
Holiday rentals in Dundee
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Top-rated holiday rentals in Dundee
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Elkhart A-Frame, Wooded Retreat near Road America
The Elkhart A-Frame is an ideal location for the adventure seeker who wants a unique and private experience that is still close to all the action. The home sits on a wooded three-acre private retreat only about a mile from the village of Elkhart Lake, Road America, and Golf Courses. This unique cabin was built in the 1970's but has been recently renovated with a fun Scandinavian modern flair. It has all the amenities for a memorable vacation stay that provides plenty of epic photo opportunities.
4.99 out of 5 average rating, 367 reviews
Wooded CABIN-Sunset & Lake Views/Kayak to Tiki Bar
Slow down at Fraser Fir log cabin, built in 1858 on Kettle Moraine Lake. In the summer, enjoy quiet moments watching the sun set from the front porch, then relax by the fire pit under a sky full of stars. Fish from the dock, kayak around the lake, or bring your boat to soak up the sun. In the winter, grab your ice-skates or ice-fishing gear and head out on the lake. With countless trails nearby, the hiking options are limitless and beautiful in every season. Your next adventure awaits.
4.94 out of 5 average rating, 124 reviews
Stay at Sunrise LLC, Like being at Grandma's
Welcome to Stay at Sunrise LLC. We offer a clean and comfortable home for your vacation enjoyment. We are in a rural area, recreation trail head is 3 miles east of us as is the Wade House, 7 miles from Road America. Large yard, Fire pit, picnic table, child swing set. Garage parking on site if arranged in advance. We do not have WIFI Phone reception for Internet is good. No Cable or Satellite TV, Over 32 antenna channels. Smoking is allowed outside of the home. No pets allowed.
4.97 out of 5 average rating, 153 reviews
The Loft at Hickory Haven-A Modern Rural Studio
The Loft at Hickory Haven is a modern country retreat made for two! Mary & Bob constructed The Loft studio in 2020 and filled it with the modern traveler's amenity wish list: A comfy king bed, central AC, a gas-fired stove, a modern bathroom, and a kitchenette with dining area. The property's rural setting offers a peaceful haven from your daily grind. Your day will start with the chirping of birds or a wild turkey sighting and end with a star-filled sky that is a site to behold! Welcome!
4.98 out of 5 average rating, 109 reviews
Lake Michigan Beach Home by Frank Lloyd Wright pro
Beautiful view and sand beach on Lake Michigan, completely private, surrounded by mature white pine trees and cedar trees. The spacious home is fully equipped with an "eat in" kitchen, dining room, and living room entertainment space, den with a see-through log-fired fireplace, screened-in porch to accommodate additional eating space, large outdoor deck with grill and fire pit. A canoe and a row boat are available for the boating enthusiast, with life jackets and other floating devices.
4.96 out of 5 average rating, 185 reviews
hot tub and sauna on 5 private acres
Looking for a peaceful retreat? Experience 5 acres of tranquil, private woodland paradise. Cool nights are perfect for warming up in the hot tub or infrared sauna which overlook the meadow. Explore hiking trails and lakes that the scenic Kettle Moraine has to offer. Grill a delicious meal and later craft perfect s’mores by campfire as the crickets sing. Unwind at SoLu winery, just a minute down the road. Near Road America, Kettle Moraine State Forest, and Dundee. Your getaway awaits!
5.0 out of 5 average rating, 286 reviews
Kettle Trails Cottage on Long Lake
Kettle Trails Cottage is the perfect getaway to relax and have fun on the water. The 3 bed/1 bath home is a cozy, comfortable landing spot to unwind. The accompanying heated Boathouse is an ideal venue for entertainment, especially when the weather keeps you indoors. Bring family and friends for the fishing, hiking, kayaking, biking, hunting and horseback riding. This property is centrally-located on the western shore of Long Lake, with forest views and amazing sunrises guaranteed.
5.0 out of 5 average rating, 17 reviews
Private 3 bedroom lake house
A beautiful spacious 3 bedroom with sofa bed (sleeps 9 guests) with lake access just steps away from the backyard. Includes washer and dryer, all cooking amenities and a grill, 3 TVs with cable (including Netflix and Disney+ capabilities), a two person canoe n 3 kayaks, hammock, board games, and books for leisure reading. Fish off the private peer. Light the bonfire in the fire pit (firewood included) by the patio onlooking the lake. Pets are allowed with a $200 pet fee.
4.85 out of 5 average rating, 121 reviews
Long Lake Chalet
This recently remodeled and tastefully furnished, PET FRIENDLY, cabin boasts a unique charm. Nestled along the shores of Long Lake in the heart of the Kettle Moraine Forest, this lakefront property offers 45’ of serene, peaceful beauty. This stunning home features a large yard, pier access and year round recreational activities. Disconnect, unwind and take in all that Kettle Moraine has to offer. Whether vacationing with family or friends this retreat is waiting for you.
4.97 out of 5 average rating, 127 reviews
Oak Haven | Theater • Game Room • Sauna • Firepit
Welcome to Oak Haven, a private 4,300 sq ft retreat surrounded by oak trees and peaceful Wisconsin beauty. 🌿 • 12-seat movie theater with plush recliners & surround sound 🎬 • Game room with pool, ping pong, shuffleboard & poker 🎱 • Infrared sauna + two outdoor fire spots for perfect nights 🔥 • Gourmet kitchen & dining for twelve 🍽️ • Minutes to Kohler golf, Kettle Moraine & Road America 🏎️ ✨ Oak Haven—where relaxation, laughter, and connection come naturally.
4.96 out of 5 average rating, 179 reviews
Outdoor Sauna | 6-BRs | Kohler-Andrae
🏖️ Private Sandy Beach on Lake Michigan 🔥 Waterfront Fire Pit for Cozy Evenings 🧖♀️ New Lakeview Sauna 🪟 Open-Concept Living with Wall-to-Wall Lake Views 🛏️ 6 Bedrooms – Sleeps Large Groups Comfortably 🍳 Fully Equipped Kitchen & Spacious Dining Area ☀️ Expansive Deck for Coffee, Sun & Scenic Relaxation 🌲 Wooded, Tranquil Neighborhood Near Kohler-Andrae State Park 🚗 Minutes to Sheboygan, Kohler, & Road America 🔐 Private Home with Seamless Self Check-In
5.0 out of 5 average rating, 119 reviews
The Blue Cobb House
My place is close to 20 minutes south of Elkhart Lake and Road America. You’ll love my place because of the outdoors space, the comfy bed, and the kitchen. My place is good for couples, solo adventurers, and business travelers. The Blue Cobb House is about 15 minutes from Kohler-Andrae State Park and 30 minutes from Harrington Beach State Park. The Kettle Moraine area is just to our west and it is filled with hiking trails.
4.98 out of 5 average rating, 324 reviewsPopular amenities for Dundee holiday rentals
Other great holiday rentals in Dundee

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The Log House
5.0 out of 5 average rating, 40 reviews
Log Cabin Luxury on a Lake
4.98 out of 5 average rating, 156 reviewsDestinations to explore
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