Search Vacation Homes in Middleton

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Vacation Homes in Middleton

COZY WATERFRONT CABIN, ON SUNSET BAY, LAKE WISCONSIN !! SUMMER AND WINTER FUN !!

10.0 out of 10, Exceptional, (91)
"Such a charming spot right on the lake! Direct access to the water, beautiful views, close to a bunch of fun bars and restaurants, and an easy drive to Devil’s Lake, Wisconsin Dells, and Madison. We stayed for a long weekend with our six month old, and it was great! Joe, the owner, is so friendly and responsive. Highly recommended!"
COZY WATERFRONT CABIN, ON SUNSET BAY, LAKE WISCONSIN !! SUMMER AND WINTER FUN !!

ONE OF A KIND vacation rental with a view

10.0 out of 10, Exceptional, (141)
"This is our second stay and will gladly come back. It is easy to maneuver around Madison and the house is a spectacular vintage 80’s home. "
ONE OF A KIND vacation rental with a view

Pet FriendlyHot tub space to relax 10min from Madison, Epic, MilitaryRidgeTrail

9.6 out of 10, Exceptional, (64)
"The property was beautiful and our group of 8 had tons of space. It was beautiful and we wish we could’ve stayed longer. We would definitely stay there again. "
Pet FriendlyHot tub space to relax 10min from Madison, Epic, MilitaryRidgeTrail

Paoli Den - Newly Remodeled!

9.8 out of 10, Exceptional, (24)
"Prefect"
Paoli Den - Newly Remodeled!

Doty ★ Walk to Everything -Hotel Quality- Downtown

9.8 out of 10, Exceptional, (33)
"Had a great stay!"
Doty ★ Walk to Everything -Hotel Quality- Downtown

The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort

10.0 out of 10, Exceptional, (15)
"I had the pleasure of spending a short weekend at The Earthhouse BnB in Mt. Horeb, and it was absolutely wonderful! The property is tucked away in a serene, peaceful location that provided the perfect escape from the hustle and bustle of everyday life. The BnB itself is charming and cozy, with unique touches that made it feel like a true home away from home."
The price is ¥15,144
¥27,295 total
includes taxes & fees
Aug 31 - Sep 1
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort

On the Yahara River, access to Madison Lakes

10.0 out of 10, Exceptional, (42)
"Beautiful home in a great setting. Really enjoyed our stay. "
On the Yahara River, access to Madison Lakes

Spacious & Modern Home w/ Deck in Oregon!

8.4 out of 10, Very Good, (5)
Spacious & Modern Home w/ Deck in Oregon!

Private Pool - HOT TUB - Sauna - Game Room - Pets

10.0 out of 10, Exceptional, (2)
"The house is great and the facilities in the house were well-functioning, and the dish washer saved us much time. The neighborhood is quiet and great views. We enjoyed our stay."
Private Pool - HOT TUB - Sauna - Game Room - Pets

Waterfront Lodi Vacation Rental on Lake Wisconsin!

9.8 out of 10, Exceptional, (16)
"Very clean! Awesome accommodations! Perfect couple of nights on the lake - kids even jumped in in early May! Washer/dryer is always an added bonus. Coffee bar a nice touch, and the kids loved the lanterns : )"
Waterfront Lodi Vacation Rental on Lake Wisconsin!

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

10.0 out of 10, Exceptional, (35)
"We had a great time being close to the lake. Everything in the house was very charming and comfortable. Would stay again for sure!"
Near DT Madison - Half Block from Lake Monona & 1 Block from Lake Loop Bike Path

Escape to tranquility – your countryside haven, and at times with a horse or two

Escape to tranquility – your countryside haven, and at times with a horse or two

Original cozy farmhouse homestead 2 blocks from the bike path and

10.0 out of 10, Exceptional, (117)
"Great house and location. Check in and out was easy and our host was very gracious. "
Original cozy farmhouse homestead 2 blocks from the bike path and

Beautifully updated home close to downtown New Glarus

10.0 out of 10, Exceptional, (59)
"Nice home, good neighborhood. Host easy to reach and very helpful."
Beautifully updated home close to downtown New Glarus

99.00 Fall Special in beautiful New Glarus

10.0 out of 10, Exceptional, (3)
"LOVELY PLACE! 3 comfy beds, nice bathrooms, living toom & large dining table easily accommodated our group. The kitchen was well stocked for us to prepare our meals. Great location, easy walking around the fun town!!"
The price is ¥47,505
¥86,777 total
includes taxes & fees
Sep 1 - Sep 2
99.00 Fall Special in beautiful New Glarus

Brand New Country Rustic Barn-R&R At It's Finest! Madison Area

9.8 out of 10, Exceptional, (22)
"It was great, good location near Madison for local dining.Loved the special touches, Christmas tree, dog bed, dog water bowls, rustic theme.Solo stove and stuff to make smores"
Brand New Country Rustic Barn-R&R At It's Finest! Madison Area

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

10.0 out of 10, Exceptional, (21)
"Barn was beautiful, clean & fun amenities."
Barnhouse! Mini Golf, Slide, Theater, Arcade/Games, Pool/Hot Tub/Sauna, Home Gym

Historic Home Near Wi Dells, Lake Wi & Party Space Avail!

8.4 out of 10, Very Good, (19)
"Plenty of sleeping options for kids.Close to Devils Head.Many restaurants within a short drive."
Historic Home Near Wi Dells, Lake Wi & Party Space Avail!

Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown

10.0 out of 10, Exceptional, (6)
The price is ¥48,520
¥85,020 total
includes taxes & fees
Sep 16 - Sep 17
Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown

One-of-a-kind house on 240 acres w/ prairie, woods & trout-stream - pet-friendly

10.0 out of 10, Exceptional, (53)
"A beautiful cabin, on a wonderful property, in a great part of the Driftless—not sure what more you could ask for... Highly recommended!"
One-of-a-kind house on 240 acres w/ prairie, woods & trout-stream - pet-friendly
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Middleton Hotel Reviews

Find out more about Middleton

Find out more about Middleton

Middleton Vacation Homes information

Number of reviews
32
Accommodation
140 Vacation Homes
Lowest Price
¥15,144
Highest Price
¥48,520