Vacation rentals in Milton

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Top-rated vacation rentals in Milton

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
Yurt in Cambridge
4.98 out of 5 average rating, 272 reviews

YurtSimple

YurtSimple is where life slows down and people unplug. It’s forest bathing in nature. It’s getting away from it all to spend time with a partner, by oneself, and sometimes with pets. You’ll be driving past YurtCation (about 300 feet past YurtCation) to get to YurtSimple. YurtCation is 20’ in diameter and YurtSimple is 16’ in diameter. Wood and charcoal are provided. You may cook on the indoor wood stove top, or visit any number of great restaurants 2 miles away. You can even order pizza delivery

Top guest favorite
A two-story blue house with a covered front porch is framed by a snowy landscape, showcasing a peaceful winter scene. The property is surrounded by a mix of bare trees and evergreens, providing a serene backdrop.
Home in Milton
4.97 out of 5 average rating, 103 reviews

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.

Guest favorite
Home in Milton
4.94 out of 5 average rating, 112 reviews

Lake House Summer Getaway

Welcome to the historic Bingham House! Enjoy everything beautiful Lake Koshkonong has to offer at this stylishly updated home. Amazing lake views throughout the inside and on the large patio. Situated on a calm canal with direct access to the lake. Expansive backyard with 150’ of canal shoreline and large hot tub. Enjoy the water on our kayaks, standup paddle-board or fishing off our dock. Prep a meal in our beautifully remodeled kitchen, on our large gas grill or by the shore on our fire pit.

Top guest favorite
A spacious hot tub features multiple massaging jets, creating bubbling water that invites relaxation. The tub is positioned on a wooden deck, offering a serene spot to unwind while enjoying the surrounding views.
Home in Milton
4.99 out of 5 average rating, 117 reviews

FirePit/Grill/Arcade Your Fall Escape Starts Here

🔥NO AIRBNB FEES🔥 Plan an unforgettable stay for a group of up to 8—and a dog or 2—at Harbor House, a spacious waterfront home with a hot tub & private dock where the Rock River emerges from 10,000-acre Lake Koshkonong offers a world of water sports—boating, kayaking, paddleboarding & more. Battle on 3 classic arcade games or ping pong table in the heated game room, gather at the firepit 12 steps from the water, and grill & dine on the deck overlooking the water. Close to Madison & Janesville.

Top guest favorite
The image displays a serene waterfront view showcasing a private pier extending over calm waters. A stylish three-story house is framed by lush greenery, offering a welcoming outdoor space. The interior features a spacious living room with comfortable seating and a modern kitchen visible in an open layout.
Home in Edgerton
4.92 out of 5 average rating, 154 reviews

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!

Guest favorite
An A-frame structure is nestled among lush green trees, showcasing large glass windows that allow for ample natural light. The contrasting wood siding complements the surrounding foliage, creating a harmonious blend with nature. A raised deck leads to the entrance, enhancing accessibility to the home.
Cabin in Fontana-on-Geneva Lake
4.94 out of 5 average rating, 187 reviews

Exquisite Modern A-frame all WithInnReach

An amazing space that truly caters to the guest experience. We've built this art piece to have our guests immerse themselves in all the amenities, from heated floors to in-ceiling speakers - all whilst losing yourself in the wood burning fireplace. At WithInnReach the attention to detail was paramount - with an emphasis of what we enjoy...amazing food through a well balanced kitchen, beautiful sound through Klipsch speakers and relaxation with floor to ceiling showers...enjoy to the fullest.

Guest favorite
A vibrant sunset paints the sky in shades of pink and orange over the water. Two figures sit on chairs, silhouetted against the colorful horizon. String lights are illuminated overhead, creating a warm ambiance. A picnic table and fire pit are visible in the foreground.
Home in Milton
4.97 out of 5 average rating, 103 reviews

Waterfront Koshkonong Home w/ Amazing Sunsets

Looking for a get away? Fun and sun on the lake? Family, friends and great memories. This 4 bed, 1.5 bath lakefront home is a perfect retreat for families and friends looking to get away from the stresses of life. Located on Lake Koshkonong in Milton, WI. Just south of Madison and north of Janesville. The sunsets from the back deck are stunning. Enjoy a campfire. There is a dock and a public boat launch around the corner. With lots of things to do, places to eat, and entertainment close by.

Top guest favorite
A cozy living area features a stone fireplace with a wooden mantel, complemented by a flat-screen television above. Soft curtains frame the windows, and warm light emanates from the fireplace, creating a relaxed ambiance. A patterned rug and comfortable seating enhance the space.
Home in Whitewater
4.96 out of 5 average rating, 178 reviews

The Modern Cozy Spacious Corner

This home is perfect for family get togethers. The basement has a game area, a living room, a queen bed and private bathroom. Duly note the queen bed downstairs is not a private bedroom. The fenced in backyard has a patio ,furniture,gas grill and a hot tub. Quiet hours begin at 9PM. Please be advised that we do have security cameras for your protection and ours.,The cameras are located on the front and back porch of the home. Please refrain from tampering with the cameras. Thanks

Top guest favorite
An open-concept living space features warm wood paneling and large glass sliding doors offering views of the river. A seating area is arranged with plush cushions, and a wooden table with bar stools is positioned nearby, inviting relaxation while enjoying the serene waterfront scenery.
Cabin in Edgerton
4.99 out of 5 average rating, 183 reviews

Waterfront modern cabin w/ kayaks

VERY romantic getaway for 2! Enjoy your own private dock, welcome to tie off your own boat or rent locally. Complimentary use of 2 kayaks. Beautiful modern riverfront cabin near Lake Koshkonong's eateries and entertainment. Soak in the gorgeous Wisconsin summer with water activities at your fingertips. The rest of the year take in the pristine wonderland views in our enclosed balcony. Only 30 minutes from Madison's world class culinary experiences, performance arts, sports & festivals.

Top guest favorite
Cabin in Fort Atkinson
4.92 out of 5 average rating, 182 reviews

Cozy Lakefront Cottage With The Best View

Location, Location, Location! Incredible views! Retreat to this cozy Lake Koshkonong cottage with vaulted ceiling and southern exposure. Enjoy spectacular sunsets and views of the 10,000 acre lake from the north shore. Fish, hunt, boat, ski, swim, snowmobile, or simply soak up the sun and take in the view from this quiet retreat on a dead-end street. Fresh paint, bedding, and furniture make this little gem very comfortable. Great Walleye ice fishing right in front of this property!

Guest favorite
Cottage in Edgerton
4.87 out of 5 average rating, 167 reviews

Rock River Rest, river cottage close to Madison!

Escape the city to our 1920s vintage riverside cottage. Nestled among centuries old Oaks, enjoy your own private sanctuary with over 100 feet of waterfront. Relax with a bonfire under the stars, sip coffee watching wildlife up close or unwind after a day kayaking from our waterfront. Perfect for couples, travelers, or business persons -- come and enjoy the scenic countryside, all with the convenience of location: we are a quick 25 minutes to Madison or a short drive from MKE + Chicago.

Guest favorite
Home in Janesville
4.99 out of 5 average rating, 153 reviews

Fully Renovated 2BR 1BA Gorgeous Exec Home #8ma-R

Enjoy your stay in Janesville, WI in this fully renovated two-bedroom cozy executive home Professionally Managed by Kevin Bush! The location is central to dining, shopping, and popular Janesville spots like the Rotary Botanical Gardens. This home will truly feel like your home away from home. Located just minutes from I39 giving you easy access for day trips to Madison, Milwaukee, Chicago, and surrounding. Please check out our listing on St. George Lane for more dates. Kevin, Host

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