Holiday Homes in Cross Plains

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Featured Holiday Homes in Cross Plains

Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!

9.8 out of 10, Exceptional, (29)
"The best thing about this house is its proximity to Madison in general and to the river. I loved taking a kayak out on the river around sunrise. Really beautiful. It's close to many fun activities in Madison too. The house itself is comfortable. Hosts are responsive and helpful. Kitchen is lovely. One helpful tip is that this house is on a busy street. There is some traffic noise at night. Not a huge deal but I wish I had known ahead of time and prepared for it. Overall a good place with...
The price is AU$818
includes taxes & fees
2 Dec - 3 Dec
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!

Barnhouse! Mini Golf, Slide, Theater, Arcade/Games, Pool/Hot Tub/Sauna, Home Gym

10.0 out of 10, Exceptional, (11)
"This was a perfect spot for our small family wedding. Our entire group loved this place. We were a little concerned if the traffic noise would be a problem, but we didn't even notice it. There were so many entertainment amenities, no one was without something to do during our stay."
Barnhouse! Mini Golf, Slide, Theater, Arcade/Games, Pool/Hot Tub/Sauna, Home Gym

Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access

10.0 out of 10, Exceptional, (98)
"Beautiful space, very relaxing. We had a great stay!"
Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access

Legacy Guest House , Mount Horeb WI

10.0 out of 10, Exceptional, (51)
"The property was as advertised. It was cute and made good use of the space available. Not overly spacious but we were comfortable with four adults. The “rules” were very clearly posted and were more than reasonable. The only feedback I would give is that it didn’t appear to have the floors well swept and countertops wiped, nor the toilets cleaned. However, they weren’t filthy by any means. Just needed to have a quick cleanup. The linens were all nice and easily accessible. We would stay again. "
Legacy Guest House , Mount Horeb WI

A Pleasant Retreat- No Cleaning Fee & New Discounts

10.0 out of 10, Exceptional, (215)
"This house was perfect for me and my adult son and daughter. We all had or own bed, the house was clean and comfortable and we absolutely loved the style of the older homes in the neighborhood. Every you could want was close by and the host was amazing. "
A Pleasant Retreat- No Cleaning Fee & New Discounts

Countryside Beauty - Min to Madison/Perfect for families/Events&Dogs! Lrg yard

10.0 out of 10, Exceptional, (142)
"We have stayed multiple times, and always enjoy the country setting; cleanliness; well equipped, large kitchen; nearby dog park; and wonderful hosts. "
Countryside Beauty - Min to Madison/Perfect for families/Events&Dogs! Lrg yard

Waterfront w/ HOT TUB + King Suite + Game Room

9.6 out of 10, Exceptional, (25)
"Fantastic place, very clean and great location. We will book this place again. "
Waterfront w/ HOT TUB + King Suite + Game Room

Hideout Haven

9.8 out of 10, Exceptional, (57)
"House was clean and very close to Baraboo. Perfect for a quick weekend trip."
Hideout Haven

ONE OF A KIND vacation rental with a view

10.0 out of 10, Exceptional, (129)
"Awesome stay with Son and Grandsons. Great place to stay."
ONE OF A KIND vacation rental with a view

Doty ★ Walk to Everything -Hotel Quality- Downtown

9.8 out of 10, Exceptional, (29)
"When I was enrolled at UW-Madison, I lived blocks from The Doty and would have loved to live at this adorable 3-bed home! It is well maintained and really did suit our location needs, near the Overture Center. Located in student rental neighborhood, I was worried it might be loud but we slept well. The beds were very comfortable. Plenty of pillows and blankets provided. We did not use the kitchen but it seemed well stocked. Had a wonderful breakfast at Marigold Kitchen. Two things I would...
Doty ★ Walk to Everything -Hotel Quality- Downtown

Near DT Madison - Half Block from Lake Monona & 1 Block from Lake Loop Bike Path

10.0 out of 10, Exceptional, (24)
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Near DT Madison - Half Block from Lake Monona & 1 Block from Lake Loop Bike Path

Family-Friendly Lake Waubesa Home: Boat + Swim!

9.8 out of 10, Exceptional, (8)
"We were there at the start of fall and the gas fireplaces were awesome both for the ambiance and warmth on cooler days. The view from the sunroom was wonderful. We spent a lot of time enjoying the view from there. It had a nice mix of modern amenities (updated kitchen and baths) and rustic charm. The neighborhood was very cute. We walked our dog quite a bit and enjoyed views of the lake side homes and the lake from all around the house. Plus there are two parks both within walking distance...
Family-Friendly Lake Waubesa Home: Boat + Swim!

Studio queen with views of Lake Monona in the heart of downtown Madison

9.0 out of 10, Wonderful, (4)
"Was in town for UWM parents weekend and wanted something more than a simple hotel room as I was going to be there for nearly a week. The Saddlery for the bill. Location was amazing. Having a kitchenette meant I could fully enjoy the great farmers market that weekend. And the view out my window of the lake was a perfect way to wake up. Manager was very responsive. Everything was as stated. TV/media set up would benefit from updating, but it actually didn’t matter as it allowed me to tuck into a...
The price is AU$465
includes taxes & fees
30 Nov - 1 Dec
Studio queen with views of Lake Monona in the heart of downtown Madison

Updated home with lake views-near Ferry, Devil's Lake, and 30 min to WI Dells!

10.0 out of 10, Exceptional, (26)
"Perfect home base for a two-family vacay. Four teenage boys and two moms and we never felt crowded. Easy drive to the Dells, Devil’s Lake, and Baraboo. Beautiful views of Lake WI from the deck and a quick walk to fishing at Memorial park and ice cream at the ferry crossing. The house was very clean, stocked with basics, and communication with the owner was so easy. Highly recommend!"
Updated home with lake views-near Ferry, Devil's Lake, and 30 min to WI Dells!

HOT TUB - 20 min to Capitol - KING Bed - Fireplace

10.0 out of 10, Exceptional, (5)
"My adult children (including SIL) and my partner and I wanted to visit Madison for the first time. While the house is a little further from downtown (20 mins.) than we might have liked, it was worth it for the size, comfort and cleanliness of the house. We had plenty of room and all of the necessities. We pretty much just slept and had breakfast at the house, but it would've been great if we'd needed to spend more time there. (I was looking forward to using the hot tub and Pacman machine,...
HOT TUB - 20 min to Capitol - KING Bed - Fireplace

Elegant Space–Premium Kitchen–Spacious & Ideal for Gathering w/ Friends & Family

10.0 out of 10, Exceptional, (12)
"This is one of the best rental homes I've ever stayed in! The owners were super accommodating and everything was labeled clearly. We stayed with a toddler and there were ample toddler toys and games, kid friendly cups and plates, and they even installed a baby gate at the top of the stairs. The neighborhood was great and quiet, with easy parking. Overall awesome, and we would love to stay here again!"
Elegant Space–Premium Kitchen–Spacious & Ideal for Gathering w/ Friends & Family

Picturesque Golf Course Home Near American Players Theatre, Taliesin & WI River

10.0 out of 10, Exceptional, (97)
"The house was awesome! We had so much fun hanging out at the house. We enjoyed checking out cave of the mounds and then a birthday celebration for my 6 year old at the house. We fed the birds, took a walk, watched football, and drank plenty of apple cider. My sister from S.C. stayed with us and we enjoyed all the Frank loyd Wright books, area architecture. It was perfect!"
Picturesque Golf Course Home Near American Players Theatre, Taliesin & WI River

Double Full Room at The Little Village

9.6 out of 10, Exceptional, (15)
"Our stay was quite pleasant. There was an issue with our thermostat when we first arrived. We texted the number provided and within thirty minutes someone had arrived to resolve the issue. Very happy with the service. "
The price is AU$185
includes taxes & fees
27 Nov - 28 Nov
Double Full Room at The Little Village

Lodge w/ Indoor Pool along Devil's Lake Park!

10.0 out of 10, Exceptional, (2)
"This was a beautiful property, serene environment and made a wonderful getaway for my husbands 50th birthday. The property owners went above nad beyond and even let us check in early ♥ Thank you!"
Lodge w/ Indoor Pool along Devil's Lake Park!

Paoli Den - Newly Remodeled!

9.8 out of 10, Exceptional, (7)
"Very clean, great communication. Great location for Madison, Shops at Paoli, New Glarus, Epic. Close to downtown Verona. Having separate parking was nice. Not having a thermostat (or one I could find) was odd. Great place overall."
Paoli Den - Newly Remodeled!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Cross Plains

Social Distance in Our Gorgeous, Private Retreat in the Woods

9.4 out of 10, Exceptional, (54)
"Unique rustic cabin. We enjoyed the space, solitude, and beautiful countryside."
Social Distance in Our Gorgeous, Private Retreat in the Woods

Brand New Cabin For Getaway Vacation - 1 Mile From Devil's Lake And Close Dells

9.8 out of 10, Exceptional, (198)
"The place was beautiful and was set up great for our group. Had an amazing time! Thank you."
Brand New Cabin For Getaway Vacation - 1 Mile From Devil's Lake And Close Dells

Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!

9.8 out of 10, Exceptional, (29)
"The best thing about this house is its proximity to Madison in general and to the river. I loved taking a kayak out on the river around sunrise. Really beautiful. It's close to many fun activities in Madison too. The house itself is comfortable. Hosts are responsive and helpful. Kitchen is lovely. One helpful tip is that this house is on a busy street. There is some traffic noise at night. Not a huge deal but I wish I had known ahead of time and prepared for it. Overall a good place with...
The price is AU$818
includes taxes & fees
2 Dec - 3 Dec
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.