Homewood Holiday Rentals

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Holiday Rentals in Homewood

Cozy Home Sweet Homewood.
10.0 out of 10, Exceptional, (4)
"Neighborhood was quiet! Rental was exactly as shown online. Was able to easily find the rental with no problem. Overall great stay."
Cozy Home Sweet Homewood.
Perfect Getaway House With Fireplace & Big Fenced Yard
7.4 out of 10, Good, (6)
"The description of this property was totally wrong. It had only one small bathroom which needs a major overhaul. The kitchen and its appliances were ancient, and the glassware was almost non existent. The host required the entire payment upfront (very unusual), and he was impossible to reach by email or phone until the day before our arrival. There were limited instructions on operating the tv or internet. The bedding and towels were awful. We left one day early due to the condition of the...
Perfect Getaway House With Fireplace & Big Fenced Yard
cozy home in Bridgeport Chicago. walking to park and river front
10.0 out of 10, Exceptional, (1)
"Staying at this VRBO house in Chicago was an absolute knockout! The location was perfect for catching the wrestling show with my friends, and the house itself was spacious, clean, and had all the amenities we needed. From comfy beds to a fully equipped kitchen, we felt right at home. The host was super accommodating and made check-in a breeze. Definitely a five-star experience – would book again in a heartbeat!"
cozy home in Bridgeport Chicago. walking to park and river front
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Amazing 4 Bedrm Twnhm-30 Miles to Dwntwn Chicago Private Off Street Parking
10.0 out of 10, Exceptional, (2)
"My family really enjoyed this townhouse. It was very nice clean, location was perfect. Would definitely stay here again. The host Sherice was very very nice, kind, friendly and patient with my family."
Amazing 4 Bedrm Twnhm-30 Miles to Dwntwn Chicago Private Off Street Parking
Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum
9.8 out of 10, Exceptional, (60)
"The location is perfect for plans to the museums and easy access to Lake Shore Drive. It also has plenty of street parking."
Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum
Elegant Mayor's Manor in Central Chicago - 9 Beds
9.6 out of 10, Exceptional, (8)
"Place was as described and worked perfect for our stay."
Elegant Mayor's Manor in Central Chicago - 9 Beds
LakeHouse
10.0 out of 10, Exceptional, (7)
"Great"
LakeHouse
Bridgeport /China Town Get Away Near Downtown
8.0 out of 10, Very good, (4)
"My sons and I stayed here for our annual trip to Chicago. We always stay in Chinatown. This place was great. All was clean. It was so quiet. The train can be heard faintly in the distance. Shower was nice. Towels were thick. The little porch was perfect for sitting outside. It was typical Chicago parking. We were always to find a spot. We hope to stay here again."
Bridgeport /China Town Get Away Near Downtown
Pink Wild Rose - Ultimate Romantic Getaway
10.0 out of 10, Exceptional, (1)
"The host was great tgey accommodated ys with a 2 hr early check in and the house was amazing"
The price is NZ$432
includes taxes & fees
20 Jun - 21 Jun
Pink Wild Rose - Ultimate Romantic Getaway
Stay near family or close to downtown, this loft in Beverly has it all!
10.0 out of 10, Exceptional, (1)
"I went with 4 other friends, and this place was super clean, came with everything we needed, and even includes a cute small gaming room! Definitely would stay again!"
Stay near family or close to downtown, this loft in Beverly has it all!
Cozy, King bed with heated bathroom!
9.8 out of 10, Exceptional, (8)
"Great"
Cozy, King bed with heated bathroom!
Stay near family or close to downtown, this cottage in Beverly has it all!
10.0 out of 10, Exceptional, (2)
"Great Stay!"
Stay near family or close to downtown, this cottage in Beverly has it all!
Luxury Condo Chicago - FREE parking
Luxury Condo Chicago - FREE parking
Fast Wi-Fi/4KTV/Free parking/Comfy beds/Getaway
The price is NZ$453
includes taxes & fees
20 Jun - 21 Jun
Fast Wi-Fi/4KTV/Free parking/Comfy beds/Getaway
Charming Crete Home with Hot Tub, Deck & Fire Pit
9.8 out of 10, Exceptional, (14)
"Plenty of room to see the family and play with great grand kids"
Charming Crete Home with Hot Tub, Deck & Fire Pit
The Comfy King Ranch /King Bed/Fast WiFi & Free Parking
9.6 out of 10, Exceptional, (39)
"Nice property with large rooms. Easy access to Chicago. Property is on busy street but sleeping in the front bedroom and no issues. Fenced backyard was nice for our dog. Would stay again if in area."
The price is NZ$676
includes taxes & fees
11 Jun - 12 Jun
The Comfy King Ranch /King Bed/Fast WiFi & Free Parking
Great suburban location! Perfect for solo or couple travelers
9.4 out of 10, Exceptional, (9)
"The accuracy of this listing is incredible! It was very clean with cute decor and a large shower. The TV and bed are huge as well!"
The price is NZ$278
includes taxes & fees
1 Jul - 2 Jul
Great suburban location! Perfect for solo or couple travelers
Cozy Apartment with Location near the University of Chicago & Lake Shore Drive
10.0 out of 10, Exceptional, (2)
"Had some trepidations about the neighborhood when I first saw it. However, neighborhood was very pleasant quiet. Apartment was very nice nicely furnished without being cluttered overall very comfortable place to stay. I would definitely consider it again if I come back to Chicago."
Cozy Apartment with Location near the University of Chicago & Lake Shore Drive
Zen Oasis of Elegance: Expansive Executive Home
Zen Oasis of Elegance: Expansive Executive Home
Cheerful 4 bedroom smart home w/ indoor fireplace
7.4 out of 10, Good, (6)
"The check in process was great and the house was very clean. It was easy to communicate with the property manager. Helped make our trip to chicago great!"
Cheerful 4 bedroom smart home w/ indoor fireplace
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See all available properties in Homewood
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.

Other types of properties in Homewood you may be interested in

Red Roof Inn PLUS+ Chicago - Willowbrook
2.5 star property
7.0 out of 10, Good, (1019)
"It was rightvoff the highway very convenient "
The price is NZ$104
includes taxes & fees
20 Jun - 21 Jun
Red Roof Inn PLUS+ Chicago - Willowbrook
The Champagne Lodge & Luxury Suites
3.5 star property
8.4 out of 10, Very good, (1017)
"Excellent "
The price is NZ$213
includes taxes & fees
10 Jun - 11 Jun
The Champagne Lodge & Luxury Suites
Sleep Inn Midway Airport Bedford Park
2.5 star property
7.4 out of 10, Good, (1025)
"It was convenient and clean"
The price is NZ$190
includes taxes & fees
1 Jul - 2 Jul
Sleep Inn Midway Airport Bedford Park
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Homewood holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Homewood. 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 Homewood. Seeing all the best attractions is bound to make you fall in love with Homewood. Who knows, you may even be tempted to extend your 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 holiday 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 Homewood short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Homewood?

Yes, there are holiday rentals close to the most popular sights in Homewood, or you can select a more secluded option if you're looking for a relaxing stay. Homewood is known for its golf courses.

What are some of the best holiday rentals that Homewood has to offer?

Cozy, King bed with heated bathroom!: This holiday home rental outside of Homewood offers a garden, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

How many holiday rentals are there in Homewood?

Expedia has 17 holiday rentals for your stay in Homewood.

What can I see and do in Homewood?

Enjoy the area's cultural attractions such as Midwest Carvers Museum, or get outdoors into nature at a spot like Centennial Park. In the wider area, you’ll find Ravisloe Country Club and Hollywood Casino Amphitheatre.

What are holiday rentals like in Homewood?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Homewood. Holiday rentals offer amenities such as patios, hot tubs and fire pits so you'll have all the comforts of home. If you're concerned about a clean environment, a holiday rental can offer a sense of privacy away from public hotel lifts and busy reception areas while still allowing you to travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for family trips.

Recent reviews of Homewood properties
Expedia verified reviews