Kathy Osterman Beach Vacation Rentals & Ski-in/Ski-out Homes

Compare Vacation Rentals & Ski-in/Ski-out Homes in Kathy Osterman Beach, Chicago, Illinois, USA

King Bed, Personal Parking & In-Unit Laundry!
Apartment
King Bed, Personal Parking & In-Unit Laundry!
From US $190 per night
10.0 (6 Reviews)
1 Bedroom 5 Guests
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New Modern Vintage Charm in Historic Neighborhood
Apartment
Modern Vintage Charm in Historic Neighborhood
From US $241 per night
New
1 Bedroom 4 Guests
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Uptown Gem
Apartment
Uptown Gem
From US $117 per night
|
10.0 (12 Reviews)
1 Bedroom 4 Guests
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Wrigleyville Inn
House
Wrigleyville Inn
From US $531 per night
|
10.0 (19 Reviews)
1 Bedroom 2 Guests
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Modern 3BR Apt in Boystown, 12-min walk to Wrigley - Stratford 1S
Apartment
Modern 3BR Apt in Boystown, 12-min walk to Wrigley - Stratford 1S
From US $517 per night
|
10.0 (4 Reviews)
3 Bedrooms 6 Guests
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House 5863 - Chicago Bed and Breakfast
Bed & Breakfast
House 5863 - Chicago Bed and Breakfast
From US $189 per night
|
9.0 (480 Reviews)
1 Bedroom 2 Guests
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North Center - Modern, Safe, Family-Friendly, Solar-Powered Apartment
Apartment
North Center - Modern, Safe, Family-Friendly, Solar-Powered Apartment
From US $226 per night
10.0 (116 Reviews)
2 Bedrooms 6 Guests
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Elegant and Chic 2Bed 2Bath steps from the lake!
Apartment
Elegant and Chic 2Bed 2Bath steps from the lake!
From US $263 per night
10.0 (4 Reviews)
2 Bedrooms 4 Guests
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Lyons' Den
House
Lyons' Den
From US $245 per night
10.0 (4 Reviews)
1 Bedroom 2 Guests
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Best Lincoln Square Location - Spacious 2 bedroom
Condo
Best Lincoln Square Location - Spacious 2 bedroom
From US $290 per night
10.0 (73 Reviews)
2 Bedrooms 4 Guests
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The Wrigleyville Deluxe -Steps from Wrigley Sleeps 10
Apartment
The Wrigleyville Deluxe -Steps from Wrigley Sleeps 10
From US $853 per night
|
10.0 (2 Reviews)
5 Bedrooms 10 Guests
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Family Friendly 2BD/2BA Near Wrigley, Lincoln Square
Condo
Family Friendly 2BD/2BA Near Wrigley, Lincoln Square
From US $464 per night
10.0 (58 Reviews)
2 Bedrooms 4 Guests
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Comfy 2BR Apartment near Wrigley Field - Grace 3
Apartment
Comfy 2BR Apartment near Wrigley Field - Grace 3
From US $500 per night
|
10.0 (2 Reviews)
2 Bedrooms 4 Guests
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Cozy Retreat, Prime Location Near Loyola & Beach!
Apartment
Cozy Retreat, Prime Location Near Loyola & Beach!
From US $197 per night
|
10.0 (2 Reviews)
1 Bedroom 4 Guests
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Stylish Chicago Retreat Walk to Loyola University
House
Stylish Chicago Retreat Walk to Loyola University
From US $584 per night
|
10.0 (1 Review)
4 Bedrooms 10 Guests
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The Holiday Lake House - 2br 2bth - 50 steps from the beach!
Apartment
The Holiday Lake House - 2br 2bth - 50 steps from the beach!
From US $347 per night
10.0 (49 Reviews)
2 Bedrooms 5 Guests
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Northside FAMLYNEST Lincoln Sq 4BR 2BA 2P Rare find
House
Northside FAMLYNEST Lincoln Sq 4BR 2BA 2P Rare find
From US $1,692 per night
|
9.7 (42 Reviews)
4 Bedrooms 9 Guests
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Wrigley Field Views & Cubs Vibes – Stay Across the Street!
Apartment
Wrigley Field Views & Cubs Vibes – Stay Across the Street!
From US $593 per night
10.0 (44 Reviews)
2 Bedrooms 4 Guests
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The Wrigleyville VIP-200 Steps from Wrigley Field
Apartment
The Wrigleyville VIP-200 Steps from Wrigley Field
From US $308 per night
|
9.7 (13 Reviews)
2 Bedrooms 6 Guests
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Spacious 2-BR Condo + Free On-Site Parking
Apartment
Spacious 2-BR Condo + Free On-Site Parking
From US $254 per night
10.0 (43 Reviews)
2 Bedrooms 4 Guests
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Comfortable & Furnished Studio Apt with Wi-Fi - Magnolia CH
Apartment
Comfortable & Furnished Studio Apt with Wi-Fi - Magnolia CH
From US $428 per night
9.7 (3 Reviews)
1 Bedroom 2 Guests
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Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
Apartment
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
From US $214 per night
10.0 (38 Reviews)
1 Bedroom 2 Guests
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Wrigley Oasis! Steps from the Field! - 3BD 1BA
Apartment
Wrigley Oasis! Steps from the Field! - 3BD 1BA
From US $131 per night
|
9.5 (40 Reviews)
3 Bedrooms 6 Guests
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The Lyons' Lair
Apartment
The Lyons' Lair
From US $239 per night
9.2 (17 Reviews)
2 Bedrooms 6 Guests
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The Wrigleyville Garden 200 Steps to Wrigley-2BR
Apartment
The Wrigleyville Garden 200 Steps to Wrigley-2BR
From US $240 per night
|
9.0 (3 Reviews)
2 Bedrooms 5 Guests
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Wrigleyville Inn - Garden Unit
Condo
Wrigleyville Inn - Garden Unit
From US $325 per night
10.0 (32 Reviews)
2 Bedrooms 4 Guests
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Wrigley 2BR, 1BA with Free Parking
Apartment
Wrigley 2BR, 1BA with Free Parking
From US $618 per night
|
9.0 (2 Reviews)
2 Bedrooms 6 Guests
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Stunning, Spacious, & Sun-soaked 2BR Uptown Condo by AllSet Turnover
Condo
Stunning, Spacious, & Sun-soaked 2BR Uptown Condo by AllSet Turnover
From US $272 per night
10.0 (30 Reviews)
2 Bedrooms 4 Guests
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Roscoe Village Family Hideaway
House
Roscoe Village Family Hideaway
From US $795 per night
|
9.0 (1 Review)
4 Bedrooms 13 Guests
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Stylish Two Bedroom - A block from Wrigley Field
Apartment
Stylish Two Bedroom - A block from Wrigley Field
From US $356 per night
10.0 (24 Reviews)
2 Bedrooms 5 Guests
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The Irving Park Hideaway – Prime Location w/Patio & Parking!
Apartment
The Irving Park Hideaway – Prime Location w/Patio & Parking!
From US $302 per night
10.0 (23 Reviews)
2 Bedrooms 4 Guests
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Modern Apartment on Quiet Street in Andersonville
Apartment
Modern Apartment on Quiet Street in Andersonville
From US $221 per night
10.0 (17 Reviews)
1 Bedroom 2 Guests
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Nice 1BR Spot, Unwind & Relax
Apartment
Nice 1BR Spot, Unwind & Relax
From US $235 per night
10.0 (10 Reviews)
1 Bedroom 2 Guests
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Lakeside Spacious Serenity: 1BR/1BA near LoyolaPark
Apartment
Lakeside Spacious Serenity: 1BR/1BA near LoyolaPark
From US $266 per night
10.0 (1 Review)
1 Bedroom 2 Guests
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2 Bed Apt w/Office, Free Parking, Near Wrigley
Apartment
2 Bed Apt w/Office, Free Parking, Near Wrigley
From US $396 per night
|
8.8 (64 Reviews)
2 Bedrooms 4 Guests
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Dorothy's
Bed & Breakfast
Dorothy's
From US $116 per night
|
8.2 (73 Reviews)
1 Bedroom 2 Guests
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Modern & Well-Located 1BR Apt
Apartment
Modern & Well-Located 1BR Apt
From US $254 per night
10.0 (1 Review)
1 Bedroom 2 Guests
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Game Day Getaway - 3BR in Vibrant Wrigleyville
Apartment
Game Day Getaway - 3BR in Vibrant Wrigleyville
From US $645 per night
|
8.7 (3 Reviews)
3 Bedrooms 8 Guests
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The Villa Toscana
Bed & Breakfast
The Villa Toscana
From US $134 per night
7.8 (602 Reviews)
1 Bedroom 2 Guests
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Great Layout – Spacious 2BR Apt
Apartment
Great Layout – Spacious 2BR Apt
From US $222 per night
10.0 (1 Review)
2 Bedrooms 4 Guests
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House 5863- Chicago's Premier Bed and Breakfast
Bed & Breakfast
House 5863- Chicago's Premier Bed and Breakfast
From US $179 per night
|
8.5 (12 Reviews)
6 Bedrooms 13 Guests
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The Guesthouse Hotel
Hotel
The Guesthouse Hotel
From US $788 per night
|
9.8 (341 Reviews)
1 Bedroom 2 Guests
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Cozy 1BR Apt in Rogers Park
Apartment
Cozy 1BR Apt in Rogers Park
From US $192 per night
10.0 (1 Review)
1 Bedroom 2 Guests
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Stylish Modern 1BR Suite Right by Loyola University - StayGia
Apartment
Stylish Modern 1BR Suite Right by Loyola University - StayGia
From US $125 per night
|
8.5 (10 Reviews)
1 Bedroom 4 Guests
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Indulging 2BR Apartment in Festive Boystown - Buckingham 1
Apartment
Indulging 2BR Apartment in Festive Boystown - Buckingham 1
From US $507 per night
8.5 (4 Reviews)
2 Bedrooms 4 Guests
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The Wrigleyville VIP- 200 steps to Wrigley- Super Clean!
House
The Wrigleyville VIP- 200 steps to Wrigley- Super Clean!
From US $652 per night
9.8 (81 Reviews)
2 Bedrooms 6 Guests
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1 Bedroom with Rooftop and Wrigley Views
Apartment
1 Bedroom with Rooftop and Wrigley Views
From US $302 per night
|
8.5 (2 Reviews)
1 Bedroom 3 Guests
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The Bright Retreat in Andersonville
Condo
The Bright Retreat in Andersonville
From US $208 per night
9.8 (62 Reviews)
1 Bedroom 4 Guests
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Perfect weekend getaway 2BR 2BA Apartment near Wrigley Field
Apartment
Perfect weekend getaway 2BR 2BA Apartment near Wrigley Field
From US $350 per night
9.8 (44 Reviews)
2 Bedrooms 4 Guests
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Luxury chicago suite
Apartment
Luxury chicago suite
From US $153 per night
|
8.0 (38 Reviews)
1 Bedroom 3 Guests
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1BR Calm & Cozy Apt in Lincoln Square - Eastwood 2S
Apartment
1BR Calm & Cozy Apt in Lincoln Square - Eastwood 2S
From US $288 per night
|
8.0 (2 Reviews)
1 Bedroom 2 Guests
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Spacious, Clean and Steps from Wrigley Field!
Condo
Spacious, Clean and Steps from Wrigley Field!
From US $417 per night
9.8 (14 Reviews)
2 Bedrooms 5 Guests
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3BR Sunny and Spacious Apartment near Restaurants - Stratford 2S rep
Apartment
3BR Sunny and Spacious Apartment near Restaurants - Stratford 2S rep
From US $1,141 per night
|
8.0 (2 Reviews)
3 Bedrooms 6 Guests
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The Lincoln Square Hideaway
Apartment
The Lincoln Square Hideaway
From US $396 per night
9.8 (10 Reviews)
2 Bedrooms 6 Guests
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Warm & Lovely 2BR Apt close to Dining & Shops - Touhy 1S
Apartment
Warm & Lovely 2BR Apt close to Dining & Shops - Touhy 1S
From US $242 per night
8.0 (1 Review)
2 Bedrooms 4 Guests
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3 -bed apartment just steps to Lake Michigan
Apartment
3 -bed apartment just steps to Lake Michigan
From US $250 per night
9.8 (10 Reviews)
2 Bedrooms 6 Guests
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Dorothy's
Bed & Breakfast
Dorothy's
From US $172 per night
7.9 (14 Reviews)
14 Bedrooms 32 Guests
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About Kathy Osterman Beach Vacation Rentals

Explore over 756 vacation rentals in Kathy Osterman Beach with SunSki Resorts. These accommodations, comprising vacation homes, cottages, cabins, and condos, boast excellent amenities at great value, ensuring comfort and luxury. Enhance your stay with SunSki Resorts in Kathy Osterman Beach for more space and value.

In search of last-minute deals or the best bargains on vacation rentals? With SunSki Resorts, you can conveniently compare various options and deals in Kathy Osterman Beach. Discover rentals with desirable amenities like swimming pools, hot tubs, and pet-friendly options. Find the ideal vacation rental in Kathy Osterman Beach tailored to your preferences. On average, these rentals offer 696.25 ft² of space, and are priced at an average of US $356 per night.

SunSki Resorts simplifies and secures the process of finding and comparing vacation rentals in Kathy Osterman Beach at prices typically 30-40% lower than hotels. Discover your perfect vacation rental and book now.

Frequently Asked Questions About Kathy Osterman Beach?

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Discover the ideal vacation rental in Kathy Osterman Beach with SunSki Resorts™. We provide an extensive selection of over 756 properties, encompassing vacation homes, private villas, cottages, and more. Explore our listings to find the perfect place to stay for your upcoming trip to Kathy Osterman Beach.

Nearby Neighborhood (12)

Neighborhood Property Count
Downtown Chicago Vacation Rentals in Chicago, Illinois 1585
The Loop Vacation Rentals in Chicago, Illinois 738
Near North Side Vacation Rentals in Chicago, Illinois 649
South Loop Vacation Rentals in Chicago, Illinois 363
River North Vacation Rentals in Chicago, Illinois 327
Lakeview Vacation Rentals in Chicago, Illinois 241
West Loop Vacation Rentals in Chicago, Illinois 198
Lincoln Park Vacation Rentals in Chicago, Illinois 145
O'Hare Vacation Rentals in Chicago, Illinois 66
Wrigleyville Vacation Rentals in Chicago, Illinois 46
Gold Coast Vacation Rentals in Chicago, Illinois 39
Magnificent Mile Vacation Rentals in Chicago, Illinois 4128

There are 756 Kathy Osterman Beach, IL Vacation Rentals

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