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 and around

Relax in this clean cozy 3 bedroom, 2 bath home in the heart of Madison. Perfect
Microwave, oven, stovetop, dishwasher

Relax in this clean cozy 3 bedroom, 2 bath home in the heart of Madison. Perfect

2.0 out of 10, (2)
"Host never showed up to let us in the property and still has not reimbursed me "
Relax in this clean cozy 3 bedroom, 2 bath home in the heart of Madison. Perfect
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 €402
includes taxes & fees
30 Jul - 31 Jul
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 €426
includes taxes & fees
30 Jul - 31 Jul
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)
"I was visiting from Chicago for a concert and was immediately sold with this property! I loved the hot tub and fireplace!! The whole house was clean and very bright! I will definitely stay again!"
Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access
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, (57)
"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
Private Pool - HOT TUB - Sauna - Game Room - Pets
Terrace/patio

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

Private Pool - HOT TUB - Sauna - Game Room - Pets
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, (26)
"The property was beautiful, safe, and in a perfect location for the event we were attending!"
The price is €345
includes taxes & fees
30 Jul - 31 Jul
One Bedroom King with Den with views of Lake Monona in the heart of downtown.
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)
"We were in town for a wedding, and this was the perfect place for us and our two young children. The space was very clean and had everything we needed for our stay. The host was extremely friendly and helpful and was quick to respond to any messages. We would definitely recommend! "
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
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
9.6 out of 10, Exceptional, (22)
"Super clean, well lit, and beautiful view! Would definitely stay again."
The price is €334
includes taxes & fees
30 Jul - 31 Jul
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 !!
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 €650
includes taxes & fees
30 Jul - 31 Jul
King Suite - Game Room - Large Groups - Yard
13 Mi to University of Wisconsin: Suburban Home
Enjoy a peaceful outdoor space with a deck, metal table, and umbrella.

13 Mi to University of Wisconsin: Suburban Home

10.0 out of 10, Exceptional, (2)
"Lovely large new home tucked into a new residential area. Ample room for 6 adults, from Austin, Fort Worth and Green Bay. About 1/2 hour to the Union Terrace, an iconic restaurant on the UW campus.."
13 Mi to University of Wisconsin: Suburban Home
Brand New Country Rustic Barn-R&R At It's Finest! Madison Area
Enjoy cooking in this kitchen with a central island, wooden cabinetry, and stainless steel appliances.

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

9.8 out of 10, Exceptional, (21)
"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
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, (4)
"Nice place. "
Country Sportsmans Paradise!! Grill, Firepit & AC - Devil's Lake and Dells area!
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
"This was our third time staying in the Governor’s Club and would recommend it to anyone looking for a destination to just relax and enjoy the amenities. We were celebrating our anniversary and they surprised us with a complimentary bottle of champagne and strawberries! How lovely! "
Rhonda 1-night trip
Posted 9 hours ago
The Madison Concourse Hotel and Governor's Club