Discover Your Perfect Old Town Vacation Homes

Best Vacation Homes in Old Town

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10.0 (1 Review)
Apartment
MTM Fully Furnished Rental in Old Town - 2 beds
  • Air Conditioner
  • Security/Safety
  • Fireplace/Heating
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10.0 (465 Reviews)
Bed & Breakfast
The Sono Chicago
  • Air Conditioner
  • Parking
  • TV
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Old Town Luxury Rentals

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Old Town Pet Friendly Vacation Rentals

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Old Town Large Vacation Homes

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Why Choose Rent By Owner for your Old Town Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

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 1791+ Rentals in Downtown Chicago

River 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 484+ Rentals in River North

Lincoln 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 143+ Rentals in Lincoln Park

Near 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 818+ Rentals in Near North Side

Gold Coast

Renowned for its historic architecture and luxury shopping, this neighborhood combines sophistication with convenience, making it an excellent base for your stay.

View 39+ Rentals in Gold Coast

Mid-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 2085+ Rentals in Mid-North District

Sheffield 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 3947+ Rentals in Sheffield Neighbors

Old 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 53+ Rentals in Old Town Triangle

Best 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

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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.

Average Temperature Daytime: 78°F to 85°F - Nighttime: 60°F to 70°F
autumn
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.

Average Temperature Daytime: 65°F to 75°F - Nighttime: 50°F to 60°F

Off-Season Highlights

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Winter (December to February)

The colder months bring fewer tourists, offering a quieter experience with opportunities to enjoy indoor cultural venues and holiday festivities.

Average Temperature Daytime: 30°F to 40°F - Nighttime: 20°F to 30°F
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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.

Average Temperature Daytime: 50°F to 60°F - Nighttime: 35°F to 45°F

Weekly Weather Forecast for Old Town

How to Book Your Old Town Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Old Town

More Top-Rated Vacation Rentals in Old Town Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

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.

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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.
  • : Visit one of the oldest zoos in the country, featuring free admission and a variety of animals that will delight children and adults alike.
  • 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.
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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

House of Glunz
House of Glunz Vacation Rentals
Second City
Second City Vacation Rentals
Old Town Triangle
Old Town Triangle Vacation Rentals
More Places to Stay Near Old Town

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:

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 2025 is over 74 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. 

4. What is the cancellation policy for vacation rentals in Old Town, Chicago?

Cancellation policies vary by listing, so it's essential to review the specific terms outlined on the booking page or contact the property owner directly to understand the details before finalizing your reservation.

5. How do I know if my chosen vacation rental in Old Town, Chicago, is available for my travel dates?

Availability can be confirmed through the listing calendar or by reaching out to the property owner, ensuring your preferred dates are open before completing your booking.

6. Are there any specific check-in or check-out procedures I should be aware of for properties here?

Check-in and check-out instructions are provided in the listing details or communicated directly from the host; reviewing these in advance will help ensure a smooth arrival and departure.

7. What amenities are typically included with vacation rentals in this part of Chicago?

Most listings include essentials such as Wi-Fi, kitchen facilities, and linens, but it’s best to verify the available amenities in each property’s description or by contacting the owner.

8. Is it possible to request special accommodations or add extra guests when booking a stay in this destination?

Special requests and additional guest accommodations can often be arranged by contacting the property owner prior to booking, but approval depends on the individual listing’s policies.