Holiday rentals in Raymond

The Crows Nest Cottage 1

Welcome to our charming 1-bedroom cottage by a serene pond. This cozy retreat features a unique basketball/pickleball court, multiple outdoor patios, and a delightful treehouse lounge area. Perfect for relaxation ! Just 5 minutes away is The Rock Sports Complex, offering top-tier activities like Topgolf, minor league baseball, an umbrella bar, hiking trails,ski hills.Whether you’re seeking tranquility or adventure, our cottage provides the ideal getaway for both.washer,dryer BOAT TOURS AVAILABLE

A Showplace of Greendale History on Apple Court

This entire 3 bedroom home is a vintage gem in Historic Greendale, Wisconsin — and it's all yours! • NO extra charge for cleaning! • FREE on-site parking for two cars • An EASY walk to charming boutiques & eateries • Located in a National Historic Landmark district • Steeped in 1930s History with Eleanor Roosevelt design features Features stylish, functional layout as part of FDR’s 1930s New Deal. Includes high speed Internet, central air conditioning, private patio for outdoor enjoyment.

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.

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.

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.

7 1/2 Acre Private Estate w/inground pool, hot tub

Any event needs to be approved. First 4 guests 10 y/o and up are included in the nightly rate. Then I charge per person per night over 4 guests. PETS ALLOWED FOR $200.00 3 Bedroom, 3 Bathroom, 3000 Sq/ft Heated Pool!!, Hot Tub!!, Fishing Pond!!, Game Room all on 7 1/2 Acres!!!!!! It is a ONE OF A KIND!! NEW REC ROOM!! 1/2 Acre Fishing pond Stocked with MANY FISH!!! Sand Beach and Pier with boat, Paddle Boards. heated in ground pool, (open May1 - October 1st), hot tub.

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!

Eagle Lake Home Steps to Beach Deck Firepit

Welcome to your dream lakeside getaway! This beautifully renovated 3BR, 1.5BA home is just steps from Eagle Lake. Enjoy an open-concept layout, vaulted ceilings, a full kitchen, and cozy furnishings. Relax on the large deck with sunset views, or explore nearby beaches, trails, and boat launches. With room for the whole family, updated amenities, and plenty of charm, it’s the perfect retreat for adventure or relaxation. Book now and make the most of your Eagle Lake escape!

Charming log cabin in the woods

This log cabin is an old hunting lodge. It is rustic, charming and quaint, nestled in the woods of Wisconsin and next to a tranquil pond. The location is close to the Johnson Park golf course and 5 miles from the beautiful Lake Michigan shore. It is a perfect place to relax, write or escape from the stress of life. In the winter a 4-wheel drive vehicle is necessary to reach the site. Please note: bathroom facilities are a close walk away. Heating from wood stove only.

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.

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**

Lakefront 2BR w/ Kayaks + Paddle Boards | Dogs OK

Lake life starts here. ☀️ Enjoy a peaceful lakefront escape with a private pier on a quiet electric-motor-only lake. Spend your days on the water and evenings grilling with lake views or relaxing by the fire pit. Just minutes from Antioch, but it feels a world away. 🚣 3 kayaks + paddle boards 🌊 Swim raft + pedal boat 🔥 Fire pit + lake views 🐾 Dog-friendly 2BR, sleeps 7. Ask about 4–6 night deals! @RockLakeEscape