Vacation Homes in Chesterton, IN
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Top Vacation Homes in Chesterton

A cozy little house along Trail Creek awaits you. Relax. Unwind. Enjoy.

Big Family House 5 Minutes from Lake Michigan/Blue Chip Casino/Brewery/Wineries!

Family Retreat-Beachwalk-Grill-AC-Free WiFi-Pool Table-Bikes-Grill-Golf Cart

Blue Chill | WalktoBeach | HotTub-all yr | Dogs OK

Hot tub & Pool in Gorgeous Wooded Community

Blue Birdhouse - No Cleaning Fee - Pet Friendly - Dunes National Park

Sweet Stay By-The-Lake in Michigan City with AC, WiFi

Red Zen | HotTub-all yr | Firepit | Grill | DogsOK

Spacious home for travelers. Big discount for monthly renters.

Golf Cart 6 bedrooms plus coach house with 1 bedroom. Summer 2026 open to book

Kid-friendly Michiana cottage! Summer dates open - including 4th of July!
Top hotels in Chesterton

Spring House Inn
Find the Best Vacation Homes in Chesterton
Why book a vacation home in Chesterton?
Vacation homes in Chesterton make for a different travel experience. Your holiday home will allow you to feel at home during your visit. You’ll usually have more space, more privacy, and extra amenities not typically included with hotel stays.
How much is a vacation home in Chesterton?
Private Chesterton rental homes range between $94 - $335 per night. Prices change based on seasonal demand, travel dates, property location, capacity, amenities, etc.
What are the cancellation and flexibility options on Travelocity?
To cancel your vacation home, you must reach out to the individual property manager. Their contact details are available in your itinerary. For more information, head over to our customer service portal. Use the ‘free cancellation’ or ‘reserve now, pay later’ filters to find the most flexible options for your bookings.
What amenities should I look out for in a vacation home?
There are some exciting amenities available in Chesterton vacation home rentals. You might look for Chesterton rental houses with a private pool or free Wi-Fi. Some popular amenities also include a private hot tub, air-conditioning, laundry facilities, and a games room.
Vacation rentals in Chesterton offer other accommodations that may interest you. Some have resort-like amenities such as a fitness center, bar/lounge, or swimming pool.
When is the best time to rent a vacation home in Chesterton?
You’ll typically get cheaper rates when staying during the off-season, . Prices are usually at their lowest for stays in . are the most popular months to visit.
Why book a vacation home with Travelocity?
Travel smart with Travelocity. Search over 1 million properties worldwide and access an incredible selection of holiday homes in Chesterton. Our members save 10% or more on select hotels, and if you find a lower price, we’ll match it with our Price Match Guarantee. Get started finding Chesterton hotels and vacation homes that best suit your stay. We also have deals for flights, and Chesterton car rentals. You’ll save even more when you bundle your items into a Chesterton vacation package!
How many vacation homes are available to book in Chesterton?
There are 740 rental homes in Chesterton. Enter your travel dates to check availability.
How do I find the best price for a vacation home in Chesterton?
Private vacation homes vary in price, and we’ll help you get the best deal possible. Use the map feature to compare rental house prices in different neighborhoods. Also, try adjusting your dates to compare nightly rates within a similar timeframe.
Chesterton Vacation Homes essential information
Accommodation | 740 Vacation Homes |
---|---|
Lowest Price | $94 |
Highest Price | $335 |
Popular accommodation | A cozy little house along Trail Creek awaits you. Relax. Unwind. Enjoy. , Big Family House 5 Minutes from Lake Michigan/Blue Chip Casino/Brewery/Wineries!, Family Retreat-Beachwalk-Grill-AC-Free WiFi-Pool Table-Bikes-Grill-Golf Cart, Blue Chill | WalktoBeach | HotTub-all yr | Dogs OK, Hot tub & Pool in Gorgeous Wooded Community, Blue Birdhouse - No Cleaning Fee - Pet Friendly - Dunes National Park, Sweet Stay By-The-Lake in Michigan City with AC, WiFi, Red Zen | HotTub-all yr | Firepit | Grill | DogsOK, Spacious home for travelers. Big discount for monthly renters., Golf Cart 6 bedrooms plus coach house with 1 bedroom. Summer 2026 open to book, Kid-friendly Michiana cottage! Summer dates open - including 4th of July!, 5BR 3.5BA Dune Side Home w/ Short Walk to the BEACH! NEW LISTING - Built in 2022 |
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