Vacation rentals in Maywood

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Quick stats about vacation rentals in Maywood

  • Total vacation rentals

    Explore 30 vacation rentals in Maywood

  • Nightly prices starting at

    Maywood vacation rentals start at $70 CAD per night before taxes and fees

  • Verified guest reviews

    Over 1,170 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    30 of Maywood vacation rentals include wifi 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

Top-rated vacation rentals in Maywood

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favourite
The living area features a comfortable sofa, paired with two woven armchairs. A rustic wooden coffee table sits at the center, adorned with a vase of fresh flowers. Natural light illuminates the space through two large windows, framed by soft curtains.
Apartment in Forest Park
4.98 out of 5 average rating, 412 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.

Superhost
A spacious living area features a gray sectional sofa arranged around a wooden coffee table. Soft lighting is provided by ceiling fixtures and wall-mounted sconces. The room leads to a set of stairs, while a TV is mounted on the wall for entertainment.
Apartment in Oak Park
4.86 out of 5 average rating, 201 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!

Top guest favourite
A bright living room features a cozy seating arrangement with a variety of armchairs and a sofa. Original art pieces adorn the walls, and a coffee table with a decorative table runner sits on a soft area rug. Light streams in through windows creating a lively atmosphere.
Apartment in Forest Park
5 out of 5 average rating, 218 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.

Top guest favourite
The exterior of a charming brick apartment building is showcased, framed by vibrant greenery. The structure features large windows and a welcoming entryway, with a well-kept lawn and flower beds enhancing its curb appeal. The clear sky provides ample natural light.
Apartment in Forest Park
4.98 out of 5 average rating, 190 reviews

1 bedroom garden apartment in Forest Park

Unique private garden apartment in our single family residence. 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 we have pets (cats/dog) in this home and also 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.

Guest favourite
An open living area features a comfortable sofa adorned with patterned pillows, set on light hardwood flooring. A dining space with a table and four chairs is visible. Natural light fills the room, enhancing the modern decor and inviting atmosphere.
Apartment in Forest Park
4.94 out of 5 average rating, 98 reviews

Luxurious apartment in great central location!

Welcome to the Troost House. This property is newly remodeled with high end finishes including Quartz counters, hardwood floors and fully equipped with brand-new stainless appliances. This 2BR 1B offers its own laundry room as well as a 1 car garage parking space. Superb location with easy access to major highways, a 5-minute walk to Blue line train station, a 3-minute drive to Loyola Medical Center, a 10-minute drive to DT Chicago, and near the heart of DT Forest Park and historic Oak park.

Guest favourite
A spacious living area is highlighted by a black sofa facing a light-colored coffee table. A vibrant area rug adds color underfoot. The walls are adorned with colorful vinyl records and framed artwork, while original woodwork details frame the open layout leading to the dining area.
Apartment in Oak Park
4.87 out of 5 average rating, 777 reviews

Rockin' 2Bed steps to shops/food/train

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

Superhost
A dining area is shown featuring a wooden table set for four with woven placemats. Brown leather chairs complement the modern aesthetic. A ceiling fan hangs above, and a mounted television is visible on the wall. Light enters through the windows, illuminating the space.
Home in Maywood
4.96 out of 5 average rating, 26 reviews

Charming Home Close to Loyola, Zoo & Chicagoland

This inviting home is perfectly situated -Minutes to Downtown Chicago: Explore iconic landmarks, shopping, dining, and entertainment just a short drive away -Brookfield Zoo: 15 minutes from the home, perfect for animal lovers and nature enthusiasts. -Loyola Hospital: A quick drive to one of the region's top medical facilities -O'Hare Airport: Only a short distance for travelers flying in or out of Chicago Age Requirement: Guest must be 25 or older to book. No Parties or Gatherings allowed

Guest favourite
A two-story apartment building is shown, featuring a light-colored exterior with dual-tone siding. Lush greenery surrounds the structure, including shrubs and grass. A staircase leads to the entrance, while the nearby homes display varying architectural styles.
Apartment in Forest Park
4.87 out of 5 average rating, 412 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.

Guest favourite
The modern kitchen features sleek white cabinetry and a granite countertop. A coffee maker is positioned beside an array of decorative items on floating shelves. The space opens to a dining area with a round table and teal chairs, creating a seamless flow between rooms.
Apartment in Forest Park
4.91 out of 5 average rating, 108 reviews

Home away from Home - Walk to train & Restaurants!

A wonderful and stylish retreat with walkability to local amenities and less than half a mile to the train which takes you into the city. The neighborhood park, pool, and fitness center is just 3 blocks away, the neighborhood grocery store is 2 blocks, and the downtown area of Forest Park is less than a mile! Leave your car in the included parking space and enjoy local restaurants and shops or hop on the train to get into the city of Chicago!

Guest favourite
The living area features a futon couch in a light tone, paired with a blue accent chair. A round coffee table sits on a patterned area rug, beneath ample natural light from large windows covered with light curtains. A small dining area is positioned nearby.
Guesthouse in Oak Park
4.89 out of 5 average rating, 128 reviews

Sunny Coach House in Historic Oak Park

This bright, cozy coach house is your ideal base in Oak Park. It was originally the coachman's quarters behind a 1909 Prairie-style house, now converted into guest lodging with all the modern amenities above a detached garage. The coach house is at the end of a long driveway (free parking included!) on a quiet street, in the heart of the Frank Lloyd Wright district, a short walk from trains to downtown Chicago.

Guest favourite
A modern living area features a gray sofa adorned with orange and gold throw pillows. An open kitchen with white cabinetry is visible in the background, complemented by a dining area with four chairs. A vibrant abstract painting adds a splash of color on the wall.
Apartment in Forest Park
4.86 out of 5 average rating, 698 reviews

Train ride to Chicago, welcome home

The garden apartment is small but mighty! It features a full kitchen and bathroom and a laundry facility onsite. You can walk 10 minutes to the blue line to Chicago. Large yard with an outdoor cabana and seating areas. Close to park and grocery store. Please make sure you are accurate on your guest count, do not put one guest when there will be 3 (for example). Welcome to my slice of heaven in Forest Park!

Top guest favourite
Apartment in Forest Park
4.98 out of 5 average rating, 103 reviews

Sunny Retreat in Forest Park

Beautiful & bright, this 2nd floor renovated 2 bedroom 1 bath unit is a perfect getaway for solo & business travelers, couples, families. Uber convenient location. Blocks from the Forest Park CTA Blue line stop. Easy access to I290. Drive or Uber to downtown Chicago. Close to restaurants, shopping & coffee. This is a strict non smokers building. Maximum 4 adults occupancy.

Popular amenities for Maywood vacation rentals

When is the best time to visit Maywood?

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Frequently Asked Questions

  • What are the best places to stay in Maywood?

    Stay in neighborhoods known for quiet streets and proximity to parks and shops, or seek vacation rentals with family-friendly amenities. Areas near community centers and markets are often recommended for convenience.

  • What are the best things to do in Maywood with kids?

    Kids can enjoy playgrounds in community parks, attend youth programs at local centers, and participate in seasonal arts or nature workshops. Family-friendly festivals and farmers markets are also popular activities.

  • What are some of the best things to do in Maywood?

    Explore parks and gardens, visit local museums or historic sites, and attend community festivals to experience Maywood’s culture. Independent shops and art spaces add to the neighborhood’s appeal.

  • How is the weather in Maywood?

    Maywood has cold winters around 19–33°F (-7–0°C) and warm, humid summers near 68–85°F (20–29°C). Rain is more frequent in spring and early summer, so packing layers and a light waterproof garment is often suggested.

  • When is the best time to visit Maywood?

    Late spring through early fall is frequently suggested for pleasant temperatures between 52–85°F (11–29°C) and vibrant outdoor events. Winter brings crisp air, so pack accordingly if visiting during colder months.

  • What are the best places to visit in Maywood?

    Maywood has locally rooted parks, community centers, and historic buildings that are often recommended for visitors. Explore green spaces, visit public art installations, or learn about local history through neighborhood landmarks.

  • What are some hiking trails in Maywood?

    Maywood has neighborhood parks with walking paths suitable for easy strolls, and larger forested areas nearby provide trails with natural scenery. These walking spaces are often frequented by locals and visitors alike.

  • What are some family activities we can do in Maywood?

    Families can explore neighborhood parks, play at community playgrounds, or attend local craft and storytime events. Seasonal fairs and markets often create opportunities for family-friendly experiences.

  • What are some of the best day trip ideas from Maywood?

    Day trips might include exploring art museums, botanical gardens, or regional nature preserves around Maywood. Urban centers nearby offer shopping districts and cultural attractions, making for diverse outings.

  • Are there any pet friendly accommodations available in Maywood?

    Maywood has a variety of vacation rentals, with some options welcoming guests traveling with pets. Many neighborhoods feature nearby parks and walking areas suitable for people with dogs.

  • What are some local tips for visiting Maywood?

    Connect with locals at neighborhood parks and farmers markets, and explore walking tours highlighting historic sites. Keeping an umbrella handy during spring is often recommended, and supporting independent shops is valued by residents.

  • What is Maywood known for?

    Maywood is known for its locally rooted history, active community spirit, and neighborhoods centered around parks and historic sites. The area also has strong connections to regional arts and civic events.

  • What are the best hidden gems to explore in Maywood?

    Explore lesser-known local parks, neighborhood art murals, or independent shops and eateries that showcase Maywood’s distinct community character. Local history exhibits and welcoming community centers are often suggested.

  • What are the best foods to try in Maywood?

    Try Maywood’s locally rooted flavors, including classic Chicago-style pizza, barbecue, and regional comfort dishes served at family eateries. Bakeries and markets may have pastries reflecting area culinary traditions.

  • What should I bring for a trip to Maywood?

    Bring comfortable walking shoes for exploring parks and neighborhoods, a light jacket for cooler evenings, and a raincoat or umbrella for spring rainfall. Sun protection is useful during warmer months.

  • What is the nightlife in Maywood like?

    Maywood’s nightlife centers around casual dining, local lounges, and community gatherings in neighborhood spaces. Live music events or open mic nights at local venues are sometimes featured.

  • What are the most popular events or festivals in Maywood?

    Maywood often hosts community gatherings, seasonal celebrations, and parades, especially around Labor Day weekend and in summer. Neighborhood festivals highlight local food, music, and cultural traditions.

  • Are there family friendly vacation rentals in Maywood?

    Many vacation rentals in Maywood are family friendly, featuring spacious layouts and amenities suited for groups. Neighborhoods near parks are popular for those traveling with children.

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