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
8.0 out of 10, Very good, (27 reviews)
"Was a very nice stay and the host was very helpful and got very quick responses "
United States
Eduardo
The price is CA $204
CA $417 total
includes taxes & fees
May 20 - May 21
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 $184
CA $358 total
includes taxes & fees
May 26 - May 27
Sunlit 1BR Apartment | Warm & Welcoming Space

Modern 3BR Apartment Near North Ave Shops

Modern 3BR Apartment Near North Ave Shops
Near North Side
The price is CA $191
CA $597 total
includes taxes & fees
May 27 - May 28
Modern 3BR Apartment Near North Ave Shops

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, (7 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 $239
CA $817 total
includes taxes & fees
May 20 - May 21
Modern West Loop Gem-City Views & Prime Location 3

Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (760 reviews)
The price is CA $211
CA $328 total
includes taxes & fees
May 25 - May 26
Kasa Magnificent Mile Chicago

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, (5 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 $364
CA $827 total
includes taxes & fees
May 26 - May 27
River North Rooftop With In and Out Parking 3

Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (17 reviews)
"Great location, comfortable room, welcoming host."
United States
Treseanne A.
The price is CA $179
CA $598 total
includes taxes & fees
May 20 - May 21
Spacious 4BR Central Apartment w/ Skyline Views

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,165 reviews)
"Spacious apartment with stunning view. A great stay!!"
United States
Tina
The price is CA $209
CA $286 total
includes taxes & fees
May 25 - May 26
Sentral Michigan Avenue

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
9.8 out of 10, Exceptional, (10 reviews)
"Great spot next to the green line train a few restaurants and a Starbucks right up the street I will book again for sure "
United States
2k G.
The price is CA $184
CA $358 total
includes taxes & fees
May 26 - May 27
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 $150
CA $295 total
includes taxes & fees
May 26 - May 27
Chic Studio in the Heart of the Gold Coast

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (478 reviews)
"Beautiful clean place. Great safe location within proximity to restaurants and transportation around the city with fantastic views. Would recommend and stay here again. "
Canada
Lissa
The price is CA $234
CA $308 total
includes taxes & fees
May 26 - May 27
Level Chicago – Old Town

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
Westchester
9.8 out of 10, Exceptional, (20 reviews)
"Great location and the place was immaculate. Host was very nice."
United States
Carl M.
The price is CA $206
CA $560 total
includes taxes & fees
May 20 - May 21
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More

Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
South Evanston
10.0 out of 10, Exceptional, (48 reviews)
"The place was awesome - very clean !! Great location !! "
United States
John R.
The price is CA $136
CA $326 total
includes taxes & fees
May 20 - May 21
Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More

LIVN Millennium Park Downtown Chicago 2BR

LIVN Millennium Park Downtown Chicago 2BR
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Excellent location... Very cleaned....it is perfect"
United States
Granada
The price is CA $368
CA $498 total
includes taxes & fees
May 25 - May 26
LIVN Millennium Park Downtown Chicago 2BR

Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley

Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
North Center
9.6 out of 10, Exceptional, (73 reviews)
"Nice property, great location, super helpful host!"
United States
Carin O.
The price is CA $197
CA $470 total
includes taxes & fees
May 20 - May 21
Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley

Cozy, Comfortable and Convenient apartment. Close to everything!

Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park
9.8 out of 10, Exceptional, (75 reviews)
"Nice, clean, safe house."
United States
Adrienne P.
The price is CA $198
CA $473 total
includes taxes & fees
May 20 - May 21
Cozy, Comfortable and Convenient apartment. Close to everything!

LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
The price is CA $188
CA $255 total
includes taxes & fees
May 25 - May 26
LIVN West Loop Chicago Queen Superior Studio

Chicago-Themed 1BR in a Central Spot near Downtown

Chicago-Themed 1BR in a Central Spot near Downtown
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Clean spacious great location easy to get everywhere "
United States
Melissa M.
The price is CA $183
CA $356 total
includes taxes & fees
May 26 - May 27
Chicago-Themed 1BR in a Central Spot near Downtown

Cozy Well-Equipped Studio Apartment

Cozy Well-Equipped Studio Apartment
Hyde Park
10.0 out of 10, Exceptional, (2 reviews)
"Wow, this is a wonderful Place to stay. The host Is very responsive and friendly The apartment is immaculate I recommend this place highly . "
United States
pnina
The price is CA $137
CA $279 total
includes taxes & fees
May 20 - May 21
Cozy Well-Equipped Studio Apartment

Cozy Boho Chicago - 10 Minutes to Downtown Chicago

Cozy Boho Chicago - 10 Minutes to Downtown Chicago
Lawndale
9.8 out of 10, Exceptional, (10 reviews)
"Wonderful space and convenient location. Really responsive host and super quiet neighborhood! "
United States
Jess S.
The price is CA $131
CA $314 total
includes taxes & fees
Jun 16 - Jun 17
Cozy Boho Chicago - 10 Minutes to Downtown Chicago
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?

ENVITAE Hotel, 4BR Luxury Modern Apartments: This vacation home rental near Maywood is located in the city center and offers a barbecue grill, air-conditioning, and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 4 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 Navy Pier 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.