Holiday Homes in Middleton

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Featured Holiday Homes in Middleton

A Pleasant Retreat- No Cleaning Fee & New Discounts
Exterior
A Pleasant Retreat- No Cleaning Fee & New Discounts
10.0 out of 10, Exceptional, (207)
"Very best Vrbo property we have ever stayed in anywhere! Checks off all the boxes as EXCELLENT."
A Pleasant Retreat- No Cleaning Fee & New Discounts
One Bedroom King with Den with views of the heart of downtown.
Exterior
One Bedroom King with Den with views of the heart of downtown.
2.0 star property
10.0 out of 10, Exceptional, (1)
"Very clean and in the heart of downtown. Quiet lovely "
The price is NZ$723
includes taxes & fees
13 Oct - 14 Oct
One Bedroom King with Den with views of the heart of downtown.
One Bedroom King with Den with views of Lake Monona in the heart of downtown.
2 bedrooms, WiFi
One Bedroom King with Den with views of Lake Monona in the heart of downtown.
8.0 out of 10, Very good, (1)
"Unit was fantastic. I wish there would have been communication regarding the construction around the building. "
The price is NZ$743
includes taxes & fees
13 Oct - 14 Oct
One Bedroom King with Den with views of Lake Monona in the heart of downtown.
Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access
View from property
Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access
10.0 out of 10, Exceptional, (92)
"thoughtful amenities, comfortable furniture, all around pleasant."
Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access
One-of-a-kind house on 240 acres w/ prairie, woods & trout-stream - pet-friendly
Interior
One-of-a-kind house on 240 acres w/ prairie, woods & trout-stream - pet-friendly
10.0 out of 10, Exceptional, (34)
"This home is so neat. Unique design. Beds were comfortable and very clean. Host had such a warm welcome note and dog treats for our Boxer, Ava. Will definately stay again. My In-Laws live nearby and this was a perfect location. We made great memories here. ❤️"
One-of-a-kind house on 240 acres w/ prairie, woods & trout-stream - pet-friendly
Studio queen with views of Lake Monona in the heart of downtown Madison
Exterior
Studio queen with views of Lake Monona in the heart of downtown Madison
The price is NZ$602
includes taxes & fees
24 Sept - 25 Sept
Studio queen with views of Lake Monona in the heart of downtown Madison
Near DT Madison - Half Block from Lake Monona & 1 Block from Lake Loop Bike Path
Marina
Near DT Madison - Half Block from Lake Monona & 1 Block from Lake Loop Bike Path
10.0 out of 10, Exceptional, (20)
"In town meeting up with family. The property is a true trip back in time. If you’re of a certain age or have memories of visiting grandparents, you’ll wonder which decade you're currently in. It’s like a living time capsule. Everything was super clean, beds ultra comfy and a great porch for coffee in the morning and a quiet neighborhood to get out and explore. Kelly was very quick responding to questions. Well hopefully be back someday!"
Near DT Madison - Half Block from Lake Monona & 1 Block from Lake Loop Bike Path
Legacy Guest House , Mount Horeb WI
Fridge, microwave, oven, stovetop
Legacy Guest House , Mount Horeb WI
10.0 out of 10, Exceptional, (47)
"What a terrific week! Home was incredibly well-equipped and cozy. We loved walking into town for drinks, dinner, & shopping. Perfect location for hiking adventures as well as the Cave, breweries, wineries, International Crane Foundation, Big Cat rescue place, Madison, and more. Host was so communicative and helpful with a small issue. Note that living room is small and there is a salon attached to front which was not in listing. Never had issues with the salon, but we were surprised by it. Main...
Legacy Guest House , Mount Horeb WI
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
Outdoor dining
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
9.8 out of 10, Exceptional, (24)
"We had a great time utilizing the outdoor deck space at the is property! It also had a spacious kitchen and a fun game-themed living space. We were a little bummed that the river water at the dock was green, making it less enticing to use the kayaks and canoe provided but I’m not sure how the property owner could control that. Location was walking distance from some fun bars and restaurants and a short drive to Madison. Close to bike trails too!"
The price is NZ$842
includes taxes & fees
6 Oct - 7 Oct
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
Social Distance in Our Gorgeous, Private Retreat in the Woods
Fridge, microwave, oven, stovetop
Social Distance in Our Gorgeous, Private Retreat in the Woods
9.4 out of 10, Exceptional, (51)
"We were in town for graduation and this provided a nice retreat from the crowds! Plenty of space and beautiful setting."
Social Distance in Our Gorgeous, Private Retreat in the Woods
Updated 3 bed home close to Downtown Madison
Fridge, microwave, oven, stovetop
Updated 3 bed home close to Downtown Madison
9.8 out of 10, Exceptional, (8)
"Luke is a great host and the house was very nice and clean. However the description says 1full bath and a half bath. The half bath is not quite what we expected and is really an extension of the laundry room in the basement which we’re not able to use at all. "
Updated 3 bed home close to Downtown Madison
Single Full Room at The Little Village in Mount Horeb
Exterior
Single Full Room at The Little Village in Mount Horeb
8.8 out of 10, Excellent, (5)
"Even though it smelled musty it was what I needed….just a place to sleep."
The price is NZ$165
includes taxes & fees
24 Sept - 25 Sept
Single Full Room at The Little Village in Mount Horeb
ONE OF A KIND vacation rental with a view
Exterior
ONE OF A KIND vacation rental with a view
10.0 out of 10, Exceptional, (125)
"A very cool 70’s vibe that we just loved! Josh was great at communicating. Very clean and just what we needed for a weekend away celebrating UW Homecoming!"
ONE OF A KIND vacation rental with a view
Beach Barn! Slide, Tiki Bar, Sauna, Hot Tub, Volleyball, Frolf, Ski/Golf
Interior
Beach Barn! Slide, Tiki Bar, Sauna, Hot Tub, Volleyball, Frolf, Ski/Golf
2.0 star property
Beach Barn! Slide, Tiki Bar, Sauna, Hot Tub, Volleyball, Frolf, Ski/Golf
Madison Luxury Home- 10 min to UW- Walk to lake Monona
Fridge, microwave, oven, stovetop
Madison Luxury Home- 10 min to UW- Walk to lake Monona
Madison Luxury Home- 10 min to UW- Walk to lake Monona
Studio Queen in the heart of downtown.
Pool
Studio Queen in the heart of downtown.
2.0 star property
The price is NZ$602
includes taxes & fees
6 Oct - 7 Oct
Studio Queen in the heart of downtown.
Doty ★ Walk to Everything -Hotel Quality- Downtown
Fridge, microwave, oven, stovetop
Doty ★ Walk to Everything -Hotel Quality- Downtown
9.8 out of 10, Exceptional, (27)
"This property was great for a conference at Monona Terrace Community and Convention Center."
Doty ★ Walk to Everything -Hotel Quality- Downtown
COZY WATERFRONT CABIN, ON SUNSET BAY, LAKE WISCONSIN !! SUMMER AND WINTER FUN !!
Smart TV, music library, stereo
COZY WATERFRONT CABIN, ON SUNSET BAY, LAKE WISCONSIN !! SUMMER AND WINTER FUN !!
10.0 out of 10, Exceptional, (81)
"The accommodations are just as they look,, comfortable, nice decor, fun games, fire out, wonderful swimming area. The rooms perfect for adults and teens. We spent the weekend on the beautiful porch and dock all weekend so when the owner mentioned the rooms are small but I thought they were great. My teenage girls only missed their full length mirror s ha ha. Everything was available for enjoying wisconsin summers. For pit for pudgy pies, grill for picking up local brats and burgers. Local...
COZY WATERFRONT CABIN, ON SUNSET BAY, LAKE WISCONSIN !! SUMMER AND WINTER FUN !!
Amazing townhouse, amazing attractions, amazing city!
Fridge, microwave, oven, stovetop
Amazing townhouse, amazing attractions, amazing city!
10.0 out of 10, Exceptional, (150)
"Our family really enjoyed our stay in this comfortable, cozy home. The downstairs rec room was a great space for our kids to play. The stairs are a bit steep, so we definitely had to supervise our toddler! All of the necessary amenities were provided for a comfortable stay, including towels, bath & kitchen items, etc. The dry erase board was fun for our kids to draw on. Location was very easily accessible and neighborhood felt safe. The host was very responsive. Would stay here again."
Amazing townhouse, amazing attractions, amazing city!
Conveniently Located just off University Avenue on Madison's West Side
Interior
Conveniently Located just off University Avenue on Madison's West Side
10.0 out of 10, Exceptional, (115)
"This is the second time we’ve stayed at this property! As before very clean, plenty of amenities towels, kitchen tools etc. Lots of space to spread out. I love the peaceful wooded lot! It is SO easy to drive back and forth to the Ironman Wisconsin triathlon course, close to downtown and the run turn around on the Howard Temin path. Is also very close to restaurants and grocery stores. Definitely would stay again! "
Conveniently Located just off University Avenue on Madison's West Side
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See all available properties in Middleton
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
Outdoor dining
Countryside Beauty - Min to Madison/Perfect for families/Events&Dogs! Lrg yard
10.0 out of 10, Exceptional, (139)
"My husband, my 21 year old dtr and I were in Wisconsin to visit multiple family members and friends in the Madison area. This house had plenty of room, it had everything we needed and was clean and comfortable. Joan even gave us fresh produce from her garden! The views of the rolling fields are beautiful and we felt like we were out in the country, yet we were only 10 minutes from a large grocery store and 20 minutes from most family."
Countryside Beauty - Min to Madison/Perfect for families/Events&Dogs! Lrg yard
A Pleasant Retreat- No Cleaning Fee & New Discounts
Exterior
A Pleasant Retreat- No Cleaning Fee & New Discounts
10.0 out of 10, Exceptional, (207)
"Very best Vrbo property we have ever stayed in anywhere! Checks off all the boxes as EXCELLENT."
A Pleasant Retreat- No Cleaning Fee & New Discounts
Barnhouse! Mini Golf, Slide, Theater, Arcade/Games, Pool/Hot Tub/Sauna, Home Gym
Fridge, microwave, oven, stovetop
Barnhouse! Mini Golf, Slide, Theater, Arcade/Games, Pool/Hot Tub/Sauna, Home Gym
10.0 out of 10, Exceptional, (9)
"We loved getting together at the house! We are a farm family and loved what you’ve done with the barn! Our favorite spaces were the theater and the heated pool! Thank you for making it so easy! We would recommend the house to everyone with kids they had a blast!"
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.