
House vacation rentals in Homewood
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Top-rated house rentals in Homewood
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Entire home: Private, Cozy Oasis in a Quiet Locale
30 minute drive from Chicago's Grant Park. Near Little Calumet and Monon trails. Appeals to nature enthusiasts, cyclists, remote workers and brewery aficionados. This 2 bedroom, 1 bathroom retreat offers comfort and convenience. Full kitchen, private backyard and comfortable living space. 3 casinos, 6 breweries: 3 Floyds, 18th Street, Fuzzyline, Byway, New Oberpfalz & Wildrose within 7 to 20 min drive. Early check-ins offered/subject to availability. Feel free to inquire on availability.

Cozy, Artsy Gem in Historic Pullman
Our home is a great getaway from the hustle and bustle of downtown. The interior, tastefully rehabbed, showcases art from local artists. The neighborhood has the same charm of the late 1800s when the house was built, and is within walking distance of the Visitor Center, Exhibition Center, Pullman Club Coffee Shop, and the National A. Philip Randolph Pullman Porter Museum, which is currently under construction. My husband and I live directly across the street makes us accessible to guests.

RetroModern Bungalow | free parking | pet friendly
Experience the city in style at Retro Modern Bungalow, the perfect pad for up to four friends. Featuring two spacious bedrooms—each with a king bed and luxury linens—a propane fire pit and a fully fenced, pup-friendly backyard. Enjoy central HVAC, speedy WiFi, and a dedicated workspace. A pack-n-play crib is available at no cost. Central location—just south of Oak Park, 15 mins from Midway airport, and 20 mins from downtown. Park for free in our garage or catch the train a few blocks away.

Cheerful 3 Bedroom, 2.5 bath central Bradley Home
A GREAT HOME AWAY FROM HOME! Conveniently located in central Bradley's family friendly Blatt Subdivision. Home sleeps six guests. 3 bedrooms, 2 queen and 2 twin beds. 2.5 bathrooms including a tub and a walk-in shower, complete with linens, toiletries and hair dryer. Additional features include a large kitchen with cooking accessories, air fryer and some essential condiments including coffee. Fenced in yard, small patio and 2 car garage. Scan QR Code in photos for Virtual Tour.

Two king beds with 3 bedroom 2 bath
4 minutes from I-57 expressway. This is a three bedroom two full bath townhome with a 2 car attached garage. King bed & 55' smart tv in the master bedroom. The Master bedroom also has a full bathroom with complimentary body wash, shampoo & conditioner. 2nd bedroom has a king size bed with king size hotel pillows. 3rd bedroom has queen bed with 55" smart tv. In closet you will find a deluxe queen size air bed with extra pillows & linens. Patio has table & chairs & charcoal grill.

The Country Life! Spacious House.
Live the Country Life in this beautiful suburban home. The entire house is yours to enjoy. Sleeps up to 12* comfortably with 4 bedrooms, 2 bathrooms and kitchen. No smoking indoors but enjoy the outdoors, barbeque in the yard or relax on the deck when weather permits. * No unauthorized events, parties, repast, gatherings or visitors; Your reservation subject to be canceled and/ or $500 FINE. No Refunds! * Extra guest fee over 8 *Small private events may be considered for a fee*

Boulderstrewn: Historic Homewood home
Charming and historic Sears Catalog House on 2/3 acre wooded lot. Less than 10 minute walk to shops and restaurants in downtown Homewood to Metra rail (and Amtrak) station with express service to Hyde Park and University of Chicago (less than a half hour) and Chicago's 3 magnificent downtown waterfront stations (~40 minutes). Fire pit in yard can be used to enjoy summer nights. No cable, but several digital antenna channels available as well as Netflix, XBox and DVDs.

Bayless Dune Lodge at West Beach - Indiana Dunes!
Bayless Dune Lodge at West Beach is a gorgeous, Lodge-themed home in Miller Beach, Indiana, a scenic community surrounded by the Indiana Dunes National Park! A short walk to one of the finest white sand beaches on Lake Michigan, the Lodge sits on nearly half an acre of land nestled into the "Bayless Dunes Nature Preserve." The property boasts a heated, in-ground swimming pool, pool-side lounge area, two outdoor dining areas, two spa-quality bathrooms and more!

Warm and comfortable inviting Suburban home !
160 year old land mark community, Framed cedar bevel siding 2 story home, front porch , 10 ft high ceilings, kitchen canned lighting home. 6 feet fence In closed yard, whole house water filtration system , Quite neighborhood with sidewalks . 19 miles to downtown Chicago , Metra train station and bus route, in walking distance . driving to the city of Chicago 5 minutes to major expressways . Host is willing to be available for any and all information 24/7.

Secluded Modern Retreat Near Beach - "Sandlot"
Stunning modern home overlooks private sand dunes on 5 wooded acres just a mile away from beautiful Lake Michigan beaches and surrounded by the Indiana Dunes National Park. Relax in our updated open-concept unique home nestled in the dunes. Enjoy the trails in the backyard, the friendly community, and local attractions near by. Just an hour to Chicago by car or the South Shore train is 1/2 mile from the house, with easy rides to Chicago and South Bend.

Cozy three bedroom home in Munster , Indiana.
Plan your next escape to Indiana or Illinois and stay in this beautifully renovated and thoughtfully appointed 3 bedroom and 1 bath home. Located in the quiet and safe suburb of Munster, Indiana, the property is just a 3 minute, easy access to the I-94 Highway. Exciting Downtown Chicago is just 30 minutes away! Walk to Riverside Park and take in the scenic view while enjoying a morning croissant and coffee from one of the quaint neighbourhood cafés.

Quiet cul-de-sac with huge fenced in backyard
3 bedroom, 2 bath ranch home on a quiet cul-de-sac. Big fenced in backyard for the kids, dog, & adults to play during the day, then relax by the fire at night. Walking distance (50 ft.) to the bar/restaurant with private entrance. 15 miles (25 mins) from downtown Chicago. And for you couples, come back home from your busy day, sit back and relax in the 8 jet jacuzzi whirlpool tub that will comfortably fit both of you.
Popular amenities for Homewood house rentals
House rentals with a pool

Elegant Executive Residence, Hot Tub/Pool/Parties!

Comfy 3BR 2BA, Liv+Fam Rm, Prime, 3-Car Parking

Pool & Beach Haven-private pool, steps to beach!

Chic Fulton Market Oasis + Curated Comfort & Style

Munster hide away

30 mins to CHI|3 Kings|BBQ Grill|TV| Spacious

Cheerful 4 bedroom 2 king size beds, 2 queen size

Friends-Inspired Vintage Vibes House near Chicago
Weekly house rentals

Romantic Escape ~ Adult Playhouse w Exotic Dungeon

The Ashlin House.

Cozy Home in Brookfield

Lakeside Loft

Cozy Getaway Home+FREE Parking+Fast Wi/Fi+Central

The Heights of Chicago

Modern Oasis Getaway Home. Free Cancellation

Fore! Peace & Love @ Golf House
Private house rentals

5 Star Upscale Entire Family Neighborhood Home

Winter Discounts! Cozy Home away from Home!

A Wonderful Getaway Home on the North Shore!

The Blue House: Family Retreat

Elegant 4BR Tudor Retreat — Spacious, Peaceful!

Beautiful , fully renovated

House in Frankfort quiet family neighborhood

Luxurious House near downtown Chicago
When is the best time to visit Homewood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ797 | ﺩ.ﺇ738 | ﺩ.ﺇ723 | ﺩ.ﺇ668 | ﺩ.ﺇ801 | ﺩ.ﺇ793 | ﺩ.ﺇ793 | ﺩ.ﺇ760 | ﺩ.ﺇ602 | ﺩ.ﺇ720 | ﺩ.ﺇ698 | ﺩ.ﺇ679 |
| Avg. temp | -3°C | -1°C | 4°C | 10°C | 16°C | 22°C | 25°C | 24°C | 20°C | 13°C | 6°C | 0°C |
Quick stats about house rentals in Homewood

Total vacation rentals
Explore 30 vacation rentals in Homewood

Nightly prices starting at
Homewood vacation rentals start at ﺩ.ﺇ184 per night before taxes and fees

Verified guest reviews
Over 1,060 verified reviews to help you choose

Family-friendly vacation rentals
30 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
30 of Homewood vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Homewood rentals

4.7 Average rating
Homewood stays receive an average rating of 4.7 out of 5 from guests
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- Lincoln Park
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- 875 North Michigan Avenue
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- Shedd Aquarium
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- Frank Lloyd Wright Home and Studio
- Oak Street Beach
- Museum of Science and Industry
- Brookfield Zoo
- Willis Tower
- University of Chicago
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- Loyola University Chicago
- The 606




