Chicago, Illinois Vacation Rentals

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1 - 20 of about 168 from 7 sites
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Location:Chicago, Illinois
Bedrooms:6
Bathrooms:2
Sleeps:16
Property Type:Condo

Amenities:Air Conditioning, BBQ, Balcony, Cable/Satellite TV, Coffee Maker, Deck, Dishwasher, Full kitchen, Garage, Hair Dryer, Internet Access, Iron, Kitchenette, Laundry, Linens, Lounge, Microwave, Oven, Patio, Pets OK, Refrigerator, Restaurant, Smoking OK, Stove, TV, Toaster & more amenities »
Activities:Canoeing, Fishing, Golf, Gym, Kayaking, Sailing, Shopping, Tennis, Zoo & more activities »

Description: Chicago Vacation Rental lenience # 2320200 This well kept property sleeps up to 16 comfortably. Enjoy the nice Wrigley Located property with great outdoor space and a sunny interior. Additional bonus includes a a huge ... more details »
Location:Chicago, Illinois
Bedrooms:4
Bathrooms:4
Sleeps:14
Property Type:Condo

Amenities:Air Conditioning, BBQ, Cable/Satellite TV, Coffee Maker, Deck, Dishwasher, Full kitchen, Hair Dryer, Iron, Laundry, Linens, Microwave, Oven, Pets OK, Refrigerator, Smoking OK, Stove, TV, Toaster & more amenities »

Description: License#2314739 This is a luxury property consistent of two units one above the other. Book one or both to accommodate the size of your group. A total of 4 bedroom 4 bath brand new construction ... more details »
Location:Chicago, Illinois
Bedrooms:5
Sleeps:14
Property Type:Vacation Home

Amenities:Air Conditioning, BBQ, Balcony, CD Player, Cable/Satellite TV, DVD Player, Deck, Dishwasher, Full kitchen, Hair Dryer, Internet Access, Iron, Laundry, Linens, Microwave, Oven, Patio, Pets OK, Playground, Refrigerator, Restaurant, Smoking OK, Stereo, Stove, TV, Toaster & more amenities »
Activities:Boating, Casino, Fishing, Hiking, Ice Skating, Miniature Golf, Shopping, Snow Skiing, Tennis, Theme Parks, Water Parks, Zoo & more activities »

Description: Beautiful Brick Single Family Rowhome in convenient Bucktown location. Bright and open family friendly layout great for entertaining. Large eat-in kitchen with deck access. Master suite w/ private outdoor deck. 2 other large bedrooms on ... more details »
Location:Twin Lakes, Wisconsin
Bedrooms:3
Bathrooms:2
Sleeps:9
Property Type:Vacation Home

Amenities:Air Conditioning, Alarm Clock, BBQ, Blender, CD Player, Cable/Satellite TV, Coffee Maker, DVD Player, Full kitchen, Hair Dryer, Internet Access, Iron, Lake View, Laundry, Linens, Microwave, Oven, Pets OK, Playground, Refrigerator, Restaurant, Screened Porch, Smoking OK, Stove, TV, Toaster, VCR & more amenities »
Activities:Amusement Parks, Beach, Boating, Bowling, Canoeing, Fishing, Golf, Hiking, Horseback Riding, Ice Skating, Jetskiing, Kayaking, Miniature Golf, Parasailing, Sailing, Scuba Diving, Shopping, Snow Skiing, Snowmobiling, Tennis, Theme Parks, Volleyball, Water Parks, Water Skiing, Zoo & more activities »

Description: 2 Story Lake-view Country Vacation home w. Volleyball and Firepit. Relaxed, Residential, Wooded area of Lake Elizabeth- the southern and larger of the two Twin Lakes. Lake View with easy 150 Ft. walk to lake. ... more details »
Location:Chicago, Illinois
Bedrooms:2
Bathrooms:2
Sleeps:6
Property Type:Apartment

Amenities:Air Conditioning, Cable/Satellite TV, Coffee Maker, Dishwasher, Full kitchen, Laundry, Linens, Pets OK, Refrigerator, Smoking OK, TV & more amenities »

Description: You will be sure to enjoy your stay in Chicago in this newly renovated, spacious, two bedroom and two bathroom oasis in the heart of Lincoln Park. Each unit is complete with dark, hardwood floors, ... more details »
Location:Hillside, Illinois
Bedrooms:3
Bathrooms:2
Sleeps:10
Property Type:Vacation Home

Amenities:Air Conditioning, Alarm Clock, Basketball Court, Blender, CD Player, Cable/Satellite TV, Coffee Maker, Computer Access, DVD Player, Dishwasher, Full kitchen, Hot Tub, Internet Access, Iron, Kitchenette, Linens, Microwave, Oven, Pets OK, Phone, Playground, Refrigerator, Restaurant, Smoking OK, Stereo, Stove, Swimming Pool, TV, Toaster & more amenities »
Activities:Amusement Parks, Basketball, Beach, Boating, Bowling, Canoeing, Casino, Golf, Gym, Shopping, Water Parks, Zoo & more activities »

Description: The Space Modern 3BD 2Bth Brick-Style Ranch! Sleeps 10!! ASK ABOUT OUR PRICE MATCHING OPTION!! Very affordable home in west suburb that offers easy access to the city. Sleeps up to 10 people. -3 Bedrooms ... more details »
Location:Michigan City, Indiana
Bedrooms:2
Bathrooms:2
Sleeps:7
Property Type:Vacation Home

Amenities:Air Conditioning, Alarm Clock, BBQ, Balcony, Basketball Court, Beachfront View, Blender, CD Player, Cable/Satellite TV, Coffee Maker, DVD Player, Deck, Dishwasher, Fireplace, Full kitchen, Internet Access, Iron, Laundry, Linens, Microwave, Oceanfront, Outdoor Shower, Oven, Patio, Pets OK, Phone, Playground, Refrigerator, Restaurant, Smoking OK, Stereo, Stove, Swimming Pool, TV, Toaster, VCR, Video Game Console & more amenities »
Activities:Basketball, Beach, Biking, Boating, Canoeing, Casino, Fishing, Golf, Hiking, Horseback Riding, Ice Skating, Jetskiing, Kayaking, Miniature Golf, Sailing, Shopping, Snow Skiing, Snowmobiling, Tennis, Volleyball, Water Parks, Water Skiing, Windsurfing, Zoo & more activities »

Description: This cottage is located in Beachwalk Resort community (tennis, private lake & beach, rental of kayaks, canoes and paddel boards, pool, boat park plus private access to Lake Michigan beach (1 block). Resort feels like ... more details »
Location:Chicago, Illinois
Bedrooms:3
Bathrooms:2
Sleeps:12
Property Type:Apartment

Amenities:Air Conditioning, BBQ, Basketball Court, Cable/Satellite TV, Coffee Maker, DVD Player, Dishwasher, Full kitchen, Hair Dryer, Internet Access, Iron, Laundry, Linens, Microwave, Pets OK, Playground, Refrigerator, Restaurant, Smoking OK, Stereo, Stove, TV, Toaster & more amenities »
Activities:Basketball, Boating, Canoeing, Casino, Golf, Hiking, Ice Skating, Kayaking, Miniature Golf, Shopping, Tennis, Theme Parks, Water Skiing, Zoo & more activities »

Description: Great location near the 90/94 expressway and the Blue line stop at Western. No cab needed from O'Hare or even Midway airports with easy access from L trains. Meticulous rehab of classic Chicago apartment. All ... more details »
Location:Barrington, Illinois
Bedrooms:6
Bathrooms:5
Sleeps:12
Property Type:Vacation Home

Amenities:Air Conditioning, Alarm Clock, BBQ, Blender, CD Player, Cable/Satellite TV, Coffee Maker, DVD Player, Deck, Dishwasher, Fireplace, Full kitchen, Garage, Hair Dryer, Hot Tub, Internet Access, Iron, Kitchenette, Laundry, Linens, Microwave, Oven, Pets OK, Phone, Playground, Refrigerator, Restaurant, Screened Porch, Smoking OK, Stereo, Stove, Swimming Pool, TV, Toaster, Towels & more amenities »
Activities:Amusement Parks, Beach, Biking, Boating, Bowling, Canoeing, Casino, Fishing, Golf, Gym, Hiking, Horseback Riding, Hunting, Ice Skating, Jetskiing, Kayaking, Miniature Golf, Racquetball, Shopping, Snow Skiing, Snowmobiling, Tennis, Water Parks, Water Skiing & more activities »

Description: Come stay in an ideal home for a holiday gathering or host a special event. Lots of space and beautiful views! Our home can be rented by room or floor. Options are main level with ... more details »
Location:Chicago, Illinois
Bedrooms:2
Bathrooms:1
Sleeps:5
Property Type:Apartment

Amenities:Coffee Maker, Linens, Microwave, TV, Wireless Internet Access & more amenities »
Activities:Restaurants

Description: Spacious, elegantly appointed and furnished Lakeview vacation/executive two bedroom, one bathroom apartment. r n r nFirst floor on a quiet tree-lined street, the entire apartment features, either oak floors or ceramic tiles, r ... more details »
Location:Chicago, Illinois
Bedrooms:2
Bathrooms:1
Sleeps:6
Property Type:Apartment

Amenities:Backyard, Child Friendly, Deck

Description: Welcome to your home away from home nestled in the Village within the City c3a2€“ Roscoe Village in Chicago, IL. Roscoe Village is a very family friendly neighborhood. This warm and welcoming first floor unit ... more details »
Location:Chicago, Illinois
Bedrooms:3
Bathrooms:2
Sleeps:6
Property Type:Apartment

Amenities:Child Friendly

Description: Chicago Guest House is the absolute BEST choice for business & leisure travelers who want to experience the sense of having arrived 'home' while they are in Chicago! n nA Vintage Beauty With All the ... more details »
Location:La Porte, Indiana
Bedrooms:2
Bathrooms:1
Sleeps:5
Property Type:Vacation Home

Amenities:Air Conditioning, BBQ, Cable/Satellite TV, Child Friendly, Coffee Maker, DVD Player, Deck, Garage, Pets OK, Shower, TV & more amenities »
Activities:Beach, Biking, Boating, Casino, Fishing, Golf, Restaurants, Shopping, Zoo & more activities »

Description: I have a very cute cozy country cottage in Laporte, Ind just steps away from PineLake. n2 bedrooms n1 Bath with standup shower nAll remodeled nSleeps 5-6 people..It has 1 queen bed, 2 twins, a ... more details »
Location:Chicago, Illinois
Bedrooms:1
Bathrooms:1
Sleeps:4
Property Type:Apartment

Amenities:BBQ, Balcony, Breakfast Bar, Cable/Satellite TV, Child Friendly, Deck, Disability Access, Fire Pit, Fireplace, Garage, Hot Tub, Lakefront, Linens, Lounge, Non-Smoking, Pets OK, Playground, Shower, Swimming Pool, TV, Towels, Utilities included, Wireless Internet Access & more amenities »
Activities:Gym, Pinball

Description: Unit not available for daily rental in July 4th Holiday ! n n n*Prices may vary depending on the season. Premium months are between April and September. n*Prices negotiable based on length of stay. ... more details »
Location:Williams Bay, Wisconsin
Bedrooms:3
Bathrooms:3
Sleeps:8
Property Type:Vacation Home

Amenities:BBQ, Child Friendly, Fireplace, Pets OK, TV, Wireless Internet Access & more amenities »
Activities:Beach, Restaurants

Description: Located in downtown Williams Bay, WI, the Williams Bay Tourist House is walking distance to restaurants, shops, the Geneva Lake beach, boardwalk, and boat launch. Also nearby are Kishwauketoe Nature Conservancy and Yerkes Observatory. The ... more details »
Location:Chicago, Illinois
Bedrooms:2
Bathrooms:2
Sleeps:5
Property Type:Apartment

Amenities:Child Friendly, Disability Access, Pets OK

Description: Unit not available for daily rental in July 4th Holiday ! n n n*Prices may vary depending on the season. Premium months are between April and September. n*Prices negotiable based on length of stay. ... more details »
Location:Lemont, Illinois
Bedrooms:4
Bathrooms:3
Sleeps:12
Property Type:Vacation Home

Amenities:Backyard, Child Friendly
Activities:Bird watching, Golf, Museums

Description: Located in Lemont, IL, home of the famous Cog Hill Golf Course, this home (circa 1868) has over 4000 S.F. and is now available to rent. The history of this home includes the Singer Family ... more details »
Location:Aurora, Illinois
Bedrooms:2
Bathrooms:1
Sleeps:4
Property Type:Vacation Home

Amenities:Air Conditioning, CD Player, Deck, Swimming Pool & more amenities »
Activities:Swimming, Yoga

Description: Casa de Teca, is natural teak home featuring truly world class views. The cozy interior is warm and welcoming. The open plan dining and living area allows for comfortable family gatherings. The fully covered wrap ... more details »
Location:Fontana, Wisconsin
Bedrooms:1
Bathrooms:1
Sleeps:2
Property Type:Vacation Home

Amenities:Air Conditioning, Child Friendly, Full kitchen
Activities:Beach

Description: Cozy 600sf cottage just steps to a great beach with pier and swim raft. Cottage has oak floors, full kitchen, separate bedroom with queen bed, full bathroom and additional loft via spiral staircase. Summer rental ... more details »
Location:Chicago, Illinois
Bedrooms:2
Bathrooms:2
Sleeps:4
Property Type:Apartment

Amenities:Child Friendly, Disability Access, Internet Access, Jacuzzi, Laundry, Pets OK, Restaurant, Sauna, Swimming Pool & more amenities »
Activities:Gym, Restaurants, Shopping, Swimming & more activities »

Description: Unit not available for daily rental in July 4th Holiday ! 1 week minimum n n n*Prices may vary depending on the season. Premium months are between April and September. n*Prices negotiable based on ... more details »
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