Holiday houses in Indian Head Park

4.89 out of 5 average rating, 112 reviews

Loft in Brookfield

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

Campervan/RV in Willow Springs

4.93 out of 5 average rating, 74 reviews

Wander Willow Springs Glamping Retreat

Nestled in the serene landscapes of Willow Springs, the Wander Willow Springs RV offers a peaceful and immersive getaway. Relax in a cozy, fully-equipped stationary RV. Unwind in nature's embrace, just 1 block from Chicagoland's largest forest preserve. Immerse yourself in the tranquility of your surroundings while savoring a cup of coffee on the outdoor patio w/fire pit, explore the forest's miles of hiking and biking trails or the village's charm from the comfort of your own private retreat

4.91 out of 5 average rating, 69 reviews

Apartment in Lemont

Burr Oak

Nestled in the Palos Forest Preserve with access to many miles of hiking and biking trails . Spacious one bedroom basement apartment with private entrance. 6 minutes to The Forge, 7 minutes to Target, 8 minutes to downtown Lemont restaurants. 4 minutes to Little Red Schoolhouse, 7 minutes to Burr Ridge shopping and dining. 22 minutes to Midway 32 minutes to O'Hare. Half hour to the Loop. 20 minutes from Ikea and Bass Pro. Very quiet cabin like setting. Ask about our extended stay discounts.

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.

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, 86 reviews

Condo in Clarendon Hills

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.

4.9 out of 5 average rating, 90 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, 4 reviews

Apartment 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.

5 out of 5 average rating, 35 reviews

Home in Bridgeview

Lofty Urban Retreat

Welcome to our urban oasis, just minutes from the heart of Chicago! Discover comfort and style in our 4-bedroom retreat, each room boasting a queen bed for a restful stay. With 2 bathrooms and full privacy, it's ideal for families or groups. Need to catch up on work? We've got you covered with a desk for your laptop. Step outside to our fenced backyard, complete with a spacious deck, perfect for lounging or dining al fresco. Your city escape awaits!

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

Apartment in Hickory Hills

4.96 out of 5 average rating, 48 reviews

Cozy Guest Suite. Private Entry+ Turo Rental

3600 sqf single family home with a Guest Apartment and private entry on the ground level. Your family will be close to everything when you stay at this centrally-located place. Centrally located off of I294, I55, I57 and I80. Easy to and from travel. In Need of a rental we have 2018 Jeep Grand Cherokee High Altitude at the house and listed Turo.

4.97 out of 5 average rating, 29 reviews

Home in Brookfield

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.

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Other great holiday rentals in Indian Head Park

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.

4.93 out of 5 average rating, 14 reviews

Private room in Lemont

Private Room in Equestrian Villa

SamuelRating, 5 stars2 days ago

Tomas was an amazing host, clean bathroom, clean room, good people, would recommend to everyone.

Private room in Franklin Park

4.96 out of 5 average rating, 126 reviews

Safe & Clean King size Bed Next to Ohare/Rosemont

PhoebeRating, 5 stars3 weeks ago

Joswe was so incredibly kind and accommodating! Being a solo traveler it felt like a home away from home. The space was clean and comfortable and felt very safe. Joswe even left freshly brewed hot coffee every morning along with breakfast! I couldn't recommend Joswe or his home enough! if I could give more stars, I would!

4.97 out of 5 average rating, 125 reviews

Private room in Berwyn

Private lower level suite suburb Chicago

TaylorRating, 5 stars2 days ago

super kind and the cutest dog, was a great stay and super clean and cozy!

4.86 out of 5 average rating, 56 reviews

Private room in Berwyn

The Quilt Room. Micro-flower farm.

TaliahRating, 5 stars3 weeks ago

The home was perfect for our trip to chicago! We will definitely come back again

Private room in Norwood Park

4.8 out of 5 average rating, 224 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.

4.94 out of 5 average rating, 62 reviews

Private room in Berwyn

Nice cozy room

Jose AlbertoRating, 5 stars6 days ago

Her attention and responsiveness make me feel like I was leaving with my mom again. This is of course, something I have never felt with any other host. I am glad to have booked this place.