Vacation Rentals in Douglas, IL: Compare 10+ Sites & Save

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1837 Best Vacation Rentals in Douglas (Starting from $95)

McCormick Place Guest House
McCormick Place Guest House
House
Chicago, IL, USA
0.8k from Douglas center

B&bs, Accommodations, Parking, Guest houses, Homestays, Romantic, Lodgings, Vacation rentals, Places to stay

12 Bedrooms28 Guests
6.4

Good

112 reviews

$136
Average price / night
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The Landmark; a comfy suite near McCormick Place
The Landmark; a comfy suite near McCormick Place
Apartment
Chicago, IL, 60616, United States
0.1k from Douglas center

AC, Heater, Internet, Kitchen, Microwave, No Smoking, Outdoor Space, Patio, Spa

1 Bedroom2 Guests
10.0

Exceptional

10 reviews

$320
Average price / night
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Modern 3BR Stay Near DT CHI
Modern 3BR Stay Near DT CHI
Apartment
Chicago, IL, USA
0.9k from Douglas center

Fireplace/Heating, Guest Services, Air Conditioner, Parking, Internet, Security/Safety

3 Bedrooms6 Guests
New to Booking
$368
Average price / night
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Cozy 2 Bedroom unit-15mins Dwtn!
Cozy 2 Bedroom unit-15mins Dwtn!
Apartment
Chicago, IL, 60616, United States
0.2k from Douglas center

AC, Crib, Free Parking, Heater, Internet, Laundry, Microwave, No Smoking, TV

2 Bedrooms4 Guests
8.0

Good

1 reviews

$265
Average price / night
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3-bedroom apartment in phenomenal Chicago with WiFi, AC
3-bedroom apartment in phenomenal Chicago with WiFi, AC
Apartment
Chicago, IL, 60616, United States
0.2k from Douglas center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

3 Bedrooms6 Guests
New to Booking
$180
Average price / night
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Affordable Private Room 2 - Shared
Affordable Private Room 2 - Shared
Apartment
Chicago, IL, USA
0.9k from Douglas center

Apartments, Accommodations, Parking, Lodgings, Places to stay

1 Bedroom2 Guests
New to Booking
$153
Average price / night
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Modern 4 Bed, 3.5 Bath Home | Near Sox & McCormick
Modern 4 Bed, 3.5 Bath Home | Near Sox & McCormick
House
Chicago, IL, 60616, United States
0.4k from Douglas center

AC, Arcade, Barbecue, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms10 Guests
10.0

Exceptional

6 reviews

$611
Average price / night
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Hamaline Luxury Guest House
Hamaline Luxury Guest House
Villa
Chicago, IL, USA
1.0k from Douglas center

Luxury, Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$289
Average price / night
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Modern Home Near McCormick Place & Downtown - Bronzeville
Modern Home Near McCormick Place & Downtown - Bronzeville
House
Chicago, IL, 60616, United States
0.4k from Douglas center

AC, Crib, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking

3 Bedrooms8 Guests
9.4

Superb

3 reviews

$419
Average price / night
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Gilean Urban Retreat
Gilean Urban Retreat
Apartment
Chicago, IL, USA
1.0k from Douglas center

Apartments, Accommodations, Parking, Lodgings, Places to stay

3 Bedrooms6 Guests
New to Booking
$566
Average price / night
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Cozy Private 1BR • 10 Min to Downtown Chicago
Cozy Private 1BR • 10 Min to Downtown Chicago
Apartment
Chicago, IL, 60616, United States
0.4k from Douglas center

AC, Free Parking, Heater, Internet, Kitchen, Laundry, No Smoking, Outdoor Space, TV

1 Bedroom2 Guests
New to Booking
$191
Average price / night
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Gather, relax, enjoy— in chic luxury home near Lake Michigan & McCormick Center
Gather, relax, enjoy— in chic luxury home near Lake Michigan & McCormick Center
House
Chicago, IL, 60616, United States
0.4k from Douglas center

AC, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Internet, Kitchen

4 Bedrooms8 Guests
10.0

Exceptional

7 reviews

$1169
Average price / night
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Affordable Private Room - Shared
Affordable Private Room - Shared
Apartment
Chicago, IL, USA
1.0k from Douglas center

Apartments, Accommodations, Parking, Lodgings, Places to stay

1 Bedroom2 Guests
New to Booking
$116
Average price / night
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3bd/2ba, King bd, Pets OK, Laundry, Fenced Yard, Near Downtwn, Hospitals, & Unis
3bd/2ba, King bd, Pets OK, Laundry, Fenced Yard, Near Downtwn, Hospitals, & Unis
Apartment
Chicago, IL, 60653, United States
0.5k from Douglas center

3 Bedrooms8 Guests
New to Booking
$129
Average price / night
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2bd/2ba, King bd, Pets OK, Laundry, Fenced Yard, Near Downtwn, Hospitals, & Unis
2bd/2ba, King bd, Pets OK, Laundry, Fenced Yard, Near Downtwn, Hospitals, & Unis
Apartment
Chicago, IL, 60653, United States
0.6k from Douglas center

AC, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms6 Guests
New to Booking
$141
Average price / night
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Villa Dubois Guest House
Villa Dubois Guest House
House
Chicago, IL, USA
1.0k from Douglas center

B&bs, Accommodations, Parking, Guest houses, Homestays, Lodgings, Vacation rentals, Places to stay

18 Bedrooms36 Guests
5.9

Review score

202 reviews

$166
Average price / night
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Free Parking! Private Rooftop! 3bd near downtown!
Free Parking! Private Rooftop! 3bd near downtown!
Apartment
Chicago, IL, USA
1.4k from Douglas center

Apartments, Accommodations, Parking, Lodgings, Places to stay

3 Bedrooms6 Guests
New to Booking
$153
Average price / night
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Large historic home minutes from downtown Chicago and the lakefront.
Large historic home minutes from downtown Chicago and the lakefront.
House
Chicago, IL, 60616, United States
0.7k from Douglas center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

5 Bedrooms8 Guests
10.0

Exceptional

11 reviews

$790
Average price / night
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Modern 3 Bedroom Close to Downtown Chicago
Modern 3 Bedroom Close to Downtown Chicago
Apartment
Chicago, IL, USA
1.6k from Douglas center

Apartments, Cheap, Accommodations, Parking, Lodgings, Vacation rentals, Places to stay

3 Bedrooms6 Guests
8.7

Fabulous

36 reviews

$349
Average price / night
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Beautiful 2 Bedroom located in a Unique Private Park. Near Beaches Near Downtown
Beautiful 2 Bedroom located in a Unique Private Park. Near Beaches Near Downtown
Apartment
Chicago, IL, 60616, United States
0.8k from Douglas center

AC, Dryer, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking, Washer

2 Bedrooms4 Guests
New to Booking
$95
Average price / night
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Stylish Urban Retreat 3 Bedroom Newly Remodeled
Stylish Urban Retreat 3 Bedroom Newly Remodeled
Apartment
Chicago, IL, USA
1.6k from Douglas center

Apartments, Cheap, Accommodations, Parking, Lodgings, Vacation rentals, Places to stay

3 Bedrooms6 Guests
9.5

Superb

10 reviews

$482
Average price / night
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Modern 3BR & 2BA Near McCormick & Downtown
Modern 3BR & 2BA Near McCormick & Downtown
Apartment
Chicago, IL, 60653, United States
1.0k from Douglas center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms6 Guests
9.2

Superb

40 reviews

$273
Average price / night
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Stylish 3 King Bed Apartment in Prime Location
Stylish 3 King Bed Apartment in Prime Location
House
Chicago, IL, 60616, United States
1.3k from Douglas center

AC, Arcade, Crib, Dryer, Elevator, Fitness Equipment, Heater, Internet, Kitchen

3 Bedrooms8 Guests
New to Booking
$525
Average price / night
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Modern 3BR Near McCormick and South Loop
Modern 3BR Near McCormick and South Loop
House
Chicago, IL, 60616, United States
1.3k from Douglas center

AC, Balcony, Crib, Dryer, Elevator, Fitness Equipment, Heater, Internet, Kitchen

3 Bedrooms8 Guests
New to Booking
$342
Average price / night
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Spacious 3BR Urban Getaway w Gym
Spacious 3BR Urban Getaway w Gym
House
Chicago, IL, 60616, United States
1.3k from Douglas center

AC, Balcony, Crib, Dryer, Elevator, Fitness Equipment, Heater, Internet, Kitchen

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$489
Average price / night
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Comfy 4BR/3BA Chicago Retreat Near Museum Campus & McCormick
Comfy 4BR/3BA Chicago Retreat Near Museum Campus & McCormick
Apartment
Chicago, IL, 60616, United States
1.3k from Douglas center

AC, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms10 Guests
New to Booking
$735
Average price / night
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Peaceful 3-bedroom apartment in charming Chicago Chinatown
Peaceful 3-bedroom apartment in charming Chicago Chinatown
Apartment
Chicago, IL, 60616, United States
1.4k from Douglas center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

3 Bedrooms7 Guests
New to Booking
$253
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Douglas.

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Frequently Asked Questions

You can explore 1837 verified vacation rentals in Douglas. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Douglas vary depending on the season, property size, and location. Rates typically start from around $95 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Douglas include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Douglas welcome pets. Currently, 42 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Douglas often include amenities such as Fireplace/Heating, Wellness Facilities, and Kitchen. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.