Westchester Rentals By Owner

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:

• Amazing Views From Beachfront Unit In the Heart of the Indiana Dunes
• Beachbum's Beachfront 1 brm efficiency apartment- Steps from Lake Mich/Dune Park
• ModernHome in HeartChesterton near IndianaDunes close to Chicago
• Chesterton Charmer: 2 Units in 1
• Charming Chesterton Home with Idyllic Location!
• Moody Modern Dunes Hot Tub Beach and Trails
• Moody Modern Dunes Hot Tub Beach and Trails
• Indiana Dunes Downtown 4 Bedroom House Dog Friendly 4 Miles to Beach
• Spacious 4 BR 10 mins to 🏝 Near Chicago Sleeps 12
• Sweet Home in Chesterton

There are many large, family-friendly vacation homes available in Westchester; however, here are the most popular family rentals listed on our site:

• Chesterton “Golf View Estate” Midwest Great Lake Beaches & Trails Of The Dunes!
• Your Midwest Dunes Vacation Tri-State Paradise!
• That 70’s Loft- Peace, Love and a Funky Stay!
• Charming Chesterton Home: w/Idyllic Location!

Yes, there are 39 self-catering vacation homes in Westchester that have hot tubs, swimming pools, & other amenities.

There are more than 39 luxury villas and vacation homes in or near Westchester. Filter by price to compare find the most expensive places to stay on Scarytravels.

Yes, there are 39 pet friendly vacation homes and places to stays that are available in or near Westchester that you may consider.