
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.
Holiday rentals for every style
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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.

#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.

#3 Charming Lake Cottage - Cypress Resort & Marine
We had a lovely stay at Cottage 3! The cottage was clean, calm, comfortable, and had a beautiful view! It was just a staircase away from the lake which was so helpful with kids. There were kayaks, paddle boards, floats, and much more which provided endless entertainment for us and our kids ranging from 2-11 years old. Amanda was so friendly, great at communication, and always available for whatever we needed. It’s a great place to stay!
Pet-friendly cottage rentals

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!

Lake Geneva Haven
Allison is very responsive and helpful with any questions we had. The house was exactly as described and located a close drive to downtown Lake Geneva and the lake. A Kwik Trip is very close and convenient for those early morning donut and coffee runs. Highly recommend!

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!!

The Lazy Dais Cottage on Pike Lake.
The home was fabulous. It was a great size. They had plenty of dishes, pots and pans, everything you could think of. It was well stocked with games and puzzles. They provided life jackets and paddle boards and kayaks. The porch was delightful to sit in and have coffee in the morning and look out at the lake. There was a a beautiful fire pit and they provided great wood. Beds were very comfortable. There is also a great restaurant/bar a block and a half away that you can walk to. I would highly recommend if your in the area to book it.

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

Nautical Lake Cottage at Petite Lake Resort, #2
Great location kids had fun playing on the beach. We had a great time and will definitely try to book again sometime.

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

Cottage on Clover. Charming, quiet walk to town.
We loved our stay at the cottage on clover! This place felt right at home and had everything we needed as a family with 3 little ones. The host did a great job communicating and you can really see the level of detail she put into her home to make you feel comfortable. This is a top tier rental in my opinion!

#2: Cute 2 bedroom cottage on the beach!
This is a small cabin, but well laid out. Be aware that there is a short walk from the busy parking lot, but not over far and it’s an easy path. The cabin is clean, quiet and right on the water. We brought two dogs and they loved the place. There is a water bowl in a cabinet by the door. Nothing to beat it in the area, and Jennifer was nothing but helpful. Would stay again.

Downtown Lake Geneva Cottage Sleeps 5
This cute cottage was perfect for a girl's getaway and it was very close to all the activities we did in lake Geneva. highly recommend.

Great getaway in Lily Lake Near Country Thunder
liked it

Waterfront Fox Lake Vacation Rental w/ Fire Pit!
We had an amazing time at this cottage! From the start, the hosts were excellent communicators and all the instructions were clear. When we got there, everything was clean and as described/seen in pictures. The area was beautiful and we absolutely love the scenery and how much we could do at the cottage. By far, the BEST Airbnb we’ve been to- and we’ve been to several. Thanks for having us! We would love to come back.

Twin Lakes Cottage: Walk to Elizabeth Lake!
Our host was friendly, informative, and flexible. She reached out mid-stay to check on us and shared several local recommendations. The house was clean, big, quiet, and homey. We felt welcome. The kitchen was well stocked with pots, pans, dishes, and flatware. Our two families had room to spread out.

4 bedroom Williams Bay <1 mile Lake Geneva Beach
Cozy cottage, walkable to restaurants and the beach!

Key House at Petite Lake Resort, #4
Amanda sent great information and instructions prior to checking in and was helpful and communicative. Beautiful place, clean, comfortable. Used the fire pit, which was enjoyable. Lots to do outdoors.
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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
- Racine North Beach
- Bradford Beach
- Grand Geneva Resort & Spa
- Richard Bong State Recreation Area
- Moraine Hills State Park
- Milwaukee County Zoo
- Wilmot Mountain Ski Resort
- Skokie Country Club
- Harrington Beach State Park
- Milwaukee Country Club
- West Bend Country Club
- Heiliger Huegel Ski Club
- Springs Water Park
- The Mountain Top Ski & Adventure Center at Grand Geneva
- Shoreacres
- Discovery World
- Sunburst
- Blue Mound Golf and Country Club