Holiday rentals in Somers

4.91 out of 5 average rating, 113 reviews

The front exterior of the home is showcased, featuring a brown wooden facade and a welcoming entry area. A small patio leads to the door, with a single chair positioned beside a window. Well-maintained grass and flower beds frame the entrance.

Home in Mount Pleasant

The Farmer's Retreat

Enjoy a stay in this cozy home that boasts the perfect balance of city and country. Many conveniences all within 10 minutes include Starbucks, Walmart, Grocery, dining and shopping. The home itself is nicely updated with a full kitchen, dining room and a large living area. Not to be left out is my favorite feature - The Spacious backyard and outdoor patio. This is a great place to run and play or just enjoy some fresh air. Great stay for whatever brings you to the Kenosha/Racine area

4.92 out of 5 average rating, 278 reviews

The image depicts a vibrant storefront building surrounded by trees and brightly colored flowers. The entrance features large windows and a doorway with a sign that indicates 15 years of celebration. A cobblestone path leads to the entrance, with a glimpse of a neighboring building in the background.

Flat in Kenosha

Cheerful Apartment in Downtown Arts District

Cheerful apartment in newly renovated building above Professional Acting Studio at edge of Kenosha's Downtown Arts District. Near Harbor, beach, 4 museums, art galleries, live entertainment, eclectic restaurants, diners, coffee shops, Trolly, bike paths, parks, lakeshore, antique stores and specialty shops, Prime Outlets, Bristol Renaissance Faire, Great America. Metra Line to Chicago, close to Milwaukee. My place is good for couples, solo adventurers, business travelers, friends and families.

4.99 out of 5 average rating, 236 reviews

An outdoor deck is furnished with a dining table surrounded by four cushioned chairs. A vase filled with fresh flowers is centered on the table. Soft lighting from hanging bulbs adds a cozy ambiance, with views of the neighborhood skyline in the background.

Flat in Kenosha

Downtown-Treetop Deck-2Bd/2Bth

Discover this one-of-a-kind, shabby-chic second-floor apartment in the heart of Downtown Kenosha — just steps from coffee shops, restaurants, museums, and the shores of Lake Michigan. Ideal for travelers who want everything within walking distance. Relax and unwind on the spacious, completely private back deck — your own hidden oasis tucked among treetops and historic neighborhood buildings. Perfect for stays up to four guests. Please note: This property is not suitable for young children.

4.85 out of 5 average rating, 828 reviews

Place to stay in Racine

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.

A bright and airy living area features a white-beamed ceiling and large windows that allow natural light to fill the space. Comfortable seating includes two soft couches, with a wooden coffee table at the center. A dining area with a large table and wicker chairs is visible in the background.

4.92 out of 5 average rating, 309 reviews

Estate on 1 Acre. Fall getaway w/Hot Tub-Sleeps 16

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.

4.95 out of 5 average rating, 130 reviews

The kitchen features light wooden cabinetry and a round dining table with four wooden chairs. A white refrigerator and microwave are positioned alongside a coffee machine on the countertop. The area is well-lit, with welcome signage subtly displayed above the sink.

Flat in Kenosha

Kenosha! Work or play, enjoy your stay!

Soft towels, fluffy pillows, complimentary breakfast, soft drinks, and more in a safe and secure environment. Only children over 13 allowed and must be accompanied by an adult. This n-smoking, pet-free 1-bedroom w/queen bed, twin mattress daybed and cot, furnished kitchen and bath apartment is on the 2nd floor of an office building. Free HI-SPD Wi-Fi and big screen Smart TV. Access to museums, universities, shopping, Chicago’s METRO train and only 37 miles from downtown Milwaukee!

A spacious outdoor patio area features a large fire pit surrounded by several seating chairs. An umbrella-covered dining table provides shaded seating, while the well-maintained lawn enhances the inviting atmosphere. Sunlight casts gentle shadows across the patio, highlighting its accessibility.

4.91 out of 5 average rating, 94 reviews

Perfect Getaway- Fire Pit, Game room, Near Lake

Make this 5-bedroom, 3.5-bath home with an incredible fire pit in Kenosha, WI your stay for a great fall getaway. Perfect for your next family reunion and/ holiday gathering for your group or getaway. Fire-pit great for those chilly fall nights and perfect for grilling s’mores. Entertaining activities for kids and adults include a music room with several instruments, a recreational room in the basement, and outdoor enjoyment. Conveniently located 2 miles from Lake Michigan.

4.95 out of 5 average rating, 105 reviews

A wooden deck steps lead to the entrance of a recently renovated home, framed by flower pots and outdoor seating. Decorative string lights are visible above, and an American flag is displayed on the left, adding to the welcoming atmosphere.

Home in Salem

Lago Amore - Channel house, pier, kayaks

A recently updated family home awaits you. Unwind with breathtaking views in the quaint Village of Paddock Lake. Kayak, go to the beach, fish with the family or ice fish and snowmobile during the winter. Bring your boat with public launch access. No matter the season, this home offers wonderful views of Paddock Lake. Centrally located between Milwaukee and Chicago, as well as Lake Geneva and Kenosha, there is always something happening just a short drive in any direction.

A cozy sunroom is featured with large windows, allowing natural light to fill the space. A comfortable gray sectional sofa provides seating, accompanied by a decorative pillow. Soft lighting fixtures and a unique chandelier add a welcoming touch to the inviting atmosphere.

4.99 out of 5 average rating, 143 reviews

6th Ave Harborside

Perfectly located near downtown Kenosha, this cozy and comfortable home makes it easy to enjoy the best of the area. Ride the bikes to the farmers market, stroll to the beach, or spend time along the marina and harbor. The large dining room invites long meals and relaxed evenings together. An ideal home base for a peaceful getaway, visiting family, or attending local events. One night stays are available on a limited basis - reach out for details!

Superhost

A modern kitchen showcases warm wood cabinets and a spacious countertop. A round dining table with four seats is positioned nearby, accentuated by a welcoming atmosphere. Ample natural light fills the room through the large window, illuminating the decorative elements and culinary tools.

4.92 out of 5 average rating, 174 reviews

Modern! Pro Cleaned, Self Check In - Sleeps 10

Enjoy your time together in this modern three bedroom one and a half bath ranch. The newly updated interior will make you feel like you have arrived. Stately hardwood floors accent the new decor. Kitchen is stocked for your inner gourmet cook. You will love all the stainless steel appliances. With our all new queen double plush beds, you will enjoy the ultimate sleep experience.