Holiday homes

Vacation Rentals Chicago Metropolitan Area, Holiday Rentals

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The Avondale Guesthouse

2973 North Elston Avenue, Hotel in Chicago, United States

Excellent
140 reviews

432 US$

min. price/night

Northside Famlynest Lincoln Sq 4Br 2Ba 2P Rare Find

2713 West Balmoral Avenue, Hotel in Chicago, United States

Excellent
39 reviews

270 US$

min. price/night

Romantic 3 Bed Home In The Heart Of The Park

5923 South Indiana Avenue, Hotel in Chicago, United States

393 US$

min. price/night

Modern Lake Geneva Condo With Year-Round Views

84-07 Red Chimney Road, Hotel in Lake Geneva, United States

Excellent
13 reviews

118 US$

min. price/night

Stunning Condo #2 - Downtown River North

811 N Sedgwick St, Hotel in Chicago, United States

Excellent
25 reviews

39 US$

min. price/night

Black Cabin Getaway In Woods I Valpo

4607 Claussen Lane, Hotel in Valparaiso, United States

Excellent
16 reviews

111 US$

min. price/night

Designer Themed 4 Bedroom In Best Location With Patio And Fireplace

329 West Schiller Street Back, Hotel in Chicago, United States

Excellent
26 reviews

759 US$

min. price/night

Blue Birdhouse - Indiana Dunes - Pet Friendly

5 West Beam Street, Hotel in Chesterton, United States

Excellent
20 reviews

196 US$

min. price/night

New Lake Como Condo With Lake Views

Lausanne Court 33, Hotel in Lake Geneva, United States

Excellent
16 reviews

182 US$

min. price/night

Large 5 Bed Lake Geneva Home 4 Blocks From Lake!

W3803 Magnolia Drive, Hotel in Lake Geneva, United States

Excellent
18 reviews

244 US$

min. price/night

Lincoln Park Living - Suite 1

West Diversey Parkway, Hotel in Chicago, United States

Excellent
25 reviews

713 US$

min. price/night

Spacious 5-Br House Near Transit W Parking

1868 South Millard Avenue, Hotel in Chicago, United States

Excellent
13 reviews

631 US$

min. price/night

Beautiful Loft Style Townhouse-Vaulted Ceilings

510 Willow Court, Hotel in Romeoville, United States

Suite 2 On Southport 4 Queen Beds

2501 North Southport Avenue, Hotel in Chicago, United States

Excellent
17 reviews

614 US$

min. price/night

Ivp Manor House By Lake Beach And Naval Base

North Sears Boulevard, Hotel in Gages Lake, United States

Excellent
9 reviews

479 US$

min. price/night

New Charming Lakeview Haven 2Br Cozy Como Cottage With Lake Views

Acacia Road N3182, Hotel in Lake Geneva, United States

118 US$

min. price/night

Family Home - 2 Bedroom, Kitchen, 1.5 Bath

4432 West Quill Lane, Hotel in Waukegan, United States

128 US$

min. price/night

Breathtaking Downtown Penthouse A - Sleeps 11

811 N Sedgwick St, Hotel in Chicago, United States

329 US$

min. price/night

Charming Lake Geneva, Wisconsin 3Br/2Bath Home - Shagbark Waters

6783 Cobble Creek Drive, Hotel in Lake Geneva, United States

Excellent
13 reviews

67 US$

min. price/night

The Black And White Suite

611 East 41St Street, Hotel in Chicago, United States

Excellent
12 reviews

313 US$

min. price/night

Beautiful Home In Beach Park Il

9873 East Yorkhouse Road, Hotel in Beach Park, United States

Excellent
12 reviews

Historic Home With Outdoor Hot Tub Near Downtown In Public Transportation Hub

3742 N. Keeler Avenue, Chicago,, Hotel in Chicago, United States

Excellent
7 reviews

Lincoln Park Living - 3 Queen Beds - Sleeps 6

1147 West Diversey Parkway, Hotel in Chicago, United States

Excellent
25 reviews

109 US$

min. price/night

The Katerina Residence

1582 Wentworth Avenue, Hotel in Calumet City, United States

150 US$

min. price/night

Cozy Rockford Home

3315 Alida Street, Hotel in Rockford, United States

Lakefront Family Retreat With Grill Steps To Beach!

9449 Lake Shore Drive, Gary, In 46403, Us, Hotel in Gary, United States

Excellent
4 reviews

495 US$

min. price/night

5 Mi To Dtwn Chicago Apartment In Garfield Park!

3461 W Adams St, Hotel in Chicago, United States

Excellent
2 reviews

162 US$

min. price/night

Beautiful Remodeled Penthouse Unit In Old Town

1556 North La Salle Street, Hotel in Chicago, United States

Excellent
10 reviews

139 US$

min. price/night

Cozy Maple House Family Lake Como Retreat

Maple Road N3348, Hotel in Lake Geneva, United States

Excellent
6 reviews

Luxe 4Br With Hot Tub & Game Room

1654 West Ohio Street, Hotel in Chicago, United States

967 US$

min. price/night

Williams Bay Retreat Walk To Lake Geneva And Town!

Williams Bay, Wi, 53191, Hotel in Lake Geneva, United States

Excellent
7 reviews

280 US$

min. price/night

New Pet-Friendly Lake Geneva Escape

West Barry Drive 3163, Hotel in Lake Geneva, United States

Excellent
3 reviews

Historic Luxury Townhouse In Downtown Chicago

71 East Bellevue Place The Townhouse, Hotel in Chicago, United States

Excellent
5 reviews

1891 US$

min. price/night

Cozy Gary Vacation Rental Steps To Beach!

1211 N Wayne St, Hotel in Gary, United States

Excellent
4 reviews

271 US$

min. price/night

Indiana Vacation Rental Near Lake Michigan

Valparaiso, United States

Excellent
3 reviews

134 US$

min. price/night

Family-Friendly Rockford Home With Private Yard!

3040 Louise St, Hotel in Rockford, United States

Good
5 reviews

185 US$

min. price/night

Home With Yard And Patio About 30 Mi To Downtown Chicago

Matteson, IL, 60443, Hotel in Matteson, United States

Excellent
3 reviews

197 US$

min. price/night

Twin Lakes Escape With Deck Less Than 1 Mi To Beach!

Twin Lakes, United States

Good
4 reviews

218 US$

min. price/night

A Terrific House For A Large Group.

4511 North Melvina Avenue, Hotel in Chicago, United States

156 US$

min. price/night

Full Building No Cleaning Fee Everythings Close

220 Cook Street, Hotel in Lake Geneva, United States

Excellent
2 reviews

Serene Lakefront Escape Boat Dock And Grill!

Twin Lakes, United States

Excellent
2 reviews

Classic Oak Park Home, 11 Mi To Downtown Chicago!

326 N Grove Ave, Hotel in Oak Park, United States

Excellent
3 reviews

639 US$

min. price/night

Spacious Luxury Retreat 8 Bed Oasis With 6 Baths

2630 South Throop Street, Hotel in Chicago, United States

Excellent
6 reviews

1636 US$

min. price/night

Chicago Home Near Navy Pier And Shedd Aquarium!

Chicago, United States

Excellent
4 reviews

159 US$

min. price/night

Farmhouse On Wells

412 South Wells Street, Hotel in Lake Geneva, United States

Excellent
2 reviews

793 US$

min. price/night

Chicago Mid-Century Gem By United Center

West Washington Boulevard, Hotel in Chicago, United States

Excellent
3 reviews

1030 US$

min. price/night

Chic 4-Bedroom Haven: Designer'S Dream Home

2655 West Huron Street, Hotel in Chicago, United States

Excellent
3 reviews

1155 US$

min. price/night

Updated Cabin On 7 Acres - Day Trip To Lake Geneva

Burlington, United States

Excellent
3 reviews

292 US$

min. price/night

Amazing 4Br 4Ba Oasis W Rooftop & Stunning Design

2223 West Race Avenue, Hotel in Chicago, United States

Excellent
2 reviews

Gorgeous A-Frame On Cedar Lake

7209 West 136Th Avenue, Hotel in Cedar Lake, United States

Excellent
2 reviews

Other Places to Stay in Chicago Metropolitan Area

Popular Areas in Chicago Metropolitan Area

Chicago Rosemont Schaumburg Schiller Park Rockford Merrillville Elk Grove Village Lake Geneva Joliet Naperville Lombard Des Plaines Bedford Park Waukegan Gurnee Oakbrook Terrace Hammond Tinley Park Hoffman Estates Arlington Heights Evanston Portage Bolingbrook Oak Brook Saint Charles Aurora Elgin Deerfield Itasca Glenview Kenosha Valparaiso Downers Grove Warrenville Lincolnshire Skokie Bourbonnais Pleasant Prairie Romeoville Lansing Bensenville Chesterton Oak Lawn Matteson Bridgeview Burr Ridge Franklin Park Lisle Northbrook Willowbrook Alsip Hillside Schererville Elmhurst Libertyville Oak Park DeKalb Morris Rolling Meadows Wheeling Mundelein Crystal Lake Addison Countryside Zion Burbank Sycamore Sturtevant Porter Niles Vernon Hills Harvey Munster Rochelle Mount Prospect Bloomingdale Markham South Holland Woodstock North Chicago Morton Grove Yorkville Monee Wood Dale Orland Park Bannockburn Carol Stream Burlington Oswego Lyons Prospect Heights Northlake Geneva Lake Forest Glendale Heights Mokena Calumet Park Manteno Loves Park Palatine Mettawa West Dundee Glen Ellyn McHenry Buffalo Grove Oak Forest River Grove Calumet City Riverwoods Antioch North Aurora Grayslake East Chicago Westchester Lemont Sandwich Westmont Algonquin Crestwood Dinwiddie Roselle Kankakee Highland Park Harvard Lake Bluff Johnsburg Shorewood Lake Zurich Villa Park Deer Park Wilmette Lincolnwood Dwight Richmond Hanover Park Mount Pleasant Wadsworth Brookfield Hampshire Bartlett Bradley Huntley Channahon Lockport Barrington Broadview Minooka Crown Point Darien Cicero Homewood Plainfield Hazel Crest Lowell Fox Lake Belvidere Gary Hebron Cedar Lake Wauconda Winthrop Harbor Austin Beach Park Berwyn Blue Island Bristol Cary Chicago Ridge Country Club Hills Dolton Dunning East Hazel Crest Elmwood Park Forest Park Fox River Grove Frankfort Gages Lake Genoa City Glenwood Hobart Ingleside Ives Grove Lake in the Hills Maywood Melrose Park Montgomery Norridge Old Mill Creek Plano Powers Lake Salem Spring Grove Streamwood Tolleston Twin Lakes Wheaton Willow Springs Wilmington (Will County) Wonder Lake Worth

Types of Accomodations in Chicago Metropolitan Area

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Chalet

Hotels near Popular Places to visit in Chicago Metropolitan Area

Midway International

Chicago O'Hare International

Chicago Rockford International

Wrigley Field Navy Pier Chicago Grant Park Michigan Avenue Chicago United Center McCormick Place Chicago Union Station

Chicago Theater

Donald E. Stephens Convention Center

Naval Station Great Lakes

Millennium Park

Six Flags Great America

Brookfield Zoo

Allstate Arena

Loyola University Chicago

Chicago Riverwalk

CIBC Theatre

Gurnee Mills

House of Blues Chicago

Art Institute of Chicago

Willis Tower Chicago

Northwestern Memorial Hospital

Hollywood Casino Amphitheatre Tinley Park

Water Tower Place Chicago

Cloud Gate

Museum of Science and Industry

Tinley Park Convention Center

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Vacation Rentals Chicago Metropolitan Area, Holiday Rentals

The Avondale Guesthouse

Northside Famlynest Lincoln Sq 4Br 2Ba 2P Rare Find

Romantic 3 Bed Home In The Heart Of The Park

Modern Lake Geneva Condo With Year-Round Views

Stunning Condo #2 - Downtown River North

Black Cabin Getaway In Woods I Valpo

Designer Themed 4 Bedroom In Best Location With Patio And Fireplace

Blue Birdhouse - Indiana Dunes - Pet Friendly

New Lake Como Condo With Lake Views

Large 5 Bed Lake Geneva Home 4 Blocks From Lake!

Lincoln Park Living - Suite 1

Spacious 5-Br House Near Transit W Parking

Beautiful Loft Style Townhouse-Vaulted Ceilings

Suite 2 On Southport 4 Queen Beds

Ivp Manor House By Lake Beach And Naval Base

New Charming Lakeview Haven 2Br Cozy Como Cottage With Lake Views

Family Home - 2 Bedroom, Kitchen, 1.5 Bath

Breathtaking Downtown Penthouse A - Sleeps 11

Charming Lake Geneva, Wisconsin 3Br/2Bath Home - Shagbark Waters

The Black And White Suite

Beautiful Home In Beach Park Il

Historic Home With Outdoor Hot Tub Near Downtown In Public Transportation Hub

Lincoln Park Living - 3 Queen Beds - Sleeps 6

The Katerina Residence

Cozy Rockford Home

Lakefront Family Retreat With Grill Steps To Beach!

5 Mi To Dtwn Chicago Apartment In Garfield Park!

Beautiful Remodeled Penthouse Unit In Old Town

Cozy Maple House Family Lake Como Retreat

Luxe 4Br With Hot Tub & Game Room

Williams Bay Retreat Walk To Lake Geneva And Town!

New Pet-Friendly Lake Geneva Escape

Historic Luxury Townhouse In Downtown Chicago

Cozy Gary Vacation Rental Steps To Beach!

Indiana Vacation Rental Near Lake Michigan

Family-Friendly Rockford Home With Private Yard!

Home With Yard And Patio About 30 Mi To Downtown Chicago

Twin Lakes Escape With Deck Less Than 1 Mi To Beach!

A Terrific House For A Large Group.

Full Building No Cleaning Fee Everythings Close

Serene Lakefront Escape Boat Dock And Grill!

Classic Oak Park Home, 11 Mi To Downtown Chicago!

Spacious Luxury Retreat 8 Bed Oasis With 6 Baths

Chicago Home Near Navy Pier And Shedd Aquarium!

Farmhouse On Wells

Chicago Mid-Century Gem By United Center

Chic 4-Bedroom Haven: Designer'S Dream Home

Updated Cabin On 7 Acres - Day Trip To Lake Geneva

Amazing 4Br 4Ba Oasis W Rooftop & Stunning Design

Gorgeous A-Frame On Cedar Lake

Other Places to Stay in Chicago Metropolitan Area

Popular Areas in Chicago Metropolitan Area

Types of Accomodations in Chicago Metropolitan Area

Hotels near Popular Places to visit in Chicago Metropolitan Area