Hotel Cancun Rosa - Vacation Rentals in Old Town

Modern 3BR City Retreat - Near Old Town From US $351
         

9.8 (11 Reviews)
Hotel
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Sophisticated 4BR Suite - Modern and Luxurious From US $373
         

10.0 (1 Review)
Hotel
  • Air Conditioner
  • Accessibility
  • Security/Safety
The Peninsula Chicago From US $803
         

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9.8 (1006 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
4BR City Retreat, Great for Business & Family From US $437
         

9.8 (6 Reviews)
Hotel
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Lincoln Park Living - Suite 1 From US $379
         

9.6 (56 Reviews)
Hotel
  • Air Conditioner
  • TV
  • Balcony/Terrace
Lincoln Park Living - 3 Queen Beds - Sleeps 6! From US $240
         

9.6 (36 Reviews)
Hotel
  • Air Conditioner
  • TV
  • Balcony/Terrace
Spacious 4BR Near Fulton Market & Riverwalk From US $812
         

9.6 (4 Reviews)
Hotel
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Sophisticated 4BR Suite - Walk to Shops, Dining & Transit From US $408
         

9.4 (10 Reviews)
Hotel
  • Air Conditioner
  • TV
  • Wheelchair Accessible

Luxury Places to Stay in Old Town

Over 4393+ Luxury Places to Stay in or Near Old Town
Wrigley 4BR Home, Sleeps 10 From US $3,786
         

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New
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: The Wolcott : Modern Elegance at Its Finest From US $3,490
         

9.4 (14 Reviews)
House
  • Air Conditioner
  • Parking
  • Designated Smoking Area

Top-Rated Vacation Rentals with a Pool in Old Town

Over 1091+ Top-Rated Vacation Rentals with a Pool in or Near Old Town
Chic 1-bedroom condo in the heart of Chicago, next to Mag Mile From US $147
         

New Luxury 3 Bdr Apt in Chicago C9 From US $1,516
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pool
3BR Luxury Modern Apartment From US $454
         

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10.0 (1 Review)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Pool
Level Chicago Old Town From US $270
         

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10.0 (1 Review)
Hotel
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  • Parking
  • Pet Friendly
Chicago Cityview Chic - Gold Coast/River North From US $199
         

Unique Chicago Penthouse Loft - Amazing Deal & Location From US $430
         

Pet-Friendly Vacation Rentals in Old Town

Over 1914+ Pet-Friendly Vacation Rentals in or Near Old Town
Lakeview/LincolnPark 2BR/1BA Updated Vintage Apartment in walkable neighborhood From US $413
         

Chicago Quick Stay From US $130
         

6.3 (47 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Internet
The Villa Toscana From US $178
         

8.0 (654 Reviews)
Bed & Breakfast
  • Parking
  • Pet Friendly
  • Security/Safety
Wrigleyville Condo, Sleeps 10, 1/2 block from Wrigley Field From US $546
         

10.0 (121 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
Wrigley Field/Lakeview -Entire Home- Large Groups! From US $777
         

10.0 (95 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
NEW LUXURY PENTHOUSE CONDO From US $631
         

10.0 (215 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
NEW LUXURY CONDO WITH PATIO DECK From US $395
         

10.0 (199 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
Large 4BR/3BA Safe Old Town Location Walk Everywhere From US $1,467
         

10.0 (75 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
See More Pet-Friendly Vacation Rentals in Old Town on PetFriendly.io

Large Vacation Homes & Villas in Old Town

Over 566+ Large Vacation Homes & Villas in or Near Old Town
4BR Old Town Chicago Loft | Walk to Wells St From US $920
         

10.0 (122 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Bootlegger House Sleeps 10-20 Free TV & Parking From US $922
         

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10.0 (4 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Magic Factory Loft 2West From US $618
         

10.0 (200 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible
5 Bedroom Wrigleyville experience right by stadium From US $942
         

10.0 (64 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Spacious 4-Level/4-Bedroom Townhouse in West Loop From US $1,217
         

Chicago Bootlegger House Sleeps 11-22 with 3 parking spots From US $988
         

10.0 (49 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Wheelchair Accessible Vacation Homes in Old Town

Over 2335+ Wheelchair Accessible Vacation Homes in or Near Old Town
Spacious 4BR Central Apartment w/Skyline Views From US $985
         

10.0 (21 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Modern River West 2BR with W&D by Zencity From US $77
         

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10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
The Publishing House B&B From US $298
         

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9.8 (208 Reviews)
Bed & Breakfast
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Dtown Penthouse 3bd VIEWS+Parking +Gym+Pool From US $875
         

10.0 (13 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
The Cornerstone - Designer 4BR Flat in Bucktown/WP From US $668
         

10.0 (11 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Luxury Loft Collection 903 - Terrace - River North From US $1,016
         

10.0 (7 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Modern West Loop Gem-City Views & Prime Location 3 From US $813
         

10.0 (7 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Modern West Loop Gem-City Views & Prime Location 4 From US $810
         

10.0 (7 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible

Old Town Vacation Rentals and Airbnb Places to Stay Under $200

Over 1310+ Old Town Vacation Rentals and Airbnb Places to Stay Under $200
Cozy 1 Bedroom Apt near Logan Sq Chicago From US $190
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Security/Safety
Modern River West 2BR with W&D by Zencity From US $76
         

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9.0 (4 Reviews)
Apartment
  • Air Conditioner
  • Wheelchair Accessible
  • Internet
Ray's Bucktown B&B From US $196
         

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9.8 (404 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Stunning 3 BR in prime Chicago location From US $179
         

Cozy Depaul/Wrigley Garden Condo +FREE Parking! From US $135
         

8.0 (1 Review)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Security/Safety

Instantly Bookable Vacation Homes in Old Town

Over 2684+ Instantly Bookable Vacation Homes in or Near Old Town
3 BD condo near to downtown, Gold Coast and Michigan Avenue. From US $303
         

Twice as Nice: Chic 2BR Stay with Style & Space From US $266
         

9.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Wrigley Field Grand Slam Suite 4 Bedrooms, 2 Bathrooms From US $1,085
         

9.0 (15 Reviews)
Condo
  • Balcony/Terrace
  • Security/Safety
  • Child Friendly
Wrigley Field All Star Suite 3 Bedrooms 2 Bath From US $951
         

9.6 (24 Reviews)
Condo
  • Air Conditioner
  • TV
  • Security/Safety
Entire Below Level Studio w/Private Sauna From US $310
         

10.0 (76 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Private Historic Coach House Wicker Park From US $432
         

10.0 (71 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

About Old Town Vacation Rentals

With more than 700 Old Town vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Hotelcancunrosa and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Old Town.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Hotelcancunrosa Old Town, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Old Town. Places to stay near Old Town are 273.76 ft² on average, with prices averaging US $445 a night.

Hotelcancunrosa makes it easy and safe to find and compare vacation rentals in Old Town with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Old Town

Type Count
Hotels 699
Resorts 1

Use these Quick Filters to Find a Vacation Rental in Old Town

Pro Tip: Hotelcancunrosa makes it easy to compare the best listings on Hotelcancunrosa homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Hotelcancunrosa 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 Old Town.

Weather in Old Town

View the weather forecast for Old Town before booking your Old Town Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Complexes around Old Town, IL


Old Town Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Old Town?
How many vacation rentals are available in Old Town?

Currently, the total number of properties listed in 2026 is over 700 in the Old Town area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Old Town.