Villa holiday rentals in Caledonia

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Top-rated villa rentals in Caledonia

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

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Guest favourite

A log-sided home is illuminated by warm lights against a snowy landscape at night. The covered porch features railing and seating, with snow blanketing the ground and surrounding trees, creating a serene winter scene.

Villa in McHenry

4.91 out of 5 average rating, 34 reviews

Fabulous Cabin

WELCOME TO WATERFRONT LOG-SIDED HOME! ARTISAN CRAFTMANSHIP HOME OFFERS A BACKYARD OASIS SITUATED , NESTLED ON A PRIVATE POND, Heated POOL(closed till April 1st), Hot tub open from Oct 15th to Apr 15thGAZEBO, FIRE PIT, FISHING! 4 BEDROOMS AND 4.5 BATHS The homes sits on the highest point in the neighborhood and has stunning views in the front & backyard! Enjoy the mornings sitting on your front porch. The main floor is completed by an office, finished walkout basement in with a custom built bar

A well-maintained lawn extends to the edge of Lake Michigan, showcasing vibrant green grass and colorful flowers. Sun loungers are positioned under a striped umbrella, providing a relaxing space with unobstructed views of the lake and sky. The tranquil turquoise water meets the horizon.

Villa in Racine

4.75 out of 5 average rating, 102 reviews

Wisconsin Lake Escape - Villa with Pvt Beach

Designed by American Architect John Randal Mcdonald in 1959, this lakefront Mid century home, perched on a bluff on Lake Michigan boasts spectacular sunrises, breathtaking 180 deg views and steps to a private beach! This designer home is a gem to recharge, escape, a honeymoon destination, a retreat, a family reunion, or a small getaway with other couples!! And if you're a digital nomad, to work in a stunning location. The sound of waves, 3 fireplaces and outdoor firepits, will rejuvenate you!

The exterior of the resort showcases a modern building set against a colorful sunset. Tall grass and shrubs line the foreground, while the lush green golf course stretches out in front. Warm lights glow from the windows, enhancing the serene atmosphere of the surroundings.

Villa in Lake Geneva

4.68 out of 5 average rating, 25 reviews

Villa Near Lake Geneva | Close to the Airport

Looking for a cozy getaway to Lake Geneva? Our comfortable two bedroom villas have got you covered! Nearby, you will find a local ski hill, plus canoeing and ziplining outfits. At the resort, you will have access to two championship golf courses, indoor and outdoor pools, and horseback riding - all catered by a local shuttle service. With the additional in-suite washer/dryer and full kitchen, you will be sure to call this property your home away from home!

A large outdoor pool is surrounded by lounge chairs and shaded areas. The clear blue water reflects the sky, and the pool area is complemented by well-maintained landscaping. Nearby buildings with a relaxed architectural style provide a welcoming backdrop.

Villa in Lake Geneva

4.65 out of 5 average rating, 57 reviews

Villa Near Lake Geneva, close to Lake

Our comfortalble one bedroom villa has got you covered on your next getaway! Nearby, you will find a local ski hill, plus canoeing and ziplining outfits. At the resort, you will have access to two championship golf courses, pools, seven on-site restaurants, a spa, and more - all serviced by a local shuttle service. With the additional in-suite washer/dryer and full kitchen, you will be sure to call this property your home away from home!

Guest favourite

A stone entrance gate with a tower stands at the beginning of a well-maintained road. Lush green trees line both sides of the driveway, providing a natural frame for the welcoming entryway to the resort.

Villa in Lake Geneva

4.9 out of 5 average rating, 80 reviews

2 Bedroom Villa at Lake Geneva's GRAND Resort

Enjoy a spacious, two-bedroom lock-off villa that sleeps up to 8 adults at the AAA 4-Diamond GRAND GENEVA RESORT, voted one of the top resorts in the Midwest by Condé Nast Traveler. Comfortable accommodations and countless resort amenities make for a fun and relaxing getaway.

Top guest favourite

An indoor heated pool is surrounded by a wooden ceiling and grassy flooring. The pool features a gentle curve and a gently sloping entry. Lounge chairs are positioned nearby, with recreational equipment visible in the background. Large windows allow natural light to fill the space.

Villa in Ringwood

4.91 out of 5 average rating, 194 reviews

Living the High Life Pool House

Relax with family & friends at our large heated indoor pool with a tiki bar, game room & stylish, cozy living space & kitchen. With tons of gathering space, you can enjoy our home in all seasons. *New third bathroom just added 3/01/25*