Vacation rentals in Maywood

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Top-rated vacation rentals in Maywood

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Guest favorite

Apartment in Forest Park

4.98 out of 5 average rating, 282 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.

Nov 2 – 9

ﺩ.ﺇ511 per night

Guest favorite

Home in Berwyn

4.92 out of 5 average rating, 237 reviews

Private apartment with retro vibe

Gunderson Getaway is a cosy one BR apartment with some retro style touches in Berwyn a block from Oak Park. 2nd floor private apartment. Wifi, cable, premium channels. Full kitchen. Queen bed plus sofa & extra single bed available. EASY free street parking right by unit. Quick drive to City. Convenient to both airports, United Center and walk to Fitzgerald’s Club. Near Blue Line, restaurants, groceries, great bakery. NO smoking, candles or glitter! Pets MUST be pre-approved and never left alone.

Sep 5 – 12

ﺩ.ﺇ332 per night

Guest favorite

Guest suite in Wood Dale

4.9 out of 5 average rating, 425 reviews

The Deer Suite

This is a one bedroom apartment within the home. NOT FOR PARTY No Smoking , ABSOLUTELY No events, parties, or large gatherings. The apartment has a separate entrance from the home main entrance. The apartment also comes with comcast high speed internet. The living room couch can be turned into a double bed, that sleeps two. Large ,shower towels and shampoo included. The apartment includes washer and dryer.The bedroom sleeps two .It is about 30min drive to Downtown-Chicago and15min to O'hare .

Oct 19 – 26

ﺩ.ﺇ440 per night

Guest favorite

Apartment in Oak Park

4.85 out of 5 average rating, 527 reviews

Long stays welcome@warm&cute vintage 2BR

This musically-inspired vintage 2 BR is perfectly placed in Oak Park and we know you'll have a rockin' vacation here. Steps to shops, cafes, train, and FL Wright home. With a cassette wall, reading nook, and many other cute touches. The apartment is a vintage brownstone with charming details, like original woodwork. Street parking available. Easy access to Chicago.The place is an older Chicago brownstone, with a lived-in feel. NO PARTIES!! Upstairs neighbors can be heard walking and moving

Sep 27 – Oct 4

ﺩ.ﺇ385 per night

Guest favorite

Apartment in Oak Park

4.91 out of 5 average rating, 102 reviews

Lovely, spacious 2bd, 1bath home w/free parking

Bring the whole family to enjoy this great place with lots of comforts and space. Beautifully decorated with reclaimed barn wood throughout the home and a completely remodeled kitchen with cute bistro table to enjoy your coffee. Wonder around this beautiful, quiet Frank Lloyd Wright neighborhood to see beautiful Victorian homes and architect or take a brisk walk to downtown Oak Park before taking in the sites in Downtown Chicago. Whether you stay for a while or a few days, welcome home!

Sep 11 – 18

ﺩ.ﺇ541 per night

Guest favorite

Guest suite in Chicago

4.98 out of 5 average rating, 110 reviews

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*

Nov 12 – 19

ﺩ.ﺇ325 per night

Guest favorite

Home in Forest Park

4.9 out of 5 average rating, 221 reviews

Charming dog friendly 2-Bath Bungalow Near Chicago

Steps from the cobblestone streets of Forest Park into our cheery bungalow, perfect for artistic souls and business travelers alike. Inside is a design savvy mix of mid-century furniture, comfy beds, and art from around the globe. Built in 1908, it boasts modern amenities you desire without sacrificing vintage charm. Minutes away from local shops, restaurants. Just off I-290, Blue Line CTA, 20. min drive to ORD, Midway & Downtown Chicago. Plus we’re dog-friendly-- bring up to 2 pups!

Jun 25 – Jul 2

ﺩ.ﺇ567 per night

Guest favorite

Apartment in Berwyn

4.87 out of 5 average rating, 136 reviews

The Green Bungalow: Charming 1-BR apt. with patio

Situated in a residential neighborhood just outside the city limits, this lovely 2nd floor apartment is blocks from the Blue Line train and highway. Our newly renovated vintage unit has a full kitchen, hardwood floors, plenty of natural light, a backyard patio and its own private entrance. Our bungalow is walking distance to cafes, restaurants, shopping, music and nightlife. Enjoy the charm of the suburbs while having easy access to all the attractions Chicago's downtown has to offer.

Jul 11 – 18

ﺩ.ﺇ392 per night

Guest favorite

Apartment in Forest Park

4.95 out of 5 average rating, 234 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. Newly remodeled but with a vintage, welcoming vibe. We're a 20-minute drive to downtown Chicago (depending on traffic). Our home is a 2-unit building. We live in the downstairs unit but the upstairs is all yours and entirely separate. 1 Dedicated Guest Parking spot (included). Additional Free Parking is available. Great wifi. 3-season back porch. Record Player (Real Vinyl!)

Oct 5 – 12

ﺩ.ﺇ486 per night

Guest favorite

Condo in Oak Park

4.88 out of 5 average rating, 163 reviews

Attractive Flat - Historic Oak Park

Attractive One Bedroom Flat for Rent in Historic Downtown Oak Park. Truly - one of the Best Locations in all of Chicago. Two Blocks from the Epicenter of this lovely city. Easy Access to Public Transportation to Downtown Chicago or the Greater Metro Area. The Elevated train -and- the Metra Train (15 Minutes by Train to Downtown) are each a quick walk. See “ property description “ For Important information for all perspective Guests:

Mar 14 – 21

ﺩ.ﺇ498 per night

Guest favorite

Apartment in Cicero

4.98 out of 5 average rating, 200 reviews

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

Quiet city side street. Walking distance to dozens of restaurants and stores. Walking distance to Public Transportation including Metra train, CTA Pink line, Direct CTA Bus to Midway Airport. You will be a short 20-minute drive to Downtown Chicago, 15 minutes to United Center or Soldier Field. Perfect for the quick getaway, the night before your flight, or even the long work assignment. Relax on the Patio with a fire pit and grill.

Jan 19 – 26

ﺩ.ﺇ450 per night

Guest favorite

Apartment in Forest Park

5.0 out of 5 average rating, 216 reviews

Like a Treehouse!

If you're coming to Illinois for any medical procedure that's no longer available in your home state, reach out to us about discounts. You'll feel like you're in a tree house in our 850 sq ft coach house, above our workshop/garage, behind our home in historic Forest Park (with "The Mayberriest Downtown!"- Chicago Magazine), right next to Oak Park. Just 8 miles west of Downtown Chicago, convenient to I-290 and the Blue Line train.

Sep 4 – 11

ﺩ.ﺇ438 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Maywood vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Maywood's top sights

Poor Boy4 locals recommend

JJ Fish & Chicken3 locals recommend

Burger King34 locals recommend

Beggars Pizza23 locals recommend

Thatcher Woods Pavilion7 locals recommend

Submarine Brothers3 locals recommend

Other great vacation rentals in Maywood

Guest favorite

Guest suite in Oak Park

4.89 out of 5 average rating, 399 reviews

Entire upstairs in Arts and Crafts Oak Park home

Dec 9 – 16

ﺩ.ﺇ426 per night

Superhost

Apartment in Berwyn

4.87 out of 5 average rating, 386 reviews

Berwyn Musical Apartment

Feb 22 – Mar 1

ﺩ.ﺇ364 per night

Guest favorite

Apartment in Oak Park

4.97 out of 5 average rating, 162 reviews

Chic Retreat in Historic Victorian House-Park Free

Jan 14 – 21

ﺩ.ﺇ495 per night

Superhost

Apartment in Maywood

4.93 out of 5 average rating, 84 reviews

Beautiful apartment close to O’Hare

Sep 21 – 28

ﺩ.ﺇ657 per night

Superhost

Home in Maywood

4.83 out of 5 average rating, 60 reviews

Maywood Relaxation

Nov 3 – 10

ﺩ.ﺇ654 per night

Guest favorite

Apartment in Forest Park

4.96 out of 5 average rating, 78 reviews

1 bedroom garden apartment in Forest Park

Mar 10 – 17

ﺩ.ﺇ403 per night

Guest favorite

Apartment in Chicago

4.97 out of 5 average rating, 30 reviews

Serene Escape with King Sleep Number Bed, No Fees!

Jan 9 – 16

ﺩ.ﺇ373 per night

Guest favorite

Apartment in Forest Park

4.86 out of 5 average rating, 14 reviews

City-Accessible Basement Retreat

Aug 15 – 22

ﺩ.ﺇ325 per night

Show all

Quick stats about vacation rentals in Maywood

Total rentals
20 properties
Wifi availability
20 properties include access to wifi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
660 reviews
Nightly prices starting at
ﺩ.ﺇ110 before taxes and fees

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 air conditioning, over 10 homes with free parking, over 10 homes with a kitchen, over 10 homes with wifi, 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 $40 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.

Vacation rentals in Maywood

Top-rated vacation rentals in Maywood

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Maywood vacation rentals

Stay near Maywood's top sights

Other great vacation rentals in Maywood

Guest suite in Oak Park

Apartment in Berwyn

Apartment in Oak Park

Apartment in Maywood

Home in Maywood

Apartment in Forest Park

Apartment in Chicago

Apartment in Forest Park

Quick stats about vacation rentals in Maywood

Total rentals

Wifi availability

Rentals with dedicated workspaces

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Do house rentals in Maywood have a kitchen?

Do house rentals in Maywood have air conditioning?

Are there family-friendly vacation rentals in Maywood?

What are the most popular amenities for House Rentals in Maywood?

Are there vacation rentals with a dedicated workspace in Maywood?

Do house rentals in Maywood have wifi?

How much does it cost to stay in house rentals in Maywood?

Do house rentals in Maywood have free parking?

Destinations to explore