50 Best Illinois Houses and Cottages – Holiday Lettings - Holiday Rentals Illinois

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  • Champaign-Urbana (1)
  • Chicago (223)
  • Cobden (3)
  • Cornell (1)
  • Cuba (2)
  • Danville (1)
  • Des Plaines (1)
  • DuPage County (4)
  • DuQuoin (1)
  • Effingham (2)
  • Elgin (1)
  • Elizabeth (1)
  • Evanston (3)
  • Fairmount (1)
  • Franklin Grove (1)
  • Freeburg (1)
  • Freeport (1)
  • Galena (16)
  • Geneva (1)
  • Glencoe (1)
  • Glenview (2)
  • Grayville (3)
  • Karbers Ridge (2)
  • Lake County (4)
  • Lake Villa (1)
  • Lima (1)
  • Lincolnwood (1)
  • Makanda (2)
  • Marion (1)
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  • Mount Carmel (2)
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  • Northbrook (2)
  • Oak Park (4)
  • Oswego (1)
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  • Sullivan (2)
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  • Utica (3)
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355 Holiday homes

Travellers going to Illinois are booking June dates now. Secure your holiday home today and have the perfect trip.

(1) Excellent 

1 / 21

Holiday condo rental

Illinois / Chicago

3 bedroomsSleeps 61 night min stay

  • 3 bedrooms
  • Sleeps 6
  • 1 night min stay

from $353 / night

$0 / week

Book Book View

from $353 / night

(1) Excellent 

1 / 11

Holiday apartment rental

Illinois / Chicago

3 bedroomsSleeps 102 nights min stay

  • 3 bedrooms
  • Sleeps 10
  • 2 nights min stay

from $217 / night

$1727 - $2961 / week

Book Book View

from $217 / night

(2) Excellent 

1 / 10

Illinois holiday apartment rental

Illinois / Chicago

2 bedroomsSleeps 63 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min stay

from $231 / night

$1614 - $2178 / week

Book Book View

from $231 / night

(32) Excellent 

1 / 57

Holiday apartment in Chicago

Illinois / Chicago

2 bedroomsSleeps 41 night min stay

  • 2 bedrooms
  • Sleeps 4
  • 1 night min stay

from $100 / night

$604 / week

Book Book View

from $100 / night

(7) Very Good 

1 / 7

Holiday apartment in Illinois

Illinois / Chicago

1 bedroomSleeps 31 night min stay

  • 1 bedroom
  • Sleeps 3
  • 1 night min stay

from $152 / night

$957 - $1027 / week

Book Book View

from $152 / night

(3) Excellent 

1 / 10

Apartment rental in Illinois

Illinois / Chicago

1 bedroomSleeps 42 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 2 nights min stay

from $260 / night

$2097 / week

Book Book View

from $260 / night

1 / 26

Holiday apartment in Illinois

Illinois / Chicago

4 bedroomsSleeps 232 nights min stay

  • 4 bedrooms
  • Sleeps 23
  • 2 nights min stay

from $202 / night

$0 / week

Book Book View

from $202 / night

(2) Very Good 

1 / 18

Holiday home in Chicago

Illinois / Chicago

3 bedroomsSleeps 9Min stay varies

  • 3 bedrooms
  • Sleeps 9
  • Min stay varies

from $140 / night

$879 - $1382 / week

Book Book View

from $140 / night

(1) Excellent 

1 / 21

Holiday home in Illinois

Illinois / Chicago

3 bedroomsSleeps 82 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min stay

from $202 / night

$1209 / week

Book Book View

from $202 / night

1 / 16

Hotel apartment rental in Chicago

Illinois / Chicago

3 bedroomsSleeps 8Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies

from $362 / night

$2517 - $4027 / week

Book Book View

from $362 / night

(6) Very Good 

1 / 27

Holiday apartment in Illinois

Illinois / Chicago

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies

from $353 / night

$2014 - $2895 / week

Book Book View

from $353 / night

(1) Excellent 

1 / 16

Holiday condo in Illinois

Illinois / Chicago

2 bedroomsSleeps 53 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min stay

from $503 / night

$3454 / week

Book Book View

from $503 / night

1 / 23

Holiday apartment rental

Illinois / Aurora

3 bedroomsSleeps 83 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min stay

from $201 / night

$1203 / week

Book Book View

from $201 / night

1 / 21

Holiday apartment in Chicago

Illinois / Chicago

2 bedroomsSleeps 123 nights min stay

  • 2 bedrooms
  • Sleeps 12
  • 3 nights min stay

from $302 / night

$2115 / week

Book Book View

from $302 / night

(15) Very Good 

1 / 39

Apartment rental in Illinois

Illinois / Chicago

Sleeps 21 night min stay

  • Sleeps 2
  • 1 night min stay

from $80 / night

$459 / week

Book Book View

from $80 / night

1 / 15

Chicago holiday apartment rental

Illinois / Chicago

2 bedroomsSleeps 63 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min stay

from $251 / night

$1755 - $2319 / week

Book Book View

from $251 / night

1 / 14

Hotel apartment rental in Chicago

Illinois / Chicago

2 bedroomsSleeps 63 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min stay

from $261 / night

$1913 - $3624 / week

Book Book View

from $261 / night

(1) Excellent 

1 / 23

Holiday home with golf nearby in Illinois

Illinois / Chicago

3 bedroomsSleeps 82 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min stay

from $1007 / night

$5035 / week

Book Book View

from $1007 / night

(3) Very Good 

1 / 13

Holiday private room in Illinois

Illinois / Chicago

2 bedroomsSleeps 41 night min stay

  • 2 bedrooms
  • Sleeps 4
  • 1 night min stay

from $90 / night

$0 / week

Book Book View

from $90 / night

1 / 29

Apartment rental in Chicago with golf nearby

Illinois / Chicago

3 bedroomsSleeps 62 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min stay

from $179 / night

$1209 - $1970 / week

Book Book View

from $179 / night

(3) Very Good 

1 / 40

Chicago holiday apartment rental

Illinois / Chicago

1 bedroomSleeps 4Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies

from $100 / night

$704 - $1480 / week

Book Book View

from $100 / night

1 / 11

Holiday apartment in Illinois

Illinois / Chicago

1 bedroomSleeps 42 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 2 nights min stay

from $152 / night

$1309 - $1838 / week

Book Book View

from $152 / night

(2) Excellent 

1 / 15

Holiday apartment in Chicago

Illinois / Chicago

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies

from $197 / night

$1158 - $1672 / week

Book Book View

from $197 / night

1 / 25

Holiday apartment in Illinois

Illinois / Chicago

2 bedroomsSleeps 71 night min stay

  • 2 bedrooms
  • Sleeps 7
  • 1 night min stay

from $252 / night

$1511 / week

Book Book View

from $252 / night

1 / 10

Condo rental in Chicago with swimming pool

Illinois / Chicago

2 bedroomsSleeps 53 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min stay

from $503 / night

$3524 / week

Book Book View

from $503 / night

1 / 12

Holiday apartment in Chicago

Illinois / Chicago

3 bedroomsSleeps 62 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min stay

from $382 / night

$2518 - $3726 / week

Book Book View

from $382 / night

1 / 8

Chicago holiday townhouse rental

Illinois / Chicago

3 bedroomsSleeps 62 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min stay

from $368 / night

$2417 - $3157 / week

Book Book View

from $368 / night

(1) Excellent 

1 / 21

Holiday hotel apartment in Chicago

Illinois / Chicago

1 bedroomSleeps 41 night min stay

  • 1 bedroom
  • Sleeps 4
  • 1 night min stay

from $222 / night

$1410 / week

Book Book View

from $222 / night

(1) Very Good 

1 / 13

Holiday apartment rental

Illinois / Chicago

2 bedroomsSleeps 81 night min stay

  • 2 bedrooms
  • Sleeps 8
  • 1 night min stay

from $96 / night

$554 - $1492 / week

Book Book View

from $96 / night

1 / 16

Holiday apartment in Chicago

Illinois / Chicago

3 bedroomsSleeps 142 nights min stay

  • 3 bedrooms
  • Sleeps 14
  • 2 nights min stay

from $202 / night

$0 / week

Book Book View

from $202 / night

(1) Poor 

1 / 51

Holiday apartment in Illinois

Illinois / Chicago

3 bedroomsSleeps 63 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min stay

from $194 / night

$1150 / week

Book Book View

from $194 / night

(1) Excellent 

1 / 22

Condo rental in Illinois

Illinois / Chicago

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies

from $96 / night

$756 - $897 / week

Book Book View

from $96 / night

1 / 7

Home rental in Evanston

Illinois / Evanston

3 bedroomsSleeps 61 night min stay

  • 3 bedrooms
  • Sleeps 6
  • 1 night min stay

from $52 / night

$0 / week

Book Book View

from $52 / night

(4) Very Good 

1 / 11

Illinois holiday apartment rental

Illinois / Chicago

2 bedroomsSleeps 53 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min stay

from $227 / night

$1259 / week

Book Book View

from $227 / night

(1) Excellent 

1 / 21

Holiday apartment in Chicago

Illinois / Chicago

2 bedroomsSleeps 43 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min stay

from $202 / night

$1128 - $1410 / week

Enquire Enquire View

from $202 / night

(3) Good 

1 / 8

Holiday apartment in Illinois

Illinois / Chicago

2 bedroomsSleeps 53 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min stay

from $202 / night

$1007 / week

Book Book View

from $202 / night

1 / 30

Holiday apartment rental

Illinois / Chicago

3 bedroomsSleeps 62 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min stay

from $152 / night

$907 - $1189 / week

Book Book View

from $152 / night

(1) Very Good 

1 / 36

Holiday apartment in Illinois

Illinois / Chicago

2 bedroomsSleeps 43 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min stay

from $161 / night

$1058 / week

Book Book View

from $161 / night

1 / 22

Holiday apartment in Illinois

Illinois / Chicago

3 bedroomsSleeps 62 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min stay

from $403 / night

$0 / week

Book Book View

from $403 / night

1 / 11

Chicago holiday home rental

Illinois / Chicago

3 bedroomsSleeps 7Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies

from $126 / night

$0 / week

Book Book View

from $126 / night

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