Ashippun Vacation Rentals

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Vacation Rentals in Ashippun

Amazing Five Bedroom Milwaukee Vacation Home!!

10.0 out of 10, Exceptional, (40)
"We have a family of 10 and this house was perfect for us. There was entertainment for all ages. Large areas for everyone to gather but also gave everyone their own space. Loved watching movies while swimming in the pool. Host was excellent to work with and process was easy. "
Amazing Five Bedroom Milwaukee Vacation Home!!

The Boat House on Pewaukee Lake| Location, Comfort, Experience

10.0 out of 10, Exceptional, (4)
"We are Pewaukee residents and known about the “boat house”for years. When we found it was available thru VRBO, we jumped on it. We had family from Texas visiting for a long week end, we reserved the boathouse. I can sum up there view of the house as fantastic. Not only was it unique, it was clean and fully equipped for their stay. Will definitely sign up for another stay."
The Boat House on Pewaukee Lake| Location, Comfort, Experience

Beautiful lakefront, Newly Remodeled Lower Level!

9.8 out of 10, Exceptional, (178)
"We loved our 3 day weekend stay here at Rebecca’s home! This place is clean, spacious and quiet! We enjoyed the clean hot tub and watching the racing on the lake! Also enjoyed a delicious complementary bottle of wine on Valentine’s Day while doing a puzzle. Had all the amenities we needed for the weekend. Thank you so very much! We appreciate all the communication and added advice of things to do in the area!Highly recommend the stay here! "
Beautiful lakefront, Newly Remodeled Lower Level!

4BR House in Glacier Hills County Park / Heart of the Kettle Moraine!

9.6 out of 10, Exceptional, (157)
"Enjoyed being close to the wedding venue. Samantha was available to answer any questions. The bedrooms were large and living space great for family. "
4BR House in Glacier Hills County Park / Heart of the Kettle Moraine!

Luxury Lakefront Home, Okauchee Lake's Finest Swim Frontage, 3 levels LakeViews

10.0 out of 10, Exceptional, (15)
"Really great location. Excellent accommodation. Clean very well equipped easy check in and out process. Only recommendation a few more blankets for beds. I’m from Fl and was in the teens needed a few extra lol. Thank you for a great home like atmosphere we were in town for our best friends funeral. "
Luxury Lakefront Home, Okauchee Lake's Finest Swim Frontage, 3 levels LakeViews

Beautiful Family Home on Quiet Lake Ashippun

10.0 out of 10, Exceptional, (12)
"We got together to celebrate one of our siblings birthday. My family is from all over and four flew into Milwaukee airport. It was a convenient location to do this. House is beautiful and roomy. Had 6 adults staying and all were comfortable and had plenty of space. We hosted our sibs party and all had a great time and were impressed with the house. Would recommend this property."
Beautiful Family Home on Quiet Lake Ashippun

Luxury Lakefront Home w Miles of Lake Views, private pier, lake toys & game room

10.0 out of 10, Exceptional, (43)
"The home was very welcoming and clean. It accommodated ages from 3-60 with all things needed for a great stay. We would definitely rent this home again should we need axon in the Future "
Luxury Lakefront Home w Miles of Lake Views, private pier, lake toys & game room

4 Bdrm 4 Bath Lake front Lake Sinissippi home

10.0 out of 10, Exceptional, (39)
"Great"
4 Bdrm 4 Bath Lake front Lake Sinissippi home

Eclectic Hubertus Home w/ Game Room & Fire Pit!

9.6 out of 10, Exceptional, (9)
"Our family was all able make the drive from southern Il, central Il, and northern Il to meet with family who live near this property. Our first time all together in one place in years! Plenty of space for everyone and then some! We got to see the area covered in beautiful snow fall. Would love to see the area again in the summer time. The game room was a big hit too!"
Eclectic Hubertus Home w/ Game Room & Fire Pit!

Waterfront on Pewaukee Lake |3BR/2BA|Private Pier

Waterfront on Pewaukee Lake |3BR/2BA|Private Pier

Charming 4-bedroom house steps from Pewaukee Lake Beach, shops & restaurants

10.0 out of 10, Exceptional, (2)
"Perfect for a family or Girls get away ! Beautiful house within walking distance to restaurants/beach. "
Charming 4-bedroom house steps from Pewaukee Lake Beach, shops & restaurants

Greenstone Cottage

10.0 out of 10, Exceptional, (16)
"Loved the property . Would recommend "
Greenstone Cottage

Spacious Pewaukee Lake/ Pier Access Home

8.6 out of 10, Excellent, (11)
"Our company needed to send workers out of town to a job site in the Delafield area. The house was perfect for our needs, close to the job site and enough beds for each person. That is always our struggle, enough beds, they will share a room but not a bed. Our employees enjoyed being able to sit out after a long day and sit around the fire pit and relax. Steve was great to work with, as we needed to book an additional week and despite having availability VRBO site showed it unavailable. We...
Spacious Pewaukee Lake/ Pier Access Home

Beautiful Historic Tudor Mansion with sandy Private Beach

9.6 out of 10, Exceptional, (30)
"We had a big crew that loves to play pickleball, jump in the pool, and blow some steam off in the sauna after an active day at the house that has it all!"
Beautiful Historic Tudor Mansion with sandy Private Beach

Pewaukee Lake | Sunsets | Dogs | Beach | Good Vibes

10.0 out of 10, Exceptional, (23)
"Kristen was an excellent host and made sure we had what we needed. The house and location were awesome and we all had a really great time."
Pewaukee Lake | Sunsets | Dogs | Beach | Good Vibes

Sunset Lake House w Hot Tub, 4 fireplaces & kids bunkroom!

9.8 out of 10, Exceptional, (9)
"We had multiple generations coming from many locations to celebrate mom’s 80 birthday. This home was large enough to accommodate all 13 for meals and gatherings very comfortably. There were spaces people could chat privately and a great room for everyone! Eleven of us slept there. We would definitely come again. "
Sunset Lake House w Hot Tub, 4 fireplaces & kids bunkroom!

Magnificently restored, charming, 8+ Bed-Victorian on a beautiful 1.5 acres.

9.8 out of 10, Exceptional, (8)
"Each year our extended family meets in Wisconsin for Christmas. This year we chose to find a location closer to Milwaukee. This recently restored Victorian worked well for our family. 8 of stayed at the house, while 8 others visited during the day. Plenty of room for the family to meet. Large kitchen and dining area. Plenty of places to park. Beautiful neighborhood. Jay our host was readily accessible and responsive prior to our visit, and we found the house very accommodating. "
Magnificently restored, charming, 8+ Bed-Victorian on a beautiful 1.5 acres.

Beautiful Waukesha Home

10.0 out of 10, Exceptional, (25)
"The house was awesome , nice neighborhood great view from kitchen. easy to get around the city. perfect place to call home while we were there. "
Beautiful Waukesha Home

3 Bedroom Okauchee Lake

9.2 out of 10, Wonderful, (10)
"Property description is accurate, yes you are staying above a very popular bar so you will hear the music late into the evening. We were there for a holiday weekend so this was just fine for us and our adult kids! Hosts communicated promptly and even provided a waffle bar and snacks! Loved being able to go downstairs and order food and drinks. We also walked to nearby restaurants, a perfect location to experience some lake life. Thank you!"
3 Bedroom Okauchee Lake

Amazing Cottage Big Cedar Lake

10.0 out of 10, Exceptional, (4)
"This home was best stocked VRBO I have ever stayed in! Great deck for morning coffee, dinner and games. Easy walk to the water! "
Amazing Cottage Big Cedar Lake
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other types of properties in Ashippun you may be interested in

The Ingleside Hotel

4.0 star property
8.6 out of 10, Excellent, (594)
"Staff was very friendly. Conveniently located, close to shopping and eateries. "
The price is CA $155
CA $175 total
includes taxes & fees
Mar 16 - Mar 17
The Ingleside Hotel

Holiday Inn Express & Suites Delafield by IHG

2.5 star property
9.4 out of 10, Exceptional, (493)
"Close to shopping and dining."
The price is CA $148
CA $167 total
includes taxes & fees
Mar 9 - Mar 10
Holiday Inn Express & Suites Delafield by IHG

Wildwood Lodge

2.5 star property
8.4 out of 10, Very good, (1001)
"Staff was very friendly, rooms were clean and comfortable. "
The price is CA $136
CA $154 total
includes taxes & fees
Mar 17 - Mar 18
Wildwood Lodge
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Can I find vacation rentals in Ashippun?

Yes, you can find vacation rentals close to well known local attractions in Ashippun, or you can choose a secluded option if you're looking for relaxation.

What are some of the best vacation rentals that Ashippun has to offer?

Amazing Five Bedroom Milwaukee Vacation Home!!: This vacation home rental near Ashippun offers an indoor pool, a fireplace, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a balcony and a garden.

What can I see and do in Ashippun?

Explore the area and family-friendly sights such as Fowler Lake Park, or get out into nature at a spot like Lac La Belle. Erin Hills Golf Course and The Octagon House are a couple of places you'll find in the larger area.

What are vacation rentals like in Ashippun?

Vacation rentals are private accommodations you can book for several days or longer in Ashippun. Vacation rentals offer extras such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a clean environment, vacation rentals can provide a sense of security away from public hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive option for family trips or small group gatherings.