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Westchester Pet Friendly Vacation Rentals

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8.1 (203 Reviews)
Hotel
Hilton Garden Inn Chesterton
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
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Why Choose Rent By Owner for your Westchester 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.

Weekly Weather Forecast for Westchester

How to Book Your Westchester 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 Westchester

More Top-Rated Vacation Rentals in Westchester 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 private outdoor spaces such as patios or decks to relax and unwind amidst nature.
  • Take advantage of outdoor grilling areas for summer barbecues and family dinners.
  • Make the most of spacious yards perfect for outdoor games and activities with loved ones.
  • Benefit from access to nearby parks or walking trails that showcase the scenic beauty of this destination.
  • Utilize outdoor furniture designed for lounging and dining in the fresh air.
  • Experience the comfort of fire pits or outdoor fireplaces during cooler evenings, ideal for gatherings.
  • Discover outdoor swimming pools or hot tubs available at select properties in the area for extra leisure and relaxation.

Top Attractions Around Westchester

What attractions are nearby?

In this scenic region, you can enjoy a variety of outdoor activities and local attractions that showcase the charm and natural beauty of Westchester, Indiana, USA, all within easy reach from your vacation rental.

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Family Activities

  • Westchester Community Park: Enjoy outdoor family activities and picnics in this scenic park with walking trails and play areas.
  • Indiana Transportation Museum: Discover local history through engaging exhibits and trains that captivate visitors of all ages.
  • The Children's Museum of Indiana: Stimulate your children's imagination with interactive exhibits designed to entertain and educate here in the region.
  • White River State Park: Experience outdoor concerts, nature exploration, and family-friendly events amidst lush surroundings in this nearby attraction.
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Adult Activities

  • Wine Tasting at Local Vineyards: Explore the region's wineries, where you can enjoy tastings and learn about the area's rich viticulture tradition.
  • Golfing at Premier Courses: Tee off at nearby golf courses that offer scenic fairways and a relaxing environment for golf enthusiasts visiting here.
  • Hiking and Nature Walks: Discover the local natural beauty by hiking through well-maintained trails that showcase the area's lush landscapes.
  • Dining at Fine Restaurants: Indulge in the region’s culinary scene by visiting acclaimed eateries known for their exceptional cuisine and welcoming atmosphere.

Other Places to Stay in Westchester, IN

Waverly Beach
Waverly Beach Vacation Rentals
Indiana Dunes Visitor Center
Indiana Dunes Visitor Center Vacation Rentals
Bailly Homestead - American Indians and Fur Traders
Bailly Homestead - American Indians and Fur Traders Vacation Rentals
Porter
Porter Vacation Rentals
Chellberg Farm
Chellberg Farm Vacation Rentals
Chesterton
Chesterton Vacation Rentals
Lustron House
Lustron House Vacation Rentals
Burns Harbor
Burns Harbor Vacation Rentals
Indiana Dunes National Park
Indiana Dunes National Park Vacation Rentals
Indiana Dunes State Park
Indiana Dunes State Park Vacation Rentals
Dune Acres
Dune Acres Vacation Rentals
Porter Beach
Porter Beach Vacation Rentals
More Places to Stay Near Westchester

Westchester Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Visit During Off-Peak Seasons: Visiting during less busy times allows you to enjoy the area's attractions and your vacation rental with more tranquility and better rates.
  • Explore Local Dining and Shopping Options: Take advantage of nearby eateries and shops to immerse yourself in the local culture without venturing far from your chosen vacation rental.
  • Coordinate Your Activities with Weather Patterns: Checking the seasonal weather helps you optimize outdoor adventures and ensures your stay is comfortable and enjoyable.
  • Connect with the Community and Event Calendar: Engaging in regional events or festivals can enrich your experience and provide a deeper connection to the destination.

Transportation Options

  • Local Bus Services: You can rely on regional bus routes to conveniently access key areas within this part of Indiana, making it easy to explore without a car.
  • Private Transportation Providers: Several local taxi and ride-sharing services are available here, offering flexible travel options for your comfort and convenience.
  • Regional Airport Access: The nearby airports provide a straightforward way to reach the region, with transportation options readily available to bring you closer to your vacation rentals.
  • Car Rentals: Renting a vehicle is a popular choice for exploring the area at your own pace, especially if you plan to visit attractions outside the immediate vicinity.

Local Customs Options

  • Local Festivals: Participating in regional festivals offers a welcoming experience and insight into the area's vibrant community traditions.
  • Food and Beverage Customs: Enjoying locally favored dishes and beverages provides a taste of the region's culinary heritage.
  • Religious Practices: Respecting local religious customs enriches your visit and fosters positive interactions with residents.
  • Community Greetings: Learning the customary ways residents greet each other helps you blend seamlessly into this destination’s social scene.

Frequently Asked Questions About Westchester?

1. What are the top vacation rentals in Westchester?

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

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

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

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

Currently, the total number of properties listed by Rent By Owner in 2025 is over 61 in the Westchester 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 Westchester. 

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

Cancellation policies vary depending on the property listing. To understand the specific terms, please review the cancellation details provided in the listing or contact the property owner directly.

5. How do I know if the vacation rental in the region is available on my travel dates?

Availability calendars are updated regularly on each listing. To confirm your dates, check the calendar or reach out to the owner for real-time availability information.

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 security deposits are specified in each listing. Review these details carefully before completing your reservation or contact the owner for clarification.

7. What amenities can I expect from vacation rentals in this destination?

Amenities vary by property but typically include essentials like Wi-Fi, parking, and kitchen facilities. For detailed information, consult the listing description or contact the owner directly.

8. How do I proceed with booking a vacation rental in the region?

Booking is straightforward—simply select your preferred dates, review the property details, and follow the booking instructions. If you have questions or special requests, reaching out to the owner ensures a smooth reservation process.