Holiday rentals in Clarendon Hills

Guest suite in Clarendon Hills

5 out of 5 average rating, 6 reviews

Deluxe cozy 3Bdrm/2Ba, 30 days+, sleeps 3-6

Lovely 3 Bedroom/ 2 Bathroom Garden Apartment, in a quiet & safe residential area w. Hinsdale Central schools. Walking distance 2 Jewel/Starbucks, easy access 2 Metra, Oakbrook Mall, restaurants, highways, 30 min 2 O'Hare/ downtown Chicago. Digital keypad check-in, parking on driveway. Great for mid term rental 3-12 months, workers, students, nurses, doctors, digital nomads, friends & families up to 6 people. We put a lot of love and care into this home and want you to have a lovely stay.

4.94 out of 5 average rating, 31 reviews

Home in Westmont

Westmont,Il 4/3 on the Lake

We may take a refundable deposit. We must say this because our direct booking site is linked. A lovely place on the lake in summer we rent entire house. This is a home that is split into a duplex. One side we have 3 bedrooms 2 baths. The other side is 1 bedroom and 1 bath. Both sides have separate entrances and decks. Enjoy the beautiful view while staying. You have access to entire house and yard except garage with this listing. This listing is for renting both sides. They do not connect.

Guest suite in Brookfield

5 out of 5 average rating, 102 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.

Apartment in Clarendon Hills

5 out of 5 average rating, 85 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, 155 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.

4.9 out of 5 average rating, 88 reviews

Home in Westmont

Chic Cottage close to Metra large enclosed yard.

Perfect for 1 - 4 in quaint Westmont. Decor is vintage chic with a focus on retro arts and collectibles. Cozy blankets and whimsical art adorn the walls. Perfect for folks who love cute quaint CLEAN and comfy not Kondo! A place to call home where the barn door closes off the Living room. A dinner for 6 in the quaint dining area. Laundry room in the home. New Grill for Summer 2024, out door furniture. Beyond pet friendly we have many accessories for Dogs.

5 out of 5 average rating, 3 reviews

Flat in Berwyn

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.

4.9 out of 5 average rating, 31 reviews

Apartment in Westmont

Hidden Gem

Apartment building was built 1976. Washer and dryer are located in the lower level in public area and coins are needed. (Coins provided). Plenty of free parking spaces just behind the building. Our Condo has two bedrooms upstairs and one downstairs. The bathroom is upstairs, so the downstairs bedroom doesn't have its own bathroom. A spiral stairs is inside the unit, you can use outer stairs too. Keys for the downstairs bedroom are the same for the upstairs

4.9 out of 5 average rating, 377 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 Clarendon Hills

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 stars1 week 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.

Private room in Naperville

4.98 out of 5 average rating, 65 reviews

Private spacious room w/dresser in a nice home

ContessaRating, 5 starstoday

⭐️⭐️⭐️⭐️⭐️ A+ Stay! Juan’s place was one of the best I’ve ever stayed in—clean, peaceful, and incredibly comfortable. His communication was excellent from start to finish, making everything easy and stress-free. If we ever come back to the area, we’ll definitely stay here again. Highly recommend it to anyone needing a great night’s rest and a relaxing stay. Thank you, Juan!

Private room in Richton Park

4.85 out of 5 average rating, 241 reviews

Urbal retreat

RobertRating, 5 stars1 week ago

The host was great, we loved the cozy room and amenities. The shower was very clean and nice. Great spot for if you’re just passing through.

4.98 out of 5 average rating, 125 reviews

Private room in Wheaton

Close To Downtown For Business & Family visits!

TheresaRating, 5 stars2 days ago

Nancy was a great host, always helpful and considerate. highly recommend staying here while in Wheaton.

4.8 out of 5 average rating, 363 reviews

Hotel room in Itasca

King Bed at Chicago Northwest + PET Friendly

JenniferRating, 5 stars2 weeks ago

had a wonderful stay. would stay again.

5 out of 5 average rating, 9 reviews

Private room in Oak Park

DT Oak Park LUXE Private BR C | Queen Bed Sleeps 2

YanitRating, 5 stars2 weeks ago

I had a great stay at this place! The location was absolutely perfect—close to grocery stores and everything I needed was easily accessible. The bedroom was definitely my favorite part: super comfy bed and a spacious closet that fit all my luggage with ease. Everything was clean and well-maintained, which made the stay even more enjoyable. Parking is on the street and not included, but there was plenty of space and could park right in front whenever I needed which was a huge plus. Would definitely stay here again!