Holiday rentals in Greendale

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Top-rated holiday rentals in Greendale

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

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Guest favourite

Home in Hubertus

4.86 out of 5 average rating, 432 reviews

Bark Lake, Entire Home, Private Lake Frontage 50ft

A 1,700 sqft home with 3 bedrooms, 2 baths, sofa bed and couch, large outdoor deck, hot tub, grill, 50 feet of lake access. Enjoy the morning sunrise from the East and relax by the waterfront and watch the sunset on the West. Bring the family and enjoy some lake life where the days linger on longer. During the Summer months we have a pier available to fish off of. There are two fire pits, one by the lake and another tucked away near the house. You will love it here, it is very calm and relaxing.

Guest favourite

Townhouse in Bay View

4.87 out of 5 average rating, 92 reviews

*CLEAN* Craftsman Lakeside 3 Bedrm Bay View Duplex

**Sparkling Clean** newly renovated historic 100 year old UPPER duplex in the highly desirable South Shore Park neighborhood of Bay View. Resembles northern Wisconsin cabin with all of the creature comforts of being close to the city of Milwaukee. Just a block off the lake/park/beach/restaurants. Super spacious living room & full size dining room with 3 separate bedrooms and a bathroom with two vanities gives all of your guests ample room to be comfortable. Pull out beds avail Sorry, no pets

Guest favourite

Home in Racine

5 out of 5 average rating, 25 reviews

The Beach house! Enjoy Beachfront Living!

BEST HOUSE ON THE BEACH! Close to marina, harbor, restaurants, downtown stores! Sip your morning coffee enjoying the beautiful sunrise from the porch of this Historical Nautical Beach home! Plenty of sleeping for up to 15 guests. Owner has 2nd lake home 2 blocks away to share in the fun w larger group! Just a short walk to the lake, concessions, 1 mile beach, charter fishing, Zoo, Walking/bike paths. Whether looking for peace and quiet or an exciting fun-filled vacation, this home has it all!

Top guest favourite

Apartment in Racine

4.97 out of 5 average rating, 233 reviews

Gorgeous Main Street Apt with Lake Views (APT2)

Gorgeous, open concept Main Street apartment on 3rd level, with views of downtown and partial views of the lake and harbor. New mini kitchen with 2 induction stove top burners, a microwave, toaster, and all the cookware and utensils needed for a getaway. Supersize custom island, comfy furnishings, and convenient to everything downtown. Unique building is connected to parking garage. Drive up to the 3rd floor - walk just 10 steps to your door - enjoy the views from above, without the climb.

Guest favourite

Guest suite in Racine

4.91 out of 5 average rating, 267 reviews

Racine theme Airbnb at the Red Birch on Erie

Home is set in a quiet neighborhood with a working vegetable farm for a backyard where deer, squirrels, geese and birds entertain. You will enjoy unobstructed, amazing sunsets along with Racine themed artwork and memorabilia, all retro and eclectic in design. It's a short drive to the Lake Michigan shoreline and just minutes away from downtown and the finest beaches! You're host has props from his Old Times photo studio that are available for photography on the grounds in special settings.

Superhost

Home in Kenosha

4.92 out of 5 average rating, 271 reviews

Where Family & Friends Gather to Create & Remember

Come gather, relax & celebrate at our 1 acre estate near beaches, dining & Carthage College! The designer interior features 5 BR/4 Bath, chef's kitchen with Viking & Subzero, Coffee/Espresso Bar, dining area for 12, 2 spacious family rooms with piano, fireplace and TVs. Enjoy dining, lounging & fun in the great outdoors w/hot tub, fire pit, basketball, pickleball, ping pong & lawn games! Beaches are walkable under a mile & near lively downtown w/ harbor, restaurants, shopping & museums.

Superhost

Home in West Allis

4.77 out of 5 average rating, 153 reviews

★Cozy Beach Themed Home★2 Beds★Spacious Parking★

Welcome to this cozy beach themed home located in the heart of West Allis. Close to public transportation and a few minutes driving to State Fair Park, Milwaukee County Zoo, Potawatomi Hotel & Casino, bars, restaurants, and more! Peaceful and quiet spot with plenty of parking on premises (up to 3 cars!) Amenities include: - Parking - TV - WiFi - Self Check in - Fresh Sheets and Towels - Additional Pillows - Shampoo & Conditioner - Soap & Hand Sanitizer - Fully Stocked Kitchen

Guest favourite

Home in West Allis

4.9 out of 5 average rating, 147 reviews

KING BED/Amazing Location/Free parking/Wi-Fi

Enjoy a fun and relaxing stay with family or friends in this stylish, cozy, and comfortable lower unit, which features: 2 bedrooms (1 king, 1 queen ) 1 bathroom Fully equipped kitchen with dining table and designated coffee bar Living room with a 65” smart TV (Netflix included) Home office space Free parking spot Located just a short drive (4 min) from I94, this home offers easy access to all the city's major attractions * the ideal base for exploring the best of Milwaukee

Guest favourite

Home in Racine

5 out of 5 average rating, 6 reviews

Scenic Waterfront Lake Michigan Escape

This stylish 1913 craftsman is perfect for family vacations, group trips or a couple's escape. Situated directly on Lake Michigan you can enjoy breathtaking views from the home and recently constructed deck. The primary bedroom features a new bathroom and magnificent views of the lake. There are three workspaces perfect for "work from home". Finish your day by relaxing in the hot tub, hammock or by the fire. The home is close to city amenities but feels like it's a world away.

Top guest favourite

Apartment in Racine

4.94 out of 5 average rating, 53 reviews

Beautiful Downtown Home - 2 Blks from Lake

Experience the ultimate in relaxation and convenience at this charming vacation rental in Racine. Perfect for a family vacation, romantic getaway, or weekend trip with friends. This 2-bdrm, 2-bath offers a top-notch location just 2 blocks from Lake Michigan and the downtown area. Step inside and discover a beautiful space with all the amenities you could need for your stay. Relax in the cozy living room or whip up a feast in the fully stocked gourmet kitchen.

Guest favourite

Home in Racine

4.88 out of 5 average rating, 48 reviews

The Main Destination

This completely rebuilt home away from home is next door to the best sports bar and grill in the city and within two blocks from five other venues and the lake. Downtown and the marina is in walking distance with all the activities of the seasons/ Designed with family gatherings, showers, vacations, birthdays, contractors , charter fisherman, and traveling businessmen in mind- or just to see the city.

Top guest favourite

Home in Kenosha

4.94 out of 5 average rating, 149 reviews

The Retreat on Lake Michigan 6 bd/4bth 4000 sq ft

*** Please for 2025 a 7-night Friday-Friday reservation is required during peak season from June 13-August 15. *** The best revenge for hard work is harder relaxation, and the ideal getaway is The Retreat, a luxurious and scenic waterfront property where you and your guests are encouraged to relax, reward, and pamper yourselves in splendor.