scenic spots.
- Visit Seasonal Attractions: Tailor your trip to include seasonal attractions that showcase the unique charm of this destination throughout the year.
- Choose Strategic Accommodation: Book a well-located vacation rental to maximize your access to top sights and minimize commute times during your visit.
Transportation Options
- Oshkosh Transit System: This local bus service offers convenient transportation around the area, making it easy for you to explore without a car.
- Rental Cars: Multiple rental car agencies operate nearby, providing flexible options for travelers seeking independence and ease of travel in this region.
- Taxi and Rideshare Services: Taxis and ride-hailing services are readily available here, offering quick and reliable transportation tailored to your schedule.
- Bike Rentals and Trails: You can enjoy cycling through scenic routes with bike rentals, giving you a healthy and eco-friendly way to discover the area’s attractions.
Local Customs Options
- Folk Music Traditions: You might notice that the local community celebrates its rich folk music heritage through annual festivals and gatherings, reflecting the area's cultural roots.
- Culinary Customs: Here, you can experience traditional Wisconsin dishes at local eateries that honor the region’s culinary history and seasonal ingredients.
- Community Events: Participating in or observing neighborhood parades and fairs offers insight into the region’s tight-knit social customs and festive spirit.
- Craftsmanship and Artisanship: The area values handcrafted goods, so exploring local markets can reveal the community’s pride in its artisanal traditions.
Frequently Asked Questions About Oshkosh?
1. What are the top vacation rentals in Oshkosh?
There are a lot of options in Oshkosh. If you plan on staying in the Oshkosh area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Oshkosh:
- WolfDen Getaway-Winnebago Channel
- The Harbor Hideaway.
- Lilly Lakeside Retreat Near Lake Winnebago – Cozy Fireplaces & Family Fun
- Entire Victorian Mansion - Near Main St & Farmer’s Mkt - Sleeps12
- Cabin Oasis on Lake Winnebago "Minutes from EAA"
- Hot tub - 4 Bedroom - 3.5 Bathrooms - Perfect Location
- Experience Oshkosh charm near EAA Aviation Museum
- Perfect Waterfront Retreat Destination on Lake Winnebago
- Goyke House- Best Lakeviews
- Beautiful home on Lake Winnebago
2. How many vacation rentals have private pools in Oshkosh?
There are 19 vacation rentals with private pools near Oshkosh. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Oshkosh are best for families?
If you are looking for a family-friendly vacation home in Oshkosh, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Oshkosh:
4. How many Rentbyowner vacation rentals are available in Oshkosh?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 426 in the Oshkosh area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Oshkosh.
5. What is the cancellation policy for vacation rentals in Oshkosh, Wisconsin?
The cancellation policies vary by listing, so it's important to review the specific terms outlined in the property listing. You can find this information in the booking details or contact the host directly for clarification.
6. How do I securely book a vacation rental in Oshkosh, Wisconsin?
Booking is handled through a secure platform that ensures your personal and payment information are protected. Follow the instructions provided on the listing page to complete your reservation safely.
7. Are there any additional fees I should be aware of when booking in the area?
Additional fees such as cleaning fees, service charges, or local taxes may apply. These will be detailed during the booking process, so reviewing the full price breakdown before confirming your reservation is recommended.
8. What amenities can I expect from vacation rentals here?
Most listings include amenities such as Wi-Fi, fully equipped kitchens, and parking. Specific features are listed on each property page, so you can choose accommodations that meet your needs.
9. How do I communicate with the host regarding my stay in this region?
Once your booking is confirmed, you can contact the host directly through the messaging system provided on the booking platform. This allows you to ask questions, request special arrangements, or coordinate check-in details.
Oshkosh Top Rated Vacation Rentals
House
10.0(22 Reviews)
3 Bedrooms
3 Baths
8 Guests
- Private Pool
Oceanfront- Fireplace/Heating
- Pool
CA $814/Night
7 Nights - CA $5,701
House
10.0(7 Reviews)
3 Bedrooms
2 Baths
4 Guests
1854 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
CA $1,006/Night
7 Nights - CA $7,040
House
10.0(1 Review)
5 Bedrooms
3 Baths
10 Guests
3000 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
CA $1,574/Night
7 Nights - CA $11,019
House
10.0(1 Review)
3 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Pool
- Kitchen
- Parking
CA $975/Night
7 Nights - CA $6,828
House
10.0(1 Review)
3 Bedrooms
4 Baths
8 Guests
1722.23 ft²
- Pool
- Parking
- Internet
- Child Friendly
CA $787/Night
7 Nights - CA $5,510
House
10.0(1 Review)
3 Bedrooms
3 Baths
6 Guests
1603.82 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Parking
CA $534/Night
7 Nights - CA $3,738
House
9.8(21 Reviews)
3 Bedrooms
3 Baths
6 Guests
1593 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
CA $827/Night
7 Nights - CA $5,787
House
9.6(12 Reviews)
2 Bedrooms
1 Bath
4 Guests
861 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
CA $442/Night
7 Nights - CA $3,096
