Owner Direct Vacation Rentals in Jackson Park

The Best Owner Direct Vacation Rentals in Jackson Park. Explore thousands of vacation home rentals, large cabins, and villas near Jackson Park

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From US $407

         

10.0 (3 Reviews)

Apartment

The Brown House - A luxurious UChicago Campus stay

• Air Conditioner
• Parking
• Security/Safety

• Chicago
• Woodlawn

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New

From US $466

         

New

House

NEW! Chicago Getaway with Pool Table & Modern Comfort

• Air Conditioner
• Parking
• TV

• Chicago
• Greater Grand Crossing

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From US $227

         

|

9.6 (1000 Reviews)

Hotel

Sophy Hyde Park

• Air Conditioner
• TV
• Wheelchair Accessible

• Chicago
• Hyde Park

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From US $405

         

10.0 (2 Reviews)

Apartment

Luxe Loft vibe with King Suite - 4BR 3Ba

• Air Conditioner
• Parking
• Pet Friendly

• Chicago
• Woodlawn

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New

From US $410

         

New

Apartment

Hyde Park Luxury Stay 5BR Near Lake & UChicago

• Air Conditioner
• Pet Friendly
• TV

• Chicago
• Kenwood

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From US $158

         

|

8.8 (1003 Reviews)

Hotel

Hyatt Place Chicago-South/University Medical Center

• Air Conditioner
• Parking
• TV

• Chicago
• Hyde Park

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From US $407

         

|

10.0 (1 Review)

Apartment

Well-Equipped Studio Apartment - Dorchester 511

• Air Conditioner
• Pet Friendly
• Security/Safety

• Chicago
• Hyde Park

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New

From US $394

         

New

House

Family-Friendly Home with Style & Space

• Air Conditioner
• Security/Safety
• Bedding/Linens

• Chicago
• Calumet Heights

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From US $82

         

3.6 (51 Reviews)

Hotel

Best Motel By OYO Chicago I-90

• Air Conditioner
• Parking
• Bedding/Linens

• Chicago
• Woodlawn

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From US $200

         

|

10.0 (1 Review)

Apartment

LuxHome Chicago 8 mins Downtown

• Air Conditioner
• Parking
• Security/Safety

• Chicago
• Grand Boulevard

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New

From US $360

         

New

House

Modern South Shore Retreat Near Lake and Museum

• Air Conditioner
• Pet Friendly
• TV

• Chicago
• South Shore

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From US $383

         

10.0 (1 Review)

Apartment

Spacious 3BDR Luxury Penthouse

• Air Conditioner
• Parking
• Security/Safety

• Chicago
• Washington Park

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New

From US $330

         

New

Apartment

City Romance Retreat Private Experience for Two

• Air Conditioner
• Security/Safety
• Bedding/Linens

• Chicago
• Chatham

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From US $213

         

10.0 (1 Review)

Apartment

Lively & Fully Furnished 1BR Apartment - Kenwood 408

• Air Conditioner
• Pet Friendly
• Security/Safety

• Chicago
• Hyde Park

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New

From US $311

         

New

Condo

Beautiful condo with elevator right into your unit in North Kenwood Hyde Park.

• Air Conditioner
• Pet Friendly
• Bedding/Linens

• Chicago
• North Kenwood

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From US $299

         

|

9.7 (18 Reviews)

Apartment

Luxurious Stay at Modern Apartment with Self Check-in Mins Frm Downtown

• Air Conditioner
• Parking
• Pet Friendly

• Chicago
• Grand Boulevard

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New

From US $108

         

New

Apartment

Renovated 1BR in Hyde Park, Near Campus

• Air Conditioner
• Security/Safety
• Bedding/Linens

• Chicago
• Kenwood

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From US $449

         

|

9.6 (5 Reviews)

House

BOUTIQUE GARDEN HOUSE CHICAGO 3-STORY sleeps 12

• Air Conditioner
• Parking
• Security/Safety

• Chicago
• Greater Grand Crossing

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From US $253

         

10.0 (18 Reviews)

Apartment

Penthouse, Lux stay near Downtown, McComick & Lake

• Air Conditioner
• Parking
• TV

• Chicago
• North Kenwood

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From US $200

         

|

9.5 (2 Reviews)

House

2 Mi to South Shore Beach Urban Retreat with Yard

• Parking
• Accessibility
• Security/Safety

• Chicago
• South Shore

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From US $319

         

|

9.3 (29 Reviews)

Apartment

The Penthouse, Lux stay near Downtown, UofC & Lake

• Air Conditioner
• Parking
• Balcony/Terrace

• Chicago
• North Kenwood

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From US $76

         

9.3 (13 Reviews)

House

Afrique Francaise de Woodlawn 1

• Air Conditioner
• Parking
• TV

• Chicago
• Woodlawn

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From US $494

         

9.3 (3 Reviews)

Apartment

Cozy & Radiant 2BR Apartment - BStone 605

• Air Conditioner
• Pet Friendly
• Security/Safety

• Chicago
• Hyde Park

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From US $107

         

9.2 (6 Reviews)

House

Shared, spacious condo near UChicago and Obama Center

• Air Conditioner
• Parking
• TV

• Chicago
• Woodlawn

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★ Pro Tip: Ownerdirect makes it easy to compare the best listings on Ownerdirect homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Ownerdirect homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Jackson Park.