Old Town Vacation Rentals & Ski-in/Ski-out Homes
Condo
- Chicago
- ·
- Old Town Triangle
- 0.18 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
Kitchen
Air Conditioner
Internet
Laundry
US $306/Night
7 Nights - US $2,144
Apartment
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
5 Guests
947.22 ft²
- Air Conditioner
- Internet
Child Friendly
Security/Safety
US $90/Night
7 Nights - US $630
Bed & Breakfast
10.0Exceptional
(530 Reviews)
1 Bedroom
1 Bath
Parking
Balcony/Terrace- Air Conditioner
- Internet
US $262/Night
7 Nights - US $1,833
Apartment
- Chicago
- ·
- Old Town Triangle
- 0.14 mi to center
9.8Exceptional
(8 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Kitchen
- Air Conditioner
- Internet
Pet Friendly
US $365/Night
7 Nights - US $2,552
Apartment
- Chicago
- ·
- Old Town Triangle
- 0.17 mi to center
9.6Exceptional
(6 Reviews)
1 Bedroom
1 Bath
2 Guests
495.14 ft²
Breakfast- Parking
- Air Conditioner
- Internet
US $285/Night
7 Nights - US $1,995
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
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $203/Night
7 Nights - US $1,418
Condo
- Chicago
- ·
- Old Town Triangle
- 0.13 mi to center
9.0Exceptional
(25 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $311/Night
7 Nights - US $2,179
Apartment
8.6Fabulous
(10 Reviews)
2 Bedrooms
1 Bath
5 Guests
950 ft²
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $195/Night
7 Nights - US $1,364
House
8.4Excellent
(43 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $277/Night
7 Nights - US $1,941
Luxury Places to Stay in Old Town
Over 80+ Luxury Places to Stay in or Near Old Town
House
- Chicago
- ·
- Old Town Triangle
- 0.12 mi to center
4 Bedrooms
2 Baths
12 Guests
10763.91 ft²
- Parking
View- Air Conditioner
- Internet
US $2,066/Night
7 Nights - US $14,462
House
10.0Exceptional
(60 Reviews)
5 Bedrooms
7 Baths
12 Guests
6200 ft²
- Parking
Spa
Ocean View- Balcony/Terrace
US $2,010/Night
7 Nights - US $14,073
House
- Chicago
- ·
- Old Town Triangle
- 0.12 mi to center
5 Bedrooms
2 Baths
12 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $1,445/Night
7 Nights - US $10,114
House
10.0Exceptional
(15 Reviews)
6 Bedrooms
6 Baths
32 Guests
4000 ft²
Hot Tub- Parking
- Ocean View
- Balcony/Terrace
US $1,355/Night
7 Nights - US $9,488
House
9.6Exceptional
(5 Reviews)
4 Bedrooms
4 Baths
18 Guests
3003.13 ft²
- Breakfast
- Parking
- Spa
- Balcony/Terrace
US $1,199/Night
7 Nights - US $8,393
House
8.3Excellent
(3 Reviews)
5 Bedrooms
4 Baths
22 Guests
3003.13 ft²
- Breakfast
- Parking
- Balcony/Terrace
- View
US $1,191/Night
7 Nights - US $8,335
House
- Chicago
- ·
- Old Town Triangle
- 0.22 mi to center
9.8Exceptional
(28 Reviews)
4 Bedrooms
3 Baths
12 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,100/Night
7 Nights - US $7,698
Apartment
8 Bedrooms
4 Baths
16 Guests
- Parking
- Air Conditioner
- Internet
- Pet Friendly
US $1,002/Night
7 Nights - US $7,015
Apartment
10.0Exceptional
(10 Reviews)
4 Bedrooms
3 Baths
12 Guests
3000 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $948/Night
7 Nights - US $6,636
Pet-Friendly Vacation Rentals in Old Town
Over 34+ Pet-Friendly Vacation Rentals in or Near Old Town
House
10.0Exceptional
(22 Reviews)
3 Bedrooms
3 Baths
14 Guests
2400 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $642/Night
7 Nights - US $4,496
House
9.5Exceptional
(30 Reviews)
4 Bedrooms
3 Baths
14 Guests
1496.18 ft²
- Breakfast
- Parking
- Balcony/Terrace
- View
US $852/Night
7 Nights - US $5,966
House
10.0Exceptional
(6 Reviews)
3 Bedrooms
2 Baths
14 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $633/Night
7 Nights - US $4,432
House
- Chicago
- ·
- Old Town Triangle
- 0.13 mi to center
4.0Average
(2 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Parking
- Air Conditioner
- Internet
- Pet Friendly
US $878/Night
7 Nights - US $6,148
House
9.8Exceptional
(115 Reviews)
4 Bedrooms
4 Baths
18 Guests
2992 ft²
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $699/Night
7 Nights - US $4,890
Condo
9.6Exceptional
(5 Reviews)
8 Bedrooms
4 Baths
16 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $877/Night
7 Nights - US $6,139
House
9.4Exceptional
(120 Reviews)
5 Bedrooms
3 Baths
22 Guests
3000 ft²
Oceanfront- Parking
- Ocean View
- Balcony/Terrace
US $742/Night
7 Nights - US $5,195
House
9.2Exceptional
(77 Reviews)
4 Bedrooms
2 Baths
14 Guests
1500 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $452/Night
7 Nights - US $3,161
House
- Chicago
- ·
- Old Town Triangle
- 0.13 mi to center
8.6Fabulous
(22 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $405/Night
7 Nights - US $2,832
Large Vacation Homes & Villas in Old Town
Over 10+ Large Vacation Homes & Villas in or Near Old Town
Apartment
10.0Exceptional
(76 Reviews)
4 Bedrooms
3 Baths
15 Guests
2500 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $1,604/Night
7 Nights - US $11,225
House
9.5Exceptional
(15 Reviews)
1 Bedroom
2 Baths
14 Guests
1194.79 ft²
- Air Conditioner
- Internet
- Child Friendly
- Security/Safety
US $705/Night
7 Nights - US $4,933
Apartment
10.0Exceptional
(40 Reviews)
4 Bedrooms
2 Baths
13 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $1,011/Night
7 Nights - US $7,077
Bed & Breakfast
9.3Exceptional
(349 Reviews)
11 Bedrooms
10 Baths
29 Guests
319.33 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $253/Night
7 Nights - US $1,768
Apartment
9.8Exceptional
(15 Reviews)
4 Bedrooms
1 Bath
12 Guests
21528 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $714/Night
7 Nights - US $4,997
House
- Chicago
- ·
- Old Town Triangle
- 0.12 mi to center
5 Bedrooms
2 Baths
12 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $1,248/Night
7 Nights - US $8,735
Condo
9.8Exceptional
(31 Reviews)
3 Bedrooms
2 Baths
10 Guests
2400 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $539/Night
7 Nights - US $3,773
House
- Chicago
- ·
- Old Town Triangle
- 0.10 mi to center
4.8Average
(5 Reviews)
4 Bedrooms
3 Baths
10 Guests
- Air Conditioner
- Child Friendly
- Laundry
Bedding/Linens
US $814/Night
7 Nights - US $5,698
House
12 Bedrooms
6 Baths
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $1,359/Night
7 Nights - US $9,513
Wheelchair Accessible Vacation Homes in Old Town
Over 12+ Wheelchair Accessible Vacation Homes in or Near Old Town
Apartment
2 Bedrooms
2 Baths
4 Guests
1147 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
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
- Parking
- Kitchen
- Air Conditioner
- Internet
US $219/Night
7 Nights - US $1,533
Hotel
- Chicago
- ·
- Old Town Triangle
- 0.18 mi to center
7.8Very Good
(1150 Reviews)
1 Bath
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $223/Night
7 Nights - US $1,564
Apartment
1 Bedroom
1 Bath
2 Guests
782 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $213/Night
7 Nights - US $1,492
Apartment
1 Bedroom
1 Bath
2 Guests
663 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $205/Night
7 Nights - US $1,435
Apartment
1 Bedroom
1 Bath
2 Guests
658 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $200/Night
7 Nights - US $1,400
Apartment
1 Bedroom
1 Bath
2 Guests
658 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $156/Night
7 Nights - US $1,092
Apartment
1 Bedroom
1 Bath
2 Guests
425 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $132/Night
7 Nights - US $924
Apartment
1 Bedroom
1 Bath
2 Guests
425 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $117/Night
7 Nights - US $819
Old Town Resorts and Airbnb Homes Under $200
Over 13+ Old Town Resorts and Airbnb Homes Under $200
Condo
- Chicago
- ·
- Old Town Triangle
- 0.19 mi to center
2 Bedrooms
1 Bath
3 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $108/Night
7 Nights - US $753
Apartment
2 Bedrooms
1 Bath
5 Guests
947.22 ft²
- Air Conditioner
- Internet
- Child Friendly
- Security/Safety
US $70/Night
7 Nights - US $490
Condo
1 Bedroom
1 Bath
2 Guests
- Air Conditioner
- Internet
- Child Friendly
- Laundry
US $163/Night
7 Nights - US $1,140
Apartment
1 Bedroom
1 Bath
2 Guests
- Air Conditioner
- Internet
- Laundry
- Bedding/Linens
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
- Parking
- Ocean View
- View
US $120/Night
7 Nights - US $842
Apartment
1 Bedroom
1 Bath
2 Guests
663 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $111/Night
7 Nights - US $777
Apartment
1 Bedroom
1 Bath
2 Guests
663 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $104/Night
7 Nights - US $728
Apartment
1 Bedroom
1 Bath
623 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $99/Night
7 Nights - US $693
Apartment
1 Bedroom
1 Bath
2 Guests
678 ft²
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $112/Night
7 Nights - US $784
Instantly Bookable Vacation Homes in Old Town
Over 22+ Instantly Bookable Vacation Homes in or Near Old Town
Apartment
- Chicago
- ·
- Old Town Triangle
- 0.15 mi to center
8.0Excellent
(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $394/Night
7 Nights - US $2,757
Apartment
6.0Good
(6 Reviews)
2 Bedrooms
1 Bath
5 Guests
950 ft²
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $220/Night
7 Nights - US $1,541
New
Apartment
- Chicago
- ·
- Old Town Triangle
- 0.13 mi to center
2 Bedrooms
1 Bath
5 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $775/Night
7 Nights - US $5,423
New
Apartment
2 Bedrooms
1 Bath
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $483/Night
7 Nights - US $3,382
Condo
9.0Exceptional
(18 Reviews)
3 Bedrooms
3 Baths
8 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $576/Night
7 Nights - US $4,031
Hotel
9.0Exceptional
(41 Reviews)
2 Baths
1200 ft²
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $276/Night
7 Nights - US $1,931
New
Condo
2 Bedrooms
2 Baths
6 Guests
- Air Conditioner
- Internet
- Child Friendly
- Laundry
US $574/Night
7 Nights - US $4,021
Apartment
10.0Exceptional
(10 Reviews)
2 Bedrooms
1 Bath
8 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
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
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $604/Night
7 Nights - US $4,225
Book a Last Minute Place to Stay in Old Town
About Old Town Vacation Rentals
Explore over 89 vacation rentals in Old Town with SunSki Resorts. These accommodations, comprising vacation homes, cottages, cabins, and condos, boast excellent amenities at great value, ensuring comfort and luxury. Enhance your stay with SunSki Resorts in Old Town for more space and value.
In search of last-minute deals or the best bargains on vacation rentals? With SunSki Resorts, you can conveniently compare various options and deals in Old Town. Discover rentals with desirable amenities like swimming pools, hot tubs, and pet-friendly options. Find the ideal vacation rental in Old Town tailored to your preferences. On average, these rentals offer 1098.98 ft² of space, and are priced at an average of US $529 per night.
SunSki Resorts simplifies and secures the process of finding and comparing vacation rentals in Old Town at prices typically 30-40% lower than hotels. Discover your perfect vacation rental and book now.
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Top Types of Ski Accommodations in Old Town
| Type | Count |
|---|---|
| Holiday Apartments | 40 |
| Vacation Homes | 30 |
| B&B | 2 |
Use these Quick Filters to Find a Vacation Rental in Old Town
★ Pro Tip: Discover Your Ideal Vacation Rental in Old Town with SunSki Resorts™. Compare a diverse array of properties, including RBO homes, vacation rentals, cottages, cabins, and more. Utilize our advanced filters to search by location, amenities, and price. Book with confidence and enjoy savings of up to 40-60% compared to a hotel stay. Create unforgettable memories with SunSki Resorts™.
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 vacation rentals in Old Town?
When organizing your trip to Old Town, don't miss the chance to explore the top-rated vacation rentals in the vicinity. With a plethora of options available, you're bound to discover the ideal accommodation for your stay in Old Town. Peruse our collection of highly-rated properties and secure your reservation today.
- 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
- Chicago’s BEST location… Lincoln Park, Lake Michigan, Wrigley Field, and more!
- 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 vacation homes or resorts in Old Town are best for families?
Choose SunSki for a wide variety of vacation rentals, including family-friendly homes, ski cabins, cottages, and more in Old Town. Enjoy great views, locations and save money with SunSki Resorts.™
- Stunning Fully Furnished 3BR/3BA Mid-Century Modern Duplex in Historic Old Town
- 3 br Spacious Home in Ideal Location w Free Parking Back Yard Pets Welcome
- A home away from home!
How many SunSkiResorts vacation rentals or resorts are available in Old Town?
Discover the ideal vacation rental in Old Town with SunSki Resorts™. We provide an extensive selection of over 89 properties, encompassing vacation homes, private villas, cottages, and more. Explore our listings to find the perfect place to stay for your upcoming trip to Old Town.
Nearby Neighborhood (10)
| Neighborhood | Property Count |
|---|---|
| Downtown Chicago Vacation Rentals in Chicago, Illinois | 1365 |
| Near North Side Vacation Rentals in Chicago, Illinois | 563 |
| River North Vacation Rentals in Chicago, Illinois | 332 |
| Lincoln Park Vacation Rentals in Chicago, Illinois | 130 |
| Rush and Division Vacation Rentals in Chicago, Illinois | 66 |
| Old Town Triangle Vacation Rentals in Chicago, Illinois | 45 |
| Gold Coast Vacation Rentals in Chicago, Illinois | 33 |
| Mid-North District Vacation Rentals in Chicago, Illinois | 24 |
| Sheffield Neighbors Vacation Rentals in Chicago, Illinois | 4153 |
| Ranch Triangle Vacation Rentals in Chicago, Illinois | 4436 |
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