Holiday rentals in Westchester

Short Drive to Hospitals/Airports/Downtown Chicago

This centrally located spacious basement apartment is 10-15 miles from Elmhurst Hospital, Loyola Med, and Downtown Chicago. Whether you are exploring the BEST BIG CITY as awarded by Condé Nast Traveler or just stopping through on your journey, this home has everything you and your family need to feel right at home in Chicago. Minutes to downtown LaGrange, the sprawling Rosemont entertainment district, and the fabulous outdoor Oak Brook Mall with tons of shopping, entertainment, and restaurants.

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!

Stunning 2bd 1bath w/free parking, W/D & fireplace

Whether you're here to visit family or friends, to attend a conference in the city or a quick getaway, your family will love renting our entire flat. It has all the comforts of home located on a beautiful block in the historic Frank Lloyd Wright District in Oak Park. Here, you will be close to The Frank Lloyd Wright Home/Studio, downtown Oak Park, amazing restaurants and attractions, the Green and Blue line trains that will take you to downtown Chicago, and major highways and shopping centers.

KNG & QN 2bdrm/free parking/desk/central location

Nothing fancy, but cozy & convenient! Your friends & family will love the entertainment style living/dining room that seats 6 and overlooks smart TV & livingroom. Spread out, cook, watch a movie, and cozy up near the fireplace while you play tunes. The KNG & QN bedrooms + sleeper sofa will sleep your crew comfortably. Pick a board game out of our large entertainment chest, read something from our library nook, get work done in the office corner, or cook in our fully equipped kitchen.

Charming Home Close to Loyola, Zoo & Chicagoland

This inviting home is perfectly situated -Minutes to Downtown Chicago: Explore iconic landmarks, shopping, dining, and entertainment just a short drive away -Brookfield Zoo: 15 minutes from the home, perfect for animal lovers and nature enthusiasts. -Loyola Hospital: A quick drive to one of the region's top medical facilities -O'Hare Airport: Only a short distance for travelers flying in or out of Chicago Age Requirement: Guest must be 25 or older to book. No Parties or Gatherings allowed

The Green Bungalow: Charming 1-BR apt. with patio

Situated in a residential neighborhood just outside the city limits, this lovely 2nd floor apartment is blocks from the Blue Line train and highway. Our newly renovated vintage unit has a full kitchen, hardwood floors, plenty of natural light, a backyard patio and its own private entrance. Our bungalow is walking distance to cafes, restaurants, shopping, music and nightlife. Enjoy the charm of the suburbs while having easy access to all the attractions Chicago's downtown has to offer.

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

Jacuzzi, King Beds, Easy Access to DT Chicago!

Our 4bd, 2.5ba house is perfect for a group of friends or family looking for a clean, modern place in a wonderful neighborhood. There is plenty of space for 10 people to sleep comfortably (4 beds), as well as 4 smart TVs (w/ complimentary Hulu & Disney+), a deck w/ a pergola, built-in grill, & firepit, a large fenced backyard, a game room (w/ ping pong and more), a jacuzzi, an office space, & much more. Great access to City of Chicago by I-290, as it's directly west of Downtown!

NEW Jade Haven in Berwyn/Riverside

Step into Jade Haven, where tranquility meets modern elegance. This serene one-bedroom, one-bath suite offers a peaceful retreat, inspired by the calming essence of jade. The space features a sleek, airy design with thoughtful touches to make you feel right at home. Fully equipped kitchen, cozy living area, the bedroom invites restful nights, while the spa-like bathroom offers a moment of quiet indulgence. Perfect for a restful getaway or a productive stay.