Old Town Holiday Rentals
Apartment
- Chicago
- ·
- Old Town Triangle
- 0.14 mi to center
9.8Exceptional
(6 Reviews)
2 Bedrooms
2 Baths
6 Guests
Fireplace/Heating
Pet Friendly
Kitchen
Air Conditioner
US $540/Night
7 Nights - US $3,779
Apartment
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
5 Guests
947.22 ft²
- Fireplace/Heating
- Air Conditioner
Internet
Child Friendly
US $90/Night
7 Nights - US $630
Bed & Breakfast
10.0Exceptional
(517 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
Balcony/Terrace
Parking- Air Conditioner
US $272/Night
7 Nights - US $1,906
Condo
Walk to Lincoln Park, North Avenue Beach, and Second City! Lovely Old Town Charm! by AllSet Turnover
- Chicago
- ·
- Old Town Triangle
- 0.16 mi to center
9.4Exceptional
(27 Reviews)
1 Bedroom
1 Bath
3 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $447/Night
7 Nights - US $3,130
Apartment
- Chicago
- ·
- Old Town Triangle
- 0.16 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
3 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $371/Night
7 Nights - US $2,598
Condo
- Chicago
- ·
- Old Town Triangle
- 0.13 mi to center
9.0Exceptional
(25 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $621/Night
7 Nights - US $4,347
Apartment
8.8Fabulous
(5 Reviews)
2 Bedrooms
1 Bath
5 Guests
950 ft²
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $371/Night
7 Nights - US $2,597
House
8.4Excellent
(43 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $622/Night
7 Nights - US $4,353
Apartment
- Chicago
- ·
- Old Town Triangle
- 0.15 mi to center
8.0Excellent
(1 Review)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $483/Night
7 Nights - US $3,381
Luxury Holiday Rentals in Old Town
Over 75+ Luxury Holiday Rentals in or Near Old Town
Condo
9.6Exceptional
(4 Reviews)
8 Bedrooms
4 Baths
16 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $1,690/Night
7 Nights - US $11,830
House
10.0Exceptional
(14 Reviews)
6 Bedrooms
6 Baths
32 Guests
4000 ft²
Hot Tub- Fireplace/Heating
Ocean View- Balcony/Terrace
US $1,660/Night
7 Nights - US $11,617
House
10.0Exceptional
(57 Reviews)
5 Bedrooms
7 Baths
12 Guests
6200 ft²
Spa- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $1,580/Night
7 Nights - US $11,060
House
9.6Exceptional
(5 Reviews)
4 Bedrooms
4 Baths
18 Guests
3003.13 ft²
- Spa
- Fireplace/Heating
- Balcony/Terrace
View
US $1,199/Night
7 Nights - US $8,393
House
8.3Excellent
(3 Reviews)
5 Bedrooms
4 Baths
22 Guests
3003.13 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
Breakfast
US $1,191/Night
7 Nights - US $8,335
House
10.0Exceptional
(19 Reviews)
3 Bedrooms
3 Baths
14 Guests
2400 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $1,137/Night
7 Nights - US $7,962
House
9.8Exceptional
(105 Reviews)
4 Bedrooms
4 Baths
18 Guests
3000 ft²
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $1,104/Night
7 Nights - US $7,730
House
8.8Fabulous
(12 Reviews)
1 Bedroom
2 Baths
14 Guests
1194.79 ft²
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $1,030/Night
7 Nights - US $7,210
Apartment
8 Bedrooms
4 Baths
16 Guests
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
US $1,002/Night
7 Nights - US $7,015
Pet-Friendly Holiday Rentals in Old Town
Over 30+ Pet-Friendly Holiday Rentals in or Near Old Town
House
10.0Exceptional
(5 Reviews)
3 Bedrooms
2 Baths
14 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $542/Night
7 Nights - US $3,792
House
9.5Exceptional
(30 Reviews)
4 Bedrooms
3 Baths
14 Guests
1496.18 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Breakfast
US $852/Night
7 Nights - US $5,966
House
- Chicago
- ·
- Old Town Triangle
- 0.21 mi to center
9.8Exceptional
(140 Reviews)
3 Bedrooms
2 Baths
6 Guests
2000 ft²
Oceanfront- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $447/Night
7 Nights - US $3,126
House
- Chicago
- ·
- Old Town Triangle
- 0.13 mi to center
4.0Average
(2 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
US $878/Night
7 Nights - US $6,148
House
9.4Exceptional
(112 Reviews)
5 Bedrooms
3 Baths
22 Guests
3000 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $729/Night
7 Nights - US $5,101
House
9.2Exceptional
(71 Reviews)
4 Bedrooms
2 Baths
14 Guests
1500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $785/Night
7 Nights - US $5,497
House
- Chicago
- ·
- Old Town Triangle
- 0.13 mi to center
8.4Excellent
(21 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $810/Night
7 Nights - US $5,671
Apartment
3 Bedrooms
3 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $249/Night
7 Nights - US $1,746
Apartment
1 Bedroom
1 Bath
2 Guests
678 ft²
- Pet Friendly
- Kitchen
- Air Conditioner
- Internet
US $112/Night
7 Nights - US $784
Large Holiday Rentals and Private Villas in Old Town
Over 11+ Large Holiday Rentals and Private Villas in or Near Old Town
Apartment
10.0Exceptional
(7 Reviews)
6 Bedrooms
3 Baths
12 Guests
3000 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $820/Night
7 Nights - US $5,740
Bed & Breakfast
9.3Exceptional
(345 Reviews)
11 Bedrooms
10 Baths
29 Guests
319.33 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $366/Night
7 Nights - US $2,562
House
- Chicago
- ·
- Old Town Triangle
- 0.22 mi to center
9.8Exceptional
(27 Reviews)
4 Bedrooms
3 Baths
12 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $875/Night
7 Nights - US $6,125
House
3 Bedrooms
3 Baths
14 Guests
2002.09 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Pet Friendly
US $259/Night
7 Nights - US $1,813
Apartment
10.0Exceptional
(75 Reviews)
4 Bedrooms
3 Baths
15 Guests
2500 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $1,376/Night
7 Nights - US $9,632
Apartment
10.0Exceptional
(38 Reviews)
4 Bedrooms
2 Baths
13 Guests
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $881/Night
7 Nights - US $6,165
Apartment
9.8Exceptional
(15 Reviews)
4 Bedrooms
1 Bath
12 Guests
21528 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $714/Night
7 Nights - US $4,997
House
- Chicago
- ·
- Old Town Triangle
- 0.12 mi to center
5 Bedrooms
2 Baths
12 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $1,248/Night
7 Nights - US $8,735
Condo
9.8Exceptional
(31 Reviews)
3 Bedrooms
2 Baths
10 Guests
2400 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $539/Night
7 Nights - US $3,773
Wheelchair Accessible Holiday Homes in Old Town
Over 12+ Wheelchair Accessible Holiday Homes in or Near Old Town
Apartment
2 Bedrooms
2 Baths
4 Guests
1147 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $223/Night
7 Nights - US $1,561
Hotel
- Chicago
- ·
- Old Town Triangle
- 0.19 mi to center
6.7Good
(520 Reviews)
15 Baths
376.74 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $244/Night
7 Nights - US $1,708
Hotel
- Chicago
- ·
- Old Town Triangle
- 0.18 mi to center
7.8Very Good
(1106 Reviews)
1 Bath
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
US $183/Night
7 Nights - US $1,284
Apartment
1 Bedroom
1 Bath
2 Guests
782 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $213/Night
7 Nights - US $1,492
Apartment
1 Bedroom
1 Bath
2 Guests
663 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $205/Night
7 Nights - US $1,435
Apartment
1 Bedroom
1 Bath
2 Guests
658 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $200/Night
7 Nights - US $1,400
Apartment
1 Bedroom
1 Bath
2 Guests
658 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $156/Night
7 Nights - US $1,092
Apartment
1 Bedroom
1 Bath
2 Guests
425 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $132/Night
7 Nights - US $924
Apartment
1 Bedroom
1 Bath
2 Guests
425 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $117/Night
7 Nights - US $819
Old Town Private Villas and Holiday Homes Under $200
Over 12+ Old Town Private Villas and Holiday Homes Under $200
Condo
- Chicago
- ·
- Old Town Triangle
- 0.19 mi to center
2 Bedrooms
1 Bath
3 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $100/Night
7 Nights - US $700
Apartment
2 Bedrooms
1 Bath
5 Guests
947.22 ft²
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $70/Night
7 Nights - US $490
Condo
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $163/Night
7 Nights - US $1,140
Apartment
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
Laundry
US $162/Night
7 Nights - US $1,136
Apartment
- Chicago
- ·
- Old Town Triangle
- 0.13 mi to center
1 Bedroom
1 Bath
2 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- View
US $120/Night
7 Nights - US $842
Apartment
1 Bedroom
1 Bath
2 Guests
663 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $111/Night
7 Nights - US $777
Apartment
1 Bedroom
1 Bath
2 Guests
663 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $104/Night
7 Nights - US $728
Apartment
1 Bedroom
1 Bath
623 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $99/Night
7 Nights - US $693
House
- Chicago
- ·
- Old Town Triangle
- 0.07 mi to center
2.5Average
(2 Reviews)
1 Bedroom
1 Bath
4 Guests
1000 ft²
- Pet Friendly
- Kitchen
- Air Conditioner
- Internet
US $149/Night
7 Nights - US $1,043
Instantly Bookable Holiday Homes in Old Town
Over 20+ Instantly Bookable Holiday Homes in or Near Old Town
Apartment
5.2Average
(5 Reviews)
2 Bedrooms
1 Bath
5 Guests
950 ft²
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $337/Night
7 Nights - US $2,358
Condo
9.0Exceptional
(18 Reviews)
2 Bedrooms
3 Baths
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $641/Night
7 Nights - US $4,490
Hotel
9.4Exceptional
(35 Reviews)
2 Baths
1200 ft²
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $697/Night
7 Nights - US $4,880
Apartment
10.0Exceptional
(10 Reviews)
2 Bedrooms
1 Bath
8 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
US $1,156/Night
7 Nights - US $8,089
Apartment
- Chicago
- ·
- Old Town Triangle
- 0.12 mi to center
10.0Exceptional
(3 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $604/Night
7 Nights - US $4,225
Condo
- Chicago
- ·
- Old Town Triangle
- 0.18 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $391/Night
7 Nights - US $2,738
House
9.8Exceptional
(17 Reviews)
1 Bedroom
1 Bath
4 Guests
555 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $540/Night
7 Nights - US $3,781
Apartment
9.8Exceptional
(10 Reviews)
3 Bedrooms
1 Bath
5 Guests
1000 ft²
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $231/Night
7 Nights - US $1,614
Apartment
9.6Exceptional
(13 Reviews)
1 Bedroom
1 Bath
4 Guests
800 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
US $292/Night
7 Nights - US $2,045
Book a Last Minute Place to Stay in Old Town
About Casai's Private Villas and Holiday Rentals in Old Town
Discover more than 84 vacation rentals available in Old Town. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Old Town.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Old Town, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Old Town. On average, places to stay near Old Town offer 1036.34 ft², with nightly prices averaging US $545.
With Casai, finding and comparing holiday rentals in Old Town is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
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Top Accommodation Types in Old Town
| Type | Count |
|---|---|
| Holiday Apartments | 38 |
| Vacation Homes | 28 |
Use these Quick Filters to Find a Holiday Rental in Old Town
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Old Town.
Weather in Old Town, IL
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
Other Places to Stay in Old Town, IL
Frequently Asked Questions About Old Town?
What are the top holiday rentals in Old Town?
With numerous options available in Old Town, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Old Town:
- The Sono Chicago
- Luxury House in the heart of Old Town with Parking
- Luxury SOHO Styled Two-Level Townhouse - Old Town
- THE COMPOUND Large Exquisite House Private Yard 'Best Location' Well Appointed
- GROUP LUX in Old Town/Gold Coast (+private roof)
- Ideal Group Getaway: Prime Location, Parking, Backyard, Sunroom & Pet-Friendly
- Walk to Lincoln Park, North Avenue Beach, and Second City! Lovely Old Town Charm! condo
- MTM Fully Furnished Rental in Old Town - 2 beds
- A home away from home!
- Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location
Which holiday homes in Old Town are best for families?
If you're searching for a family-friendly holiday home in Old Town, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Old Town:
- Spacious 2 Bedroom unit with a Free Parking Spot
- Old Town Chicago at it's finest! Pet Friendly & Recently Renovated Top-Floor Condo Has Everything You Need for a Perfect Windy City Getaway condo
- Charming 2-bedroom apartment in fabulous Chicago with AC
How many Casai.nz holiday rentals are available in Old Town?
As of 2026, Casai boasts over 84 properties listed in the Old Town area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Old Town.
Nearby Neighborhood (10)
| Neighborhood | Property Count |
|---|---|
| Downtown Chicago Vacation Rentals in Chicago, Illinois | 1295 |
| Near North Side Vacation Rentals in Chicago, Illinois | 566 |
| River North Vacation Rentals in Chicago, Illinois | 350 |
| Lincoln Park Vacation Rentals in Chicago, Illinois | 133 |
| Rush and Division Vacation Rentals in Chicago, Illinois | 54 |
| Old Town Triangle Vacation Rentals in Chicago, Illinois | 40 |
| Gold Coast Vacation Rentals in Chicago, Illinois | 35 |
| Mid-North District Vacation Rentals in Chicago, Illinois | 24 |
| Sheffield Neighbors Vacation Rentals in Chicago, Illinois | 4082 |
| Ranch Triangle Vacation Rentals in Chicago, Illinois | 4385 |
People Also Ask
Finding the best prices in Old Town
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