Chenequa Holiday Rentals

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Holiday Rentals 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)
"The property was exactly what we needed for a convenient extended weekend. Very spacious house with ample parking and all the amenities we were looking for. "
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.

Stunning Log Cabin Getaway Near Lake Beulah *Pool Table*Grill

9.8 out of 10, Exceptional, (90)
"Relaxing weekend with a mom and daughter, and daughter-in-law. We were looking for a relaxing weekend with reading, good eating and drinking and nearby small town shops. And we got it all. 1bedroom downstairs, large Master on the main floor. A lot of spaces to relax, the property is gorgeous. The kitchen is impressive. Communication was easy, quick and helpful."
Stunning Log Cabin Getaway Near Lake Beulah *Pool Table*Grill

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$839
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

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

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

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

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

Rock River Haven - charming, spacious, peaceful

10.0 out of 10, Exceptional, (31)
"This was the perfect spot to get together and have a nice quiet weekend with my family. Will definitely stay here again the next time I'm in town."
Rock River Haven - charming, spacious, peaceful

Comfy Cozy Casa in Milwaukee, WI

7.0 out of 10, Good, (2)
"We came to Milwaukee for Harley Homecoming. We were gone most of the days. This property is upstairs in a shared building. Very clean. Very prompt responses from the host. Would stay again. Quiet Neighborhood."
Comfy Cozy Casa in Milwaukee, WI
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 Chenequa you may be interested in

Holiday Inn Express Milwaukee-West Medical Center, an IHG Hotel

2.5 star property
7.6 out of 10, Good, (1060)
"i love coming here the only thing i had an issue was my balcony door was broke so i couldn’t go outside other than that 10/10 definitely recommend!"
The price is AU$154
includes taxes & fees
1 Dec - 2 Dec
Holiday Inn Express Milwaukee-West Medical Center, an IHG Hotel

Country Inn & Suites by Radisson, Milwaukee West (Brookfield), WI

3.0 star property
8.8 out of 10, Excellent, (1010)
"."
The price is AU$172
includes taxes & fees
26 Nov - 27 Nov
Country Inn & Suites by Radisson, Milwaukee West (Brookfield), WI

Sonesta Milwaukee West Wauwatosa

3.5 star property
7.6 out of 10, Good, (1137)
"Older hotel but very clean friendly staff."
The price is AU$152
includes taxes & fees
12 Dec - 13 Dec
Sonesta Milwaukee West Wauwatosa
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

Black Friday: Members save 30%+

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

Frequently asked questions

Can I find a holiday rental in Chenequa?

Yes, there are holiday rentals close to the most popular sights in Chenequa, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Chenequa has to offer?

Amazing Five Bedroom Milwaukee Vacation Home!!: This holiday home rental outside of Chenequa offers an indoor pool, a fireplace and a BBQ 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 that you can cook with friends or family. Kick off your shoes and enjoy yourself with a balcony and a garden.

What’s there to see and do in Chenequa?

While exploring the area, visit family-friendly sights like Springs Water Park, or get outside and enjoy nature at Pewaukee Lake. In the wider area, you’ll find Lac La Belle and Pewaukee Lake Beach.

What’s a holiday rental in Chenequa like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chenequa. Holiday rentals offer extras like WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of privacy away from shared hotel lifts and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for small groups.