Holiday Homes in Middleton

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Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sept - 28 Sept

Featured Holiday Homes in Middleton

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 AU$678
includes taxes & fees
1 Sept - 2 Sept
Two bedroom suite with city views in the heart of downtown Madison
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 AU$720
includes taxes & fees
1 Sept - 2 Sept
Two Bedroom with views of Lake Monona in the heart of downtown Madison
Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access
Relax in a serene hot tub surrounded by a lush garden and a meandering stone pathway.

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

10.0 out of 10, Exceptional, (115)
"My husband and I live hear Chicago and wanted a quick getaway and this beautiful apartment felt like a home away from home. The hosts thought of every detail when designing this fun and very functional space (even the shower soap was a special luxury!) The bed was incredibly comfortable and the fireplace added warmth and coziness. We would love to stay here again!"
Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access
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
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
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!
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
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 AU$575
includes taxes & fees
1 Sept - 2 Sept
One Bedroom King with Den with views of Lake Monona in the heart of downtown.
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 AU$556
includes taxes & fees
1 Sept - 2 Sept
One Bedroom King with Den with views of the heart of downtown.
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, (87)
"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 house on 240 acres w/ prairie, woods & trout-stream - pet-friendly
Step up to a cozy living area with a comfortable sofa and matching bench, surrounded by a dining space and large window.

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

10.0 out of 10, Exceptional, (49)
"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
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
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, (21)
"Prefect"
Paoli Den - Newly Remodeled!
A Pleasant Retreat- No Cleaning Fee & New Discounts
Stroll through the beautifully maintained garden, surrounded by a variety of flowering plants and shrubs.

A Pleasant Retreat- No Cleaning Fee & New Discounts

10.0 out of 10, Exceptional, (240)
"This home was perfect for our family and was so cute and clean. But the owners are what made it so special. They greeted us and showed us around the house. They made sure you felt at home. "
A Pleasant Retreat- No Cleaning Fee & New Discounts
Original cozy farmhouse homestead 2 blocks from the bike path and
Relax on the patio surrounded by lush greenery and enjoy the peaceful atmosphere.

Original cozy farmhouse homestead 2 blocks from the bike path and

10.0 out of 10, Exceptional, (115)
"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
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. "
The price is AU$1,171
includes taxes & fees
4 Aug - 5 Aug
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
Country Sportsmans Paradise!! Grill, Firepit & AC - Devil's Lake and Dells area!
Cozy dining area with a wooden table and chairs, surrounded by mounted animal heads and antlers.

Country Sportsmans Paradise!! Grill, Firepit & AC - Devil's Lake and Dells area!

10.0 out of 10, Exceptional, (5)
"Amazing its like we were in a different state and it felt like our home paradise and us being Hunter's on top of it ,, and the prise was reasonable for a 4 day stay, wow, i would give this 10 ☆"
Country Sportsmans Paradise!! Grill, Firepit & AC - Devil's Lake and Dells area!
Studio queen with views of Lake Monona in the heart of downtown Madison
Stunning urban landmark with a prominent central dome.

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

9.4 out of 10, Exceptional, (9)
"The property location is great, walking distance to great restaurants, the Farmers market, and close to walking/running trails. "
The price is AU$431
includes taxes & fees
1 Sept - 2 Sept
Studio queen with views of Lake Monona in the heart of downtown Madison
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, (13)
"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 AU$290
includes taxes & fees
24 Aug - 25 Aug
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort
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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