Holiday rentals in Westmont

4.91 out of 5 average rating, 154 reviews

Home in Glen Ellyn

Home in Glen Ellyn

Beautiful 5 bedroom, 2.5 bath home in Glen Ellyn, fully furnished with everything you may need for a wonderful stay! Located in the peaceful suburbs of Glen Ellyn, the area is perfect for families or friends who would like a comfortable getaway. Located 40 minutes from downtown Chicago and Midway airport and 30 minutes from O'Hare airport. Located nearby major highways and shopping centers. Large, private and completely enclosed backyard perfect for kids to play in or a relaxed evening of BBQ!

Guest suite in Brookfield

5 out of 5 average rating, 104 reviews

Charming Chicago suburb! 1 bedroom apartment.

Enjoy your stay just west of Chicago in our 1880 updated 1st floor of a 2 flat. You get a one bedroom apartment with queen bed, private kitchen and bath, separate office for work, plus 2 porches for you to enjoy. Brookfield is a charming village with unique restaurants, bars, salon and day spa, coffee shops, library and the train to Chicago--all within a 5 minute walk. We want you to feel at home; but before you book understand that you may not smoke ANYTHING in the unit or on the property.

5 out of 5 average rating, 29 reviews

Home in Lombard

Spacious Home in Chicago Suburbs

Enjoy your stay in Chicagoland in this gorgeous, newly updated home. After a full day of sightseeing in the Windy City or hitting the local shops and attractions, this is a restful homebase to return to. The spacious fenced-in backyard and patio, a comfortable and tastefully furnished basement, and the full kitchen with amenities provide the perfect environment to unwind. You’ll find plenty of seating, sleeping accommodations for nearly a dozen, and an open layout that fosters connection.

4.99 out of 5 average rating, 659 reviews

Guest suite in Geneva

A Suite within a Cozy cottage in Geneva Illinois.

Cozy private suite in the lower level. Guests have the suite to themselves. The bathroom is adjacent to the room and is private. There is a small fridge, a coffee maker, and a microwave oven. We are in Geneva, Illinois. We are LGBTQ+friendly. Our space is ideal for shorter stays and visitors on the go . Not suitable for staycations. Quiet area. Hosts live on the upper level and guests pass through our space to get to the suite. In a bind we can accommodate a 3rd guest and a pet. Welcome.

5 out of 5 average rating, 3 reviews

Home in Westmont

Cute & Cozy Westmont, IL House Near the Best Areas

Beautiful 2 bedroom 1 bath house with a 2 car garage, private driveway and plenty of parking. With a nice back yard in one of Westmont's prime location close to great restaurants, shopping areas, easy access to expressways and airports in a great quiet neighborhood. Fully furnished with high-speed internet Wifi and stocked with essentials to make your stay comfortable. Near Morton Arboretum, Metra Station, Yorktown Center, upscale Oakbrook Center and a short commute to downtown Chicago.

Apartment in Clarendon Hills

5 out of 5 average rating, 86 reviews

Apartment in Clarendon Hills.

Newly renovated Suite in multi family home in Clarendon Hills. Main level: fully equipped kitchen/island, dining area, living room & family room with fireplace. Upper level: Bedroom 1 - king size bed, walk in closet, private bathroom/shower. Bedroom 2 - queen bed, closet. Bedroom 3 - size bed, closet. Living room has a pull-out sofa bed. Family room with gas fireplace, access to deck/outdoor area. Easy access to restaurants, shopping (Oak Brook Mall minutes away), Metra, O’Hare.

4.99 out of 5 average rating, 157 reviews

Flat in Aurora

Penthouse In The Historic Hobbs

Experience luxury and historic charm at the Penthouse in the Historic Hobbs. Built in 1892, and restored in 2023, this new one bedroom corner unit offers a panoramic view of the Aurora skyline. Cook a delicious meal in the fully stocked kitchen. Dine at the bespoke table in the window bay under the iconic onion dome. Relax on the cozy sofa and enjoy a movie on the big screen TV. Rest in the plush king-sized bed. This urban retreat is near coffee, shopping, art and entertainment.

4.95 out of 5 average rating, 57 reviews

Home in Westmont

Charming Home in Westmont, Close to Chicago!

Very peaceful neighborhood! This house has the best location in the Western Suburbs of Chicago. Walking distance to downtown Westmont and train station. A few minutes drive to malls, parks and everything...eight minutes drive to downtown Downers Grove. 30 minutes drive to downtown Chicago. This house has an appealing open floor plan and a well equipped kitchen. Each bedroom has its own TV. Lower level game room has the most popular board games, toys and an air hockey table.

4.69 out of 5 average rating, 13 reviews

Home in Westmont

"Big" Tiny House yard 20 minutes from Chicago

Established Westmont BNB owners introduce "Tiny" launching March 15th 2025 She is a beauty gorgeous hardwood floors, large bedroom walk in closer. One Bedroom with walk I closet home, attached garage with laundry. Enclosed yard. the cutest house on the block, don't blink she is popular already! Sleeps 3 guests two in the full size one on the Sleeper sofa. couch tv wifi glorious kitchen sunny breakfast nook! Full kitchen and Bathroom, central air and heat and parking spot.

4.91 out of 5 average rating, 106 reviews

Home in Downers Grove

Games, Grounds, Goodness in DG

Our family loves games and when travelling it is great to have entertainment for the whole family. Our game room includes a video arcade game with over 400 options, boardgames and more! Maybe simple cards or puzzles are your preference--we have them all in this fully furnished home with large backyard to play in. Bedroom 1--bunk bed with full on bottom, twin on top Bedroom 2--queen bed with room for a play pen Stay for a weekend or longer and know fun will be had!

Guest house in Villa Park

4.92 out of 5 average rating, 124 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!

4.9 out of 5 average rating, 379 reviews

Tiny home in Burr Ridge

Less is more! Pet friendly Tiny Home near Chicago!

Less is more--see for yourself how big 250 square feet can really feel! For those who would love to try tiny living and a minimalist lifestyle, this is the perfect getaway. This tiny house has everything you will need to fall in love with tiny living! There is a fenced yard, grass area for furry friends, free parking and is close to hiking trails, restaurants, shops, breweries, bars, and Chicago! Check us out on Insta: @LessIsMore_TinyHome

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Other great holiday rentals in Westmont

Private room in West Lawn

4.85 out of 5 average rating, 392 reviews

The Red Room

SydneRating, 5 stars2 weeks ago

Family is very kind and very welcoming especially for solo travelers. Spent my first night relaxing with the family and even going for a walk. definitely recommend this place!

Private room in La Grange Park

4.88 out of 5 average rating, 58 reviews

Hidden Gem, Perfect Private Bed/Bath in La Grange

JoshuaRating, 5 stars2 weeks ago

Wow. what a little gem this place truly is. Katrina and family were the most kindest and accommodating hosts. A beautiful neighborhood, safe, clean and was easy to get to. Highly recommended and will visit again, I thoroughly enjoyed the stay. Welcoming atmosphere with a beautiful energetic.

Private room in Woodridge

4.83 out of 5 average rating, 12 reviews

Master Room w/private bath in a ranch

LaioRating, 5 stars3 months ago

Sophie is a 5 star host! That is my second time at Sophie's house, and if I have the opportunity, I'll do it again. Recommend to everyone.

4.99 out of 5 average rating, 217 reviews

Private room in Elmhurst

Chic Oasis near Downtown Chicago

Bella Rating, 5 stars2 weeks ago

Thank you Jan for welcoming me into your home. Jan communicated very well throughout the stay. She went above and beyond to make sure we enjoyed our stay. Bless you!

Private room in North Riverside

4.93 out of 5 average rating, 215 reviews

The Albany Park Room at the Cape Cod in Riverside

GianfrancoRating, 5 stars2 weeks ago

I had an amazing experience staying at this Airbnb! From the moment I arrived, everything exceeded my expectations. The space was spotless, beautifully decorated, and exactly as described—if not better. The bed was incredibly comfortable, and all the little touches (like fresh towels and local recommendations) made it feel like a home away from home. The host was outstanding—friendly, responsive, and genuinely committed to making sure I had a great stay. Check-in and check-out were seamless, and they went above and beyond to accommodate any questions I had. The location was perfect: quiet and peaceful, but still close to restaurants, shops, and everything I wanted to explore. Whether you’re traveling for business or a getaway, I highly recommend this place. I’ll definitely be coming back!

Private room in Villa Park

4.85 out of 5 average rating, 306 reviews

BK's Stay'zzz

TravisRating, 5 stars1 week ago

Stayed at Brad’s a second time. Didn’t expect to stay another night but he was very accommodating to my last minute scheduling

Private room in Norwood Park

4.8 out of 5 average rating, 223 reviews

Skyline Room, near Medical Ctr, Upstairs

ThoRating, 5 stars5 months ago

Enjoyed my stay, very clean and comfortable. Very convenient and close to airport, train station, bus stop, etc. The host is amazing and responsive to guest’s needs.