Discover Your Perfect Chatham Vacation Homes

Chatham Luxury Rentals

New
Apartment
Luxury off the Lake
  • Air Conditioner
  • Pet Friendly
  • Bedding/Linens
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Chatham Pet Friendly Vacation Rentals

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8.4 (8 Reviews)
Apartment
Charming 3BD 2BTH Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
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Why Choose Rent By Owner for your Chatham 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 Chatham Vacation Rentals

Where are the best neighborhoods to stay in Chatham?

When seeking the perfect neighborhood to stay in Chatham, Chicago, Illinois, you’ll find a vibrant community that offers both comfort and convenience. The area’s diverse atmosphere provides a welcoming environment for travelers looking to explore the city while enjoying a relaxing retreat. Whether you prefer a quiet residential setting or a lively local scene, Chatham's neighborhoods are ideal for discovering authentic Chicago experiences. Booking your vacation rental here ensures easy access to local amenities and a genuine connection to the heart of the city, making your visit memorable and hassle-free.

Greater Grand Crossing

This vibrant neighborhood provides a unique blend of local culture and accessible amenities, making it an ideal choice for your stay. Here, you'll find comfortable vacation rentals close to key community spots, offering an authentic Chicago experience.

View 471+ Rentals in Greater Grand Crossing

Princeton Park

Nestled within the region, this area offers a peaceful setting with convenient access to the city's attractions. Your stay in Princeton Park guarantees a relaxing environment combined with easy travel to the heart of Chicago.

View 112+ Rentals in Princeton Park

Best Times to Visit Chatham

When should you plan your Vacation Rentals stay?

Timing your visit to this destination can significantly enhance your experience, so consider the seasonal patterns and local climate when choosing the best time to book your vacation rentals in the area.

Peak Season Highlights

summer
Summer (June to August)

During the warm summer months, you'll enjoy the lively atmosphere and pleasant weather in this part of Chicago, making it an ideal time for outdoor activities.

Average Temperature Daytime: 85°F - Nighttime: 65°F
autumn
Fall (September to November)

Experience the stunning fall foliage and cooler temperatures, which create a cozy environment perfect for exploring local surroundings.

Average Temperature Daytime: 70°F - Nighttime: 50°F

Off-Season Highlights

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Winter (December to February)

The winter season offers a quieter experience with colder temperatures, ideal if you prefer less crowded accommodations and a peaceful retreat.

Average Temperature Daytime: 35°F - Nighttime: 20°F
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Spring (March to May)

As the region awakens from winter, the mild spring weather provides a refreshing setting for those seeking a more relaxed visit before the busy summer season.

Average Temperature Daytime: 60°F - Nighttime: 40°F

Weekly Weather Forecast for Chatham

How to Book Your Chatham 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 Chatham

More Top-Rated Vacation Rentals in Chatham 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 a private outdoor space with a patio or deck for relaxing and entertaining during your stay.
  • Take advantage of well-maintained gardens or landscaped yards that add charm to your outdoor experience.
  • Make the most of outdoor dining areas equipped with tables and seating, perfect for meals al fresco.
  • Benefit from access to a backyard fire pit for cozy evenings with friends or family.
  • Explore nearby outdoor recreational facilities, such as parks and walking trails, easily accessible from your rental.
  • Spend time in a spacious yard suitable for outdoor activities or children's play.
  • Look for properties with parking spaces designed for outdoor use, ensuring convenience during your visit.

Top Attractions Around Chatham

What attractions are nearby?

Explore the vibrant neighborhood with nearby parks, cultural attractions, and dining options that offer an authentic Chicago experience, all within easy reach from your vacation rental in this welcoming part of the city.

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Family Activities

  • Pullman National Monument: Discover the history of the area through this historic site, offering educational tours that are perfect for exploring with family.
  • Lake Michigan Beaches: Enjoy a day of sun and sand along the nearby shores, ideal for building sandcastles and relaxing by the water.
  • The Illinois Science Council’s Museum: Engage your family with interactive exhibits designed to inspire curiosity and learning about science and technology.
  • Chicago Sculpture Park: Stroll through this outdoor gallery where your family can admire contemporary sculptures while enjoying the fresh air in the region.
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Adult Activities

  • Visit the Chatham Business District: Explore local shops and eateries that showcase the vibrant community spirit unique to this part of Chicago.
  • Enjoy outdoor activities at Cottage Grove Park: Relax or take part in recreational pursuits amidst the greenery and open spaces ideal for unwinding here.
  • Discover cultural events at nearby community centers: Engage with neighborhood programs and performances that highlight the area's rich local culture.
  • Experience local cuisine at neighborhood restaurants: Savor authentic flavors and diverse menus that reflect the culinary diversity of this region.

Other Places to Stay in Chatham, IL

Chatham Fields
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Dauphin Park
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Garden Homes
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Chatham Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Cuisine: Savor the authentic flavors and diverse dining options available nearby to immerse yourself in the regional culinary scene.
  • Visit Community Events: Check out local events or festivals to experience the vibrant culture and connect with residents during your stay.
  • Plan Convenient Transportation: Utilize nearby public transportation or consider renting a vehicle to explore the area's attractions with ease.
  • Choose Central Locations: Select vacation rentals that are centrally located to maximize your access to popular spots and activities here.

Transportation Options

  • Chicago Transit Authority (CTA) Bus and 'L' Train: You can efficiently navigate the area with the extensive CTA public transportation network, providing convenient access to key attractions and neighborhoods.
  • Metra Commuter Rail: The Metra offers commuter rail services connecting here to downtown Chicago and beyond, ideal for those seeking a reliable, regional transit option.
  • Rideshare Services: Companies like Uber and Lyft operate frequently in this part of Chicago, offering a flexible and comfortable way to travel within the region.
  • Rental Cars: Numerous car rental agencies are available nearby, giving you the freedom to explore this destination and its surrounding areas at your own pace.

Local Customs Options

  • Respect for Community Gatherings: In this neighborhood, participating in local events and respecting community gatherings are highly valued and reflect the area's close-knit spirit.
  • Traditional Dining Etiquette: When dining at regional eateries, it's customary to greet servers warmly and appreciate homemade dishes, showcasing your respect for local customs.
  • Celebration of Cultural Events: Engaging in and observing annual cultural celebrations demonstrates appreciation for the area's rich heritage and diversity.
  • Respect for Local Heritage: Visitors are encouraged to honor local history by adhering to guidelines when visiting historical sites or landmarks in this region.

Frequently Asked Questions About Chatham?

1. What are the top vacation rentals in Chatham?

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

2. Which vacation homes in Chatham are best for families?

If you are looking for a family-friendly vacation home in Chatham, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Chatham:

3. How many Rentbyowner vacation rentals are available in Chatham?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 256 in the Chatham 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 Chatham. 

4. What is the cancellation policy for booking a vacation rental in this area?

The cancellation policy varies by property. Please review the specific listing details and contact the host directly to understand the terms and any applicable fees.

5. How do I find available dates and secure my reservation in Chicago's neighborhood?

You can check availability and make your booking through the listing page. Be sure to confirm your dates quickly, as availability may change, especially during peak seasons.

6. Are there any additional fees I should be aware of when booking vacation rentals here?

Additional fees such as cleaning, service charges, or security deposits are often outlined on the listing page. Review these details carefully before confirming your reservation to ensure transparency.

7. What amenities can I expect from a vacation rental in this part of Chicago?

Listings typically specify the amenities available, including Wi-Fi, parking, kitchens, and laundry facilities. Check the property description for a comprehensive list tailored to each rental.

8. Is there a minimum stay requirement for booking a vacation rental nearby?

Minimum stay policies differ depending on the property. Details are provided on each listing, so reviewing these before booking will help you plan your trip accordingly.