Vacation rentals in Crestwood

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Top-rated vacation rentals in Crestwood

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.

Nov 12 – 19

G$16,831 GYD per night
Guest favorite

Bungalow in Chicago

4.89 out of 5 average rating, 100 reviews

Relax.Relate.Release in our Bungalow

Relax in our spacious Bungalow. Relate in the essence of another Chicago gem. Release your inner thoughts during your stay. Hardwood floors set this space as you travel the first level. Traveling to the second level you are met with carpet for a short while. This home is great for family, couples, individuals, short and long stays. Close to major highways, bus transportation and walk/bike paths. Very quiet tree-lined neighborhood. About 20mins to downtown and close to south suburbs of Chicago.

Jun 9 – 16

G$36,631 GYD 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.

Jan 24 – 31

G$17,638 GYD per night

Popular amenities for Crestwood vacation rentals

Other great vacation rentals in Crestwood

Guest favorite

Home in Chicago Ridge

4.89 out of 5 average rating, 44 reviews

Quiet cul-de-sac with huge fenced in backyard

Nov 27 – Dec 4

G$31,342 GYD per night
Superhost

Apartment in Chicago

4.91 out of 5 average rating, 35 reviews

Ultra Modern Beverly Suite

May 4 – 11

G$24,954 GYD per night
Guest favorite

Home in Oak Forest

4.91 out of 5 average rating, 74 reviews

Cheerful three bedroom, 2 full bath in Oak Forest

May 3 – 10

G$57,258 GYD per night
Guest favorite

Apartment in Chicago Ridge

4.86 out of 5 average rating, 14 reviews

Peaceful two bedroom condo

Apr 30 – May 7

G$28,886 GYD per night
Guest favorite

Home in Worth

4.94 out of 5 average rating, 32 reviews

Worth It! 3 bedroom ranch home

Mar 20 – 27

G$37,871 GYD per night
Guest favorite

Townhouse in Calumet Park

4.83 out of 5 average rating, 65 reviews

Calumet Park Townhouse/ Chell's Hideaway

Aug 21 – 28

G$30,058 GYD per night
Guest favorite

Condo in Palos Hills

4.87 out of 5 average rating, 54 reviews

~King Bed, Updated, Fast Wi-Fi, Near Hospitals~

Feb 22 – Mar 1

G$33,557 GYD per night
Superhost

Condo in Evergreen Park

4.8 out of 5 average rating, 90 reviews

Evergreen Park Condo with balcony and Jacuzzi tub

Dec 19 – 26

G$27,091 GYD per night
Guest favorite

Home in Calumet Park

4.94 out of 5 average rating, 17 reviews

My quaint little escape

Nov 22 – 29

G$27,475 GYD per night
Guest favorite

Condo in Chicago Ridge

4.96 out of 5 average rating, 55 reviews

Industrial Sheek Gem

Aug 10 – 17

G$35,851 GYD per night
Guest favorite

Home in Munster

4.97 out of 5 average rating, 30 reviews

Entire home: Private, Cozy Oasis in Quiet Locale

Jan 18 – 25

G$26,707 GYD per night
Guest favorite

Home in Lansing

4.83 out of 5 average rating, 59 reviews

Easter at The Walter Experience

Aug 10 – 17

G$21,123 GYD per night

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