Discover Your Perfect New Chicago Vacation Homes

New Chicago Pet Friendly Vacation Rentals

5.0 (2 Reviews)
Cottage
Spacious 3BR House With Firepit & Grill, Near Beach
  • Pet Friendly
  • Security/Safety
  • Barbecue/Outdoor Cooking
View Availability
See More Pet-Friendly Vacation Rentals in New Chicago on PetFriendly.io

Why Choose Rent By Owner for your New Chicago 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.

Best Times to Visit New Chicago

When should you plan your Vacation Rentals stay?

Choosing the optimal time to visit here ensures you enjoy the best weather and local experiences, making your stay in this destination truly memorable and aligning perfectly with your vacation plans.

Peak Season Highlights

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Summer (June to August)

During the summer months, the area experiences warm weather, making it an ideal time for outdoor activities and exploring the region's natural beauty. Booking vacation rentals in this season ensures you'll enjoy longer daylight hours and vibrant local events.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 60°F to 70°F
autumn
Fall (September to November)

Autumn offers pleasant temperatures and colorful foliage, attracting visitors seeking a scenic retreat. Securing a vacation rental during this season allows you to enjoy the region’s picturesque landscapes and mild weather.

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 winter months bring cooler temperatures and fewer tourists, providing a peaceful environment for those who prefer quieter accommodations. This is a great time to find deals on vacation rentals in the area.

Average Temperature Daytime: 30°F to 40°F - Nighttime: 20°F to 30°F
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Early Spring (March to April)

As the region transitions from winter to spring, fewer visitors venture here, creating opportunities for affordable stays. The weather begins to warm, making it suitable for early-season outdoor activities.

Average Temperature Daytime: 45°F to 55°F - Nighttime: 35°F to 45°F

Weekly Weather Forecast for New Chicago

How to Book Your New Chicago 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 New Chicago

More Top-Rated Vacation Rentals in New Chicago 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 outdoor dining with a spacious patio or picnic area available at many properties.
  • Take advantage of private or shared access to scenic waterfronts and lakes for fishing or boating.
  • Relax in your own outdoor hot tub or spa, perfect for unwinding after exploring the region.
  • Benefit from well-maintained gardens or lush lawns that provide a peaceful outdoor setting.
  • Utilize outdoor grills or BBQ facilities to prepare meals al fresco with family and friends.
  • Explore nearby walking trails, bike paths, or nature reserves directly accessible from your rental.
  • Make use of outdoor fireplaces or fire pits ideal for cozy gatherings under the stars.

Top Attractions Around New Chicago

What attractions are nearby?

Within this charming area, you can explore a variety of outdoor activities and scenic spots that showcase the natural beauty of the region, making it an ideal destination for relaxation and adventure during your stay.

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Family Activities

  • Indiana Dunes National Park: Discover outdoor adventures with scenic hikes, beach activities, and wildlife viewing right near your vacation rental here.
  • Lakefront Recreation: Enjoy family-friendly fun on the shores of Lake Michigan, including swimming, picnicking, and relaxing by the water.
  • Local Nature Centers: Explore educational programs and nature trails that provide engaging experiences for children and adults alike in the region.
  • Community Parks and Playgrounds: Spend quality time at nearby parks featuring playgrounds, sports fields, and open spaces perfect for family outings.
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Adult Activities

  • Visit the Indiana Dunes National Park: Explore scenic hiking trails, enjoy birdwatching, and relax on the sandy dunes along Lake Michigan here in the region.
  • Enjoy a round of golf at local courses: Take advantage of the area's well-maintained golf courses to unwind and perfect your swing amidst picturesque surroundings.
  • Discover local breweries and wineries: Sample craft beers and regional wines that highlight the area's emerging beverage scene, perfect for adult tasting experiences.
  • Explore waterfront dining options: Savor delicious meals at restaurants overlooking Lake Michigan, offering a relaxing atmosphere and stunning views.

New Chicago Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Activities in Advance: Take time to explore local attractions and outdoor activities to maximize your experience during your stay in this area.
  • Choose the Right Vacation Rental: Select a property that offers convenient access to key sites and amenities, ensuring a comfortable and hassle-free visit.
  • Discover Hidden Gems: Talk to locals or do some research to find lesser-known spots that provide an authentic taste of the region's charm.
  • Travel Off-Peak: Visiting during less busy times can enhance your experience with lower costs and more personalized attention at your vacation rental here.

Transportation Options

  • Personal Vehicles: Renting or using your own car offers you the flexibility to explore this area and its surroundings at your own pace.
  • Public Transit: The region provides bus services that connect key spots, making it a convenient option for getting around without hassle.
  • Taxi and Rideshare Services: Reliable taxi companies and rideshare apps are readily available for quick, on-demand transportation within the destination.
  • Shuttle Services: Local shuttle options operate regularly, providing easy access to popular local attractions and nearby cities.

Local Customs Options

  • Local Festival Celebrations: Participating in the area's traditional festivals offers an authentic glimpse into the community's heritage and customs.
  • Chowder Bowls Etiquette: When enjoying local seafood dishes, it's customary to share and appreciate the region's culinary traditions with neighbors and visitors alike.
  • Indigenous Heritage Respect: Recognizing and honoring the indigenous history of this destination is a meaningful way to connect with its cultural roots.
  • Community Hospitality: Warm welcomes and friendly interactions embody the genuine hospitality you can expect here during your stay.

Frequently Asked Questions About New Chicago?

1. What are the top vacation rentals in New Chicago?

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

2. How many vacation rentals have private pools in New Chicago?

There are 6 vacation rentals with private pools near New Chicago. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in New Chicago are best for families?

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

4. How many Rentbyowner vacation rentals are available in New Chicago?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 259 in the New Chicago 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 New Chicago. 

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

Cancellation policies vary by property listing, so it is important to review the specific terms outlined in the reservation details or contact the property owner directly to understand the cancellation timeframe and any applicable fees.

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

Additional fees such as cleaning, service charges, or taxes may apply depending on the property. Details are typically provided during the booking process or detailed within the listing, so reviewing these specifics will ensure you have all the necessary information before confirming your reservation.

7. How do I know if my chosen vacation rental in this destination is available for my preferred dates?

Availability is updated in real-time on the listing page. If your dates are not shown as available, you can contact the host directly through the platform for clarification or to inquire about flexible check-in options.

8. What amenities are usually included in vacation rentals here?

Amenities vary by property but often include essentials like Wi-Fi, fully equipped kitchens, parking, and laundry facilities. You can find a detailed list of amenities on each listing to ensure the accommodation meets your needs.

9. How do I contact the property owner or manager if I have questions before booking?

You can reach out to the owner or manager directly through the messaging system provided on the booking platform. It's recommended to clarify any concerns or special requests prior to completing your reservation to ensure a smooth stay.