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Maywood Holiday Rentals

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Our top choices for Maywood holiday rentals

1. 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, (31 reviews)
"Pros: Quiet neighborhood, felt safe going in and out of the house. Upstairs bathroom shower was amazing. Cons: warmer in living room, stained pillows, couches and floors felt like dust mites all over( simple fix) All in all it was a good stay."
United States
Amal
The price is HK$1,165
HK$2,379 total
includes taxes & fees
17 Aug - 18 Aug
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

2. Chic Suite/Mins to L Train /Laundry/Free Parking

Chic Suite/Mins to L Train /Laundry/Free Parking
Oak Park
9.6 out of 10, Exceptional, (68 reviews)
"Very nice stay. Close to everything. Host very helpful. "
United States
Tamela S.
The price is HK$904
HK$2,058 total
includes taxes & fees
18 Aug - 19 Aug
Chic Suite/Mins to L Train /Laundry/Free Parking

3. Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI

Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI
Berwyn
9.0 out of 10, Wonderful, (18 reviews)
"It's a great place to stay, honestly, the hosts are nice and there to help you as well.The place is big, it has good A/C, and lots of space for different activities.Finally, there's lots of parking available in case you are using a car."
United States
Juan Pablo T.
Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI

4. Cozy, Comfortable and Convenient apartment. Close to everything!

Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park
9.8 out of 10, Exceptional, (77 reviews)
"The host responded quickly to my requests. Apartment was clean. Kitchen well stocked with cooking, utensils, spices, etc. He registered my car so I coiud park on the street without any problem. Close to the Blue Line stop to take the "L" into downtown Chicago."
United States
Michael
The price is HK$988
HK$2,524 total
includes taxes & fees
18 Aug - 19 Aug
Cozy, Comfortable and Convenient apartment. Close to everything!

5. Stylish Luxe King bed w/Free Parkng near DT Oak Pk

Stylish Luxe King bed w/Free Parkng near DT Oak Pk
Oak Park
9.6 out of 10, Exceptional, (110 reviews)
"Very clean, spacious living area, and convenient location"
United States
Clara B.
The price is HK$1,172
HK$2,447 total
includes taxes & fees
19 Aug - 20 Aug
Stylish Luxe King bed w/Free Parkng near DT Oak Pk

6. 1BR Apartment - Walk to Shops - Downtown OAK PARK

1BR Apartment - Walk to Shops - Downtown OAK PARK
Oak Park
9.2 out of 10, Wonderful, (43 reviews)
"Clean and close to all we needed."
United States
Steve O.
The price is HK$1,003
HK$2,127 total
includes taxes & fees
1 Sept - 2 Sept
1BR Apartment - Walk to Shops - Downtown OAK PARK

7. Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking

Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking
Northlake
10.0 out of 10, Exceptional, (22 reviews)
"Great host and had everything you would need."
United States
Mj2green J.
The price is HK$1,177
HK$1,427 total
includes taxes & fees
12 Aug - 13 Aug
Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking

8. At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.6 out of 10, Exceptional, (11 reviews)
"Great place, clean, and very accommodating! "
United States
Theresa
The price is HK$1,744
HK$2,867 total
includes taxes & fees
23 Aug - 24 Aug
At Home in Oak Park

9. 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
9.6 out of 10, Exceptional, (21 reviews)
"Great location and the place was immaculate. Host was very nice."
United States
Carl M.
The price is HK$1,450
HK$3,464 total
includes taxes & fees
12 Aug - 13 Aug
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

10. Historic Oak Park Home

Historic Oak Park Home
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (5 reviews)
"The owner was awesome. Convenient parking and beautiful area! Will definitely make a reservation again."
United States
Janette
The price is HK$1,835
HK$2,972 total
includes taxes & fees
18 Aug - 19 Aug
Historic Oak Park Home

11. Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill

Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
Belmont Cragin
9.2 out of 10, Wonderful, (5 reviews)
"Excellent place to stay for a family trip. Lovely neighborhood. Check in was a breeze. Very responsive with any questions I had!"
United States
Traci
The price is HK$711
HK$3,213 total
includes taxes & fees
19 Aug - 20 Aug
Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill

12. Vintage Urban Retreat

Vintage Urban Retreat
Oak Park
10.0 out of 10, Exceptional, (15 reviews)
"It was a very nice neighborhood, with many restaurants and retail establishments in proximity. We really enjoyed our stay and our host was an excellent when it comes to communication."
United States
Tim P.
The price is HK$1,519
HK$4,244 total
includes taxes & fees
12 Aug - 13 Aug
Vintage Urban Retreat

13. 4BR Retreat w/ Theater, Arcade, Gym and Firepit

4BR Retreat w/ Theater, Arcade, Gym and Firepit
Belmont Cragin
10.0 out of 10, Exceptional, (3 reviews)
"Great location, safe and quiet. Perfect for our family of 6!"
United States
Jason
The price is HK$1,305
HK$5,091 total
includes taxes & fees
17 Aug - 18 Aug
4BR Retreat w/ Theater, Arcade, Gym and Firepit

14. Oak Park Victorian by FLW Studio

Oak Park Victorian by FLW Studio
Oak Park
10.0 out of 10, Exceptional, (32 reviews)
"Would stay there again"
United States
Margaret L.
The price is HK$1,769
HK$4,576 total
includes taxes & fees
12 Aug - 13 Aug
Oak Park Victorian by FLW Studio

15. First floor of Historic Oak Park Villa, Grge:2Cars

First floor of Historic Oak Park Villa, Grge:2Cars
Oak Park
9.6 out of 10, Exceptional, (26 reviews)
"Very clean, comfortable and nicely located!"
United States
Steve P.
The price is HK$1,835
HK$3,394 total
includes taxes & fees
18 Aug - 19 Aug
First floor of Historic Oak Park Villa, Grge:2Cars

16. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,250 reviews)
"Great property and location."
United States
Michael
The price is HK$1,186
HK$1,623 total
includes taxes & fees
31 Aug - 1 Sept
Sentral Michigan Avenue

17. LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.6 out of 10, Excellent, (54 reviews)
"Hot tub was very nice!"
United States
Jeff
The price is HK$1,412
HK$2,929 total
includes taxes & fees
24 Aug - 25 Aug
LUXE 3 BR, 2 BA + Hot Tub

18. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
7.8 out of 10, Good, (13 reviews)
"Great location and super clean!"
United States
Erica
The price is HK$1,930
HK$2,761 total
includes taxes & fees
8 Sept - 9 Sept
Kasa Lake Shore Chicago

19. 1F - ❤️ Trendy 2BR Apartment in Logan Square!

1F - ❤️ Trendy 2BR Apartment in Logan Square!
Logan Square
10.0 out of 10, Exceptional, (101 reviews)
"Very clean and comfortable, wonderful communication with host. Great location! "
United States
Stacey E.
The price is HK$1,412
HK$2,743 total
includes taxes & fees
28 Aug - 29 Aug
1F - ❤️ Trendy 2BR Apartment in Logan Square!

20. Sleeps 7 • Huge Projector • Designated Workspace

Sleeps 7 • Huge Projector • Designated Workspace
Irving Park
10.0 out of 10, Exceptional, (6 reviews)
"Great location and easy on street parking. "
United States
Lori A.
The price is HK$600
HK$2,361 total
includes taxes & fees
1 Sept - 2 Sept
Sleeps 7 • Huge Projector • Designated Workspace
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

Search for holiday rentals in Maywood on Expedia! You can easily find your home rentals, villas, holiday apartments in Maywood using one of the methods below:

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Look no further and take a look at our great range of rental properties in Maywood!

Frequently asked questions

Can I find a holiday rental in Maywood?

Yes, there are holiday rentals close to the most popular sights in Maywood, or you can select a more secluded option if you're looking for a relaxing stay. 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 are some of the best holiday rentals that Maywood has to offer?

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed: This highly rated holiday home rental in Maywood offers a patio, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave.

How many holiday rentals will I find in Maywood?

With 8 Expedia holiday rentals, you're guaranteed 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. United Center and Wrigley Field are other popular places to visit in the area.

What’s a holiday rental in Maywood like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Maywood. Holiday rentals offer extras such as laundry facilities and kitchens so your stay will be comfortable. If you're concerned about cleanliness, a holiday rental can provide a sense of privacy away from shared hotel lifts and lobbies packed with people while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for family gatherings.