Vacation rentals in Homewood

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Homewood

Guests agree: these stays are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favorite

Farm stay in De Motte

4.94 out of 5 average rating, 113 reviews

Cozy barn loft on organic vegetable farm

Find peace and restoration in this beautiful barn loft at Perkins' Good Earth Farm. The loft has a bedroom, separate shower and toilet spaces, work area, sitting room, kitchen space, and heating/cooling fresh air system. Located above our farm store, the loft provides privacy for you while giving you access to fresh fruits & veggies, locally sourced meats, homemade soups & salads from our farm kitchen, and so much more. You can also walk our farm trails, visit the veggies, or enjoy a campfire.

Mar 21 – 28

$73 per night

Guest favorite

Apartment in Homewood

5.0 out of 5 average rating, 39 reviews

Charming Garden Apartment

Make yourself at home in a charming apartment with all the amenities! Lose yourself birding or reading a book surrounded by lush gardens. Take a short walk to lovely downtown Homewood to enjoy shopping & dining or catch the train to Chicago. After a day of exploring, a king-sized sleep number bed and lush bathroom features will pamper you! A fold-down sofa creates an additional bed. Dogs are welcome! This suite has a kitchenette with a convection toaster oven, induction cooktop, and fridge!

Dec 22 – 29

$95 per night

Guest favorite

Home in Lansing

4.84 out of 5 average rating, 64 reviews

The Walter Experience

Come indulge in your private oasis located 35 mins from DT chicago. Ideal for Business Travelers(close to I 90/94), Couples ( Perfect Getaway ) and Small Families or friends( Relax & Replenish). Tour our town or neighboring towns ( indiana state line 2 mins away-Munster/Hammond/ Schererville -Lower taxes,Gas,etc. Local entertainment (shows or other events) Complimentary early check in may be extended. Depending on availability, Home is thoroughly cleaned and sanitized before arrival.

Sep 26 – Oct 3

$87 per night

Superhost

Home in Homewood

4.91 out of 5 average rating, 35 reviews

Charming Homewood Away from Home

Keep it simple at this peaceful and centrally-located place. Cozy and Charming brick ranch nested on a quiet street. Minutes from the metra line taking you to downtown Chicago or visit the neighborhood shopping in downtown Homewood. No smoking and no parties. We are unable to accommodate a party of any size because of our agreement with our neighbors. Driveway is narrow. Limit 2 cars. No extra guest without notice. Extremely strict neighbors! We follow all cancellation rules.

Dec 20 – 27

$145 per night

Guest favorite

Apartment in Homewood

4.84 out of 5 average rating, 19 reviews

High-End Oasis Close to Fun

Escape to our inviting 2nd-floor High-End condo, just a short 37-minute drive from the vibrant heart of Downtown Chicago, Millennium Park, and Navy Pier. Immerse yourself in the charm of our neighborhood, surrounded by custom homes, golf clubs, and family-friendly entertainment. Many dining options all within a 2-minute drive or a quick Uber ride. Large balcony with seating for six and 2 minutes from the Metra Train Station for a fast trip to Chicago. Be one of our first guests!

Dec 20 – 27

$166 per night

Superhost

Home in Homewood

4.91 out of 5 average rating, 106 reviews

Peaceful & Private Hot Tub Vacation Home Getaway

A Rare gem 💎in the heart of Homewood. This Quaint 2-bedroom remodeled home is charming, sophisticated and discrete. It is minutes away from the Metra station, golf course and downtown Homewood shops. The energy is very calm and quiet ☯️. This is the home away from home where details are everything and the pictures do not capture the essence of this luxurious space. Experience the love, the joy and the peace that continues to leave its mark. Peace and Love - Michael and KP💞

Aug 20 – 27

$194 per night

Superhost

Home in Homewood

4.95 out of 5 average rating, 19 reviews

Our Homewood Home

Hi. We want to thank you for considering staying at our home in Homewood. We set this home up for us to use when we are in Chicago as a family for business or pleasure. We live out of state and needed a comfortable and quiet home where we and our 4 kids could stay for extended periods of time. This home is in a very quiet neighborhood, with amazing neighbors and a very large backyard. We hope you will enjoy it as much as we do. Scan the QR code for virtual tour.

Mar 30 – Apr 6

$250 per night

Guest favorite

Tiny home in Burr Ridge

4.92 out of 5 average rating, 237 reviews

Less is more! Pet friendly Tiny Home near Chicago!

Less is more--see for yourself how big 250 square feet can really feel! For those who would love to try tiny living and a minimalist lifestyle, this is the perfect getaway. This tiny house has everything you will need to fall in love with tiny living! There is a fenced yard, grass area for furry friends, free parking and is close to hiking trails, restaurants, shops, breweries, bars, and Chicago! Check us out on Insta: @LessIsMore_TinyHome

Nov 19 – 26

$112 per night

Guest favorite

Apartment in Blue Island

4.93 out of 5 average rating, 262 reviews

Charming Unique 2 Bdrm Apartment in Victorian Home

My place is close to the excitement and culture of the beautiful city of Chicago. It is a short walk to Metra trains with a 25 minute ride downtown. You’ll love my place because of the diverse, comfortable, quiet, tree lined neighborhood where you can relax and feel secure. It is close to expressways, golf courses and a local park with walking path. The apartment is not available to guests without previous positive reviews.

Nov 2 – 9

$137 per night

Guest favorite

Townhouse in Country Club Hills

5.0 out of 5 average rating, 16 reviews

Luv Happii House

Truly enjoy home away from home at the Luv Happii House, a Charming, vintage style canna friendly townhouse. Perfect for a weekend getaway, business trip, work from home alternative, content creation, or cozy home base while exploring everything Chicago and the South Suburbs of Chicago have to offer including nearby The Credit Union 1 Amphitheater and Tinley Park Convention Center.

Dec 15 – 22

$146 per night

Superhost

Home in Whiting

4.8 out of 5 average rating, 225 reviews

Whiting Getaway

Nicely situated in the quiet and safe city of Whiting IN, near the bustling Whihala Beach on Lake Michigan, just down the street from Wolfe Lake and the Wolfe Lake Pavilion, within 2 miles of The Horseshoe Casino and just 20 minutes (17.5 miles) from downtown Chicago, this house offers a perfect location for a complete vacation. Come and enjoy all that the 'region' has to offer

Apr 22 – 29

$80 per night

Guest favorite

Cottage in Merrillville

4.89 out of 5 average rating, 183 reviews

The Hideaway

This cozy cottage (lodging only, renters only) located 30 minutes from Chicago is located on a private 3 acre property. It’s a private detached cottage that sleeps four. One king size bedroom (sheets supplied), large full bathroom with deep tub (towels supplied), full kitchen (dishes, pots and pans ect supplied) and private parking. Also has its own fire pit for enjoyment.

Jun 3 – 10

$95 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Homewood vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Homewood's top sights

Blueberry Hill Pancake House4 locals recommend

Grady's Snack N' Dine4 locals recommend

Flossmoor Station Restaurant & Brewery5 locals recommend

Other great vacation rentals in Homewood

Superhost

Home in Matteson

4.86 out of 5 average rating, 50 reviews

Tranquil 2 bedroom ranch home

Dec 16 – 23

$160 per night

Guest favorite

Home in Munster

4.97 out of 5 average rating, 33 reviews

Entire home: Private, Cozy Oasis in Quiet Locale

Oct 19 – 26

$116 per night

Guest favorite

Guest suite in Homewood

4.96 out of 5 average rating, 54 reviews

Cozy/Romantic Game Room Suite w/Outdoor Hot Tub

Oct 25 – Nov 1

$155 per night

Guest favorite

Home in Oak Forest

4.91 out of 5 average rating, 75 reviews

Cheerful three bedroom, 2 full bath in Oak Forest

Jun 5 – 12

$238 per night

Guest favorite

Home in Chicago

4.92 out of 5 average rating, 85 reviews

Boho Chic Coach House 30Min to downtown W/ Parking

Mar 1 – 8

$99 per night

Guest favorite

Home in Olympia Fields

5.0 out of 5 average rating, 9 reviews

Exquisite Getaway Home

Dec 6 – 13

$235 per night

Guest favorite

Guest suite in Orland Park

4.99 out of 5 average rating, 70 reviews

Private Guest Suite 2 Cozy Rooms

May 25 – Jun 1

$99 per night

Guest favorite

Home in Munster

5.0 out of 5 average rating, 12 reviews

Cozy Farmhouse in Munster

Jun 7 – 14

$93 per night

Show all

Quick stats about vacation rentals in Homewood

Total rentals
30 properties
Wifi availability
30 properties include access to wifi
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
30 properties are a good fit for families
Total number of reviews
630 reviews

Frequently Asked Questions

How much does it cost to stay in house rentals in Homewood?
Experience the best of Homewood with our house rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there family-friendly vacation rentals in Homewood?
Homewood has more than 30 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Are there pet-friendly vacation rentals in Homewood?
Four-legged friends are welcome in Homewood. Choose from more than 10 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Homewood?
Yes! Work meets play with ease at over 20 vacation rentals in Homewood featuring dedicated workspaces. Stay connected and productive in your home away from home.

Vacation rentals in Homewood

Top-rated vacation rentals in Homewood

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Homewood vacation rentals

Stay near Homewood's top sights

Other great vacation rentals in Homewood

Home in Matteson

Home in Munster

Guest suite in Homewood

Home in Oak Forest

Home in Chicago

Home in Olympia Fields

Guest suite in Orland Park

Home in Munster

Quick stats about vacation rentals in Homewood

Total rentals

Wifi availability

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

How much does it cost to stay in house rentals in Homewood?

Are there family-friendly vacation rentals in Homewood?

Are there pet-friendly vacation rentals in Homewood?

Are there vacation rentals with a dedicated workspace in Homewood?

Destinations to explore