
Cottage holiday rentals in Caledonia
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Top-rated cottage rentals in Caledonia
Guests agree: These cottages are highly rated for location, cleanliness and more.
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Popular amenities for Caledonia cottage rentals
Cottage rentals with a hot tub

The Coral Cottage
I loved the home , our stay was very nice and peaceful experience being. The host was very kind and flexible with our needs ! Very happy with our stay !

The Yellow Cottage @ Cottages on Petite Lake
great place and I loved being able to bring our dogs. they loved the gated yard to run around in while we chilled in the hot tub. we'd love to visit sometime in the summer to check out more of the lake activities.

#4 Adorable Lake Cottage-Cypress Resort & Marine
This was our second visit to Amanda’s and just like the first time, it left my boys with fun memories. We will be back next summer.

Lakeside Pewaukee Cottage
We were impressed by the cleanliness and open feeling of the place. It was a little smaller than we expected and had very limited seating but fit our group of 3 ok. I can’t imagine it being comfortable for a larger group though unless you’re only using the place to sleep! Overall it was a pleasant experience, beds were comfortable, kitchen well-appointed and the hot tub was nice, but we did feel that the price, once the cleaning fee was added on, was a little steep.

#8 Hillside Cottage at Cypress Resort & Marine
This was my second time staying at this lakehouse, and it was just as great as I remembered. I absolutely love the peaceful surrounding area—it's a perfect spot to relax and enjoy nature. The hosts were very responsive and helpful, answering any questions I had right away. Everything in the listing was exactly as described, and the check-in instructions were clear and easy to follow. The house was clean, comfortable, and had everything I needed. I’m already looking forward to coming back again!

The Blue Roof Cottage @ Cottages on Petite Lake
David was great, cabin lovely, peaceful surroundings. We will definitely be back!

#4 The Cozy Cottage
The place was beautiful. The house is a bit old but we didn’t mind it, it made it feel homey in a way. My friends and I loved the hot tub, would love to come back again.

#3 The Little Blue Cottage @ The Cottages on Petit
Love the rustic feel of the place, easily accessible amenities. Small and intimate, but also enough room for a couple.
Pet-friendly cottage rentals

The Butterfly Cottage
We took our family on a long weekend vacation to explore Lake Geneva and this was such a perfect lake side cottage that was only 20 mins from Lake Geneva. It was so nice to come home to a quiet spot to fish and relax. The cabin is so clean, cozy, cute and had more then everything we needed.

Twin Lakes Bungalow
My husband and I were looking for a weekend escape from Chicago and we really lucked out with this space!! We have a large dog and wanted a home with a private fenced in yard and he absolutely loved it here. The yard was massive, and the house was quaint and private. Easy walking to restaurants, bars and the lake! Jess was a beyond amazing hostess, and was extremely responsive and friendly. She left us a bottle of wine which was a HUGE plus :) we spent a majority of our time in the backyard with our dog (it was a vacation for him), but we also went to a Sand Bar, George’s, Manny’s and the ice cream shop!! We loved it all and will be back!!

Charming Lakeside Cottage
We had a wonderful stay at Jenna’s place. A perfect location on the lake, fantastic backyard and plenty of amenities. Would definitely love to return!

A vintage charming 2-bedroom cottage!
I had a wonderful stay at this beautiful, historic cottage and would highly recommend it. The host has thought of everything to make your experience one full of beauty, comfort, fun, relaxation and ease. As a writer and artist looking for a small town, private retreat, it was a perfect location and living experience, very inspiring and productive. Williams Bay is charming, with great local services including a convenient yoga studio, grocery and salon--all within walking distance of the gorgeous lakefront. This is a gem.

Hilltop Cottage
Quite neighborhood and a beautiful place. Very nice place.

COZY Cottage | 4 BEDS | Fenced yard
Great house in a great location. Hope to stay again someday.

Cozy 2 bedroom cottage on lake Delavan with kayaks
Had a great stay! Place was beautiful and the location was great! Tiffany was very responsive :) The second bedroom was smaller than anticipated but it made sense due to the size of the house. The private beach you have access to is less than a minute walk and we caught some good fish over there. Overall had a great stay and would highly recommend staying here!

NEW! Renovated Home in Downtown Lake Geneva
Short, but sweet stay for business. The rental was exactly as described and spotless. Will definitely be back if I'm in the area again. Thank you!
Private cottage rentals

Updated Twin Lakes Cottage, Walk to Lake Mary
We had a great stay in Twin Lakes near Mary Lake. The home was very clean and the area was quiet. The beds linens and pillows were very comfortable. We had enough room for 7. Two baths and laundry worked out great. There was a nice patio and fire pit to use. It was walkable to the small town of Twin Lakes. Although we did not visit the local establishments this time. We had friends to visit in Lindenhurst which was an easy 30 minute drive into IL We would recommend this location for anyone visiting southern WI and northern IL. Supplies were minimal but sufficient for making meals at the house. There was a gas grill available as well. We hope to visit again sometime.

Cozy cottage w/stunning views
We were looking for a peaceful getaway & we got just that! The host was very responsive with any questions 😊

Private 1BR Cottage with City Views
Cris’s cottage was perfect for a weekend getaway for Milwaukee! The location was awesome - right by walking paths & places to grab a beer. Definitely recommend!

Lakefront Views, Free Water Sports!!
Very great get away I’m a fisherman and caught some really big fish. Water was clean lots to do on the chain of lakes. Only 9 mins from McDonald’s and Walmart in case anyone needs last minute stuff. Chris and Shannon were very knowledgeable of the area. Great place for peace. Sunset is on bedroom window side. (Loved to see this as I was just getting up) neighbors were friendly. Love the fact we had water toys like paddle boat kayaks and paddle board for use even though I didn’t use them I was fishing my 3 days there. There’s a dock and water at dock is about 2’-3’. Would highly recommended them. Overall it was a great stay and will be coming back again. To all who is looking at this you will love this environment. I consider this place a happy place getaway. Caught cat fish, drum,bass,,walleye Maybe rent a boat and explore the chain of lakes next time. Thank you Shannon and Chris for the great experience

The Lily Pad at Lake Wandawega
This stay is amazing for quiet mornings with coffee on the deck. It’s right on the water with the ability to kayak and paddle board. The amenities are amazing and it’s the perfect place for a couples getaway weekend. Close distance for day trips to Lake Geneva or concerts at Alpine Valley!

Connie's Cottage on the Lake.
Absolutely fantastic property and fantastic host. Very responsive, understanding, flexible, friendly! I booked the cottage to celebrate my mother's birthday and we had the absolute best time. In terms of amenities, the house had everything needed to cook our feasts ; plenty of cutlery, cups, glasses, pans, bowls , spices! Great dishwasher too. Although our trip fell on a windy few days we still had plenty to do to keep ourselves entertained from the karaoke microphones and games to flying kites with our kid, making s'mores at the fire pit and playing air hockey. Well worth the money and highly recommend to anyone that wants a peaceful getaway. Thank you Connie!

Cottage on Lake Delavan- beach, parks, boat launch
The lakehouse was in a nice location and very private. Definitely would recommend staying here if your looking for a place that is quiet.

Lakefront Cottage with Gorgeous Sunsets
Josh is a great host, very responsive. The lakehouse is a cute weekend getaway. The sunsets are gorgeous and the house is cozy and heats up well (we stayed when it was chilly outside).
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- Six Flags Great America
- Erin Hills Golf Course
- Milwaukee Public Museum
- Alpine Valley Resort
- Geneva National Resort & Club
- Illinois Beach State Park
- Bradford Beach
- Racine North Beach
- Grand Geneva Resort & Spa
- Moraine Hills State Park
- Richard Bong State Recreation Area
- Milwaukee County Zoo
- Wilmot Mountain Ski Resort
- Skokie Country Club
- Harrington Beach State Park
- Milwaukee Country Club
- West Bend Country Club
- Springs Water Park
- Heiliger Huegel Ski Club
- Shoreacres
- The Mountain Top Ski & Adventure Center at Grand Geneva
- Discovery World
- Old Elm Club
- Bob O'Link Golf Club