Holiday Homes in Chenequa

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Featured Holiday Homes in Chenequa

Amazing Five Bedroom Milwaukee Vacation Home!!

10.0 out of 10, Exceptional, (37)
"Went for our annual golf trip. Perfect house for the 6 of us. Never had to leave the house after our rounds!"
Amazing Five Bedroom Milwaukee Vacation Home!!

Beautiful lakefront, Newly Remodeled Lower Level! ^^

9.8 out of 10, Exceptional, (173)
"We had a wonderful stay; only complaint was that we couldn't get the outside light to work in the back, by the hot tub. Would definitely come again!"
Beautiful lakefront, Newly Remodeled Lower Level! ^^

Pewaukee Lake Home: Sunsets, Dogs & Good Vibes

10.0 out of 10, Exceptional, (22)
"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 Home: Sunsets, Dogs & Good Vibes

Relax Near Everything in Milwaukee

10.0 out of 10, Exceptional, (35)
"We stayed here for the weekend while visiting our daughter at Wisconsin Lutheran College along with the grandparents. The house was clean and it had everything we expected. Very quiet neighborhood. Communication was great! He even checked in a couple times (via text) to make sure everything was okay. We will probably be staying here again in the future for other visits. Highly recommend!"
Relax Near Everything in Milwaukee

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

10.0 out of 10, Exceptional, (5)
"Beautiful home and property, lots of space to spread out and have privacy. "
Magnificently restored, charming, 8+ Bed-Victorian on a beautiful 1.5 acres.

Modern and Convenient Waukesha Home with Hot Tub

8.0 out of 10, Very good, (1)
"This home worked great for our group while in town visiting Carroll University. It was close to downtown and campus. I would stay here again."
The price is AU$497
includes taxes & fees
2 Dec - 3 Dec
Modern and Convenient Waukesha Home with Hot Tub

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!

Fall Deals! - Mins to Froedert/State Fair - Dogs!

9.6 out of 10, Exceptional, (8)
"Our family of 6 older adults (48-71) were in town for a funeral. CUTE home 20 minutes from everything we had to attend. Close to the interstate. Easy booking, quick response from the owner/host. The patio was a great gathering place as we had very comfortable weather. Mr. Ackley promptly addressed an issue that arised after hours on a Friday!!! That is a great host! Give this cozy home a try!"
Fall Deals! - Mins to Froedert/State Fair - Dogs!

Beautiful Waukesha Home

10.0 out of 10, Exceptional, (21)
"Beautiful home in a quiet neighborhood. Very clean property with all the amenities needed for our son’s wedding weekend. Host was very responsive and accommodating. Would definitely stay again if in the area. "
The price is AU$854
includes taxes & fees
1 Dec - 2 Dec
Beautiful Waukesha Home

Family Friendly Sandy Beach Lake Home! Your 3Bed, 2Bath Escape For All Seasons!

10.0 out of 10, Exceptional, (31)
"We loved our stay here. We wanted a quiet place to stay for an extended weekend and this was the perfect spot. My kids loved the pier, the kayaks, and the bikes. I loved the giant couch and the view! The pictures didn't show off how amazing this house really is so when I walked in I literally said "Wow!". The house had everything you could possibly need. Thank you for letting us stay at your property. We will definitely be back again. "
Family Friendly Sandy Beach Lake Home! Your 3Bed, 2Bath Escape For All Seasons!

🌊 Well Appointed Home Steps from Pewaukee Lake + KING Bed 🌊

9.6 out of 10, Exceptional, (10)
"Lovely unit very clean, and great hosts!"
🌊 Well Appointed Home Steps from Pewaukee Lake + KING Bed 🌊

Historic, Vintage, Classy, 11 bed, 5+ bath!

10.0 out of 10, Exceptional, (6)
" We were immediately impressed with the property! It was beautiful and well appointed.The host was responsive."
Historic, Vintage, Classy, 11 bed, 5+ bath!

Classic Brookfield Home ~ 14 Mi to Milwaukee!

9.2 out of 10, Wonderful, (13)
"Plenty of space and beautiful landscaping that we all enjoyed. The woodwork and decorations add so much character. "
Classic Brookfield Home ~ 14 Mi to Milwaukee!

Cozy Pet Friendly Home w/ Private Yard & King Bed - Near Wauwatosa

10.0 out of 10, Exceptional, (11)
"Perfect for our time in Milwaukee. The fences in yard was great for our dogs. "
Cozy Pet Friendly Home w/ Private Yard & King Bed - Near Wauwatosa

W172-Lannon · Charming Muskego House, Walk to Lake & Restaurants

9.6 out of 10, Exceptional, (5)
"Home needs a few fixes, but easy to do. Overall good property . Convenient placement with lots to do and many restaurants and convenient stores for provisions. "
The price is AU$430
includes taxes & fees
2 Dec - 3 Dec
W172-Lannon · Charming Muskego House, Walk to Lake & Restaurants

Modern 3 BR Minutes to WI Statefair, MKE Zoo, Brewers, & Hospital

10.0 out of 10, Exceptional, (13)
"My father, brother, 2 nieces and i travelled together to visit my Grandma for her 100th birthday. It was wonderful to be able to stay together in this very special home — beautiful decorated and very well kept. Great location. Incredibly relaxing and easy to navigate. We would love to stay again when visiting the Milwaukee/West Allis area. "
Modern 3 BR Minutes to WI Statefair, MKE Zoo, Brewers, & Hospital

Meadow Hill: Central, dog friendly home on 2 acres

10.0 out of 10, Exceptional, (2)
"My family and I rented this property to attend a family members wedding in Milwaukee. We also travel with our two dogs and wanted a quiet spacious place. The property was very clean and provided all the amenities listed. Beds were very comfortable! The property manager was responsive and promptly addressed any questions. The property is secluded yet conveniently located near food and shopping. We also had numerous deer visit the backyard during our visit and many deer bed in the timber behind...
Meadow Hill: Central, dog friendly home on 2 acres

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

10.0 out of 10, Exceptional, (1)
"We had a wonderful weekend. This home was perfect for our family. Will definitely book this place again."
Charming 4-bedroom house steps from Pewaukee Lake Beach, shops & restaurants

Nice three 3 bedroom unit with free parking and wi-fi

6.0 out of 10, (18)
"Could use updated, but was clean and comfortable."
The price is AU$313
includes taxes & fees
30 Nov - 1 Dec
Nice three 3 bedroom unit with free parking and wi-fi

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
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 property types in Chenequa

Amazing Five Bedroom Milwaukee Vacation Home!!

10.0 out of 10, Exceptional, (37)
"Went for our annual golf trip. Perfect house for the 6 of us. Never had to leave the house after our rounds!"
Amazing Five Bedroom Milwaukee Vacation Home!!

Beautiful lakefront, Newly Remodeled Lower Level! ^^

9.8 out of 10, Exceptional, (173)
"We had a wonderful stay; only complaint was that we couldn't get the outside light to work in the back, by the hot tub. Would definitely come again!"
Beautiful lakefront, Newly Remodeled Lower Level! ^^

Pewaukee Lake Home: Sunsets, Dogs & Good Vibes

10.0 out of 10, Exceptional, (22)
"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 Home: Sunsets, Dogs & Good Vibes
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.