Discover Your Perfect Washington Square Vacation Homes

Best Vacation Homes in Washington Square

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10.0 (479 Reviews)
Bed & Breakfast
The Sono Chicago
  • Air Conditioner
  • Parking
  • TV
View Availability
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9.8 (370 Reviews)
Bed & Breakfast
Ray's Bucktown B&B
  • Air Conditioner
  • Parking
  • Balcony/Terrace
View Availability
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9.8 (186 Reviews)
Bed & Breakfast
The Publishing House B&B
  • Air Conditioner
  • TV
  • Wheelchair Accessible
View Availability

Why Choose Rent By Owner for your Washington Square 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 Washington Square Vacation Rentals

Where are the best neighborhoods to stay in Washington Square?

Staying in the vibrant neighborhoods surrounding Washington Square in Chicago offers you a unique blend of local charm and urban excitement. Located in the heart of the city, these areas provide convenient access to cultural attractions, diverse dining options, and lively community events. Whether you're seeking a bustling atmosphere or a more relaxed setting, choosing a vacation rental nearby ensures you'll experience the true essence of this dynamic part of Chicago. With trusted and reliable accommodations available, your stay in Washington Square promises both comfort and an authentic neighborhood experience.

Downtown Chicago

In the heart of the city, downtown offers convenient access to the region's vibrant attractions, making it an ideal choice for those seeking to explore Chicago from a central location.

View 2287+ Rentals in Downtown Chicago

Magnificent Mile

Known for its shopping and entertainment options, this area provides a lively backdrop for your stay, perfectly suited for travelers wanting to experience the city's upscale scene.

View 4128+ Rentals in Magnificent Mile

The Loop

As the city's cultural and business hub, The Loop is perfect if you want to be immersed in Chicago’s iconic architecture and vibrant urban energy.

View 1324+ Rentals in The Loop

River North

This neighborhood boasts a thriving arts scene and bustling nightlife, making it an exciting base for visitors eager to enjoy Chicago’s creative spirit.

View 384+ Rentals in River North

Hyde Park

Famous for its academic institutions and cultural landmarks, Hyde Park offers a more relaxed environment, ideal for travelers interested in exploring the intellectual side of the city.

View 110+ Rentals in Hyde Park

Lincoln Park

With its lush parks and scenic lakefront, Lincoln Park provides a peaceful retreat within the city, perfect for those wanting a blend of outdoor activities and local charm.

View 186+ Rentals in Lincoln Park

O'Hare

Proximity to one of the busiest airports makes this area a strategic choice for travelers needing quick access to flights while still experiencing the region’s vibrant atmosphere.

View 76+ Rentals in O'Hare

Lakeview

Known for its lively neighborhoods and diverse entertainment options, Lakeview is well-suited for visitors looking to enjoy both urban excitement and a friendly, community vibe.

View 318+ Rentals in Lakeview

Best Times to Visit Washington Square

When should you plan your Vacation Rentals stay?

Choosing the optimal time to visit here can enhance your experience and ensure you enjoy the best available vacation rentals in this vibrant region.

Peak Season Highlights

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Summer (June to August)

During this period, the area experiences warm and lively days, making it ideal for enjoying outdoor activities and events. You can expect higher demand for vacation rentals as visitors flock here to enjoy the vibrant summer atmosphere.

Average Temperature Daytime: Approximately 80°F to 88°F - Nighttime: Around 65°F to 70°F
autumn
Fall (September to November)

Early fall brings mild weather and colorful foliage, attracting many looking to experience the region's natural beauty. Vacation rentals tend to fill quickly as visitors seek comfortable stays during this scenic season.

Average Temperature Daytime: Ranging from 70°F to 78°F - Nighttime: Between 55°F and 60°F

Off-Season Highlights

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Winter (December to February)

The winter months see a slowdown in bookings with cooler temperatures, offering a quieter experience for travelers seeking peaceful stays in cozy accommodations within this destination.

Average Temperature Daytime: Typically 30°F to 40°F - Nighttime: Around 20°F to 28°F
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Spring (March to May)

Late spring brings gradually rising temperatures and fewer tourists, providing an excellent opportunity to explore comfortably while enjoying lower rates on vacation rentals.

Average Temperature Daytime: From 55°F to 68°F - Nighttime: Between 40°F and 50°F

Weekly Weather Forecast for Washington Square

How to Book Your Washington Square 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 Washington Square

More Top-Rated Vacation Rentals in Washington Square 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

  • Enjoy access to landscaped outdoor spaces where you can unwind and relax amidst the city’s vibrant atmosphere.
  • Many properties offer private balconies or patios, perfect for enjoying morning coffee or evening sunsets.
  • Take advantage of communal courtyards designed for socializing or quiet reflection during your stay.
  • Look for accommodations with outdoor grilling areas or picnic spots to enhance your outdoor dining experience.
  • Some rentals feature scenic views of the surrounding neighborhood, providing a picturesque backdrop for your visit.
  • Outdoor seating arrangements are common, giving you a comfortable spot to read or simply enjoy the fresh air.
  • Access to nearby parks or green spaces is often included, offering opportunities for outdoor recreation in the area.

Top Attractions Around Washington Square

What attractions are nearby?

Here, you can enjoy a variety of nearby activities that showcase the vibrant culture and local charm of the region, making your stay in Washington Square, Chicago, Illinois, USA, truly memorable.

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Family Activities

  • Washington Square Park: Enjoy a family picnic or playtime at this iconic park known for its scenic beauty and open green spaces.
  • Chicago History Museum: Discover the rich history of the region through engaging exhibits that captivate visitors of all ages.
  • The Art Institute of Chicago: Immerse your family in world-class art collections and interactive programs suitable for young explorers.
  • Millennium Park: Experience outdoor concerts, captivating public art installations, and family-friendly activities just nearby here.
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Adult Activities

  • Visit the Chicago History Museum: Dive into the region’s rich heritage through engaging exhibits showcasing the area’s evolution over time.
  • Explore the Lincoln Park Zoo: Enjoy a leisurely day observing a variety of animals at one of the oldest free zoos in the country, right here in the region.
  • Experience a performance at the Harris Theater: Attend a concert or theatrical show in this modern venue known for its diverse cultural programming in the city center.
  • Stroll through Millennium Park: Admire iconic public art installations and serene green spaces while soaking up the vibrant atmosphere of this famous urban park.

Washington Square Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Dining Options: Take advantage of the area's diverse culinary scene to enjoy authentic regional flavors close to your vacation rental.
  • Plan Your Transit Routes: Familiarize yourself with local transportation options to easily navigate between attractions and maximize your stay here.
  • Visit Nearby Parks and Green Spaces: Spend quality time outdoors at parks in the area to relax and experience the natural beauty surrounding your accommodation.
  • Discover Unique Neighborhoods: Immerse yourself in the local culture by exploring neighboring districts, offering a richer experience during your visit.

Transportation Options

  • Chicago Transit Authority (CTA) Rail System: You can conveniently access the city's attractions via the extensive CTA train network, which connects to this neighborhood and beyond.
  • Bus Services: Multiple bus routes serve the area, providing affordable and reliable transportation options for exploring Chicago and nearby neighborhoods.
  • Metra Commuter Rail: The Metra lines offer quick and efficient travel to downtown Chicago and other regional destinations, ideal for day trips from your vacation rental.
  • Rideshare Services: Popular rideshare options are readily available here, offering flexible and direct travel within the city and surrounding areas at your convenience.

Local Customs Options

  • Respect for Local Art and Culture: You’ll find that appreciating the vibrant arts scene here is key to understanding this destination’s unique identity.
  • Celebration of Community Events: Participating in neighborhood festivals and local gatherings offers a genuine way to connect with residents of this area.
  • Politeness in Interactions: Courteous communication is highly valued, reflecting the friendly spirit of this region’s community.
  • Adherence to Dining Customs: Embracing local dining etiquette, such as shared meals and casual conversations, enhances your experience here.

Frequently Asked Questions About Washington Square?

1. What are the top vacation rentals in Washington Square?

There are a lot of options in Washington Square. If you plan on staying in the Washington Square area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Washington Square:

2. How many Rentbyowner vacation rentals are available in Washington Square?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 3865 in the Washington Square 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 Washington Square. 

3. What is the cancellation policy for vacation rentals in this area?

Cancellation policies vary by property; you should review the specific listing details or contact the owner directly to understand the terms and any associated fees.

4. Are there any additional fees I should be aware of when booking a rental here?

Additional fees such as cleaning, service charges, or security deposits are listed with each property. Be sure to review these details on the listing or inquire with the host for clarification.

5. How do I know if my chosen vacation rental is available for my travel dates?

Availability is updated regularly on the listing page. If your dates are flexible, contacting the property owner can help confirm availability or suggest alternative options.

6. What amenities are typically included in vacation rentals in this neighborhood?

Most rentals offer essential amenities like Wi-Fi, kitchen essentials, and linens. Specific amenities are detailed on each listing, so reviewing the property description will provide a complete list.

7. Is it possible to communicate directly with the property host before booking?

Yes, you can reach out to the host through the messaging platform to ask questions about the property, clarify details, or request additional information before finalizing your booking.

Best Vacation Homes in Washington Square