Holiday rentals in Troy

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Top-rated holiday rentals in Troy

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

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Top guest favourite
A wooden dock extends toward a calm lake, featuring a covered boat and a sunbathing area with a chair. A yellow floating mat lies nearby, and the water reflects the surrounding greenery. Swimmers can be seen enjoying the gentle waves in the distance.
Home in Mukwonago
4.97 out of 5 average rating, 34 reviews

Lake House Retreat on Phantom Lake

A cozy secluded retreat like being "up North" without having to go up North. Quiet private road, and quiet lake. Great swimming and fishing off the dock in this sandy bottom lake with clean spring fed water, and large grassy area for lawn games and relaxing. Great for families, ladies retreats, golf groups, or concert goers. Only 5 mins to grocery stores. Lots of space in the house, and lots of space for spending time outside on the deck or the dock or lawn by the lake. Feel free to inquire!

LocationFamilyView

Top guest favourite
An outdoor fire pit surrounded by wooden benches and chairs is visible in a spacious green area. The cabin in the background features a red exterior and large windows framed by trees, offering a serene spot for gathering.
Home in Elkhorn
4.98 out of 5 average rating, 197 reviews

Red Lodge|Hot Tub, Game Room, Near Lake, Free Dog!

Conveniently located amidst Southeast Wisconsin's best attractions, The Red Lodge is a contemporary-styled retreat that offers the space and family-friendly amenities to keep everyone entertained for hours. Enjoy an 👾 room, a secondary game room, a hot tub, a fire 🔥 pit, and a BBQ pit. Rent a boat right in the neighborhood at Lauderdale Lakes. Bike and hike at Kettle Moraine State Forest. Visit Lake Geneva for golfing and shopping—a quick 20-25 min drive away. Alpine Valley is minutes away!

LocationValueOutdoor spaces

Guest favourite
An expansive wooden deck offers a welcoming outdoor space, featuring a dining table surrounded by chairs and a cozy rattan chair. A large umbrella stands in one corner, while lush greenery and blue skies create a serene backdrop.
Cabin in Elkhorn
4.97 out of 5 average rating, 330 reviews

The Retreat: 5 Acre Log Cabin

Escape to this beautiful 5-acre country retreat, located a short drive from Lauderdale Lakes, Alpine Valley, and Lake Geneva. The cabin features two kitchens, two family rooms, a year around outdoor hot tub, a game room, and five bedrooms with comfortable king-sized beds. The master suite also includes a steam room for added luxury. Spend your days enjoying the great outdoors with a game of beach volleyball or roasting marshmallows around a bonfire, while taking in the fresh midwestern air.

FamilyLocationBack garden

Superhost
Home in East Troy
5.0 out of 5 average rating, 4 reviews

The Lodge - Camp Kettlewood

Once a Girl Scout mess hall and nurse’s station, the Scout Lodge has been thoughtfully restored for a new era of memory-making. With three bedrooms and 4 queen size beds, a full kitchen, and a modern bath tucked inside its original walls, it’s the perfect space for groups to unwind and relax. Inside you’ll find an open-concept living area with vaulted ceilings and a fireplace. The full kitchen makes shared meals easy, and a back deck overlooking the pond offers a peaceful place to unwind.

LocationFamilyOutdoor spaces

Top guest favourite
Cottage in Burlington
4.98 out of 5 average rating, 103 reviews

The Butterfly Cottage

Your summer get-away is perfect at The Butterfly Cottage on Honey Lake! Relax and enjoy the serenity of the lake and all the natural beauty of the season! This is a cozy cottage on Honey Lake, just 4 miles from downtown Burlington and 13 miles from Lake Geneva. Alpine Valley for concerts and skiing, fishing on Honey Lake or nearby Browns Lake as well as shopping in Lake Geneva are the highlights of the area! There are hiking/walking trails all around as well as rustic roads to explore.

FamilyLocationSleep quality

Top guest favourite
Home in Elkhorn
5.0 out of 5 average rating, 39 reviews

Private House on 5 acres - Walk to Alpine Valley

Valley Oasis is a private 3 bedroom 2 bath home located on 5 acres next to the entrance of Alpine Valley Resort. Far enough off the road to enjoy the quiet beauty of nature. Woods located behind the house and a field next to it. Enjoy the outdoors on the deck, have dinner in the screened in porch, enjoy a fire in the fire pit, or warm up by the fireplace. You will have access to the entire house and immediate yard. The garage is not accessible. No smoking in the home. No parties allowed.

LocationFamilyAmenities

Guest favourite
The striking A-frame exterior features large triangular windows that allow natural light to flood the interior. The patio area includes seating for relaxation and a hot tub, set against a backdrop of lush surrounding trees, enhancing the connection with nature.
Cabin in Bloomfield
4.95 out of 5 average rating, 88 reviews

Modern A-Frame Lake Cabin w/ Pickleball Ct.4Bd 3Ba

Escape to this stunning A-frame home in Genoa City, Wisconsin, where tranquility meets adventure. Just minutes away from Nippersink golf course, Lake Geneva and Wilmot Ski Resort. Nearby Cabin offers a range of amenities designed to enhance your stay. Including a private pickleball court, hot tub, kayaks, and many more. Providing private lake access, and a private pier, this spacious vacation rental is the perfect getaway for families and groups looking to unwind and explore.

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Top guest favourite
The cottage features a charming facade with a combination of blue siding and stonework. Two sets of double doors are framed by large windows, allowing natural light to fill the entrance. Flower beds line the pathway leading to the front door, enhancing the welcoming appearance.
Home in Elkhorn
4.98 out of 5 average rating, 164 reviews

Cozy Country Cottage near Lake Geneva, WI

Our Cozy Cottage features 3 comfortable bedrooms and nightly magnificent sunsets. Nestled on a country road, the house offers plenty of space to rest after visiting Lake Geneva, Lauderdale lakes, biking at Kettle Moraine or site seeing in the area. It’s close to Walworth County fair grounds where the flea market, Das Fest and Rib Fest are held. This is country living with plenty of opportunity to enjoy the beautiful outdoors or the peace and quiet of the countryside.

ValueLocationBiking

Top guest favourite
The exterior of the classic A-frame cabin, featuring a striking red facade, is set against a backdrop of lush greenery. A wooden walkway leads to a seating area with two chairs. A deck is visible, providing an inviting space to relax outdoors.
Home in Palmyra
4.99 out of 5 average rating, 104 reviews

A-Frame in forest on bike trail!

Classic A-Frame, in the woods. Borders the Kettle Moraine State Forest on 3 sides. Exterior: 2 acres, fully-fenced and dog-friendly. Hop on the "Connector" mountain bike trail right out the backyard. Or take a hike on the nearby Ice Age trail, Bald Bluff, John Muir, Nordic, or snowmobile trails. Interior: 1,500 square feet, 2 levels, open concept main living area with loft ceiling, wood-burning fireplace, 2 arcade machines, outdoor firepit, frisbee golf stand, etc.

FamilyValueGrill

Guest favourite
A Mid Century modern two-story home is shown, featuring a green exterior and large windows. A stone pathway leads to the entrance, surrounded by well-maintained grass and plants. The front porch is equipped with a railing, and steps provide access to the main door.
Home in Elkhorn
4.9 out of 5 average rating, 41 reviews

Eclectic Lake Wandawega Cabin

Enjoy Lake Wandawega in our unique home that combines Mid Century modern aesthetics with a vintage, eclectic vibe. Located just steps away from Lake Wandawega, bring your kayak or paddle board for a delightful adventure from the community lake access. Play a friendly game downstairs or head outside to a rustic outdoor space complete with a fire pit perfect for enjoying the outdoors. Perfect for year round enjoyment. 15 minutes from Kettle Moraine and Alpine Valley.

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Guest favourite
Home in East Troy
5.0 out of 5 average rating, 6 reviews

Historic 1868 Farmhouse Kettle Moraine Getaway

Escape to an elegantly restored 1868 Italianate manor on 4.5 private acres. Once home to the Johnston Cookie family, this farm blends old-world charm with modern luxury. Whether it’s a family reunion or a romantic retreat, enjoy high tin ceilings, a designer chef’s kitchen, and a master suite with a clawfoot tub. Located in the heart of Kettle Moraine hiking, skiing, and concerts are just minutes away. Relax, unplug, and rejuvenate.

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Top guest favourite
Home in Burlington
4.96 out of 5 average rating, 46 reviews

Long Lake Retreat - Cottage in Burlington, WI

Long Lake Retreat Kick back and soak up the laid-back lake life at our cozy cottage right on the water in beautiful Burlington, Wisconsin! Just a short drive from downtown Burlington, Waterford, and Lake Geneva, you'll find great local spots to eat, shop, and explore. But with a lake out your back door and nature all around, you might just spend your whole trip outside! Come unwind, unplug, and enjoy lake life!

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Popular amenities for Troy holiday rentals