Vacation rentals in Glenwood

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Top-rated vacation rentals in Glenwood

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

Guest favorite

Apartment in Chicago

4.92 out of 5 average rating, 166 reviews

Handicap accessible apartment w/Level-2 EV Charger

Just 12.5 miles from downtown in the extremely quiet Chicago neighborhood of Hegewisch. Walking distance to the South Shore train line, which can easily get you to Chicago museums and entertainment, or attractions in NW Indiana. Private parking in back also gives you the option of driving anywhere and then walking directly to your door, and outside cameras are present for security. Banks, restaurants, grocery, convenience, and liquor stores are all 1 block of the apartment for all your needs.

Aug 16 – 23

$94 per night
Guest favorite

Farm stay in De Motte

4.94 out of 5 average rating, 109 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.

Sep 26 – Oct 3

$73 per night
Superhost

Home in Richton Park

4.84 out of 5 average rating, 207 reviews

Spacious home near Chicago, fenced yard for pets

Modern single family home with over 2100 sqft of space including 3 bedrooms, & 2.5 bathrooms. Located in a quiet neighborhood with free parking, our home has easy access to trains & major highways. We're a short ride from Downtown Chicago, Midway Airport, Tinley Park Convention Center, Hollywood Casino Amphitheatre, universities, shopping & dining. Enjoy a fully stocked kitchen, washer/dryer, WIFI, smart tv & spacious deck. Come unwind in a cozy living space during your trip to Illinois! 5279

Dec 11 – 18

$299 per night

Popular amenities for Glenwood vacation rentals

Other great vacation rentals in Glenwood

Guest favorite

Home in Munster

4.97 out of 5 average rating, 30 reviews

Entire home: Private, Cozy Oasis in Quiet Locale

Dec 3 – 10

$110 per night
Superhost

Home in Homewood

4.91 out of 5 average rating, 33 reviews

Charming Homewood Away from Home

Oct 28 – Nov 4

$134 per night
Guest favorite

Home in Hammond

4.8 out of 5 average rating, 87 reviews

Spacious home 28 miles from Downtown Chicago

Jul 21 – 28

$248 per night
Superhost

Home in Homewood

4.95 out of 5 average rating, 19 reviews

Our Homewood Home

Mar 11 – 18

$250 per night
Guest favorite

Townhouse in Country Club Hills

5.0 out of 5 average rating, 14 reviews

Luv Happii House

Nov 1 – 8

$166 per night
Guest favorite

Home in Munster

4.9 out of 5 average rating, 81 reviews

Cozy House with Gazebo

Dec 11 – 18

$153 per night
Guest favorite

Home in Munster

4.93 out of 5 average rating, 69 reviews

Cozy three bedroom home in Munster , Indiana.

Dec 24 – 31

$148 per night
Guest favorite

Guest suite in Orland Park

4.99 out of 5 average rating, 67 reviews

Private Guest Suite 2 Cozy Rooms

May 26 – Jun 2

$92 per night
Guest favorite

Apartment in Hammond

4.96 out of 5 average rating, 45 reviews

Wolfe Lake Getaway

Mar 1 – 8

$66 per night
Guest favorite

Home in Olympia Fields

5.0 out of 5 average rating, 6 reviews

Exquisite Getaway Home

Jan 1 – 8

$224 per night
Guest favorite

Home in Park Forest

4.98 out of 5 average rating, 43 reviews

King bed comfy 3 BR Entire home in Suburban Area

Jul 26 – Aug 2

$214 per night
Guest favorite

Home in Chicago

4.92 out of 5 average rating, 84 reviews

Boho Chic Coach House 30Min to downtown W/ Parking

Jun 28 – Jul 5

$105 per night

Destinations to explore

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  4. Cook County
  5. Glenwood