House holiday rentals in Caledonia

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Popular amenities for Caledonia house rentals

House rentals with a pool

Guest favourite
Home in Lake Geneva
5 out of 5 average rating, 33 reviews

Cozy cabin getaway near Lake Como and Lake Geneva

DanielRating, 5 stars2 weeks ago
Sasha’s place was even better than expected. We all felt at home and it was very relaxing. We had plenty of room to accommodate all of the guests.
Guest favourite
Home in Fontana-on-Geneva Lake
5 out of 5 average rating, 16 reviews

Abbey Springs Home! Hot Tub + Golf Cart

KathyRating, 5 stars2 months ago
A wonderful home that was well appointed, clean & a great location! We hosted Easter here with my adult Kids and grandson. We all enjoyed the beautiful surroundings and all the wildlife-many deer and even a coyote! So much room and a great layout for us to enjoy the home together!
Guest favourite
Home in Mequon
5 out of 5 average rating, 11 reviews

Vacation home: heated inground pool on 4+ acres

AvremiRating, 5 stars1 month ago
Was a wonderful stay at the home, will definitely go back again in the summer for a nice swim in the beautiful pool! If you are looking for a little getaway in a quiet area with a home that's both comfortable and modern I highly recommend this stay!
Top Guest favourite
Home in Lake Geneva
5 out of 5 average rating, 40 reviews

Newly Updated Modern Lake Condo

LaurenRating, 5 stars1 month ago
Loved this house! It was in a great location, a few mins away from town, walking distance to Lake Como and super easy to find and navigate. Everyone had a great time. Only drawback was a tiny kitchen for multiple people but the rest of the living areas were great!
Top Guest favourite
Home in Woodstock
4.88 out of 5 average rating, 66 reviews

Grand 1800s Victorian Gem: Updated/by Downtown

MarshaRating, 5 stars2 days ago
The stay was fantastic! The house is old but beautiful, gave us a very unique vibe, from every little details. Included amenities are great and of course we love the espresso maker and the kids have the most fun in the pool. Just sad we missed the fire pit due to lack of time. Last but not the least Deirdre is a very kind and responsive host, she made sure that we are comfortable and enjoy our stay even just for a short period. She made things/requests happen. I will give her and her place more than 5 stars if I could. Thank you!!
Guest favourite
Home in Lake Geneva
4.96 out of 5 average rating, 77 reviews

Relaxing getaway/StepsToLake/Pool/Tennis/nearDT/WD

CindyRating, 5 stars5 days ago
We only stayed for one night so weren't able to take advantage of all the community amenities, but the house was very comfortable and we had a good night's sleep. Seemed like a peaceful retreat just outside of the main shopping/dining area of Lake Geneva. We would return!
Top Guest favourite
Home in Whitewater
5 out of 5 average rating, 81 reviews

Nestled in the Southern Kettle Moraine Forest

DianaRating, 5 stars1 week ago
The property was better than the description… Chris and Jarvis made us feel “like we were staying with friends” … The landscaping on the property is gorgeous and everywhere you went there would be something interesting to see … The animals on the property were wonderful for me, I left my “mini-farm” for this trip, it was very soothing to walk out and watch the animals as I was missing mine. The interior design was very tasteful, slightly different, but much better than the pictures. The extra’s - muffins, bread, bacon, fresh farm eggs, and an assortment of drinks - were above and beyond any Airbnb property I have stayed at!! I have to add … if you’re planning to stay for the Kettle Moraine 100 - this property is less than 10-minutes to the start/finish and within 25 minutes or less to all crew accessible aid stations! I really hope to have another opportunity to stay at this property and explore the surrounding areas.
Superhost
Home in Lake Geneva
5 out of 5 average rating, 6 reviews

Oasis on Oak | Private In-Ground Pool | Hot Tub

ADAMRating, 5 stars3 weeks ago
House was great and matches the description and photos. House is spacious, good for a group of 6-7 people and private from other neighbors. It’s also less than 10 minutes from downtown Lake Geneva. It is an ideal house if you are looking for a quiet weekend retreat, close to the areas activities. In addition, the host is responsive and helpful. Looking forward to our next stay with you all!

Weekly house rentals

Top Guest favourite
Home in Trevor
5 out of 5 average rating, 24 reviews

2BR Lake House | Lake Toys | Views | Dog Friendly

KristinRating, 5 stars5 days ago
My husband and I really enjoyed our week stay at Rock Lake. The big deck with a screened in lounge was perfect for Summer evenings. We used the lake toys and enjoyed bon fires. We will definitely come back!
Top Guest favourite
Home in Milwaukee
5 out of 5 average rating, 75 reviews

Entire Cozy Cottage! Pet Friendly, No Cleaning Fee

MayraRating, 5 stars2 days ago
Absolutely loved our stay! The place was beautiful—clean, cozy, and stocked with all the essentials. The location was perfect, super close to the cutest local cafés and restaurants. There was even a super helpful binder with local recs and info that made getting around easy. The host was warm and welcoming from the start. I’d 10/10 recommend this spot and would definitely stay here again!
Guest favourite
Home in Oak Creek
4.84 out of 5 average rating, 87 reviews

Spacious Ranch Home Oak Creek close to Airport

EmilyRating, 5 stars3 weeks ago
Great place to stay. Great for family. Plenty of room to spread out and relax. Quiet neighborhood. Close enough to Milwaukee to go to attractions, but far enough away to get away from the bussle of the city traffic. Will definitely look to stay here again when we are back in the area.
Top Guest favourite
Home in Salem
5 out of 5 average rating, 32 reviews

Lago Amore - Channel house, pier, kayaks

GregoryRating, 5 stars2 weeks ago
Wish we had time to book a longer stay! Regardless, it was a perfect place for my son and I to stay and do some kayaking and fishing on Paddock Lake. The deck was really a nice touch with the cafe lights. It was really nice to have access to a dock to launch our kayaks and fish from.
Superhost
Home in Milwaukee
4.82 out of 5 average rating, 22 reviews

Cozy house near mke airport, quiet neighborhood

AdrianRating, 5 stars3 weeks ago
The property was great and Rebecca will message if anything was needed, but everything was perfect. Great by location and lots of restaurants and close to downtown
Top Guest favourite
Home in Racine
4.98 out of 5 average rating, 41 reviews

Mid-Century Modern Dream Getaway

CatherineRating, 5 stars1 month ago
This was a beautiful house and a beautiful location. My family had a great time exploring the rooms and enjoying the views out the many windows. Lovely trees and lawn space. The design elements of the house were so fun, this felt like a house I would tour - it was cool to stay in!
Guest favourite
Home in Milwaukee
5 out of 5 average rating, 9 reviews

Cozy Milwaukee cottage (whole house), sleeps 6

KarenRating, 5 stars2 weeks ago
We were vising family who lived just a few blocks over and we were able to walk back and forth to their place a few times everyday. The neighborhood felt very safe and it was nice and quiet. We really enjoyed the outdoor sitting area and used it quite a bit to hang out outside and play cards. The stairs really are steep but seemed doable. The only concern I had was with the very small landing at the top the stairs. We had a quick group discussion to make sure everyone was careful with the are, and ended up having no problems with it.
Guest favourite
Home in Waukesha
4.98 out of 5 average rating, 86 reviews

Brand New Studio w. Private Entry + Garden Patio

AdrienneRating, 5 stars3 weeks ago
Hubby and I stayed Friday and Saturday night. The room was perfect for us. Not too big and not too small. Plenty of amenities in the room to make us feel welcome. We didn't get a chance to sit out on in the backyard, but the view was beautiful.

Private house rentals

Guest favourite
Home in Cudahy
4.92 out of 5 average rating, 85 reviews

Upgraded! 4BR in Milwaukee near airport & downtown

DonnaRating, 5 stars1 week ago
This is an older home that has been redone so cute. We loved how much charm it had. It was clean and had everything we needed. Nice yard. Quiet neighborhood and the location worked great for us.
Superhost
Home in Racine
5 out of 5 average rating, 10 reviews

North Beach Bungalow

MarshaRating, 5 stars2 days ago
The place was spotless and very cozy. Loved the deck and all the seating areas. Just wish that it wasn’t on Main Street because of the noise. I didn’t realize that there wasn’t a lot to do in Racine except for the beach. The downtown area was really dead. There were a few restaurants around the river and port area but that was about it.
Guest favourite
Home in Bay View
4.97 out of 5 average rating, 36 reviews

2Bdrm home next to Humboldt Park

AnnaRating, 5 stars3 months ago
Jean‘s House is charming—it was very clean and comfortable. Woodwork was beautiful and so many of the original features of the home have been kept in excellent condition or renovated to make it a great mixture of a vintage aesthetic with the modern comforts. You cannot do without a car if staying here. But if you have a car it’s a convenient base for doing things in Milwaukee. Great list of recommendations (At Random is a great little cocktail venue).
Guest favourite
Home in Milwaukee
4.92 out of 5 average rating, 38 reviews

Cozy home

MarleeRating, 5 stars1 week ago
Quiet neighborhood close to all our destinations. Duplex but never ran into anyone else. Always parking available near house. Inside was peaceful and clean. Just the getaway we needed.
Guest favourite
Home in Glendale
4.92 out of 5 average rating, 26 reviews

Bass & Sparrow - Spa Retreat on the MKE River

CamilleRating, 5 stars1 month ago
You would have no idea this place is in Milwaukee. It truly felt so secluded, like you were hours away from downtown. The hot tub, sauna, river right there…might has well been at a resort. Truly one of the most memorable weekends and we can’t wait to reserve another stay with Brad!
Guest favourite
Home in Racine
4.86 out of 5 average rating, 50 reviews

The Main Destination

KevinRating, 5 stars2 months ago
Rhoda is an excellent host! Very helpful, friendly and accomadating! She went above and beyond for us! The house is very clean and comfortable.
Guest favourite
Home in South Milwaukee
5 out of 5 average rating, 17 reviews

Small Mid-century Ranch

LaureneRating, 5 stars1 week ago
Fabiana is an excellent host that had everything you would need for your stay. Very thoughtful about all the things she makes available to her quests. Super comfortable bedding, plush towels and items for every need in the kitchen. Definitely will stay again when in the Milwaukee area. Highly recommended ~ nice home, full garage, great backyard , cozy back porch all on a very quite dead end street
Guest favourite
Home in Kenosha
4.85 out of 5 average rating, 40 reviews

Backyard Oasis- 5BDRM, Firepit, Safe Area, By Lake

PatriciaRating, 5 stars2 days ago
Such a beautiful and spacious house - my grandkids came by and really enjoyed the foosball and air hockey in the basement, and my musical brother and sister used the piano and guitars for us all. The kitchen was very well equipped with everything we needed. The neighborhood was quiet, and being a residential area, it was handy to have street parking as well as the driveway for our meal and game times. Downtown was just a couple of turns away, easy to get to. If I ever lure my whole family back to Kenosha, I will definitely rent this again. Thanks Leida!

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