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

Lakefront Plymouth Cottage w/ Private Hot Tub
Beautiful place, good restaurants in Elkhart Lake and five minutes away from Road America. We stayed here while attending the races. Peaceful, did not hear any of the noise from the track.

Colorful Cottage w/ Hot Tub - Steps to Long Lake!
This was a charming and unique place. The grounds are really lovely. It's right on the main road that runs alongside the lake, but we never heard any traffic. Plenty of parking in the driveway, nice size, fully equipped kitchen, and the owner proactively texted me to invite any questions I might have. Easy, manageable checkout tasks. The restaurants right down the street were really good! There isn't a grocery store nearby, but we brought everything we would need so not an issue.

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.

Clementine Cottage
Clementine cottage was Everything presented on air b&b and beyond. They thought of all the details and the house was one of the cleanest air b&b’s I have ever stayed at. No harsh chemical smells or fabric softener, linens so comfy. Loved the privacy of the yard and bikes in the garage to get to the lake. One of the Best stays I have had. The hosts are friendly and communicative. Loved our experience and will be back to see friends again.
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.

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!

Private 3 bedroom lake house
Awesome place. We 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!

Cottage Escape near Private Browns Lake Beach
The cottage was fabulous. From the moment we opened the front door, it had such a positive vibe! It was clean and bright. Very inviting. Also two awesome workspaces. — as I found myself having to set up my work laptop while I was there. The outdoor space was very inviting with fabulous places to swing and listen to the birds. The private beach was quite the added surprise! Spectacular view of sunsets over the water. So peaceful!

BeachDaze! A Lake Michigan Property
Great place to get away for a bit! Right on the beach with a great view! Had a blast!

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.
Private cottage rentals

Kalbus Cottage Lake Winnebago
Very nice place, we liked it very much, good location, very quiet, beautiful views, nice house and everything you need to have for a very good rest. We are very satisfied, everything is as in the photo, even better in the best.

Hummingbird Haven Cottage on Lake Koshkonong
Beautiful stay! My sister and I stayed here with four of her friends for her chill bachelorette weekend and it was perfect! The cottage was very nice and clean, within walking distance to a few places to eat, and the host was super responsive. I highly recommend booking your stay here! I've already told my husband that we should go sometime and my sister already wants to go back too.

The Green Heron Cottage full kitchen - King bed
The cutest old house ever. So sweet and had all the character you’d want in a house. I have nothing bad to say about the property and I would definitely recommend.

Lake Country Guest Cottage
1 million stars! This cottage was absolutely a dream for my sister and me. The only downside was that we were not able to stay longer due to our own travel plans. Gorgeous property fabulous house, incredible location! Every single detail was thought of in this gorgeous cottage. Don't hesitate, just book it, you won't regret it.

Stunning Lakefront Cottage with Private Beach
I can’t recommend this amazing lakefront property enough! The location is unbeatable. It's right on the lake with stunning views and beautiful surroundings that truly made the stay feel peaceful and serene. The house itself is spacious, beautifully furnished, and immaculately clean. It felt like a home away from home, with all the comforts you could possibly need. The amenities were a real highlight, from the complimentary coffee and snacks to the thoughtful gift basket upon arrival. The hosts went above and beyond to make sure we had everything we needed, and they even provided fantastic local recommendations for dining and activities. The backyard is a dream—private lake frontage, tons of seating, lots of nature to see. It's the perfect spot to relax and unwind, and there’s plenty of space to move around inside and out.

Lakefront Cottage with Private Beach
Sarah did an awesome job making sure we had what we needed and was a very kind and awesome host! The home is peaceful and has a beautiful view. Thanks again for the hospitality!

Cozy one bedroom cottage near lake Michigan!
Very private and quiet! Clean, tidy, well-stocked kitchen and bathroom. 15 minute brisk walk to North Point Overlook. Easy drive to area restaurants and attractions. Kohler museums are a must!

Pristine Beach Access, Arcade near Kohler-Andrae
We are so glad we picked Jeremy’s place for our last minute Memorial Day weekend trip. It was in a beautifully, secluded and calm place, with a short drive to Sheboygan that had plenty of restaurants and things to do. Although the weather wasn’t great for the beach, our youngest still had a great time playing in the sand with a sweatshirt on. It also was extremely helpful to have a kitchen full of all the necessary, utensils and cooking items, even for the kids. Highly recommend this location if you’re looking for a peaceful getaway with the family. Oh, and I must call out Jeremy’s amazing communication skills, and proactiveness.
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- Erin Hills Golf Course
- Milwaukee Public Museum
- Alpine Valley Resort
- Kohler-Andrae State Park
- Whistling Straits Golf Course
- Bradford Beach
- Richard Bong State Recreation Area
- Racine North Beach
- Milwaukee County Zoo
- Milwaukee Country Club
- The Bull at Pinehurst Farms Golf Course
- Harrington Beach State Park
- West Bend Country Club
- Springs Water Park
- Heiliger Huegel Ski Club
- Pine Hills Country Club
- Discovery World
- Blue Mound Golf and Country Club
- Sunburst