Holiday rentals in Stoughton

Cozy Magnolia Style 2-Bedroom Home with Loft

Cozy 2BR 1900's bungalow with beautiful backyard. Step into the Magnolia style living and dining room with decorative crown molding and new floors. Large bedroom with plenty of storage and finished attic for the kids or additional guests. Mudroom with laundry and relaxing front porch add to this spacious home. Outside is the true GEM, with adorable patio area just waiting for fire pit gatherings. Located close to parks, canoe/kayak launch, eateries, and shopping. Quick drive to downtown Madison!

Peaceful Pines on 59~Welcome! 5 bdrm river front!

Relax, unwind and play on 4+ acres of beautiful nature: green space, woods, the Rock River, gardens and fresh clean air! Enjoy life from the back deck or rocking on the front porch. Stroll down the tree covered lane to fish from our shoreline, watch river traffic, picnic in the cabin, untie your watercraft from our pier and go travel the river and Lake Koshkonong, play a variety of outdoor games, grill dinner outside and end the day around the firepit. Hosts live in the lower level apartment.

Spacious Home/Fenced Yard/10 Min to Madison

Bring the whole crew! This spacious McFarland home has 3 bedrooms, 2.5 baths, with MANY places to sleep (11 different sleeping spots, including a pullout couch for 2). Enjoy a private fenced backyard — perfect for kids, pets, and evening hangs. Just 15-20 minutes from downtown Madison, Camp Randall, and the Capitol, with free parking and a quiet neighborhood vibe. Perfect for Badger weekends, family reunions, and group getaways. Please note: no parties allowed. Book early — it fills up fast!

Fun Lake Kosh Private Pier, Decks, Fire Pit, Grill

Gather at the White House: a stylish lake house with private pier, 4Br/2.5bath/beds for 15 people, fire pit, gas grill, huge yard, 2 wooded acres. Lake Koshkonong is one of WI’s largest, famous for its boat-up restaurants/bars, fishing, and water sports all accessible from our private pier. Located along 39/90hwy - 90 mins to Chicago/30 min to Madison. Perfect for entertaining: fully stocked, professionally cleaned, open floorplan, 3-story outdoor living, dining & patio, playroom & much more!

Rustic Lake Home Retreat

Our home is located just across the street from the lake. We have lake access via a private beach everyone in the area uses. We do not have a dock for your use. Make left out of the house to Lake Shore Dr. Then left to walking path located 100 feet up on the right side. When using the beach please be mindful of others who may be using it as well. Use proper etiquette, respect others, leash your dogs, and ensure you clean up the area when you leave. PETS NEGOTIABLE, BY INQUIRY ONLY

Quiet country retreat

Peaceful solitude or exciting sightseeing? You’ll have the best of both worlds at this quiet country home located just outside Madison on 10 magnificent acres. After, enjoying your morning coffee, take a stroll on the grounds and enjoy the sweeping views of the pastoral landscape. Then head into Wisconsin’s state capital (23 minutes by car) for an exciting day of sightseeing. Or visit the quaint town of Cambridge (8 minutes by car) to explore its unique pottery and antique shops.

25min to Capitol - KING Suite - Game Room - Groups

🔸Large groups & families - 1 King, 2 Queen, 2 twin beds, and 2 queen floor mattresses 🔹Game room w/ 85" TV, ping pong, foosball, stick hockey, arcade game & board games 🔸Private yard w/ concrete patio, lounge furniture, gas fire pit & corn hole 🔹Highchair & pack n’ play - free to use 🔸Fully stocked kitchen w/ island seating 🔹You'll find "The Kohl Center, UW-Madison, Camp Randall Stadium, State Street, The Capitol, & The Alliant Energy Center" within a 25 minute drive

Beautiful Lake Home- On Lake Waubesa

Beautiful home on Lake Waubesa. Our home is a perfect location, offering a quiet and relaxing neighborhood while only being 15 minutes to the Wisconsin Capital building and downtown Madison. Room for 8 adults plus children! Spend the day enjoying the lake and indulging in the beautiful views from the patio. Quick commute to Camp Randall, Kohl Center, UW Madison, State Street, Monona Terrace and Alliant Energy Center. Downtown dining offers a variety of incredible food choices.

The Orchard House at Pied Beauty Farm

In a complex world that makes so many demands your time and attention, the Orchard House is a simple, Nordic-inspired refuge where you can be restored, reconnected, and refreshed. Midweek special: $1000 for 5 nights, Sunday evening through Friday morning. The Orchard House is a private retreat set on 30 acres in the Wisconsin countryside, just 20 minutes from Madison. A wood -fired hot tub set in a secluded forest clearing is available year round for outdoor soaking.

Main St 2 Bdrm - Walk to coffee & sushi!

* Be sure to check out our winter extended stay discounts for 3+ nights! * Welcome to historic downtown Oregon! Nestled in a picturesque setting, this elegant retreat combines modern comfort with historic charm. You'll be steps away from locally owned coffee and gift shops, a wine reserve & restaurants! With convenient access to Madison (14 mi), experience the best of both worlds – small-town tranquility and urban excitement. Whether for work or leisure, welcome home!

Bees on Main: sweeter than ever

Located in the heart of Stoughton's Downtown Historic District, "Bees on Main" is a lovingly renovated upstairs apartment. You'll find the Opera House, Chorus, and Stoughton's wonderful shops, restaurants, pubs, and galleries only steps away. The Yahara River and Fairgrounds are within a few blocks, and there's space on the private deck to safely store your bikes or kayaks if you want to enjoy the great outdoor activities and nature surrounding Stoughton.

Nothing Else Like It!

There is absolutely nothing else like it available, and you’ll agree as soon as you step foot inside! This beautifully designed home makes your stay comfortable with it's high end furnishings, bedding, towels, mattresses and dishes. Kick back and relax in this calm, stylish space. Fully fenced backyard great for dogs, entertaining and room for kids to play. Private work space available too! All bedrooms have room darkening shades!