Middleton Vacation Rentals

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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Middleton Vacation Homes

One Bedroom King with Den with views of Lake Monona in the heart of downtown.
Saddleback building features a brick facade and multiple windows on each floor.

One Bedroom King with Den with views of Lake Monona in the heart of downtown.

9.6 out of 10, Exceptional, (27)
"The property was beautiful, safe, and in a perfect location for the event we were attending!"
The price is CA $384
CA $507 total
includes taxes & fees
Sep 1 - Sep 2
One Bedroom King with Den with views of Lake Monona in the heart of downtown.
Pet FriendlyHot tub space to relax 10min from Madison, Epic, MilitaryRidgeTrail
Relax in this serene room with a high ceiling, ceiling fan, and large window offering a view of the backyard and deck.

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

9.6 out of 10, Exceptional, (61)
"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
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort
Two-story house with a garage on the ground floor, surrounded by a well-maintained lawn and stone wall.

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

10.0 out of 10, Exceptional, (14)
"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 CA $142
CA $255 total
includes taxes & fees
Aug 24 - Aug 25
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort
ONE OF A KIND vacation rental with a view
Stylish building surrounded by lush greenery, featuring a glass facade and brick architecture.

ONE OF A KIND vacation rental with a view

10.0 out of 10, Exceptional, (139)
"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
Waterfront Lodi Vacation Rental on Lake Wisconsin!
Enjoy a serene lake view from the deck, where you can sit and relax with a table and chairs.

Waterfront Lodi Vacation Rental on Lake Wisconsin!

10.0 out of 10, Exceptional, (14)
"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!
Two Bedroom with views of Lake Monona in the heart of downtown Madison
Enjoy cooking in this kitchen with a large island and windows offering a view of the outdoors.

Two Bedroom with views of Lake Monona in the heart of downtown Madison

10.0 out of 10, Exceptional, (7)
"We loved everything about this property. Would definitely stay there again."
The price is CA $480
CA $634 total
includes taxes & fees
Sep 1 - Sep 2
Two Bedroom with views of Lake Monona in the heart of downtown Madison
Private Pool - HOT TUB - Sauna - Game Room - Pets
Terrace/patio

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

10.0 out of 10, Exceptional, (1)
"The Sun Prairie house perfectly met the goals for our family gathering of six adults and golden retriever for social and private space and so many entertainment options! The house was spotless, the neighborhood quiet, with Woodmans close by for shopping. We had 5 days of sunshine, golfing nearby courses, enjoying afternoon pool time, evening hot tub, and bug-free outdoor dining-so private and relaxing! We never ran out of room for food/drinks in the large volume fridge (loved the beverage...
Private Pool - HOT TUB - Sauna - Game Room - Pets
Two bedroom suite with city views in the heart of downtown Madison
Enjoy a meal at the kitchen island with a cutting board, or relax in the adjacent seating area with a view of the city skyline.

Two bedroom suite with city views in the heart of downtown Madison

9.8 out of 10, Exceptional, (33)
"Perfect for a weekend in Madison. A good location close to everything. "
The price is CA $453
CA $598 total
includes taxes & fees
Sep 1 - Sep 2
Two bedroom suite with city views in the heart of downtown Madison
One Bedroom King with Den with views of the heart of downtown.
Standing tall with a historic central dome, this building offers a glimpse into the past.

One Bedroom King with Den with views of the heart of downtown.

2.0 star property
10.0 out of 10, Exceptional, (23)
"Super clean, well lit, and beautiful view! Would definitely stay again."
The price is CA $370
CA $489 total
includes taxes & fees
Sep 1 - Sep 2
One Bedroom King with Den with views of the heart of downtown.
Doty ★ Walk to Everything -Hotel Quality- Downtown
Enjoy cooking in this well-equipped kitchen with a dishwasher, oven, and gas stove.

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
Paoli Den - Newly Remodeled!
Enjoy cooking in this well-equipped kitchen with a microwave, coffee maker, and kettle.

Paoli Den - Newly Remodeled!

9.8 out of 10, Exceptional, (23)
"Prefect"
Paoli Den - Newly Remodeled!
Beautifully updated home close to downtown New Glarus
Relax on the inviting front porch with Adirondack chairs, surrounded by a serene garden and a tranquil water feature.

Beautifully updated home close to downtown New Glarus

10.0 out of 10, Exceptional, (58)
"It was so good to come back to a clean and cozy house each evening after spending the day at the World Dairy Expo."
Beautifully updated home close to downtown New Glarus
Escape to tranquility – your countryside haven, and at times with a horse or two
Relax on the patio with a sofa and two chairs, shaded by a covered area.

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
Near DT Madison - Half Block from Lake Monona & 1 Block from Lake Loop Bike Path
Relax in a cozy space with a neatly made bed, wooden headboard, and two bedside tables.

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

10.0 out of 10, Exceptional, (33)
"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
Spacious & Modern Home w/ Deck in Oregon!
Enjoy cooking in this kitchen with a central island, stainless steel sink, microwave, and gas range.

Spacious & Modern Home w/ Deck in Oregon!

7.0 out of 10, Good, (2)
"Awesome...very clean property.Plenty of space for eight people...Quiet neighborhood"
Spacious & Modern Home w/ Deck in Oregon!
Premium 3BR | Quick to Downtown
Enjoy cooking in this well-equipped kitchen with a central island, ample counter space, and integrated appliances.

Premium 3BR | Quick to Downtown

10.0 out of 10, Exceptional, (10)
"Beautiful furnishings, very clean, Well stocked. Would definitely stay there again. The host was very responsive."
The price is CA $453
CA $1,096 total
includes taxes & fees
Aug 11 - Aug 12
Premium 3BR | Quick to Downtown
Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown
Interior

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

10.0 out of 10, Exceptional, (5)
The price is CA $454
CA $796 total
includes taxes & fees
Aug 12 - Aug 13
Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown
King Suite - Game Room - Large Groups - Yard
Enjoy cooking in this well-equipped kitchen with a refrigerator, microwave, and double oven.

King Suite - Game Room - Large Groups - Yard

10.0 out of 10, Exceptional, (9)
"Our family enjoyed our stay in Madison. The house was great and our host was very responsive. I would highly recommend this duplex for your trip. "
King Suite - Game Room - Large Groups - Yard
Beautifully remodeled 2 bed 104 Berkley Verona #6
Experience the unique charm of Mine City Excavation, a functional building with a spacious porch area and easy access to parking.

Beautifully remodeled 2 bed 104 Berkley Verona #6

9.6 out of 10, Exceptional, (24)
"The apartment is well maintained and Joel was helpful. We’d stay again if we need a place to stay in Verona"
Beautifully remodeled 2 bed 104 Berkley Verona #6
COZY WATERFRONT CABIN, ON SUNSET BAY, LAKE WISCONSIN !! SUMMER AND WINTER FUN !!
Cozy cabin interior with a seating area, dining table, and large window offering a view of the surrounding trees.

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

10.0 out of 10, Exceptional, (89)
"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 !!
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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Top Middleton Hotel Reviews

The Madison Concourse Hotel and Governor's Club

The Madison Concourse Hotel and Governor's Club

10/10 Excellent
"The most comfortable beds EVER. I even took a picture of the tags so I can get the same exact one! Love this hotel! My rant has stayed there at least 10 times and will keep coming back!"
Stephanie 2-night trip
Posted 7 hours ago
The Madison Concourse Hotel and Governor's Club