Homewood Vacation Rentals

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Our top choices for Homewood vacation rentals

3.0 star property
4.0 out of 10, (68)
"Good "
United States
Abel
$94 nightly
The price is $106
Dec 17 - Dec 18
Total with taxes and fees
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
2.0 star property
Stylish Apartment near Chicago Downtown
8.4 out of 10, Very Good, (12)
"The place was well maintained and very clean with no issues and the host was great and fast to respond."
United States
Tenika P.
Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!

Apartment in Hyde Park

Modern Studio Near UChicago
9.6 out of 10, Exceptional, (11)
"Clean room and convenient location! "
United States
Gabriela
$144 nightly
The price is $160
Jan 1 - Jan 2, 2026
Total with taxes and fees
Modern Studio Near UChicago

Apartment in Hyde Park

Modern 1BR in Historic HydePark
8.4 out of 10, Very Good, (13)
"The location couldn't be beat. The beds were super comfortable and the room was perfect for my husband and I. We'll definitely stay here again!"
United States
Lisa O.
$150 nightly
The price is $165
Dec 17 - Dec 18
Total with taxes and fees
Modern 1BR in Historic HydePark

Vacation Home in South Shore

LakeHouse
9.4 out of 10, Exceptional, (26)
"This was a cute place with a lot of space. Nice backyard with areas to chill. The grand piano is beautiful and in tune!"
United States
Kenna C.
LakeHouse
9.8 out of 10, Exceptional, (15)
"Wonderful property and nice owners. I definitely recommend and will stay again if I'm ever in the area."
United States
Karen D.
$178 nightly
The price is $199
Dec 18 - Dec 19
Total with taxes and fees
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
9.6 out of 10, Exceptional, (17)
"Nice and cozy place to stay. We enjoyed our secluded area during our time here."
United States
Allison A.
$92 nightly
The price is $103
Dec 30 - Dec 31
Total with taxes and fees
Beautiful Rustic Cabin for Two!
9.8 out of 10, Exceptional, (34)
"We loved it!!! Perfect space for the 3 of us area is beautiful!! "
United States
Aaliyah G.
$196 nightly
The price is $209
Dec 21 - Dec 22
Total with taxes and fees
Less is more! Pet friendly Tiny Home near Chicago!

Vacation Home in Calumet Heights

A Home Away From Home!
9.6 out of 10, Exceptional, (14)
"Great place to stay. Host responded quickly to questions. Location was good and neighbor was quite. "
United States
Marchand J.
A Home Away From Home!
7.6 out of 10, Good, (4)
"Only issue was the water pressure in the bathroom was very very low. "
United States
Derrick M.
$319 nightly
The price is $341
Dec 17 - Dec 18
Total with taxes and fees
Charming 2-bedroom apartment in marvelous Blue Island with WiFi
9.4 out of 10, Exceptional, (3)
"All the necessities with no personal touches. Keys from lockbox to open second door were not needed as the second door is always open. Impeccable communication with host. Great location, close to restaurants and train to Millennium Station. Coffee service was excellent, just be sure to find extra pouches in cabinet. Bathtub faucet could not be turned far enough to prevent leaking. TV remote not great and I couldn’t get CNN or MSNBC. I’d stay here again. "
United States
lost whale press
$168 nightly
The price is $183
Dec 17 - Dec 18
Total with taxes and fees
Explore Hyde Park: 2BR Apt on Blackstone Ave
8.8 out of 10, Excellent, (15)
"Clean, nice"
United States
Autumn R.
Luxury Apartment in Bronzeville, Just Minutes from Downtown - RSV Now!
10.0 out of 10, Exceptional, (12)
"We were in town for a concert at Soldier Field, and overall tourism activities in Chicago. The bnb was very clean, and as advertised. "
United States
Griffin H.
1-bedroom condo next to Chicago Midway International Airport
9.8 out of 10, Exceptional, (27)
"Perfect for what we needed"
United States
Richard G.
Penthouse Condo in Chicago featuring Zero Gravity Massage Chair
9.6 out of 10, Exceptional, (74)
"Enough room for a quick get away"
United States
wendy C.
Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum
10.0 out of 10, Exceptional, (2)
"Great House, and everything is brand new! Loved the sheets and the towels, and the beds were all super comfy. The outdoor fire pit was a nice touch and made our night a great experience. "
United States
Jim A.
$2,184 nightly
The price is $2,446
Dec 17 - Dec 18
Total with taxes and fees
Spacious 5-Bedroom Golf Course Home Perfect for Getaways & Special Occasions
9.4 out of 10, Exceptional, (21)
"The owners were SUPER helpful and their communication was SUPERB!"
United States
Juan B.
Mayors Manor, Zen Garden Oasis, Hot Tub & Sauna in Central Chicago, 8-12 guests

Apartment in Bronzeville

Toca Bella ~ 7mins to Downtown
9.8 out of 10, Exceptional, (20)
"The place is nice and clean. Public transportation is very close by so you can hop on CTA and visit McCormick Place and Downtown with ease. We loved the neighborhood and the architecture too. My wife says that it probably beats Baltimore’s."
United States
Luis
Toca Bella ~ 7mins to Downtown
10.0 out of 10, Exceptional, (4)
"Great place to stay host was very communicative which made the stay a lot easier highly recommend "
United States
Alcario B.
South Shore Chicago Condo-1 Block to Lake-WiFi-AC-Elevator-420 Friendly
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 Homewood Hotel Reviews

Find out more about Homewood

Everything you need to know about Homewood vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Homewood vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Homewood vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Homewood vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Homewood. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Homewood in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $103 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Homewood rentals

At Expedia, we put the best Homewood vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Homewood rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Homewood vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Homewood. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Are there vacation rentals in Homewood?

Yes, we offer vacation rentals near the most popular sights in Homewood, or you can go with a more remote option if you'd like a relaxing place to stay. Homewood is known for its golf courses.

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

A Home Away From Home!: This vacation home rental outside of Homewood offers a fireplace, a garden, 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 vacation rentals are there in Homewood?

Expedia has 16 vacation rentals for your stay in Homewood.

What can I see and do in Homewood?

Explore the area and family-friendly sights such as Odyssey Fun World, or get out into nature at a spot like Centennial Park. In the larger area, you’ll find Ravisloe Country Club and Credit Union 1 Amphitheatre.

What are vacation rentals like in Homewood?

Vacation rentals are privately owned accommodations you can stay in for a couple days or more in Homewood. Vacation rentals feature extras like kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about cleanliness, a vacation rental can offer a sense of seclusion away from public hotel elevators and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive option for a family trip.