Chicago Luxury Vacation Rentals
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Beach access
Lakefront Rooftop Parking
- BBQ facilities
- Free parking
- Air conditioning
- Flat-screen TV
- Mini-bar
- Terrace
Featuring lake views, the 3-bedroom Lakefront Rooftop Parking Chicago villa invites guests to visit the private research University of Chicago, located around 10 minutes away by car.
Lakefront Rooftop Parking
- BBQ facilities
- Free parking
- Air conditioning
- Flat-screen TV
- Mini-bar
- Terrace
Lakefront Rooftop Parking
Featuring lake views, the 3-bedroom Lakefront Rooftop Parking Chicago villa invites guests to visit the private research University of Chicago, located around 10 minutes away by car.
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Popular choice
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Beach access
Hamaline Luxury Guest House
- Cookware/ Kitchen utensils
- Free parking
- VIP check-in/ -out
- Air conditioning
- Massage
- Garden area
Along with Wi-Fi and a car park, Hamaline Luxury Guest House Chicago villa offers proximity to the super - tall skyscraper "Willis Tower", located 6 km away.
Hamaline Luxury Guest House
- Cookware/ Kitchen utensils
- Free parking
- VIP check-in/ -out
- Air conditioning
- Massage
- Garden area
Hamaline Luxury Guest House
Along with Wi-Fi and a car park, Hamaline Luxury Guest House Chicago villa offers proximity to the super - tall skyscraper "Willis Tower", located 6 km away.
Luxury 9 Bedroom Villa Mins From Downtown And The Lake
- Free parking
- Air conditioning
- Flat-screen TV
- Heating
Luxury 9 Bedroom Villa Mins From Downtown And The Lake Chicago, located a 6-minute walk from Roman Susan, can host up to 19 guests.
Luxury 9 Bedroom Villa Mins From Downtown And The Lake
- Free parking
- Air conditioning
- Flat-screen TV
- Heating
Luxury 9 Bedroom Villa Mins From Downtown And The Lake
Luxury 9 Bedroom Villa Mins From Downtown And The Lake Chicago, located a 6-minute walk from Roman Susan, can host up to 19 guests.
Cheap Chicago Vacation Rentals
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Great deal
A Home Away From Home!
- Cookware/ Kitchen utensils
- Flat-screen TV
- Tea and coffee facilities
Located a 16-minute walk from Bronzeville Children's Museum, A Home Away From Home! Chicago gives access to various tourist sites in the vicinity.
A Home Away From Home!
- Cookware/ Kitchen utensils
- Flat-screen TV
- Tea and coffee facilities
A Home Away From Home!
Located a 16-minute walk from Bronzeville Children's Museum, A Home Away From Home! Chicago gives access to various tourist sites in the vicinity.
Emmanuel Haven
- Cookware/ Kitchen utensils
- Free parking
- Security
- Air conditioning
- Flat-screen TV
- Patio
Located just 400 metres from Faith Tabernacle M.B. Church, the 5-bedroom Emmanuel Haven Villa Chicago provides access to various tourist attractions in the vicinity.
Emmanuel Haven
- Cookware/ Kitchen utensils
- Free parking
- Security
- Air conditioning
- Flat-screen TV
- Patio
Emmanuel Haven
Located just 400 metres from Faith Tabernacle M.B. Church, the 5-bedroom Emmanuel Haven Villa Chicago provides access to various tourist attractions in the vicinity.
Heavenly Abode
- Cookware/ Kitchen utensils
- Flat-screen TV
- Ironing facilities
- Tea and coffee facilities
Offering a Jacuzzi, the 1-bedroom Heavenly Abode Villa Chicago is located around a 25-minute walk from Nat King Cole Park.
Heavenly Abode
- Cookware/ Kitchen utensils
- Flat-screen TV
- Ironing facilities
- Tea and coffee facilities
Heavenly Abode
Offering a Jacuzzi, the 1-bedroom Heavenly Abode Villa Chicago is located around a 25-minute walk from Nat King Cole Park.
Pet Friendly Vacation Rentals Chicago
Modern 4Br Near Six Flags & Naval Base
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Tea and coffee facilities
- Patio
Located about a 25-minute walk from the sprawling amusement park "Six Flags Great America", the 5-bedroom Modern 4Br Near Six Flags & Naval Base Villa Gurnee gives access to various tourist sites in the vicinity. This 2-bathroom villa hosts up to 10 guests and provides them with private car parking.
Modern 4Br Near Six Flags & Naval Base
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Tea and coffee facilities
- Patio
Modern 4Br Near Six Flags & Naval Base
Located about a 25-minute walk from the sprawling amusement park "Six Flags Great America", the 5-bedroom Modern 4Br Near Six Flags & Naval Base Villa Gurnee gives access to various tourist sites in the vicinity. This 2-bathroom villa hosts up to 10 guests and provides them with private car parking.
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Guest favorite
Urban Oasis In Chicago'S Best Suburb
- Cookware/ Kitchen utensils
- Free parking
- Security
- Air conditioning
- Flat-screen TV
- Luggage storage
Hosting up to 6 guests, the 3-bedroom Urban Oasis In Chicago'S Best Suburb Naperville villa offers a convenient location around 10 minutes' drive from the Classic Riverwalk Urban Park.
Urban Oasis In Chicago'S Best Suburb
- Cookware/ Kitchen utensils
- Free parking
- Security
- Air conditioning
- Flat-screen TV
- Luggage storage
Urban Oasis In Chicago'S Best Suburb
Hosting up to 6 guests, the 3-bedroom Urban Oasis In Chicago'S Best Suburb Naperville villa offers a convenient location around 10 minutes' drive from the Classic Riverwalk Urban Park.
5 Star Luxury Stay Near Chicago O'Hare
- Cookware/ Kitchen utensils
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Garden area
The 3-bedroom 5 Star Luxury Stay Near Chicago O'Hare Des Plaines villa is located 3.9 km from Flick Park, giving access to various tourist spots nearby.
5 Star Luxury Stay Near Chicago O'Hare
- Cookware/ Kitchen utensils
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Garden area
5 Star Luxury Stay Near Chicago O'Hare
The 3-bedroom 5 Star Luxury Stay Near Chicago O'Hare Des Plaines villa is located 3.9 km from Flick Park, giving access to various tourist spots nearby.
Chicago Vacation Rentals Oceanfront
Luxury 4Br Near Six Flags & Naval Base
- BBQ facilities
- Free parking
- Housekeeping
- Air conditioning
- Flat-screen TV
- Terrace
Situated just a 5-minute walk from Clearview Park, Luxury 4Br Near Six Flags & Naval Base Villa Waukegan entices guests with views of the garden.
Luxury 4Br Near Six Flags & Naval Base
- BBQ facilities
- Free parking
- Housekeeping
- Air conditioning
- Flat-screen TV
- Terrace
Luxury 4Br Near Six Flags & Naval Base
Situated just a 5-minute walk from Clearview Park, Luxury 4Br Near Six Flags & Naval Base Villa Waukegan entices guests with views of the garden.
Elegant Executive Residence Hot Tub Pool Parties!
- Free parking
- Air conditioning
- Flat-screen TV
Staying at the 1-bedroom Elegant Executive Residence Hot Tub Pool Parties! Bartlett villa, guests can visit Bartlett Park District T, which is nearly 25 minutes' walk away.
Elegant Executive Residence Hot Tub Pool Parties!
- Free parking
- Air conditioning
- Flat-screen TV
Elegant Executive Residence Hot Tub Pool Parties!
Staying at the 1-bedroom Elegant Executive Residence Hot Tub Pool Parties! Bartlett villa, guests can visit Bartlett Park District T, which is nearly 25 minutes' walk away.
Wolfsbane - Upscale 2 Bedroom Villa At Petite Acres
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Tea and coffee facilities
- Sauna
- Garden area
Wolfsbane - Upscale 2 Bedroom Villa At Petite Acres New Buffalo, located 2.2 km from Galien River County Nature Park, invites guests to relax in a sauna.
The area is popular for those who like cycling and fisheries.
Wolfsbane - Upscale 2 Bedroom Villa At Petite Acres
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Tea and coffee facilities
- Sauna
- Garden area
Wolfsbane - Upscale 2 Bedroom Villa At Petite Acres
Wolfsbane - Upscale 2 Bedroom Villa At Petite Acres New Buffalo, located 2.2 km from Galien River County Nature Park, invites guests to relax in a sauna.
The area is popular for those who like cycling and fisheries.
Chicago Vacation Rentals with Private Pool
Dogwood - Upscale 2 Bedroom Villa At Petite Acres
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Tea and coffee facilities
- Sauna
- Garden area
Offering access to entertainment venues such as the full - service Oselka's Snug Harbor Marina, situated around 25 minutes' walk away, the 2-bedroom Dogwood - Upscale 2 Bedroom Villa At Petite Acres New Buffalo can host up to 4 guests. Pampering guests with a sauna, this property features views of the lake and is nestled 2.2 km from Galien River County Nature Park.
Guests can enjoy cycling and fisheries, which can be arranged onsite.
Dogwood - Upscale 2 Bedroom Villa At Petite Acres
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Tea and coffee facilities
- Sauna
- Garden area
Dogwood - Upscale 2 Bedroom Villa At Petite Acres
Offering access to entertainment venues such as the full - service Oselka's Snug Harbor Marina, situated around 25 minutes' walk away, the 2-bedroom Dogwood - Upscale 2 Bedroom Villa At Petite Acres New Buffalo can host up to 4 guests. Pampering guests with a sauna, this property features views of the lake and is nestled 2.2 km from Galien River County Nature Park.
Guests can enjoy cycling and fisheries, which can be arranged onsite.
Goldenrod - Upscale 2-Bedroom Villa At Petite Acres
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Tea and coffee facilities
- Sauna
- Garden area
The 2-bedroom Goldenrod - Upscale 2-Bedroom Villa At Petite Acres New Buffalo is nestled within 7 km of the outdoor Hesston Steam Museum and provides a sauna.
There is cycling and fisheries available on-site.
Goldenrod - Upscale 2-Bedroom Villa At Petite Acres
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Tea and coffee facilities
- Sauna
- Garden area
Goldenrod - Upscale 2-Bedroom Villa At Petite Acres
The 2-bedroom Goldenrod - Upscale 2-Bedroom Villa At Petite Acres New Buffalo is nestled within 7 km of the outdoor Hesston Steam Museum and provides a sauna.
There is cycling and fisheries available on-site.
Larkspur - Upscale 2 Bedroom Villa At Petite Acres
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Tea and coffee facilities
- Sauna
- Garden area
The comfortable 3-star Larkspur - Upscale 2 Bedroom Villa At Petite Acres New Buffalo hotel is within 10 minutes' drive of Galien River County Nature Park and boasts a casino, a sauna, and a golf course.
Guests can access a casino to add excitement to their stay. The area is known for cycling and fisheries.
Larkspur - Upscale 2 Bedroom Villa At Petite Acres
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Tea and coffee facilities
- Sauna
- Garden area
Larkspur - Upscale 2 Bedroom Villa At Petite Acres
The comfortable 3-star Larkspur - Upscale 2 Bedroom Villa At Petite Acres New Buffalo hotel is within 10 minutes' drive of Galien River County Nature Park and boasts a casino, a sauna, and a golf course.
Guests can access a casino to add excitement to their stay. The area is known for cycling and fisheries.
Wild Indigo - Upscale 2 Bedroom Villa At Petite Acres
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Tea and coffee facilities
- Sauna
- Garden area
The 2-bedroom Wild Indigo - Upscale 2 Bedroom Villa At Petite Acres New Buffalo is located within a 7-km distance of the outdoor Hesston Steam Museum and provides guests with a sauna for a more relaxing stay.
Cycling and fisheries can be enjoyed nearby and a fitness room is available onsite.
Wild Indigo - Upscale 2 Bedroom Villa At Petite Acres
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Tea and coffee facilities
- Sauna
- Garden area
Wild Indigo - Upscale 2 Bedroom Villa At Petite Acres
The 2-bedroom Wild Indigo - Upscale 2 Bedroom Villa At Petite Acres New Buffalo is located within a 7-km distance of the outdoor Hesston Steam Museum and provides guests with a sauna for a more relaxing stay.
Cycling and fisheries can be enjoyed nearby and a fitness room is available onsite.
Windflower - Upscale 2 Bedroom Villa At Petite Acres
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Tea and coffee facilities
- Sauna
- Garden area
The 2-bedroom Windflower - Upscale 2 Bedroom Villa At Petite Acres New Buffalo entices active guests with access to a fitness area and is located about 25 minutes on foot from New Buffalo Railroad Museum.
Relax at a sauna, where you can enjoy the rest in full. There is a casino, along with cycling and fisheries to diversify guests' leisure.
Windflower - Upscale 2 Bedroom Villa At Petite Acres
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Tea and coffee facilities
- Sauna
- Garden area
Windflower - Upscale 2 Bedroom Villa At Petite Acres
The 2-bedroom Windflower - Upscale 2 Bedroom Villa At Petite Acres New Buffalo entices active guests with access to a fitness area and is located about 25 minutes on foot from New Buffalo Railroad Museum.
Relax at a sauna, where you can enjoy the rest in full. There is a casino, along with cycling and fisheries to diversify guests' leisure.
Witch Hazel - Upscale 2 Bedroom Villa At Petite Acres
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Tea and coffee facilities
- Sauna
- Garden area
The 2-bedroom Witch Hazel - Upscale 2 Bedroom Villa At Petite Acres New Buffalo boasts a sauna and is nearly a 25-minute stroll from entertainment sites such as the full - service Oselka's Snug Harbor Marina. The New Buffalo villa hosts up to 4 guests and provides a casino for their enjoyment.
If you would like stay in shape, try cycling and fisheries at the New Buffalo accommodation.
Witch Hazel - Upscale 2 Bedroom Villa At Petite Acres
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Tea and coffee facilities
- Sauna
- Garden area
Witch Hazel - Upscale 2 Bedroom Villa At Petite Acres
The 2-bedroom Witch Hazel - Upscale 2 Bedroom Villa At Petite Acres New Buffalo boasts a sauna and is nearly a 25-minute stroll from entertainment sites such as the full - service Oselka's Snug Harbor Marina. The New Buffalo villa hosts up to 4 guests and provides a casino for their enjoyment.
If you would like stay in shape, try cycling and fisheries at the New Buffalo accommodation.
Woodsage - Upscale 2 Bedroom Villa At Petite Acres
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Tea and coffee facilities
- Sauna
- Garden area
Offering a sauna for a relaxing experience, the luxurious Woodsage - Upscale 2 Bedroom Villa At Petite Acres New Buffalo is located a 25-minute walk from the full-service Oselka's Snug Harbor Marina. Providing guests with Wi-Fi and a private parking lot, the 2-bedroom villa is 3.9 km from Whittaker Woods Golf Course.
There are a casino provided for guests' enjoyment, along with a fitness room for guests to stay fit. Onsite sport activities include cycling and fisheries.
Woodsage - Upscale 2 Bedroom Villa At Petite Acres
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Tea and coffee facilities
- Sauna
- Garden area
Woodsage - Upscale 2 Bedroom Villa At Petite Acres
Offering a sauna for a relaxing experience, the luxurious Woodsage - Upscale 2 Bedroom Villa At Petite Acres New Buffalo is located a 25-minute walk from the full-service Oselka's Snug Harbor Marina. Providing guests with Wi-Fi and a private parking lot, the 2-bedroom villa is 3.9 km from Whittaker Woods Golf Course.
There are a casino provided for guests' enjoyment, along with a fitness room for guests to stay fit. Onsite sport activities include cycling and fisheries.
Are you in a hurry?
Here is a quick list of Vacation Rentals in Chicago, selected based on their rating
| Name of hotel | Accommodation Rating | Price, $ | |
| Lakefront Rooftop Parking |
7.5 / 10 (11 Reviews) |
From 301$ | |
| Hamaline Luxury Guest House |
7.1 / 10 (14 Reviews) |
From 336$ | |
| Modern 4Br Near Six Flags & Naval Base |
10.0 / 10 (6 Reviews) |
From 361$ |
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