Holiday Homes in Middleton

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Featured Holiday Homes in Middleton and around

A Pleasant Retreat- No Cleaning Fee & New Discounts
10.0 out of 10, Exceptional, (215)
"We needed a place for a group of family members to stay to prepare food and decorations for a 60th birthday party at a nearby location. We had everything we needed and our hosts provided other prep items that aren’t commonly found in a rental home. The location was ideal (near a grocery store for forgotten items) and so comfortable!"
A Pleasant Retreat- No Cleaning Fee & New Discounts
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
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 €510
includes taxes & fees
1 Dec - 2 Dec
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
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
Single Full Room at The Little Village in Mount Horeb
8.6 out of 10, Excellent, (7)
"Quaint and affordable."
The price is €107
includes taxes & fees
24 Nov - 25 Nov
Single Full Room at The Little Village in Mount Horeb
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
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!
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
Historic Home Near Wi Dells, Lake Wi & Skiing with Party Space!
8.8 out of 10, Excellent, (13)
"I loved the vibe of this house. So much character and nicely updated. We loved walking to the ferry, the ice cream stand, and taking a ride across the lake. It was the perfect stay for our weekend trip to Baraboo and Devil’s Lake. "
Historic Home Near Wi Dells, Lake Wi & Skiing with Party Space!
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
COZY WATERFRONT CABIN, ON SUNSET BAY, LAKE WISCONSIN !! SUMMER AND WINTER FUN !!
10.0 out of 10, Exceptional, (83)
"My college friends and I had the most lovely time at this cozy cabin! Everything was as mentioned in the description, the lake and views were stunning. We hiked nearby and happened upon the outdoor market in Baraboo. Saturday night dinner at Fish Tales just down the road was excellent. Highly recommended, will be back next year!"
COZY WATERFRONT CABIN, ON SUNSET BAY, LAKE WISCONSIN !! SUMMER AND WINTER FUN !!
Amazing townhouse, amazing attractions, amazing city!
10.0 out of 10, Exceptional, (156)
"Ben and Sara were great hosts - very communicative! Perfect little house and we loved watching sports on the big tv downstairs!"
Amazing townhouse, amazing attractions, amazing city!
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
Conveniently Located just off University Avenue on Madison's West Side
10.0 out of 10, Exceptional, (117)
"We were here for the PSU- Wisconsin game and the house worked great. Maybe just a new shower curtain liner in the upstairs bathroom 😁"
Conveniently Located just off University Avenue on Madison's West Side
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!
Waters Edge Private Cottage
8.0 out of 10, Very good, (6)
"For people 'of a certain age' like us, there was NO TV for 3 days because we do Not has streaming services.....so there was absolutely NO television option. It was in the fine print/description, we just didn't realize that meant NO TV options at all, so be aware of that. That being said, the location and view was ideal and beautiful!"
Waters Edge Private Cottage
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
Lakefront 4BR ‘Up North’ Outdoor Getaway - Best Sunset View on The Lake
9.6 out of 10, Exceptional, (10)
"We visited in late October, early November, so we didn't do much on the lake, but there is a cute park with a playground nearby! The house was clean and accommodating, even had a high chair for our use which was helpful with a 15 month old. We made all our meals in the house and found cooking utensils/dishes to be a little sporadic, but that was our only complaint. Stephen was a wonderful host who communicated clearly and quickly whenever we had questions! The view of the lake is gorgeous!"
Lakefront 4BR ‘Up North’ Outdoor Getaway - Best Sunset View on The Lake
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!
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 Middleton

Countryside Beauty - Min to Madison/Perfect for families/Events&Dogs! Lrg yard
10.0 out of 10, Exceptional, (142)
"We enjoyed having lots of room to spread out with space to gather be also have privacy for our group. Very quiet, rural setting but just minutes away from Madison and many activities. "
Countryside Beauty - Min to Madison/Perfect for families/Events&Dogs! Lrg yard
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 €510
includes taxes & fees
1 Dec - 2 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
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.