Vacation Rentals in Oakland, IL
PRICE PER NIGHT
ACCOMMODATION TYPES
Lakefront - Kenwood - Oakwood Luxury 4 Bd/2.5 Ba
10
Excellent
·
Oakland
·
4 br
·
Outdoor Space · Air Conditioning · Fireplace ·
From
$368/nightProperty
House · 4 Beds · 3 baths
Amenities
Air Conditioning
Fireplace
Dishwasher
Furnished
In Unit Laundry
Wifi
Oven
Residents Lounge
Other spaces
Balcony, Kitchen
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9.8
Excellent
·
Grand Boulevard
·
1 br
·
Sleeps 5
·
On Site Laundry · Fitness Center · High Ceilings ·
From
$107/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
On Site Laundry
Fitness Center
High Ceilings
Air Conditioning
Fireplace
Furnished
In Unit Laundry
Wifi
Other spaces
Kitchen
Chi~Bronzeville Luxury TH 10Mins To DWTWN- Modern Updates
No reviews
·
Grand Boulevard
·
3 br
·
Sleeps 6
·
On Site Laundry · Smoking Allowed · Hardwood Floor ·
From
$337/nightProperty
Apartment · 3 Beds · 2 baths
Amenities
On Site Laundry
Smoking Allowed
Hardwood Floor
Free Parking
Air Conditioning
Fireplace
Dishwasher
Furnished
Other spaces
Kitchen
Langley
No reviews
·
Grand Boulevard
·
1 br
·
Sleeps 2
·
On Site Laundry · Assigned Parking · Hardwood Floor ·
From
$80/nightProperty
House · 1 Bed · 1 bath
Amenities
On Site Laundry
Assigned Parking
Hardwood Floor
Free Parking
Air Conditioning
Furnished
In Unit Laundry
Wifi
Other spaces
Workspace, Balcony, Kitchen
Unique and Chic Townhome
No reviews
·
Grand Boulevard
·
3 br
·
Sleeps 3
·
Pool · Fitness Center · Waterfront ·
From
$166/nightProperty
House · 3 Beds · 4 baths
Amenities
Pool
Fitness Center
Waterfront
Air Conditioning
Fireplace
Dishwasher
Furnished
In Unit Laundry
Other spaces
Workspace, Kitchen
Just Minutes from Downtown Chicago
8
Very good
·
Grand Boulevard
·
1 br
·
Sleeps 6
·
Hardwood Floor · Air Conditioning · Fireplace ·
From
$169/nightProperty
House · 1 Bed · 2 baths
Amenities
Hardwood Floor
Air Conditioning
Fireplace
Dishwasher
Furnished
In Unit Laundry
Wifi
Other spaces
Kitchen
Just Minutes from Downtown Chicago
10
Excellent
·
Grand Boulevard
·
1 br
·
Sleeps 6
·
Hardwood Floor · Air Conditioning · Fireplace ·
From
$169/nightProperty
House · 1 Bed · 2 baths
Amenities
Hardwood Floor
Air Conditioning
Fireplace
Dishwasher
Furnished
In Unit Laundry
Wifi
Other spaces
Kitchen
Bronzeville beauty close to all amenities
10
Excellent
·
Douglas
·
3 br
·
In Unit Laundry · Furnished · Wifi ·
From
$393/nightProperty
House · 3 Beds · 3 baths
Amenities
In Unit Laundry
Furnished
Wifi
Other spaces
Kitchen
Cozy Beautiful Condo
No reviews
·
Kenwood
·
1 br
·
Furnished · Wifi ·
From
$99/nightProperty
Condo · 1 Bed · 1 bath
Amenities
Furnished
Wifi
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Trendy 1- Bedroom Apartment 10 mins to Downtown!
10
Excellent
·
Douglas
·
1 br
·
Sleeps 3
·
Hardwood Floor · Air Conditioning · Furnished ·
From
$63/nightProperty
House · 1 Bed · 1 bath
Amenities
Hardwood Floor
Air Conditioning
Furnished
Wifi
Oven
Business Center
Other spaces
Kitchen
Spacious 3 bed Chicago condo
No reviews
·
Grand Boulevard
·
Studio
·
Beach · Waterfront · Air Conditioning ·
From
$223/nightProperty
Condo · Studio
Amenities
Beach
Waterfront
Air Conditioning
Fireplace
Dishwasher
Furnished
In Unit Laundry
Wifi
Other spaces
Balcony, Kitchen
Chateau Noir - Eclectic 2 BR / 2 BA Condo in the ♥️ of Bronzeville
No reviews
·
Grand Boulevard
·
2 br
·
Sleeps 6
·
Oven · Furnished · Wifi ·
From
$250/nightProperty
Condo · 2 Beds · 2 baths
Amenities
Oven
Furnished
Wifi
Other spaces
Kitchen
Penthouse Spa Condo @ Bronzeville
10
Excellent
·
Grand Boulevard
·
3 br
·
Beach · Lake · Waterfront ·
From
$328/nightProperty
Condo · 3 Beds · 2 baths
Amenities
Beach
Lake
Waterfront
Air Conditioning
Fireplace
Furnished
In Unit Laundry
Wifi
Other spaces
Balcony, Kitchen
Enjoy this 4bedroom smart home with rooftop
No reviews
·
Kenwood
·
4 br
·
Beach · Lake · Waterfront ·
From
$400/nightProperty
House · 4 Beds · 4 baths
Amenities
Beach
Lake
Waterfront
Mountains
Fireplace
Dishwasher
Furnished
In Unit Laundry
Other spaces
Kitchen
The Penthouse, Luxury stay near Downtown, Hyde Park, U of Chicago & Lake
10
Excellent
·
Kenwood
·
2 br
·
Fitness Center · Beach · Lake ·
From
$240/nightProperty
Apartment · 2 Beds · 2 baths
Amenities
Fitness Center
Beach
Lake
Waterfront
Air Conditioning
Dishwasher
Furnished
In Unit Laundry
Other spaces
Balcony, Kitchen
Modern 4 Bedroom Greystone | White Sox
7.8
Very good
·
Douglas
·
4 br
·
Sleeps 9
·
Hardwood Floor · Air Conditioning · Fireplace ·
From
$362/nightProperty
House · 4 Beds · 2 baths
Amenities
Hardwood Floor
Air Conditioning
Fireplace
Dishwasher
Furnished
Wifi
Oven
Fitness Center
Other spaces
Balcony, Kitchen
Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum
9.7
Excellent
·
Grand Boulevard
·
2 br
·
Sleeps 8
·
Fitness Center · Beach · Lake ·
From
$105/nightProperty
Apartment · 2 Beds · 1 bath
Amenities
Fitness Center
Beach
Lake
Waterfront
Air Conditioning
Furnished
In Unit Laundry
Wifi
Other spaces
Workspace, Kitchen
Cozy Gem 15mins to DOWNTOWN!
8.4
Very good
·
Douglas
·
2 br
·
Sleeps 5
·
On Site Laundry · Hardwood Floor · Outdoor Space ·
From
$111/nightProperty
Condo · 2 Beds · 1 bath
Amenities
On Site Laundry
Hardwood Floor
Air Conditioning
Furnished
In Unit Laundry
Wifi
Oven
Other spaces
Balcony, Kitchen
Charming Chicago Garden Unit
9.8
Excellent
·
Douglas
·
1 br
·
Sleeps 2
·
Air Conditioning · Dishwasher · Furnished ·
From
$180/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
Air Conditioning
Dishwasher
Furnished
In Unit Laundry
Wifi
Oven
Fitness Center
Other spaces
Kitchen
Spacious Duplex Condo/3BR/2.5 Bath
No reviews
·
Grand Boulevard
·
3 br
·
Sleeps 6
·
Workspace · Air Conditioning · Dishwasher ·
From
$276/nightProperty
Condo · 3 Beds · 3 baths
Amenities
Air Conditioning
Dishwasher
Furnished
In Unit Laundry
Wifi
Oven
Other spaces
Workspace, Kitchen
Remodeled 4 Bedroom 2 Bath Near The Lake
9.4
Excellent
·
Kenwood
·
4 br
·
Sleeps 10
·
Air Conditioning · Fireplace · Dishwasher ·
From
$309/nightProperty
Apartment · 4 Beds · 2 baths
Amenities
Air Conditioning
Fireplace
Dishwasher
Furnished
In Unit Laundry
Wifi
Oven
Other spaces
Balcony, Kitchen
Chicago Vacation Rental Near Lake Michigan!
No reviews
·
Douglas
·
2 br
·
Sleeps 4
·
Beach · Free Parking · Dishwasher ·
From
$183/nightProperty
Apartment · 2 Beds · 2 baths
Amenities
Beach
Free Parking
Dishwasher
Furnished
In Unit Laundry
Wifi
Oven
Other spaces
Kitchen
NEW! 2-Story Modern Apt ~ 5 Mi to Dtwn Chicago!
10
Excellent
·
Grand Boulevard
·
4 br
·
Sleeps 8
·
Ceiling Fan · Toiletries · Central Heat ·
From
$185/nightProperty
Apartment · 4 Beds · 3 baths
Amenities
Ceiling Fan
Toiletries
Central Heat
Walk In Closets
Tv
Free Parking
Dishwasher
Wifi
Other spaces
Kitchen
2-Story Modern Apt about 5 Mi to Dtwn Chicago!
No reviews
·
Grand Boulevard
·
4 br
·
Sleeps 8
·
Free Parking · Dishwasher · Furnished ·
From
$400/nightProperty
Apartment · 4 Beds · 3 baths
Amenities
Free Parking
Dishwasher
Furnished
In Unit Laundry
Wifi
Other spaces
Kitchen
Updated: March 29, 2023
Learn about vacation rentals in
Oakland
Browse 1 vacation rentals near Oakland in Chicago, Illinois. If you’re interested in touring around Chicago, and you want to stay in the Oakland neighborhood, use our interactive map to find your next rental. You can see pictures of Oakland vacation rentals, view amenities and features, browse by property types, and more. Whether you’re looking for a Oakland staycation, weekend getaway, or a long vacation, we’ve got you covered. The lowest vacation rental price in Oakland is $368 per night and goes up to as much as $368 per night. Use the date filters at the top to select your travel dates and view availability.
1 of the vacation rentals near Oakland are houses.
The average bathroom count for a vacation house near Oakland is
3. The average price for vacation houses near Oakland is $368 per night. There are 1 vacation homes under this price. The most common
amenities for vacation rentals near Oakland are: outdoor space, residents lounge, and dishwasher. To find vacation properties that might be a good option for large groups or families, use our filters for bedroom count, bathroom count and more.
4+ bed rentals
1 available
Getting around Oakland
Walking
7/10
Grab your reusable bags–many shops and stores are within walking distance.
Driving
7/10
This area is close to freeways and has adequate parking options.
Transit
7/10
Popular public transit options are just a short walk from this location.
Points of interest in Oakland
Groceries
8/10
At least one grocery store within a 15-minute walk
Shopping
6/10
Variety of shops within walking distance
Cafes
5/10
Some cafés within walking distance
Restaurants
6/10
Variety of restaurants within walking distance
Parks
8/10
Large amount of park space nearby
Nightlife
4/10
Some bars within walking distance
Which price range for vacation rentals is considered a good deal in Chicago, IL area?
Vacation Rental Price Information in Chicago, IL
The graph shows the percentages of vacation homes in each price bucket. Chicago, IL has the largest percentage (40.00%) of homes in $50 - $100 price range.
$0 - $50
1
units
$50 - $100
2
units
$250 - $300
1
units
$300 - $350
1
units
Vacation Rentals in Oakland, IL FAQ
How many vacation rentals in Oakland are available?
There are currently 1 vacation rentals in Oakland available. Choose from nightly rentals, monthly rentals, weekend rentals, and weekly rentals to find your perfect stay in Oakland.
What types of vacation rental properties are available in Oakland, IL?
As of March 29, 2023, there are 1 vacation houses for rent in Oakland and no vacation condos and apartments for rent in Oakland, IL. Check each listing to view photos and get more details about pricing and available amenities.
Are there any vacation rentals in Oakland, IL with more than 1 bedroom?
Yes, there are 1 Oakland vacation rentals with more than 1 bedroom. To view a more detailed amenity list, click on the available properties on Vacations by Zumper.
How many pet friendly Oakland vacation rentals are available?
As of March 29, 2023, there are no pet friendly vacation rentals in Oakland, Illinois available. For more information about pet policies regarding dogs and cats, view the property listing or contact the leasing agent.
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