Best Vacation Homes in Old Town
10.0
Fireplace/Heating
Pet Friendly
Kitchen
Air Conditioner
10.0- Fireplace/Heating
- Air Conditioner
Internet
Child Friendly
10.0- Fireplace/Heating
Balcony/Terrace
Parking- Air Conditioner
10.0- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
10.0- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
10.0- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
9.4- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
9.0- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
Old Town Luxury Rentals
9.6- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
- Fireplace/Heating
View- Pet Friendly
- Air Conditioner
10.0
Spa- Fireplace/Heating
Ocean View- Balcony/Terrace
10.0
Hot Tub- Fireplace/Heating
- Ocean View
- Balcony/Terrace
10.0- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
9.6- Spa
- Fireplace/Heating
- Balcony/Terrace
- View
8.3- Fireplace/Heating
- Balcony/Terrace
- View
Breakfast
10.0- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
Old Town Pet Friendly Vacation Rentals
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
9.5- Fireplace/Heating
- Balcony/Terrace
- View
- Breakfast
10.0- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
9.0- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
9.8- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
9.4
Oceanfront- Fireplace/Heating
- Ocean View
- Balcony/Terrace
9.2- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
8.4- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
Old Town Large Vacation Homes
10.0- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
9.2- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
9.8- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
8.8- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
10.0- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
9.8- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
9.8- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
Why Choose Rent By Owner for your Old Town Vacation Rental Homes?
What makes our Vacation Rentals special?
Popular Areas for Old Town Vacation Rentals
Where are the best neighborhoods to stay in Old Town?
Old Town in Chicago, Illinois, offers a vibrant and historically rich neighborhood perfect for your stay. When choosing a place to stay in this area, you'll enjoy easy access to the neighborhood’s charming streets, diverse dining options, and local attractions. The neighborhood's central location makes it an ideal base for exploring all that Chicago has to offer, while providing a cozy, neighborhood feel. Booking vacation rentals here ensures a convenient and comfortable experience, with trusted options that blend the charm of Old Town with modern amenities for a memorable visit.
Downtown Chicago
Staying near the heart of the city offers convenient access to the region's vibrant urban scene and iconic skyline. This area is ideal for those seeking a lively atmosphere with easy transportation options, making it a prime choice for your stay.
View 1316+ Rentals in Downtown ChicagoRiver North
Known for its trendy galleries and lively nightlife, this neighborhood is perfect if you want to experience the region’s artistic charm and modern amenities just steps from your accommodation.
View 339+ Rentals in River NorthLincoln Park
Famous for its scenic parks and relaxed vibe, this neighborhood provides a peaceful retreat with plenty of outdoor activities and cultural attractions within reach.
View 140+ Rentals in Lincoln ParkNear North Side
Offering proximity to the city's major attractions and upscale dining options, this area is ideal for travelers looking to explore the region while enjoying high-end accommodations.
View 562+ Rentals in Near North SideGold Coast
Renowned for its historic architecture and luxury shopping, this neighborhood combines sophistication with convenience, making it an excellent base for your stay.
View 37+ Rentals in Gold CoastMid-North District
This area's vibrant community life and eclectic atmosphere provide a charming setting for those seeking an authentic local experience in the region.
View 3956+ Rentals in Mid-North DistrictSheffield Neighbors
A lively neighborhood known for its diverse culture and musical heritage, it's a great choice if you want to immerse yourself in the area's artistic and social scene.
View 4082+ Rentals in Sheffield NeighborsOld Town Triangle
Nestled in the historic core, this neighborhood offers a blend of vintage charm and modern comforts, ideal for travelers wanting a cozy yet accessible location for their stay.
View 45+ Rentals in Old Town TriangleBest Times to Visit Old Town
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit here ensures you can enjoy the vibrant atmosphere and local events, making your stay in this destination truly memorable.
Peak Season Highlights
Summer (June to August)
During the warmest months, you can enjoy lively city events and outdoor activities that showcase the vibrant culture of the area.
Fall (September to November)
This season offers mild weather and beautiful autumn foliage, making it an ideal time for exploring local attractions and enjoying scenic views.
Off-Season Highlights
Winter (December to February)
The colder months bring fewer tourists, offering a quieter experience with opportunities to enjoy indoor cultural venues and holiday festivities.
Spring (March to May)
Early spring can be unpredictable, but it’s a great time to benefit from lower rates while witnessing the city's seasonal rebirth and blooming parks.
Weekly Weather Forecast for Old Town
How to Book Your Old Town Vacation Rental Home
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Old Town
Common Vacation Rentals Amenities
What amenities can you expect?
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- You can enjoy a private outdoor patio or balcony to relax after exploring the city.
- Many properties feature access to nearby parks where you can unwind amidst greenery and open space.
- Expect outdoor dining areas or BBQ grills for memorable meals under the open sky.
- Some rentals offer communal courtyards or shared gardens that foster a sense of community.
- You might find outdoor seating and lounge areas to soak up the local atmosphere.
- Look for accommodations with easy access to sidewalks and scenic streets perfect for strolling.
- Certain properties include outdoor parking spaces, providing convenience during your stay in the area.
Top Attractions Around Old Town
What attractions are nearby?
Within this vibrant neighborhood, you can explore a variety of activities nearby that showcase the best of local culture and entertainment, making your stay in Old Town truly memorable.
Family Activities
- Chicago History Museum: Engage your family with interactive exhibits and engaging storytelling that bring the area's rich history to life in a family-friendly setting.
- The Second City: Enjoy a comedy show suitable for all ages, offering a fun and memorable experience right here in the region’s renowned entertainment district.
- North Avenue Beach: Relax by Lake Michigan on this scenic beach, perfect for swimming, picnicking, and building sandcastles, all within easy reach of the neighborhood's vacation rentals.
Adult Activities
- Architectural Boat Tour: Experience a scenic boat cruise along the Chicago River that highlights the stunning architecture and history of this historic area.
- Wicker Park Shopping and Dining: Explore eclectic boutiques, trendy cafes, and gourmet restaurants that embody the vibrant spirit of the neighborhood.
- Chicago History Museum: Delve into the rich past of the city through engaging exhibits and interactive displays just a short distance from your accommodation.
- Nightlife and Entertainment: Enjoy live music venues, cocktail bars, or theater performances that showcase the lively entertainment scene within the district.
Other Places to Stay in Old Town, IL
Old Town Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Dining and Shops: Take advantage of the area's vibrant culinary scene and boutique stores to experience authentic flavors and unique souvenirs during your stay.
- Plan Your Transportation: Use public transit options or walk to easily navigate between popular attractions and enjoy the charming streets of this historic neighborhood.
- Visit Top Cultural Spots: Dedicate time to discover the region’s cultural landmarks, museums, and theaters that showcase its rich history and artistic heritage.
- Choose a Prime Location for Your Vacation Rental: Select a vacation rental in a central part of here to maximize convenience and immerse yourself fully in the local atmosphere.
Transportation Options
- Chicago Transit Authority (CTA) buses and trains: You can conveniently navigate this area using the extensive CTA network, which offers reliable transportation options for exploring Chicago and nearby neighborhoods.
- Divvy bike-sharing system: Explore the region at your own pace on a Divvy bike, with numerous stations available right here to provide an eco-friendly and flexible way to get around.
- Taxis and ride-sharing services: Taxis and popular ride-sharing apps like Uber and Lyft are readily accessible, offering a quick and comfortable way to reach local attractions and destinations within the city.
- Walking: Given the compact layout of this neighborhood, walking is often the most enjoyable method to experience the charm and ambiance of the area firsthand.
Local Customs Options
- Respect for Local Artisans and Crafts: You’ll find that supporting local artisans and their crafts is a cherished custom here, reflecting a deep appreciation for regional culture in this vibrant neighborhood.
- Greetings and Personal Interactions: Greeting neighbors and shopkeepers with a friendly smile or a simple "hello" is customary, fostering a welcoming atmosphere in the area.
- Cultural Festivals and Parades: Participating in or observing neighborhood festivals and parades showcases the community's pride and rich traditions that you can experience during your stay.
- Preservation of Historic Architecture: Respecting the historic buildings and adhering to local guidelines when exploring or staying in old town areas demonstrates appreciation for the region’s architectural heritage.
Frequently Asked Questions About Old Town?
1. What are the top vacation rentals in Old Town?
There are a lot of options in Old Town. If you plan on staying in the Old Town area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Old Town:
- The Sono Chicago
- Large 4BR/3BA Safe Old Town Location Walk Everywhere
- 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
- Archways at the Lincoln Park Zoo 2bed/2ba
- Family Friendly 2 Bedroom Full Kitchen Free Laundry Work Space
- Chicago’s BEST location… Lincoln Park, Lake Michigan, Wrigley Field, and more!
2. Which vacation homes in Old Town are best for families?
If you are looking for a family-friendly vacation home in Old Town, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Old Town:
3. How many Rentbyowner vacation rentals are available in Old Town?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 88 in the Old Town area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Old Town.
