
House vacation rentals in Homewood
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Top-rated house rentals in Homewood
Guests agree: these houses are highly rated for location, cleanliness, and more.

Cozy, Clean, 1 Bedroom w/ Kitchen & Prking, for 4
Enjoy our historic district three-flat w/ free parking in upscale, safe Oak Park just 3 blocks to the train, easy access to Chicago. Enjoy some tranquil time in our little eco suburban farm. Check out the gardens and visit our 6 friendly chickens. This non-smoking unit with full kitchen is perfect for tourists, families, or business travelers. We require no check-out chores. Easy highway and airport access. No parties. Booking age, 25 or at least one 5 ⭐️ review. Visit profile for more units.

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.

Retro Modern Bungalow | fire pit | free parking
Experience the city in style at our Retro Modern Bungalow, the perfect pad for up to 4 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.

Boho Chic Coach House 30Min to downtown W/ Parking
Whether your looking to stay near family or be close to Downtown. This place has it ALL! This coach house is located in Mt greenwood which is one of the safest neighborhoods in the City of Chicago. It is home to many police, firefighters and teachers. Downtown is a quick 30 minute drive and there are also many bars and restaurants in walking distance. The home has been totally renovated and stocked with all the essentials. All you need to do now is pack your bags and enjoy your vacation.

The Gray Warbler single family lake view home
Stunning 3 bedroom 2 bathroom home! Breathtaking lake views from all living spaces! Nestled in a serene location this fully remodeled retreat with all brand new furnishings offers a perfect getaway. Comfortable, brand new adjustable base mattresses, clean, modern bathrooms with new tile showers and a tub, well equipped kitchen with new granite counters and stainless appliances open to our living room with 65" HD smart TV and Verizon 5G. Enjoy our arcade with Golden Tee and Mrs. Pac-Man!

Lockports Famous Hideaway ~ 2bdrm Guest House Flat
A history buff’s dream filled with antiques & artifacts relating to Chicago, Joliet, Lockport, the I & M Canal & "Route 66"! *Note: Pricing is based on "Double Occupancy". Extra charges per person apply after 2 guests. Can accommodate up to 6 guests. Family & Business Friendly. The entire upstairs 1,500 sq ft vintage 2-bedroom house apartment is all your own space. The flat is NOT shared with other guests/host. Private-entrance/self-check-in. Have a 'historic' stay at the "Hideaway"!

The Dune Den! Huge Yard/Firepit/Near Town+Dunes
Right in-between The Dunes National Park and downtown Chesterton, you will be close to everything when you stay at this centrally-located home. Things to look forward to: Less than 10 minutes to the Dunes and beaches or head 3 minutes the other way to downtown for food, drinks and plenty of small town fun. This charismatic home greets you with all new furniture, front porch, HUGE fenced yard, and local decor. You will fall in love with this family town so bring the kids!

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.

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.

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.

Updated, bright, and modern, 3 bedroom home.
You will be comfortable in this newly remodeled three bedroom, two bathroom home. ✶ 6.7Miles to Olivet Nazarene University ✶ 8.4Miles to Riverside Medical ✶ 11Miles to Kankakee River State Park ✶ 43Miles to Midway Airport The home FEATURES: *Safe, quiet, walkable neighborhood *3 Bedroom; 1 King, 1 Queen, 2 twin beds *Spacious fully equipped kitchen with coffee station *Washing Machine, Dryer & Dishwasher * Fast Wi-Fi

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

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

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

Munster hide away

Spacious 2BR in The Loop + 5-Star Comfort

Friends-Inspired Vintage Vibes House near Chicago

A Glass House in a Gated Nudist Resort

King Queen Bunk Bed Cozy Munster MiniGolfHouse

Lake Escape in Nudist Paradise
Weekly house rentals

Dream Stay - Modern Bungalow Near Downtown

Experience Chicago from Our 3-Story Retreat

Relax city

Lakeview Estate

Midway Airport • 3BR Home • 5 Beds • Free Parking

House in Frankfort quiet family neighborhood

Home away from home

Laurna Dune
Private house rentals

Beachfront-Lake Michigan-Indiana Dunes-5BD/3BR

The Ashlin House.

Lakeside Loft

Spacious Serene Escape~ 20 mins IN Dunes

The Blue House: Family Retreat

Luxury Meets Comfort

The Jefferson House

1 Block to Beach/next door to the National Park
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.ﺇ845 | ﺩ.ﺇ881 | ﺩ.ﺇ1,058 |
| 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 970 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

4.6 Average rating
Homewood stays receive an average rating of 4.6 out of 5 from guests
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- Lincoln Park
- Millennium Park
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- United Center
- Navy Pier
- 875 North Michigan Avenue
- Humboldt Park
- Shedd Aquarium
- Guaranteed Rate Field
- The Field Museum
- Oak Street Beach
- Wicker Park
- Lincoln Park Zoo
- Garfield Park Conservatory
- Frank Lloyd Wright Home and Studio
- The Beverly Country Club
- Museum of Science and Industry
- Brookfield Zoo
- Willis Tower
- Washington Park Zoo
- The 606
- Raging Waves Waterpark
- Villa Olivia
- Chicago Cultural Center




