
Holiday houses in Maywood
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Top-rated holiday rentals in Maywood
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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.

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.

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!

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.

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.

Cozy, 1 Bedroom Apt. w/ Kitchen & Parking for 4
Enjoy our historic district three-flat w/ free parking in upscale, safe Oak Park just 3 blocks to the train, easy access to Chicago. Enjoy some tranquil time in our little eco suburban farm. Check out the gardens and visit our 6 friendly chickens. This non-smoking unit with full kitchen is perfect for tourists, families, or business travelers. We require no check-out chores. Easy highway and airport access. No parties. Booking age, 25 or at least one 5 ⭐️ review. Visit profile for more units.

Gorgeous Studio 15 Minutes From Ohare!
Private, cozy and spacious studio apartment. This wonderful apartment is clean and ready to be your home away from home in Chicago! Full kitchen and bath! Spacious Backyard! Free Parking! On a beautiful treelined street in the Dunning neighborhood. Great for couples & business travelers! Close to great restaurants and parks, Rosemont Convention Center (10 minutes), O’ Hare Aiport (15 minutes), Downtown (35-45minutes). *Travel times are non rush hour and can increase depending on time/events*

Retro Modern Bungalow | free parking | fire pit
Experience the city in style at Retro Modern Bungalow, the perfect pad for up to 4 friends. Featuring two spacious bedrooms—each with a king bed and luxury linens—a propane fire pit and a fully fenced, pup-friendly backyard. Enjoy central HVAC, speedy WiFi, and a dedicated workspace. A pack-n-play crib is available at no cost. Central location just south of Oak Park, 15 mins from Midway airport, and 20 mins from downtown. Park for free in our garage or catch the train a few blocks away.

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.

Romantic King Bed/1 free parking/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

Vintage Chicago-Style 1 bed, Cable & NFL PASS 40-1
→ Introducing our newly renovated and furnished apartment unit nestled in the charming Oak Park Art District. Richly characteristic brick building, Chicago style, situated in a safe and quiet neighborhood. ★ Property Features: • One block away: Oak Park Art District • Vintage Chicago style brick building • Safe, quiet neighborhood • Newly renovated and furnished • Smart TV with Cable • Free Laundry Room • Free Parking for short stays, long stays limit spots please confirm.**

Beautiful apartment close to O’Hare
Keep it simple at this peaceful and centrally-located place. Eighteen min away from the airport and twenty min away from Downtown Chicago. This second floor apartment have everything you need in a quiet location. Just 5 Minutes from I 290 expressway. Great Neighborhood and friendly Neighbors, You will love it! Please keep in mind that this is a snail apartment and that there is an incline set of stairs on the front and a more confortable second set of stairs on the back porch.
Popular amenities for Maywood holiday rentals
Other great holiday rentals in Maywood

Basement Private Office Studio

Master On-Suite Bedroom Near Downtown Chicago

Egyptian Room - Free Parking, 1 block to CTA

Antique Filled Home

The Albany Park Room at the Cape Cod in Riverside

Room within a Cozy Cottage

Private Room “A”

Walk to Train | Private BR B | Queen Bed Sleeps 2
When is the best time to visit Maywood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $211 AUD | $211 AUD | $216 AUD | $198 AUD | $216 AUD | $211 AUD | $213 AUD | $204 AUD | $195 AUD | $190 AUD | $202 AUD | $206 AUD |
| Avg. temp | -3°C | -1°C | 4°C | 10°C | 16°C | 22°C | 25°C | 24°C | 20°C | 13°C | 6°C | 0°C |
Frequently Asked Questions
Do house rentals in Maywood have a kitchen?
Absolutely! We offer over 10 house rentals with a kitchen in Maywood. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Maywood have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Maywood. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Maywood?
Maywood has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for House Rentals in Maywood?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with a kitchen, over 10 homes with air conditioning, over 10 homes with wifi, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there vacation rentals with a dedicated workspace in Maywood?
Yes! Work meets play with ease at over 10 vacation rentals in Maywood featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Maywood have wifi?
Absolutely! We offer over 10 house rentals with wifi in Maywood. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Maywood?
Experience the best of Maywood with our house rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Maywood have free parking?
Absolutely! We offer over 10 house rentals with free parking in Maywood. Enjoy a tailored experience with all the comforts you desire.
Quick stats about holiday rentals in Maywood

Total holiday rentals
Explore 20 holiday rentals in Maywood

Nightly prices starting at
Maywood holiday rentals start at $70 AUD per night before taxes and fees

Verified guest reviews
Over 1,000 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Maywood holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Maywood rentals

4.6 Average rating
Maywood stays receive an average rating of 4.6 out of 5 from guests
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- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Grant Park
- Navy Pier
- 875 North Michigan Avenue
- Soldier Field
- Six Flags Great America
- Humboldt Park
- Shedd Aquarium
- Guaranteed Rate Field
- The Field Museum
- Wilmot Mountain Ski Resort
- Wicker Park
- Lincoln Park Zoo
- Garfield Park Conservatory
- Oak Street Beach
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Brookfield Zoo
- Illinois Beach State Park
- Willis Tower
- Washington Park Zoo




