Best Vacation Homes in Ashippun
House
10.0(17 Reviews)
2 Bedrooms
1 Bath
6 Guests
760 ft²
Oceanfront
Fireplace/Heating
Ocean View
Balcony/Terrace
R5,653/Night
7 Nights - R39,573
House
10.0(1 Review)
3 Bedrooms
4 Baths
12 Guests
3831.95 ft²
- Fireplace/Heating
Pet Friendly
Parking
Internet
R6,334/Night
7 Nights - R44,335
Bed & Breakfast
9.8(83 Reviews)
1 Bedroom
1 Bath
Breakfast- Parking
Air Conditioner- Internet
R1,941/Night
7 Nights - R13,593
Apartment
10.0(5 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
Kitchen- Air Conditioner
R6,556/Night
7 Nights - R45,890
Apartment
10.0(1 Review)
2 Bedrooms
1 Bath
8 Guests
796.53 ft²
- Fireplace/Heating
- Parking
- Internet
Child Friendly
R4,421/Night
7 Nights - R30,941
Apartment
9.8(10 Reviews)
2 Bedrooms
1 Bath
8 Guests
800 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
R4,269/Night
7 Nights - R29,882
Apartment
9.8(6 Reviews)
1 Bedroom
1 Bath
6 Guests
750 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
View
R3,239/Night
7 Nights - R22,672
House
9.6(30 Reviews)
2 Bedrooms
1 Bath
6 Guests
1000 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
R10,485/Night
7 Nights - R73,391
Ashippun Luxury Rentals
House
10.0(3 Reviews)
8 Bedrooms
5 Baths
17 Guests
10700 ft²
Private Pool- Oceanfront
Hot Tub- Fireplace/Heating
R55,564/Night
7 Nights - R388,948
House
10.0(8 Reviews)
5 Bedrooms
5 Baths
13 Guests
8100 ft²
- Hot Tub
Spa- Fireplace/Heating
- Balcony/Terrace
R52,959/Night
7 Nights - R370,724
House
9.6(36 Reviews)
8 Bedrooms
8 Baths
20 Guests
10500 ft²
- Private Pool
- Hot Tub
- Spa
- Fireplace/Heating
R42,643/Night
7 Nights - R298,508
House
10.0(2 Reviews)
4 Bedrooms
4 Baths
8 Guests
3200 ft²
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R42,231/Night
7 Nights - R295,614
House
10.0(1 Review)
4 Bedrooms
3 Baths
8 Guests
4800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R32,032/Night
7 Nights - R224,224
House
10.0(28 Reviews)
5 Bedrooms
4 Baths
12 Guests
3800 ft²
- Hot Tub
- Spa
- Fireplace/Heating
- Ocean View
R30,008/Night
7 Nights - R210,052
New
House
5 Bedrooms
3 Baths
12 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
R29,692/Night
7 Nights - R207,852
House
10.0(9 Reviews)
4 Bedrooms
3 Baths
8 Guests
3600 ft²
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R21,457/Night
7 Nights - R150,205
Ashippun Pet Friendly Vacation Rentals
House
10.0(23 Reviews)
2 Bedrooms
1 Bath
4 Guests
900 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R3,635/Night
7 Nights - R25,450
House
9.8(5 Reviews)
3 Bedrooms
2 Baths
6 Guests
1905.21 ft²
- Spa
- Fireplace/Heating
- Pet Friendly
- Parking
R4,746/Night
7 Nights - R33,223
House
10.0(11 Reviews)
2 Bedrooms
1 Bath
6 Guests
1200 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
R5,839/Night
7 Nights - R40,879
Apartment
9.3(3 Reviews)
2 Bedrooms
1 Bath
8 Guests
1194.79 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Parking
R2,481/Night
7 Nights - R17,364
Cabin
10.0(5 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R4,327/Night
7 Nights - R30,279
Apartment
10.0(5 Reviews)
2 Bedrooms
1 Bath
7 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R4,307/Night
7 Nights - R30,147
House
10.0(25 Reviews)
3 Bedrooms
2 Baths
8 Guests
1800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R11,315/Night
7 Nights - R79,212
House
10.0(18 Reviews)
4 Bedrooms
2 Baths
8 Guests
1800 ft²
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R20,506/Night
7 Nights - R143,540
Ashippun Large Vacation Homes
House
10.0(127 Reviews)
4 Bedrooms
3 Baths
13 Guests
2500 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
R9,550/Night
7 Nights - R66,859
House
9.8(9 Reviews)
3 Bedrooms
2 Baths
10 Guests
2002.09 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Breakfast
R5,953/Night
7 Nights - R41,673
House
10.0(101 Reviews)
5 Bedrooms
3 Baths
13 Guests
4140 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R15,526/Night
7 Nights - R108,681
House
8.6(5 Reviews)
8 Bedrooms
7 Baths
25 Guests
788.45 ft²
- Fireplace/Heating
- View
- Breakfast
- Parking
R1,621/Night
7 Nights - R11,344
House
10.0(41 Reviews)
4 Bedrooms
3 Baths
10 Guests
3500 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R13,828/Night
7 Nights - R96,790
House
10.0(9 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R11,063/Night
7 Nights - R77,442
House
9.8(45 Reviews)
3 Bedrooms
2 Baths
100 Guests
1900 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R4,792/Night
7 Nights - R33,553
House
9.8(7 Reviews)
3 Bedrooms
1 Bath
10 Guests
- Fireplace/Heating
Pool- Pet Friendly
- Kitchen
R2,411/Night
7 Nights - R16,868
Why Choose Rent By Owner for your Ashippun 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 Ashippun
When should you plan your Vacation Rentals stay?
Choosing the right time to vacation here can enhance your experience and help you make the most of your stay in this inviting region.
Peak Season Highlights
Summer (June to August)
During the summer months, you can enjoy warm weather and longer daylight hours, making it ideal for outdoor activities in this region.
Average Temperature Daytime: 78°F to 85°F - Nighttime: 55°F to 65°F
Fall (September to November)
This season offers pleasant temperatures and vibrant foliage, perfect for exploring the area's natural beauty and serene surroundings.
Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F
Off-Season Highlights
Winter (December to February)
The colder months bring snow and quiet tranquility, creating a cozy atmosphere for a peaceful getaway in this destination.
Average Temperature Daytime: 20°F to 30°F - Nighttime: 10°F to 20°F
Early Spring (March to May)
As nature begins to awaken, the weather remains cool, offering fewer crowds while still providing scenic views of budding flora.
Average Temperature Daytime: 40°F to 55°F - Nighttime: 30°F to 40°F
Weekly Weather Forecast for Ashippun
How to Book Your Ashippun 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 Ashippun
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 areas where you can savor meals with scenic views of the surrounding landscape.
- Take advantage of spacious yards or gardens perfect for relaxing or family activities.
- Many properties feature fire pits, ideal for cozy evenings under the stars.
- Access to private or community pools provides a refreshing way to unwind during your stay.
- The region often offers outdoor recreational spaces such as hiking or biking trails nearby.
- Some rentals include boat docks or water access for exploring local lakes and waterways.
- Outdoor seating and lounging areas are common, giving you a comfortable spot to enjoy the fresh air.
Top Attractions Around Ashippun
What attractions are nearby?
In this charming area, you can enjoy a variety of outdoor activities such as hiking, fishing, and exploring scenic parks that showcase the natural beauty of the region.
Family Activities
- Oconomowoc Lake Park: Enjoy a family picnic and outdoor fun at this scenic park, perfect for relaxing in the natural beauty of the area.
- Sunny Slope Park: Explore hiking trails and open spaces where children can play, making it an ideal spot for outdoor adventures in the region.
- Historic Downtown Oconomowoc: Discover charming shops and kid-friendly eateries within walking distance, offering a taste of local culture and entertainment.
- Lake Country Playhouse: Catch a family-friendly live performance or theater production, providing entertaining cultural experiences here in the region.
Adult Activities
- Explore the nearby lakes and waterways: Engage in kayaking, fishing, or simply enjoying a peaceful boat ride on the scenic waters that surround this charming area.
- Visit local parks and nature preserves: Discover the region's natural beauty through walking trails, birdwatching, and outdoor relaxation in well-maintained parks.
- Experience regional culinary delights: Savor authentic Wisconsin flavors at nearby eateries that showcase the area's renowned local produce and cuisine.
- Enjoy outdoor recreational activities: Take advantage of bike trails, golf courses, or hunting opportunities that offer an active way to experience the region's outdoors.
Ashippun Travel Tips
How Can You Make the Most of Your Stay?
- Plan Ahead for Local Events: Keep an eye on the area's event calendar to align your stay with local festivals or community gatherings, enhancing your experience in this charming Wisconsin destination.
- Explore Nature Nearby: Take advantage of the region’s natural beauty by visiting nearby parks and outdoor spaces that offer scenic views and tranquil settings perfect for relaxation.
- Communicate with Hosts: Reach out to your hosts early to get personalized tips about the best spots and hidden gems in the area that may not be widely advertised.
- Pack Accordingly: Prepare for the climate by packing versatile clothing suitable for outdoor activities and variable weather conditions here in this Wisconsin destination.
Transportation Options
- Car Rentals: You can explore the area and its surroundings conveniently by renting a car, providing flexibility for your travel plans here.
- Public Transit: Local bus services offer an affordable transportation option to navigate through this region efficiently.
- Taxi Services: Taxis are readily available for quick and direct travel within the destination and nearby locations.
- Bike Rentals: For a scenic and eco-friendly way to experience the area, bike rentals are a popular choice among visitors here.
Local Customs Options
- Local Dairy Traditions: You’ll find that the area embraces its dairy farming heritage through community events and local cuisine, offering an authentic taste of Wisconsin’s rich agricultural roots.
- Seasonal Celebrations: Participating in seasonal festivals and parades is a common custom here, reflecting the region’s close-knit community spirit and love for celebrating the changing seasons.
- Respect for Nature: The community places importance on outdoor appreciation and conservation, making it customary to engage in local outdoor activities while respecting the natural landscape.
- Community Gatherings: Regular neighborhood gatherings and local markets highlight the region’s friendly atmosphere, providing opportunities to connect with residents and experience local hospitality firsthand.
Frequently Asked Questions About Ashippun?
1. What are the top vacation rentals in Ashippun?
There are a lot of options in Ashippun. If you plan on staying in the Ashippun area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Ashippun:
- Sunsets on the lake at Mill Pond Cottage-Pickleball, Water Sports, Hiking &more
- Victorian Lake Home
- Spacious Lake House with Beautiful Views and 123 Feet of Swimming Frontage
- Nagawicka Woods-Beautiful Lake Country Ranch Home
- Piper's Retreat: 4 bed, 2.5 bath by Erin Hills Golf, Glacier Hills, Holy Hill
- Exquisite Newly Renovated Historic Lake Country Home - Maison La Belle
- Pet-friendly, Kid-friendly Farmhouse near Holy Hill, Ice Age Trail, State Forest
- Charming Historic Upper Walk to Downtown, Festivals & Beach
- Rock River Haven - charming, spacious, peaceful
- One-of-a-kind Blue Tree House Retreat Holy Hill Getaway Hiking Trails
2. How many vacation rentals have private pools in Ashippun?
There are 8 vacation rentals with private pools near Ashippun. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Ashippun are best for families?
If you are looking for a family-friendly vacation home in Ashippun, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Ashippun:
4. How many Rentbyowner vacation rentals are available in Ashippun?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 167 in the Ashippun 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 Ashippun.
5. What is the cancellation policy for vacation rentals in Ashippun, Wisconsin?
Cancellation policies vary by listing, so it is important to review the specific terms on each property’s page or contact the owner directly for detailed information regarding cancellations and potential fees.
6. How do I secure my reservation at a vacation rental in this Wisconsin region?
Reservations are confirmed once you complete the booking process on the listing page and receive a confirmation from the host. It’s recommended to review any booking requirements or deposits needed before finalizing your reservation.
7. Are there any additional fees I should be aware of when booking a vacation rental here?
Additional charges such as cleaning fees, service fees, or local taxes may apply depending on the property. Be sure to check the detailed pricing section of each listing for a comprehensive breakdown of costs.
8. What amenities can I expect at vacation rentals in the area?
Amenities vary between properties, but many offer essentials like Wi-Fi, kitchen facilities, and parking. For specific amenities, review each listing thoroughly or reach out to the owner for clarification.
9. Is there a minimum stay requirement for booking a vacation rental in this destination?
Minimum stay requirements differ among properties; some may require a night or two, especially during peak seasons. Details are available on the individual listing pages or can be confirmed by contacting the host directly.
Ashippun Top Rated Vacation Rentals
Other
10.0(41 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
R5,033/Night
7 Nights - R35,240
Apartment
10.0(1 Review)
1 Bedroom
1 Bath
4 Guests
- Hot Tub
- Pool
- Breakfast
- Parking
R3,383/Night
7 Nights - R23,681
Apartment
10.0(1 Review)
1 Bedroom
1 Bath
6 Guests
- Hot Tub
- Pool
- Breakfast
- Parking
R3,326/Night
7 Nights - R23,284
Hotel
9.2(863 Reviews)
1 Bath
- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
R2,074/Night
7 Nights - R14,519
Hotel
9.2(171 Reviews)
1 Bath
- Pool
- Balcony/Terrace
- Breakfast
- Parking
R2,168/Night
7 Nights - R15,181
Hotel
9.0(675 Reviews)
1 Bath
- Hot Tub
- Fireplace/Heating
- Pool
- Breakfast
R1,977/Night
7 Nights - R13,841
R1,800/Night
7 Nights - R12,601
Hotel
8.8(431 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Breakfast
- Kitchen
R3,163/Night
7 Nights - R22,143
