Holiday rentals in Caledonia

4.96 out of 5 average rating, 229 reviews

Cottage in Poynette

Lake Wiscosnin Cozy Cottage

Relax and unwind at this cozy cottage on the Wisconsin River with fantastic views. Enjoy the park right across the street with fishing, a picnic pavilion, beach and playground for your kids. Public boat launch is only a block away. Full laundry and eat in kitchen features quartz counter tops and makes you feel like you're home away from home. Many local restaurants and bars within driving distance, as well as wine tasting and 2 ski resorts. Keurig and a propane grill provided. CableTV and Wifi

4.95 out of 5 average rating, 110 reviews

Home in Baraboo

Cottage Near Devil's Lake

Perfect Location! Under ten minutes to almost everything. Our cozy and romantic getaway is nestled in the scenic Baraboo Bluffs, just minutes to Devil's Lake, Devil's Head Resort, Historic Downtown Baraboo, wineries, distilleries & more. Take the picnic set to Devil's Lake or Parfrey's Glen, then relax on the patio for smores and yard games around the fire pit. Finish the evening snuggled up with wine & vinyl on the player. We have ample parking so bring the boat, we'd love to help you getaway.

Guest suite in Sun Prairie

4.88 out of 5 average rating, 336 reviews

Entire Lower Level, Countryside Garden Suite

Welcome to our home! We have upgraded our Garden (lower) Level to host travelers much like ourselves and long-term guests. The view of our backyard is incredible! You will find yourself lost in the country, yet less than ten minutes from all the excitement that Madison has to offer. Along with a private drive and entrance, you will have 1,000 square feet of comfort all to yourselves. This property is perfect for a quiet getaway we all need from time to time. All designed with you in mind.

4.93 out of 5 average rating, 171 reviews

Home in Briggsville

The Lake House on beautiful Mason Lake

"The Lake House" is located on beautiful Mason Lake in Briggsville, WI. Our home is a freshly remodeled 2 bedroom, 1 bathroom lake house with 36 ft. of lake frontage. The property has a huge fenced in back yard, concrete patio and a new pier (2021) for outside fun. We can accommodate two vehicles on the black top driveway, public street parking and a large public parking lot for boat / rec. trailers right across the street. The property is also located on a ATV/UTV and snowmobile trail system.

4.92 out of 5 average rating, 189 reviews

Home in Poynette

Island View Hideaway-Peaceful, On Water, Sandbars!

Rent this furnished cottage to enjoy the beauty of nature on the Wisconsin River and Lake Wisconsin. Conveniently located on the Lake Wisconsin waterfront between Madison and the Wisconsin Dells, just 1.5 hours from Milw and 3 hours from Chicago. We are pet friendly for well behaved dogs with a $25/night pet fee per dog. Beautiful views out the large living room windows look onto green, sandbars, islands and the undeveloped distant shores of the Wisconsin River as it opens up into Lake WI.

4.9 out of 5 average rating, 111 reviews

Home in Merrimac

Lakefront A-Frame | Stunning Views | Private Dock

Escape to our A-frame lake house on a private double lot on Lake WI! What You’ll Love: ✅ Wall of windows – floods the home with natural light ✅ Private dock – great for fishing, swimming & boating ✅ 2 wood-burning fireplaces – cozy up after outdoor fun ✅ Game area w/ pool table – family-friendly entertainment ✅ Secluded & peaceful – enjoy nature in total privacy Prime Location: 🚗 15 min → Devil’s Head Ski Resort 🎿 🚗 20 min → Devil’s Lake State Park 🏞️ 🚗 45 min → Madison & WI Dells 🌆

4.91 out of 5 average rating, 163 reviews

Bungalow in Baraboo

Close to Wisconsin Dells freshly renovated home!

Beautiful bungalow located 15 minutes away from Lake Delton and all Wisconsin Dells attractions. And 4 minutes from gorgeous Devils Lake park. 15 minutes from all 3 different winter activities. Place has a beautiful sunroom, where you can enjoy a quiet neighborhood and read a book on the swing chair. House comes with a full kitchen, air fryer, coffee maker etc. Wi-Fi and electric fireplace. Fire pit with comfy chairs. We have variety of board games. House could accommodate up to 9 people.

4.94 out of 5 average rating, 103 reviews

Home in Portage

Grandma's House: Spring is Springing!

Welcome to Grandma's House, a single level home nestled in the beautiful hills of Caledonia, between Portage and Baraboo. Three bedrooms, sleeps 8, full kitchen, dining room, living room and an attached 2-car garage. Just 4 miles from I90/94, Grandma's House enjoys easy access to Portage, Baraboo and Wisconsin Dells. 2023 renovations include, new vanity mirror in bathroom, new queen hide-a-bed with memory foam mattress (no bar at the back), and new queen bed with pillow- top mattress.

4.91 out of 5 average rating, 247 reviews

Guest house in Poynette

Simple Cabin*Lake View rustic cabin in rural WI

The Simple Cabin on Lake Wisconsin is a simple and clean space. It would be ideal for an individual or couple who are enjoying the beautiful outdoors by day, and would like a bed by night. It is 350 sq ft for the entire cabin consisting of bedroom, small full bathroom, and living area. You will enjoy 180 degrees of across-the-water views. It's a great hub for hiking with the following all within 15 - 35 minutes: Devil's Lake, Parfrey's Glen, Gibralter Rock (ice age tr) & Mirror Lake.

4.95 out of 5 average rating, 102 reviews

Earthen home in Ontario

Straw Clay Cabin on a Sustainable Farm

This Earthen house is made of sand, straw and clay. Nestled in a valley it is a peaceful and unique getaway. The cabin has four comfortable single beds and electricity, a wood stove for winter. Outside a fire pit and grill. A hand washing sink inside; and port-o-let toilet outside. You may be able to drive in (weather/road condition depending). It is a short walk to our Bakery (Sat. 9 am until 2 pm) Please arrive before dark. We are LGBTQ owned and operated. BIPOC welcome.

4.91 out of 5 average rating, 185 reviews

Cabin in Merrimac

Lakeview Cabin> Unique Mid-Century Tucked in Bluff

Nestled in the bluffs of Caledonia, this cabin offers a true Wisconsin experience! Floor to ceiling windows boast amazing water views of Lake Wisconsin, all while you reside in the charm of the mid-century architecture of this cabin. Minutes from the bluffs of Devil's Lake which offer some of Wisconsin's best hiking, biking, walking trails, and swimming! Plus, a short drive from Baraboo or Wisconsin Dells, where you can check out shops, restaurants and local attractions!

4.89 out of 5 average rating, 114 reviews

Tent in Kendall

Driftless Glamping on a Bluff

Rustic camping in the Driftless Region on the top of a bluff in a 20ft. Bell Tent. Relax, without having to pack, set up camp, and tear down and put away when you get home, more time to do things you enjoy. Go trout fishing, walk or ride the Omaha Trail Tunnel, Elroy- Sparta Trail, or the 400 Trail. Necedah Wildlife Refuge, Buckhorn, Castle Rock, Wisconsin Dells, Amish scenic drive, and Wildcat State Park with canoeing down the Kickapoo River are all within 30 minutes.

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Other great holiday rentals in Caledonia

4.93 out of 5 average rating, 76 reviews

Cabin in Merrimac

Enjoy sunsets at a fully equipped & secluded cabin

FaithRating, 5 stars1 week ago

The location was just perfect. My group loved the beautiful surroundings and being in a peaceful area. The place was clean and it was exactly what we were looking for. If you or your family is looking for a cabin like experience, this is the place for you. Lots of fun games already there, ready to play. Had such a great time. The host was quick with responses and very helpful.

4.94 out of 5 average rating, 103 reviews

Home in Portage

Wisconsin River Valley Farmhouse: Fire Pit & View

LorettaRating, 5 stars3 weeks ago

We enjoyed our stay at this peaceful farm house. To sit outside and take in the beautiful view was refreshing.

4.97 out of 5 average rating, 66 reviews

Home in Portage

Vintage Home Close to Ski Hills, Curling and Dells

JaniyahRating, 5 stars1 week ago

Very nice stay at this home! SARA was very informative and helpful with instructions! Nice spacious home, with lots of games to do inside ! Great home to stay in!!! Was very pleased!

5 out of 5 average rating, 3 reviews

Home in Baraboo

Traveling RN's! 5 blocks from St Clare Hospital!

MatthewRating, 5 stars5 months ago

For me this place has been great. The host went above and beyond. While it isn’t surrounded by activities, everything is within a mile so mostly walkable. But since it’s winter I mostly drive. Parking insights great. The home is charming and I’ll be staying longer because I enjoyed it so much.

5 out of 5 average rating, 20 reviews

Cabin in Blue River

New Secluded Cabin Quiet Getaway

PawelRating, 5 stars1 week ago

Great! Amazing! Beautiful! I would give even ten stars if this would be possible. House located in very stunning and peaceful area, perfect for getaway! Just nature and you! House itself its very clean and well finished, pretty much everything that you need its in there! And host is taking care of everything above and beyond! Can’t wait to visit again! Definitely recommend this house, listing and host! It was a pure pleasure to spend a time there. Thank you Corey!

5 out of 5 average rating, 20 reviews

Home in Baraboo

Secluded Cabin wGame Room! Fire Pit! Baraboo/Dells

BridgetRating, 5 stars4 days ago

My group loved Charlie’s place. It had ample space for me & my girlfriends celebrating our 40th birthdays and an expecting mom. We used the game room, had a fire, and checked out the winery & distillery in town. We brought our bikes & got to check the beautiful scenery nearby. I highly recommend!