Holiday rentals in Maywood

4.99 out of 5 average rating, 353 reviews

Walk to Oak Park from Our Sunny Turn of the Century Apt

Soak up the vintage charm of this apartment dating back to 1908. This newly remodeled space is an elegant retreat, featuring 10-foot ceilings, local art treasures, and plush linens. A relaxing outdoor lounge area awaits after a busy day exploring. Pets are welcome on a case by case basis (contact host). The space is a charming two bedroom, one bathroom first-floor unit in a two unit historic home built in 1908. The apartment combines historic details with modern conveniences such as central heat and air, a dishwasher and washing machine and dryer access. The Monroe House is a stone’s throw from historic Oak Park and just three blocks from the CTA Blue Line making downtown Chicago a 25 minute train ride away. The condo includes additional amenities such as: •Smart TV for watching any account may you have (Netflix, Hulu etc...) •Central Air conditioning •Front and back porches for your enjoyment •Washer and dryer on site Just to the east lies historic Oak Park, and an array of attractions such as: •Brookfield Zoo •Chicago Architecture Foundation •Ernest Hemmingway Museum and Birthplace •Frank Lloyd Wright Home and Studio •Frank Llyod Wright’s Unity Temple •Oak Park Conservatory After taking in the local attractions, Chicago is only a train ride away, and it offers such noteworthy experiences as: •Shedd Aquarium •Architecture River Cruise •Skydeck Chicago •Navy Pier •The Field Museum •John Hancock Observatory •Adler Planetarium •Art Institute of Chicago •The Museum of Science and Industry You will have access to the entire unit and the basement so you can use the washing machine and dryer. We also have a back patio with a chiminea, patio table that seats 6, and a grill/smoker. You are welcome to use the backyard at anytime during your stay. We live in the top unit and are as available as you need. That being said, we very much respect your privacy and will not be checking in with you in person unless you request it. It is located in the Madison district, with acclaimed restaurants, pubs, and unique boutiques. Downtown Chicago is a 25-minute train ride away. The local brewery across the street offers delicious beers and creative meals for the whole family. We have a parking pad located behind our building. You can fit two cars on your side of the parking pad if they are parked in tandem. Some street parking is also available. We are located .4 miles from the CTA Blue Line train - Forest Park Stop. It is about a 6 - 10 minute walk from the flat. You can also take an Uber/Lyft into the city. It is about a 15 - 25 minute ride and it costs between $15 and $25. We are located about one mile from the Metra Station (Union Pacific West) and CTA Green Line - Oak Park Stop. Third bed is a queen sleeper sofa. We provide sheets and blankets for the sleeper sofa. You can smoke in the backyard. An ashtray is provided.

4.94 out of 5 average rating, 123 reviews

Flat in Melrose Park

KNG+QN 2bdrm/1parking space /18 min O’hare/Alstate

Top/2nd floor apartment+ parking spot in adjacent lot & playground up street Shampoo & body wash, extra towels, coffee & tea, WI-FI, books & board games, fully stocked kitchen for cooking, toaster oven, ice, iron & iron board, workspace, large screen TV 17 min-airport 18 min-Allstate arena 30 min-DT Chicago Early check-in/late checkout possible Walk to restaurants & bars/shopping & groceries/movie theater & Plaza 3 grocery stores within 10 min walk. Oak Brook/Oak Park/Rosemont shopping~ 20 min

4.97 out of 5 average rating, 144 reviews

1 bedroom garden apartment in Forest Park

Unique private garden apartment in our single family residence. Great location approximately 8 miles directly west of downtown Chicago. Close to shopping, dining, entertainment and public transportation to the city. One bedroom & best for 2 people but could sleep 3 ($50 fee) for short stays. It's important to note that this is a garden/ground/lower level apartment. The ceilings are relatively low at 6.5'. This would not be the best space for tall people. Free parking in front of the house.

4.87 out of 5 average rating, 119 reviews

City-Accessible Basement Retreat

Discover a perfect mix of small-town charm and city life in this cozy basement unit. Situated just a 7-minute walk from the train station, downtown Chicago is easily accessible for work/leisure. The neighborhood is a treasure trove of local restaurants, bars, and stores, ensuring you're never far from what you need. A convenient gas station/store is right behind your home for quick needs. Ideal for a simple, connected lifestyle with the city’s pulse at your doorstep. Your urban retreat awaits!

4.99 out of 5 average rating, 156 reviews

Sunny 1 bedroom apartment 1 block from restaurants

This sunny second floor apartment perched in an 1890’s farmhouse offers traditional charm with many contemporary touches. It showcases a variety of original art. Located on a quiet street but just steps away from restaurants, bars and shops, off-street parking is included. Two nearby trains provide easy access to downtown Chicago and O’Hare Airport. An enclosed porch directly off the kitchen overlooks a beautiful prairie garden. You can relax on the backyard patio with gas grill and fire pit.

4.97 out of 5 average rating, 311 reviews

Flat in Cicero

COZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy

Located on a tranquil city side street, this property is walking distance to numerous restaurants and stores. Enjoy easy access to public transportation, including Metra train, CTA Pink Line, and a direct CTA bus to Midway Airport. Downtown Chicago is a mere 20-minute drive away, with the United Center and Soldier Field just 15 minutes away. Ideal for a quick getaway, an overnight stay before your flight, or an extended work assignment. Unwind on the patio, complete with a fire pit and grill.

Guest suite in Brookfield

5 out of 5 average rating, 103 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.

Superhost

Flat in Oak Park

4.82 out of 5 average rating, 123 reviews

Circle Back Modern Apartment

Sit on your leafy private patio and enjoy your coffee before heading out to the city- or wind down at the end of the day with a cold beer. Steps to coffee shops, neighborhood pubs, and the Blue Line train this beautifully updated and decorated apartment is the perfect landing pad for your Chicago adventure. FREE off-street parking, free in-unit laundry, a cute coffee station- basically every amenity we could think of! This will be the place you want to stay every time you visit Chicago.

4.82 out of 5 average rating, 284 reviews

Home in Forest Park downstairs.

Enjoy a private ground floor apartment which is centrally-located with easy access , to the city. You will have a functional kitchen, laundry facility outside your back door and fast internet. Forest Park is located about 20 minutes from downtown Chicago and about 30 minutes from O’Hara international airport. You are within walking distance of many boutiques, restaurants, parks and also public transportation. Please make a note that there will be a $30 per guest fee if more than four.

4.97 out of 5 average rating, 116 reviews

Home in Oak Park

Garden Unit, King & Queen, Kitchenette & Parking

Our comfy, recently remodeled garden unit is 3 blocks to the train with free parking in upscale, safe, walkable Oak Park. Enjoy some time in our little urban farm. Check out the gardens and visit our 4 friendly hens. This non-smoking studio with a kitchenette is perfect for tourists, families, or business travelers. We require no check-out chores. Easy highway and airport access. No parties, 4 guests max allowed. Minimum age to book is 25. Visit my profile for additional units

4.92 out of 5 average rating, 101 reviews

Flat in Maywood

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.

4.95 out of 5 average rating, 325 reviews

Mid-Century Charm. Near Chicago. Low Cleaning Fee!

Step back in time a bit with our charming 2nd floor walk-up in a quiet, safe suburb. Parking included on-site. Vintage, welcoming vibe. We're a 20-30 minute drive to downtown Chicago (depending on traffic). The unit is on the 2nd Floor and is separate from the rest of the house (we live on the 1st floor). 1 Dedicated Guest Parking spot (included). Additional Free Parking is available. Great wifi. 3-season back porch. Record Player (Real Vinyl!)

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Other great holiday rentals in Maywood

4.99 out of 5 average rating, 139 reviews

Private room in Elmhurst

Cozy room with private bathroom.

RiyaRating, 5 stars1 week ago

We had a wonderful stay at this beautiful home, 30 min away from Chicago downtown which came equipped with all the basic amenities we needed for a comfortable visit. The house was spotless, the bed was cozy, and the neighborhood was quiet and pleasant perfect for a relaxing getaway. The hosts were incredibly warm and welcoming. They gave us a quick tour of the place upon arrival, making sure we felt at home. They were flexible with our late checkin and In the mornings, they offered us breakfast, which was a lovely touch. They also went out of their way to suggest local tourist spots, including some great tips and tricks for finding parking downtown — something we really appreciated. Having a dedicated parking spot in the driveway was super convenient, especially after long days of exploring. Overall, the hospitality, cleanliness, and thoughtful touches made this a truly memorable stay. We’d definitely love to return and highly recommend this place to anyone visiting the area.

Superhost

Hotel room in Itasca

4.8 out of 5 average rating, 364 reviews

King Bed at Chicago Northwest + PET Friendly

JenniferRating, 5 stars2 weeks ago

had a wonderful stay. would stay again.

4.95 out of 5 average rating, 382 reviews

Private room in Oak Park

Antique Filled Home

LaurentRating, 5 stars2 days ago

Tom and Grace were very welcoming. They encouraged us to think of their home as ours. It was lovely, on a lovely street in the relaxing and lovely town of Oak Park. Close to the metro trains. Close to Oak Park downtown. Convenient to downtown Chicago. Loved eating in front porch. Great parking spot. Did not use the car all week. Walking neighborhood. A lovely stay all around.

4.92 out of 5 average rating, 273 reviews

Hotel room in Rosemont

Relaxing Standard Room l Free Airport Shuttle

AlexeiRating, 5 stars2 weeks ago

easy check-in, super clean, friendly staff. parking is easy and affordable. will definitely be staying again!

Superhost

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.

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 stars3 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!