Maywood Vacation Rentals

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Our top choices for Maywood vacation rentals

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Maywood
8.2 out of 10, Very good, (22 reviews)
"Easy to access, big place, great for a group that needs to have several rooms and beds. Would definitely stay again"
United States
JOSE S.
The price is CA $207
CA $423 total
includes taxes & fees
Apr 14 - Apr 15
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Sunlit 1BR Apartment | Warm & Welcoming Space

Sunlit 1BR Apartment | Warm & Welcoming Space
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Host was very friendly and informative. Place was clean and close to lots of fun. Trains loud and busy but knew that going in. "
United States
Tyler B.
The price is CA $157
CA $323 total
includes taxes & fees
Apr 2 - Apr 3
Sunlit 1BR Apartment | Warm & Welcoming Space

Modern Comfort: 1BR Unit w/ Laundry

Modern Comfort: 1BR Unit w/ Laundry
Downtown Chicago
9.4 out of 10, Exceptional, (16 reviews)
"Great host comfortable bed close to restaurants and parks"
United States
Alana C.
The price is CA $96
CA $244 total
includes taxes & fees
Apr 14 - Apr 15
Modern Comfort: 1BR Unit w/ Laundry

River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.6 out of 10, Exceptional, (4 reviews)
"We had a very comfortable stay here. The hosts are exceptionally communicative and helpful. Loved having a place to park my car, and the hosts set it up so my license plate was recognized at the gate so that parking was free. The unit was very clean and spacious. Note, the kitchen does not have pots or pans to cook, so plan on eating out!"
United States
Jennifer M.
The price is CA $223
CA $642 total
includes taxes & fees
Apr 14 - Apr 15
River North Rooftop With In and Out Parking 3

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,117 reviews)
"Clean spacious my go to vacation spot all year around "
United States
xavier
The price is CA $164
CA $234 total
includes taxes & fees
Apr 2 - Apr 3
Sentral Michigan Avenue

Modern West Loop Gem-City Views & Prime Location 3

Modern West Loop Gem-City Views & Prime Location 3
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
"Loved the place 4 bedroom & 4 bathrooms was ideal for our stayGreat locationLoved the well stocked convenience store a block away "
United States
Tina Y.
The price is CA $202
CA $776 total
includes taxes & fees
Apr 22 - Apr 23
Modern West Loop Gem-City Views & Prime Location 3

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (8 reviews)
"Great communication and hosts. Location and unit was perfect."
United States
Greg C.
The price is CA $157
CA $323 total
includes taxes & fees
Apr 2 - Apr 3
West Loop Living – Bright 1BR

Chic Studio in the Heart of the Gold Coast

Chic Studio in the Heart of the Gold Coast
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
"The communication was really effective and made for a smooth check in and check out process. Host was friendly and made great recommendations, 10/10 would stay again!"
United States
Seynabou
The price is CA $149
CA $296 total
includes taxes & fees
Apr 28 - Apr 29
Chic Studio in the Heart of the Gold Coast

The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (5 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The price is CA $168
CA $347 total
includes taxes & fees
Apr 2 - Apr 3
The Oak Park Loft

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (453 reviews)
"Would definitely stay again. Everything was great!"
United States
Michelle
The price is CA $314
CA $403 total
includes taxes & fees
Apr 6 - Apr 7
Level Chicago – Old Town

Premium Urban 4BR - Perfect Mix of Comfort & Location

Premium Urban 4BR - Perfect Mix of Comfort & Location
Near North Side
10.0 out of 10, Exceptional, (1 review)
"Nice place, clean property, great views "
United States
Zach L.
The price is CA $184
CA $611 total
includes taxes & fees
Apr 15 - Apr 16
Premium Urban 4BR - Perfect Mix of Comfort & Location

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (187 reviews)
"Nice area if you are renting a car, be aware that you would have to pay for street parking or go over a few blocks and park in a parking lot."
United States
Daysha
The price is CA $199
CA $348 total
includes taxes & fees
Apr 15 - Apr 16
Kasa River North Chicago

Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (12 reviews)
"Great location, comfortable room, welcoming host."
United States
Treseanne A.
The price is CA $217
CA $658 total
includes taxes & fees
Apr 26 - Apr 27
Spacious 4BR Central Apartment w/ Skyline Views

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Worth
9.4 out of 10, Exceptional, (58 reviews)
"Home was exactly what we were needing fir our stay. Host was responsive and timely. "
United States
Stephanie H.
The price is CA $216
CA $468 total
includes taxes & fees
Apr 7 - Apr 8
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"The service was top notch at this property. The hosts were super responsive and professional. The location was incredible. Loved being able to cook in the apartment. The apartment was newly renovated and very urban chic. "
United States
Michelle R.
The price is CA $189
CA $256 total
includes taxes & fees
Apr 8 - Apr 9
LIVN West Loop Chicago Queen Superior Studio

Cozy & Furnished 2BR Unit

Cozy & Furnished 2BR Unit
Lincoln Square
9.2 out of 10, Wonderful, (17 reviews)
"Very cozy, amenities in great condition."
United States
Kaitlin T.
The price is CA $136
CA $323 total
includes taxes & fees
Apr 5 - Apr 6
Cozy & Furnished 2BR Unit

2-bedroom apartment just 2 minutes drive to Wrigley Field

2-bedroom apartment just 2 minutes drive to Wrigley Field
North Center
9.6 out of 10, Exceptional, (65 reviews)
"Great host, quick communication, and wonderful place to stay in Chicago. Well thought out and made our stay enjoyable. Highly recommend, we will book it again next time we are in Chicago. "
United States
Justin P.
The price is CA $187
CA $459 total
includes taxes & fees
Apr 5 - Apr 6
2-bedroom apartment just 2 minutes drive to Wrigley Field

Just remodeled apartment close to airport and mall

Just remodeled apartment close to airport and mall
Elk Grove Village
10.0 out of 10, Exceptional, (16 reviews)
"Very nice place to stay in secure neighborhood "
United States
Christina F.
The price is CA $188
CA $356 total
includes taxes & fees
Apr 3 - Apr 4
Just remodeled apartment close to airport and mall

2BR Apartment Beautifully Furnished

2BR Apartment Beautifully Furnished
Lakeview
10.0 out of 10, Exceptional, (9 reviews)
"We loved the place. The feeling of home away from home."
United States
Sataish
The price is CA $157
CA $347 total
includes taxes & fees
Apr 2 - Apr 3
2BR Apartment Beautifully Furnished

5 Minutes to Wrigley and Beach - Games and Arcades - Garage - Sleeps 10

5 Minutes to Wrigley and Beach - Games and Arcades - Garage - Sleeps 10
Lakeview
9.2 out of 10, Wonderful, (5 reviews)
"This was a wonderful stay! The apartment was clean, well furnished, and the communication with the manager was wonderful. My son and I really enjoyed the video games, especially golden tee. The location is fantastic, giving us access to most everything in the Lincoln Park area, as well as Wrigley Field. I can’t recommend this enough. We had a wonderful time!"
United States
Matthew B.
The price is CA $193
CA $517 total
includes taxes & fees
Apr 8 - Apr 9
5 Minutes to Wrigley and Beach - Games and Arcades - Garage - Sleeps 10
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Maywood Hotel Reviews

Find out more about Maywood

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Maywood. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a vacation rental in Maywood?

Yes, there are vacation rentals close to top local attractions in Maywood, or you can choose a secluded option if you're looking for relaxation. Maywood is known for its shopping and restaurants. Make sure you have time to check out the festivals while you're in the area.

What's the top vacation rental that Maywood has to offer?

Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!: This vacation home near Maywood is on a lake and equipped with air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals will I find in Maywood?

With 8 Expedia vacation rentals, you're sure to find just the right place for your Maywood stay.

What’s there to see and do in Maywood?

While exploring the area, visit family-friendly sights like Galloping Ghost, or get outside and enjoy nature at Millennium Park. Wrigley Field and Michigan Avenue are other popular places to visit in the area.

What’s a vacation rental in Maywood like?

Vacation rentals are privately owned properties you can stay in for a few weeks or just a few days in Maywood. Vacation rentals feature extras like kitchens and laundry facilities so your stay will be comfortable. If you're concerned about a sanitized environment, a vacation rental can provide a sense of seclusion away from shared hotel elevators and lobbies packed with people while still allowing you to travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for a small group gathering.