Holiday houses in Raymond

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Top-rated holiday rentals in Raymond

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Guest favourite
The living area features a blue couch complemented by a yellow armchair, arranged around a coffee table. A rug with a modern pattern covers the floor, adding warmth. Wall art and plants contribute to the inviting ambiance, while dimmable lights enhance the space.
Condo in Kenosha
4.9 out of 5 average rating, 282 reviews

Spacious 2-BDRM/ Safe area Great for work & vacay

You will enjoy this carefully designed, well-decorated and well-furnished basement apartment. It is roomy (over 950 feet), pleasant, private and quiet in a residential area. Whether you ( 1-4 guests) come for work, business, family or a special function, its full kitchen, classy bathroom, extra-comfortable king and queen size beds, blender, high-speed internet and ergonomic chairs (2nd on demand) as well as free parking will add comfort and extra ease to your stay, and make it one to remember.

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Place to stay in Racine
4.84 out of 5 average rating, 812 reviews

Wisconsin Treehouse Getaway!

Featured in Timeout Magazine as Chicago's Top 10 Airbnbs, and in other outlets as Wisconsin's most romantic and top 5 Airbnbs, this space has an immersive nature experience, overlooking a creek and woods with all modern comforts. Imagine yourself in a cabin in the woods to unplug and recharge, waking up to chirping birds as if in a Treehouse! 3 miles to Lake Michigan & dwntn. lf we're home, a complimentary Chai! Come, make lifelong memories at Racine's Best Kept Secret No local bookings.

Top Guest favourite
An outdoor patio is shown with a red umbrella providing shade over a black table and four metal chairs. A barbecue grill is positioned nearby, with a view of a green lawn and a distant red barn visible in the background.
Home in Racine
4.98 out of 5 average rating, 112 reviews

Farm House Retreat w/ Private Backyard & Garage

Comfort, convenience and country views await you! Relax on the private patio and soak up the beautiful scenery. Minutes from the lakefront, Racine Zoo and short drive to Milwaukee, you'll enjoy this completely updated home. Cook a meal in the fully stocked kitchen and kick back in the comfy family room. Whether you are here to visit family, attend special events or business travel, you'll find everything you need here. And if you're a little country at heart, the view will not disappoint.

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Tiny home in Muskego
5 out of 5 average rating, 3 reviews

Tiny House on Century Farmstead

Stay comfortably in Muskego at this 1-bedroom tiny house on a century farm. The delightful space features a cozy full bed, kitchenette, bathroom, porch, and fire pit. Guests enjoy a pleasant indoor climate thanks to heating and AC and a screened in porch when the weather is pleasant. Whether you’re relaxing after a day of exploring or simply unwinding, this tiny house offers a fantastic retreat. Experience our farm with chickens, ducks and turkeys right outside your 125 sqft tiny home.

Top Guest favourite
The exterior of the home features a two-story brick structure with large screened windows and arched entrances. Lush greenery surrounds the property, complemented by vibrant fall foliage. A spacious patio area with seating is visible, set against a backdrop of mature trees and a well-maintained lawn.
Guest suite in Wind Lake
4.92 out of 5 average rating, 36 reviews

The Secret Garden

Take it easy at this unique and tranquil getaway in the lower level private garden apartment of our family home! Includes full kitchen; large great room with big screen TV, sleeper sofa, and foosball table; large patio outside surrounded by beautiful gardens; 2 bedrooms with king size beds and private wooded views; generously sized bathroom with full bath. A mere 30-40 minute drive from Lake Geneva, downtown Milwaukee, and more! Come enjoy your stay at our garden cottage space!

Top Guest favourite
Home in Wind Lake
5 out of 5 average rating, 22 reviews

Lakeside Inn

Welcome to your lakeside escape. Wake up to sunlight pouring through the windows. Sip coffee while overlooking the water. Enjoy boating, kayaking and swimming in the summer and fishing, skating and the calmness of perfect snowfalls in the winter. Wind down while enjoying a golden sunset from your very own pier. Enjoy open living spaces perfect for cooking, gathering and making memories. A cozy, welcoming retreat, you'll love in every season. Lake life awaits, come visit!

Top Guest favourite
Guest suite in South Milwaukee
4.99 out of 5 average rating, 94 reviews

Historic Hawthorne House

Nestled just steps from Grant Park Beach & Lake Michigan, the scenic Seven Bridges Trail, and the lush Grant Park Golf Course, this unique rental offers a blend of history, charm and comfort. Only a 10 minute drive to Mitchell International Airport and an easy 20 min drive to downtown Milwaukee. Whether you're here to unwind in nature, explore the local parks, enjoy a peaceful lakeside stay, or enjoy the best that Milwaukee has to offer this home has everything you need.

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A wooden dining table is surrounded by six matching spindle-back chairs. A light-colored table runner runs across the center, complemented by a simple candle holder. Sunlight pours in from a nearby window, illuminating the warm wood floors and creating a cozy dining space.
Home in Caledonia
4.72 out of 5 average rating, 29 reviews

Convenient Countryside Oasis

Escape to the serene countryside with our charming abode, offering a tranquil retreat from the hustle and bustle of city life. Just a stones throw away from downtown, this cozy 3 bedroom home boasts beautiful wood floors, creating a warm and inviting ambiance for your stay. Despite its secluded setting, our rental is conveniently located just a short distance from downtown Milwaukee, offering easy access to a myriad of attractions and entertainment options.

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Home in Milwaukee
5 out of 5 average rating, 4 reviews

Historic Walker’s Point Home • Sleeps 10 • Garage

Welcome to Rosa Luna, a beautifully restored late-1800s cottage in the heart of Walker’s Point. Enjoy vintage charm, original hardwood floors, 3 bedrooms, a spacious skylit attic retreat with 2 double beds, a private fenced backyard, and secure 2-car garage parking. Minutes from downtown, Bay View, restaurants, coffee, nightlife, Summerfest, and sporting events—it’s the perfect home base for your Milwaukee getaway for families or groups of friends.

Top Guest favourite
Home in Greenfield
4.97 out of 5 average rating, 38 reviews

Cozy, Cute, & Clean !

Cozy, Cute, and Clean! SHORT TERM fully furnished rental available in a quiet neighborhood of Greenfield! 20 minutes or less drive to: Downtown Milwaukee, Lake Michigan, Brady Street, Am-Fam Field, UW-Milwaukee, Marquette University; Advocate-Aurora, Ascension, & Froedtert Hospitals, stores, restaurants, and just 40 mins from the IL border! Utilities included In-Unit Washer/Dryer **Perfect for Travel Nurses/Techs, and Business Professionals**

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Home in Muskego
4.88 out of 5 average rating, 8 reviews

Relax at Muskego Lakehouse – 30 mins to Downtown!

Unwind with the whole family at this charming Cape Cod-style lake house! With plenty of beds and ample outdoor seating, it's the perfect spot to relax by the water, soak in the fresh air, or cozy up indoors with stunning lake views. The property features a private dock and a small beach area for endless fun. Cast a line off the pier, take in the breathtaking sunset from the spacious deck, and create unforgettable memories by the lake!

Top Guest favourite
Home in Burlington
4.97 out of 5 average rating, 37 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!

Popular amenities for Raymond holiday rentals

  1. Airbnb
  2. United States
  3. Wisconsin
  4. Racine County
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