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Vacation Rental Properties

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Roscoe Village Inn | Chicago Vacati...

$ 194 per night
Chicago’s Trendy North Side Roscoe Village Inn offers charming vacation rentals in C [more]
Chicago’s Trendy North Side Roscoe Village Inn offers charming vacation rentals in C [more]

Roscoe Village Inn | Vacation Renta...

$ 199 per night
Chicago’s Trendy North Side Roscoe Village Inn offers charming vacation rentals in C [more]
Chicago’s Trendy North Side Roscoe Village Inn offers charming vacation rentals in C [more]

The Wrigley Flats 2nd FL | Vacation...

$ 299 per night
WALK to WRIGLEY FIELD Are you looking for a vacation rental home that is near Wrigley Fiel [more]
WALK to WRIGLEY FIELD Are you looking for a vacation rental home that is near Wrigley Fiel [more]

The Wrigley Flats | Vacation Rental...

$ 299 per night
Are you looking for a vacation rental home that is near Wrigley Field? Then you have found [more]
Are you looking for a vacation rental home that is near Wrigley Field? Then you have found [more]

Chicago Guest House | Vacation Rent...

$ 150 per night
SIMPLY ADORABLE! This Lakeview vacation rental home is distinctive, warm & inviting; c [more]
SIMPLY ADORABLE! This Lakeview vacation rental home is distinctive, warm & inviting; c [more]

Chicago Guest House | Vacation Rent...

$ 218 per night
EXPERIENCE SOMETHING UNIQUE! This Wrigleyville vacation rental home is distinctive, warm & [more]
EXPERIENCE SOMETHING UNIQUE! This Wrigleyville vacation rental home is distinctive, warm & [more]

Chicago Guest House | Vacation Rent...

$ 218 per night
FULL of CHARM & CHARACTER! This Wrigleyville vacation rental home is distinctive, warm [more]
FULL of CHARM & CHARACTER! This Wrigleyville vacation rental home is distinctive, warm [more]

Chicago Guest House | Vacation Rent...

$ 319 per night
VINTAGE CHARM WITH MODERN AMENITIES! This Wrigleyville vacation rental home is distinctive [more]
VINTAGE CHARM WITH MODERN AMENITIES! This Wrigleyville vacation rental home is distinctive [more]

Chicago Guest House on Newport Ave ...

$ 207 per night
COZY & COMFORTABLE! This Wrigleyville vacation rental home is distinctive, warm & [more]
COZY & COMFORTABLE! This Wrigleyville vacation rental home is distinctive, warm & [more]

Chicago Guest House | Wrigleyville ...

$ 375 per night
BEAUTIFUL & SPACIOUS This Wrigleyville vacation rental home is distinctive, warm & [more]
BEAUTIFUL & SPACIOUS This Wrigleyville vacation rental home is distinctive, warm & [more]
11
Houseboat Sweet Caroline (1)

Houseboat Sweet Caroline: Amazing W...

From $ 225 per night
Features: Master bedroom with double bed and ensuite bathroom. Stateroom with full bed and [more]
Features: Master bedroom with double bed and ensuite bathroom. Stateroom with full bed and [more]
50
MV Patriot (1)

M/V Patriot: Absolutely Amazing Flo...

From $ 249 per night
This is it! The one you’ve been waiting for. A vacation rental so unique, so unbelie [more]
This is it! The one you’ve been waiting for. A vacation rental so unique, so unbelie [more]