Holiday Homes in Stoughton

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Featured Holiday Homes in Stoughton

A Pleasant Retreat- No Cleaning Fee & New Discounts

10.0 out of 10, Exceptional, (215)
"We needed a place for a group of family members to stay to prepare food and decorations for a 60th birthday party at a nearby location. We had everything we needed and our hosts provided other prep items that aren’t commonly found in a rental home. The location was ideal (near a grocery store for forgotten items) and so comfortable!"
A Pleasant Retreat- No Cleaning Fee & New Discounts

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

10.0 out of 10, Exceptional, (98)
"Beautiful space, very relaxing. We had a great stay!"
Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access

Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!

9.8 out of 10, Exceptional, (29)
"The best thing about this house is its proximity to Madison in general and to the river. I loved taking a kayak out on the river around sunrise. Really beautiful. It's close to many fun activities in Madison too. The house itself is comfortable. Hosts are responsive and helpful. Kitchen is lovely. One helpful tip is that this house is on a busy street. There is some traffic noise at night. Not a huge deal but I wish I had known ahead of time and prepared for it. Overall a good place with...
The price is AU$803
includes taxes & fees
1 Dec - 2 Dec
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!

Waterfront w/ HOT TUB + King Suite + Game Room

9.6 out of 10, Exceptional, (25)
"Fantastic place, very clean and great location. We will book this place again. "
Waterfront w/ HOT TUB + King Suite + Game Room

Executive Lakefront Home 30 Minutes From Madison!

10.0 out of 10, Exceptional, (85)
"Beautiful property. Very well equipment. "
Executive Lakefront Home 30 Minutes From Madison!

Lakeside Retreat at Lake Ripley - Sandy Beach, Dock, Kayaks, & More

10.0 out of 10, Exceptional, (18)
"Plenty of room for everyone and nice location for our weekend getaway. Far enough from the hustle and bustle but close enough to have things to do! Enjoyed an afternoon of antiquing and exploring Madison which is a short drive. Grocery store and gas station located within minutes of the property. Relaxing lake side location and views. Would definitely recommend!"
Lakeside Retreat at Lake Ripley - Sandy Beach, Dock, Kayaks, & More

Fully Renovated 2BR 1BA Gorgeous Executive Home

10.0 out of 10, Exceptional, (15)
"This is a nice clean place in a quiet neighborhood. Had the feeling of “coming home” to this house. It has all the things, dishware, appliances, linens, etc. Will definitely stay here on our next Janesville visit. Also Kevin the host responded to us in a very timely manner, always appreciated!! "
The price is AU$560
includes taxes & fees
24 Nov - 25 Nov
Fully Renovated 2BR 1BA Gorgeous Executive Home

ONE OF A KIND vacation rental with a view

10.0 out of 10, Exceptional, (129)
"Awesome stay with Son and Grandsons. Great place to stay."
ONE OF A KIND vacation rental with a view

Paoli Den - Newly Remodeled!

9.8 out of 10, Exceptional, (7)
"Very clean, great communication. Great location for Madison, Shops at Paoli, New Glarus, Epic. Close to downtown Verona. Having separate parking was nice. Not having a thermostat (or one I could find) was odd. Great place overall."
Paoli Den - Newly Remodeled!

Eagle's Landing on the Rock River, Pontoon available for additional fee

10.0 out of 10, Exceptional, (10)
"Great property! Want to return next summer for a family vacation."
Eagle's Landing on the Rock River, Pontoon available for additional fee

Amazing townhouse, amazing attractions, amazing city!

10.0 out of 10, Exceptional, (156)
"Ben and Sara were great hosts - very communicative! Perfect little house and we loved watching sports on the big tv downstairs!"
Amazing townhouse, amazing attractions, amazing city!

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

10.0 out of 10, Exceptional, (24)
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Near DT Madison - Half Block from Lake Monona & 1 Block from Lake Loop Bike Path

Conveniently Located just off University Avenue on Madison's West Side

10.0 out of 10, Exceptional, (117)
"We were here for the PSU- Wisconsin game and the house worked great. Maybe just a new shower curtain liner in the upstairs bathroom 😁"
Conveniently Located just off University Avenue on Madison's West Side

HOT TUB - 20 min to Capitol - KING Bed - Fireplace

10.0 out of 10, Exceptional, (5)
"My adult children (including SIL) and my partner and I wanted to visit Madison for the first time. While the house is a little further from downtown (20 mins.) than we might have liked, it was worth it for the size, comfort and cleanliness of the house. We had plenty of room and all of the necessities. We pretty much just slept and had breakfast at the house, but it would've been great if we'd needed to spend more time there. (I was looking forward to using the hot tub and Pacman machine,...
HOT TUB - 20 min to Capitol - KING Bed - Fireplace

Elegant Space–Premium Kitchen–Spacious & Ideal for Gathering w/ Friends & Family

10.0 out of 10, Exceptional, (12)
"This is one of the best rental homes I've ever stayed in! The owners were super accommodating and everything was labeled clearly. We stayed with a toddler and there were ample toddler toys and games, kid friendly cups and plates, and they even installed a baby gate at the top of the stairs. The neighborhood was great and quiet, with easy parking. Overall awesome, and we would love to stay here again!"
Elegant Space–Premium Kitchen–Spacious & Ideal for Gathering w/ Friends & Family

Lakefront 4BR ‘Up North’ Outdoor Getaway - Best Sunset View on The Lake

9.6 out of 10, Exceptional, (10)
"We visited in late October, early November, so we didn't do much on the lake, but there is a cute park with a playground nearby! The house was clean and accommodating, even had a high chair for our use which was helpful with a 15 month old. We made all our meals in the house and found cooking utensils/dishes to be a little sporadic, but that was our only complaint. Stephen was a wonderful host who communicated clearly and quickly whenever we had questions! The view of the lake is gorgeous!"
Lakefront 4BR ‘Up North’ Outdoor Getaway - Best Sunset View on The Lake

3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe

10.0 out of 10, Exceptional, (135)
" This home sits on a hill looking west. The home is spacious with a nice back yard and firepit. Close to New Glarus. The rooms are big and very clean. The kitchen has everything you need. Communication with the owner was awesome. Would definitely stay again."
3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe

Family-Friendly Lake Waubesa Home: Boat + Swim!

9.8 out of 10, Exceptional, (8)
"We were there at the start of fall and the gas fireplaces were awesome both for the ambiance and warmth on cooler days. The view from the sunroom was wonderful. We spent a lot of time enjoying the view from there. It had a nice mix of modern amenities (updated kitchen and baths) and rustic charm. The neighborhood was very cute. We walked our dog quite a bit and enjoyed views of the lake side homes and the lake from all around the house. Plus there are two parks both within walking distance...
Family-Friendly Lake Waubesa Home: Boat + Swim!

Cozy Lakefront House

9.8 out of 10, Exceptional, (12)
"Very clean, great place to stay!"
Cozy Lakefront House

New Luxury & Spacious House in the Heart of Janesville

2.0 star property
9.0 out of 10, Wonderful, (2)
"Nice place and great location to downtown. The only concern with this property are the stairs. They are very narrow and slick. Other then that we had a great stay."
The price is AU$846
includes taxes & fees
24 Nov - 25 Nov
New Luxury & Spacious House in the Heart of Janesville
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 Stoughton

Peaceful lake house on Lake Kegonsa!

5.0 out of 10, (2)
"We stayed at this property for a weekend in the summer. It was nice to be right on the water, and the neighbors were all quiet and nice. One neighbor has a beautiful garden that attracts birds and makes for a relaxing spot for morning coffee. The location is ideal for anyone looking to bike. There is a great trail next to the house that goes to downtown Madison."
Peaceful lake house on Lake Kegonsa!

Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!

9.8 out of 10, Exceptional, (29)
"The best thing about this house is its proximity to Madison in general and to the river. I loved taking a kayak out on the river around sunrise. Really beautiful. It's close to many fun activities in Madison too. The house itself is comfortable. Hosts are responsive and helpful. Kitchen is lovely. One helpful tip is that this house is on a busy street. There is some traffic noise at night. Not a huge deal but I wish I had known ahead of time and prepared for it. Overall a good place with...
The price is AU$803
includes taxes & fees
1 Dec - 2 Dec
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!

Conveniently Located just off University Avenue on Madison's West Side

10.0 out of 10, Exceptional, (117)
"We were here for the PSU- Wisconsin game and the house worked great. Maybe just a new shower curtain liner in the upstairs bathroom 😁"
Conveniently Located just off University Avenue on Madison's West Side
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.