Holiday rentals in Westchester

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Top-rated holiday rentals in Westchester

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

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Top guest favourite
A modern kitchen showcases dark wood cabinetry and stainless steel appliances, including a refrigerator and gas stove. A granite countertop extends into a bar area with three metal stools. A microwave and kettle are placed on the counter, illuminated by overhead lighting.
Guest suite in Wood Dale
4.91 out of 5 average rating, 534 reviews

The Deer Suite

This is a one bedroom apartment within the home. NOT FOR PARTY No Smoking , ABSOLUTELY No events, parties, or large gatherings. The apartment has a separate entrance from the home main entrance. The apartment also comes with comcast high speed internet. The living room couch can be turned into a double bed, that sleeps two. Large ,shower towels and shampoo included. The apartment includes washer and dryer.The bedroom sleeps two .It is about 30min drive to Downtown-Chicago and15min to O'hare .

Superhost
A dining area is presented with a long glass table set for six, surrounded by tall upholstered chairs. The space features a decorative rug beneath the table and wall art made of natural materials, with soft lighting illuminating the room.
Home in Elmhurst
4.79 out of 5 average rating, 121 reviews

Luxe 3BR, 2BA + Hot Tub

Discover our delightful raised ranch offering 3BR, 2 Full BA, and an updated kitchen. The open living and dining area is bathed in natural light, while the cozy family room awaits for relaxation. Attached garage. Relax in the sprawling backyard with upper and lower decks, a great hot tub. Easy access to I-294 and I-88, close to Elmhurst Hospital, 20 mins to chi. Indulge in snacks and coffee from the kitchen's bar for a perfect stay. Book now and cherish memorable moments in this tranquil haven!

Guest favourite
A spacious artist loft features a living area with hardwood floors and large windows allowing natural light. A leather sofa is positioned in the center, with stylish chairs nearby. The open kitchen is visible in the background, along with a modern dining space under soft lighting.
Loft in Brookfield
4.91 out of 5 average rating, 138 reviews

1920s fully updated unique open artist loft space

True artist living loft space!!! One of a kind space in a safe area of the western suburbs close to the city and easy commute to shops stores. very close to trains buses and expressways. Private parking lot. No unit above or below. Quiet and private spacious updated wide open loft. Hardwood floors throughout forced heat and ac slated steel designer bathroom.. Double oven dishwasher electric cooktop sub zero fridge microwave and toaster oven. Ceiling fans two beds. Can sleep 6 for added cost

Guest favourite
Home in Northlake
4.79 out of 5 average rating, 19 reviews

Garden Suite 10 Min to O’Hare w/ Yard & Grill

Relax in our Cozy-Chic Garden Suite, minutes from O’Hare & Rosemont! Private backyard with grill, gated parking, snacks, drinks & games for a cozy stay.🏡 Need transportation?🚗We offer chauffeur services, including seamless airport pickup/drop-off or full-stay transportation tailored to your plans! Celebrating a birthday or special occasion? We offer professional on-site makeup services & can decorate the suite for your event upon request perfect for surprises, and memorable moments. 💄🎉

Home in Villa Park
5 out of 5 average rating, 4 reviews

Cozy 5BD Home with Scandinavian Vibes

✨ Newly Renovated Spacious Scandinavian-Style Home Near Chicago Airport ☀️ Enjoy your stay in this beautiful, fully equipped 5-bd, 2-bath home featuring modern Scandinavian-style furniture, rattan details, thoughtful touches, and all the comforts you need for a relaxing getaway. This spacious and inviting house is just a short drive from Chicago O’Hare Airport and downtown, offering both convenience and comfort yet it remains peaceful and quiet, so you won’t hear the noise of passing planes.

Guest favourite
A comfortable living area is presented with a light-colored sofa draped with a soft blanket. A wooden coffee table sits center stage on a patterned rug. Two decorative lamps illuminate the space, and a bookshelf with various books and a dartboard is positioned against the wall.
Flat in Melrose Park
4.97 out of 5 average rating, 106 reviews

KNG+QN/1 free parking/18 min to O’hare & Allstate

-18 minutes to O’Hare/Allstate Arena -35 minutes to DT Chicago -King & QN 2 bedroom + sleeper sofa/1 bath apartment decorated with a playful & bright nautical theme & vintage accent pieces. -Board games, books, darts, & large screen TV for entertainment. -Tea & Coffee station -Free designated parking space -walk to local restaurants at corner or playground w/outside seating up the street. -Nothing fancy, but convenient! urban/suburbia vibe in quieter corner of busy central area

Top guest favourite
A spacious bed with patterned bedding rests against a geometric accent wall painted in dark blue and vibrant yellow. Two nightstands with lamps are positioned on either side, contributing to the cozy and modern aesthetic of the room.
Flat in Maywood
4.94 out of 5 average rating, 155 reviews

Cozy guest studio, great for couples!

This unique place has a style all its own. Enjoy this beautiful, cozy guest studio with modern touches and well furnished living area, small kitchenette with mini fridge and microwave to reheat a quick bite before heading to the city, full bathroom with rainfall shower and handheld sprayer to help you relax after a long day. Flat screen TV with Xfinity streaming device so you can connect your accounts and enjoy your favorite shows and movies for a quiet stay in.

Guest favourite
The exterior of the vintage garage apartment is shown, featuring a bright yellow facade with two white garage doors. A large window is positioned above the doors, with greenery surrounding the property, contributing to the charming appearance.
Guest house in Villa Park
4.92 out of 5 average rating, 138 reviews

Eclectic Coach House Apartment

Vintage Charmer! 1935 Sears Craftsman Coach House garage apartment. Beautiful safe neighborhood surrounded by historic homes and just steps from the Illinois prairie path, parks, brewery's/bars, restaurants and more! With an eclectic boho chic vibe, featuring full kitchen and on site private washer/dryer. Overlooking an accessible lovely backyard! Close to airports and easy access to public transportation/major highways. Just 30 min from the Chicago Loop!

Guest favourite
A cozy living area features a plush gray sofa accompanied by light-colored ottomans. A glass coffee table sits on a multicolored rug, adding warmth to the space. Natural light filters through sheer curtains, enhancing the modern design complemented by a mounted flat-screen television.
Flat in Berwyn
5 out of 5 average rating, 25 reviews

NEW Jade Haven in Berwyn/Riverside

Step into Jade Haven, where tranquility meets modern elegance. Welcome to Jade Haven your serene retreat of calm and comfort.Inspired by the soothing essence of jade, this one-bedroom suite blends modern elegance with spa-like tranquility. Enjoy a fully equipped kitchen, cozy living area, a serene bedroom designed for restful nights and peaceful mornings. The space features a sleek, airy design with thoughtful touches to make you feel right at home.

Top guest favourite
A single-story brick home with a well-maintained front yard features green shrubs and a neat pathway leading to the entrance. Large windows allow natural light to illuminate the interior, while a tree provides shade near the entrance.
Home in Brookfield
4.98 out of 5 average rating, 57 reviews

Cozy Home in Brookfield

Discover tranquility just minutes from the busy city life! Nestled in the heart of Brookfield, IL, our charming home offers the perfect blend of suburban serenity and urban convenience. Just an 8-minute walk from the train station, you'll find easy access to downtown Chicago while enjoying the peaceful atmosphere of our neighborhood. Pets are allowed, but no exotic pets and no cats or dogs with a bite history.

Top guest favourite
A welcoming living room is highlighted by a comfortable sectional sofa with decorative pillows. A patterned area rug covers the hardwood floor, and a reading nook features a unique egg chair. Artwork adorns the walls, complemented by greenery from potted plants.
Home in Lombard
4.99 out of 5 average rating, 127 reviews

Modern Boho house in Lombard 7 min to Metra

Kick back and relax in this calm, stylish space. Visiting family in Chicagoland area? Traveling for work? Lombard is centrally located 30 min to everywhere! The house is only 6 min to Oakbrook Shopping and Business Center and upscale shopping and fabulous restaurants like RH with rooftop restaurant, 8 min to Yorktown Shopping Center. Whatever your travel purpose is, we will be happy to host you! Welcome home!

Guest favourite
Home in Elmhurst
5 out of 5 average rating, 6 reviews

Elmhurst Luxury 4BR w/ Pool, Fenced Yard, Downtown

✨ Beautiful & Spacious Home with Pool ✨ Perfect for families and groups, this home offers 3 bedrooms and 1 bath on the main floor, plus a luxurious master suite upstairs with a walk-in shower, huge closet, and laundry room. Enjoy the open-concept living room, fully equipped kitchen, and a stunning backyard with a pool the ideal spot for relaxation and fun during your stay!

Popular amenities for Westchester holiday rentals

  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Westchester