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Chesterton vacation rentals

We found 1,362 vacation rentals — enter your dates for availability

Discover a selection of 30 homes and other vacation rentals in Chesterton that are perfect for your trip. Whether you’re staying in a vacation home with your kids and pets or just with friends, you'll have the amenities you expect and more, which might include air conditioning and a pool. Whatever you're looking for, you'll be sure to find a rental to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Vacation rentals with weekly discounts - Chesterton

Showing deals for:Jul 17 - Jul 24

Image gallery for Blocks from the beach with giant covered deck, firepit, and grill!

☀️
9.6 out of 10, Exceptional, (5 reviews)
Exceptional
(5 reviews)

Blocks from the beach with giant covered deck, firepit, and grill!

Gary

8% off
Price is $187
$1,306 for 7 nights
All fees included
Blocks from the beach with giant covered deck, firepit, and grill!

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Find out more about Chesterton

Why visit Chesterton

  • Outdoor Adventures: Chesterton is a paradise for outdoor enthusiasts, featuring beautiful beaches and parks for hiking, biking, and relaxation.
  • Charming Downtown: The downtown area offers a delightful atmosphere for family outings and romantic strolls, filled with shops and dining options.
  • Lake Michigan Beaches: Just a short drive away, enjoy stunning beaches that provide scenic views and recreational activities.
  • Diverse Accommodations: Choose from cozy cottages, stylish apartments, or spacious vacation homes to suit your needs.
  • Memorable Experiences: Chesterton’s blend of natural beauty and community vibes ensures an unforgettable vacation.

Popular types of accommodation in Chesterton

Planning a getaway to Chesterton? You're in for a treat. Explore a variety of accommodations, including houses, cozy cottages, and stylish apartments. Whether you’re seeking spacious house rentals or comfortable bedroom options, Chesterton has something for everyone. Discover the perfect Indiana apartment for your stay and enjoy a memorable experience in this charming town. Let the adventure begin.

  • Houses: The top choice for visitors in Chesterton, offering spacious and comfortable accommodations ideal for families or groups.
  • Cottages: A charming option, these cozy retreats provide a quaint atmosphere perfect for a relaxing getaway.
  • Apartments: A practical choice for travelers, offering all the amenities of home in a convenient location.
  • Condos: Stylish and modern, these rentals offer a blend of comfort and luxury for a delightful stay.
  • Cabins: Embrace nature with our rustic cabins, ideal for those seeking a peaceful escape in the woods.**

Top attractions in and around Chesterton

Chesterton, Indiana, is perfect for outdoor enthusiasts seeking scenic adventures. With its beautiful beaches, national and state parks, and urban parks, there's plenty to explore. Whether you’re traveling with family or friends, you'll find numerous attractions that cater to outdoor experiences and relaxation. Don’t miss the chance to enjoy Chesterton’s natural beauty and make lasting memories on your vacation.

  • Indiana Dunes National Park: Explore stunning sand dunes, diverse ecosystems, and scenic trails. This national park offers adventurous hiking, breathtaking views of Lake Michigan, and opportunities for birdwatching and nature photography.
  • Lake View Beach: Enjoy relaxing beach vibes at this picturesque spot featuring soft sands and gentle waves. It's perfect for sunbathing, swimming, and picnicking with family and friends.
  • Indiana Dunes Visitor Center: Discover interactive exhibits and helpful resources about the park. The center is a great starting point for family-friendly adventures and outdoor activities in the dunes.

Things to do recommended for couples

For a romantic getaway in Chesterton, Indiana, visit Anderson's Winery, just 6 miles away, for a cozy atmosphere filled with entertainment. Alternatively, explore Shady Creek Winery, 15 miles from town, where you can sip fine wines and enjoy a charming setting perfect for couples.

Things to do recommended for families

Your family vacation in Chesterton, Indiana, will be filled with fun. Enjoy thrilling rides at Deep River Water Park, relax at Marquette Park, and satisfy your sweet tooth at Albanese Candy Factory. These local attractions promise adventure, relaxation, and delicious treats for everyone.

Things to do recommended for groups

Groups visiting Chesterton can shop at the Lighthouse Place Premium Outlets for a fun retail experience, hike the scenic Cowles Bog Trailhead for outdoor adventure, and enjoy a captivating performance at the Chicago Street Theatre, perfect for culture and entertainment.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Chesterton

If you're traveling with a group, with family, bringing your pets, or planning an extended stay, be sure to filter your options based on your key priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Chesterton with a group: Think about how many bedrooms you'll require, as well as features like a complete kitchen or outdoor area for group gatherings. Luckily, you can easily filter for all of these options and more on Vrbo.
  • Traveling to Chesterton with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with finding suitable amenities like a private swimming pool. Additionally, think about how close you are to family-friendly attractions.
  • Taking your pets with you to Chesterton: For many families, a trip wouldn’t feel complete without their furry companion by their side. If you can relate, explore Vrbo listings that welcome pets. Many of these pet-friendly properties offer amenities like food bowls and beds to ensure that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Chesterton: If you're in search of vacation rentals that offer discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like parking, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in and around Chesterton

Chesterton, Indiana, offers a delightful blend of relaxing getaways and outdoor adventures. Explore the charming downtown area, perfect for family outings and romantic strolls. Just a short drive away, you'll find beautiful beaches along Lake Michigan that invite recreation and scenic views. Whether you're seeking a family-friendly atmosphere or a peaceful retreat, Chesterton and its surroundings provide an unforgettable vacation experience filled with diverse vibes and stunning landscapes.

  • Michigan City: Located 11 miles from Chesterton, Michigan City is a vibrant city known for its beautiful scenery and outdoor adventures. Visitors can enjoy the stunning landscapes of nearby national and state parks, where hiking and nature walks abound. The area offers a variety of recreational activities, including playgrounds for families and wellness retreats for relaxation. Don't miss the chance to visit the iconic Indiana Dunes, where you can soak up the sun on the beach or explore the unique coastal ecosystem. Michigan City is a perfect blend of adventure and tranquility, making it an ideal stop for nature lovers.
  • Portage: Just 6 miles from Chesterton, Portage is a charming city that invites travelers to explore its scenic views and outdoor opportunities. With its expansive recreational areas, Portage is perfect for families and adventure seekers alike. Enjoy educational experiences at local venues or spend time at the playgrounds scattered throughout the city. Nature lovers will appreciate the proximity to national and state parks, as well as the picturesque dunes that provide ample hiking and exploration opportunities. Portage is a welcoming destination for anyone looking to enjoy the great outdoors.
  • Porter: Nestled in the area around Chesterton, Porter is a quaint village that offers a delightful escape for those seeking natural beauty and outdoor fun. With its recreational areas and fairgrounds, Porter is perfect for family outings or community events. Visitors can explore local landmarks such as the nearby national and state parks, as well as the iconic dunes that provide a stunning backdrop for outdoor activities. Whether you’re enjoying a fairground show or taking in the fresh air, Porter is a charming destination that beautifully complements your Chesterton adventure.

Booking with Vrbo is simple

Are you hoping to save on your next getaway? Staying flexible with your travel dates can help, as prices tend to vary. Additionally, booking a longer stay often leads to significant savings. To find the perfect Vrbo property that fits your budget, take advantage of our filters to narrow down options by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers an easy-to-use platform for planning your travels. You can create new trips, continue from where you last stopped, or view and manage your travel arrangements all in one place. Your saved or booked properties are neatly organized into categories: Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Tranquil Chesterton will entice you

The riverfront, beaches and lake are a perfect backdrop to your vacation home in Chesterton. Travelers to this relaxing city praise the coffeehouses, bird watching and shopping. Take in top local attractions like Indiana Dunes National Park and Lake Michigan. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.

Sightseeing in and around Chesterton

Do you want to find attractions to visit in the city? Venture out of your vacation home and experience everything that Chesterton has to offer. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Washington Park Zoo (11.6 mi / 18.6 km)
  • The Course at Aberdeen (11.9 mi / 19.1 km)
  • Deep River Water Park (12.9 mi / 20.8 km)
  • Shady Creek Winery (14.5 mi / 23.3 km)
  • Legacy Hills Golf Club (16.1 mi / 26 km)
  • Anderson's Winery (6.1 mi / 9.9 km)

Exploring the natural landscape of Chesterton

Travelers enjoy Chesterton for its beaches and lakeside setting. Whether you're an outdoor enthusiast or just want to take in the scenery, Chesterton is a great place to get outside. These are some of the area's noteworthy sights, all within 30 miles (48.2 km) of the city center:

  • Indiana Dunes National Park (2.7 mi / 4.3 km)
  • Indiana Dunes Visitor Center (1.7 mi / 2.7 km)
  • Dune Acres Beach (3.5 mi / 5.6 km)
  • Waverly Beach (3.5 mi / 5.7 km)
  • Kemil Beach (5.7 mi / 9.1 km)
  • Dunbar Beach (6 mi / 9.7 km)

Seasonal weather in Chesterton

If warm-weather activities are high on your list, July, August, June and September are the hottest months to visit, when temperatures average 70°F.

Transportation to and around Chesterton

The nearest airport is in Chicago Midway Airport (MDW), located 37 mi (59.6 km) from the city center. If you're unable to find a flight that fits your schedule, you might consider flying into Chicago O'Hare Intl. Airport (ORD), which is 50.2 mi (80.7 km) away.

Frequently asked questions

What is the best area to stay in Chesterton, Indiana, United States of America when booking a vacation rental?
When considering a vacation rental in Chesterton, Indiana, the downtown area is an excellent choice. This vibrant neighborhood offers a charming small-town atmosphere with easy access to local shops, eateries, and cultural attractions. A great point of interest nearby is the Chesterton European Market, which takes place on Saturdays and features a variety of local vendors offering fresh produce, handmade goods, and delicious food. Additionally, the nearby Coffee Creek Watershed Preserve provides beautiful trails and scenic views, superb for nature lovers.

Another appealing area is the proximity to the Indiana Dunes National Park, which boasts stunning sandy beaches and an array of outdoor activities. Staying close to the park allows visitors to easily explore its diverse ecosystems and enjoy hiking, birdwatching, and relaxing by the shores of Lake Michigan. In terms of vacation rentals, Chesterton has a variety of properties available, ranging from cozy cottages to spacious homes, providing plenty of options to suit different preferences and group sizes.
How much does it cost to rent a vacation home in Chesterton?
Prices for vacation rentals in Chesterton vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Chesterton to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Chesterton vacation house rentals?
You can find great discounts on house rentals in Chesterton on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Chesterton?
For renting a beach house in Chesterton, consider the picturesque area near Indiana Dunes National Park. This region features a variety of vacation rentals, many of which are located just a short walk from the sandy shores of Lake Michigan. Properties in this area often come equipped with amenities such as spacious decks for outdoor dining, fire pits for cozy evenings, and fully stocked kitchens that cater to families and groups looking for a home-away-from-home experience.

Particularly, the neighborhoods around the West Beach area provide charming cottages and modern homes that offer easy access to both the beach and the scenic trails of the national park. Many rentals here include features like outdoor showers, grills, and large yards, ideal for enjoying the summer sun. The proximity to local attractions such as the quaint downtown Chesterton, with its shops and restaurants, adds to the appeal, allowing travelers to explore local flavors and crafts during their stay.

Additionally, the nearby Coffee Creek Watershed Preserve offers opportunities for hiking and birdwatching, making it a great spot for nature enthusiasts. Rentals in this vicinity often provide a peaceful retreat with quick access to both the natural beauty of the dunes and the vibrant community life of Chesterton.
What is the most popular type of vacation rental accomodation in Chesterton?
In Chesterton, vacation houses are the most popular rental option, with around 27 available throughout the area. These houses typically feature multiple bedrooms, fully equipped kitchens, and spacious living areas, making them ideal for families or groups. Many also come with outdoor spaces, such as patios or gardens, where guests can relax after a day of exploring local attractions like the Indiana Dunes National Park and the charming downtown area. Additionally, there are several cottages, apartments, mobile homes, and cabins available, providing a variety of choices for travelers seeking different experiences.
Are there any family house rentals in Chesterton?
In Chesterton, Indiana, there are numerous family-friendly house rentals available, with around 37 options to choose from. This charming town offers a variety of neighborhoods, each providing unique accommodations suitable for families. Many of these homes boast spacious living areas, fully equipped kitchens for preparing family meals, and cozy outdoor spaces where children can play safely.

Travelers will find that many properties come with amenities such as Wi-Fi, air conditioning, and laundry facilities, ensuring a comfortable stay. Chesterton is also conveniently located near attractions like the Indiana Dunes National Park, where families can enjoy hiking, picnicking, and stunning views of Lake Michigan.
Can I rent a vacation home with a pool or hot tub in Chesterton?
In Chesterton, Indiana, there are several vacation homes available for rent that feature pools and hot tubs. This charming town, located near the stunning Indiana Dunes National Park, offers a mix of outdoor activities and local attractions. Many of the rental properties come equipped with private pools, hot tubs, and spacious outdoor areas, superb for relaxation after a day of exploring. Travelers can expect amenities such as fully equipped kitchens, comfortable living spaces, and sometimes even game rooms or fire pits, making these homes ideal for family gatherings or group getaways.
Can I find long-stay vacation rentals in Chesterton?
A long-stay vacation rental in Chesterton is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Chesterton?
In Chesterton, there are several pet-friendly house rentals available, offering a welcoming environment for travelers with furry companions. Many of these rentals are equipped with amenities such as spacious backyards, fully equipped kitchens, and comfortable living areas, making them ideal for families or groups.

The area around Chesterton features convenient access to local parks like Dogwood Park and the expansive Indiana Dunes National Park, where pet owners can enjoy scenic trails and open spaces for walks and playtime. Additionally, the charming downtown area includes pet-friendly cafes and shops, enhancing the overall experience for those traveling with pets. See all pet-friendly rentals in Chesterton.
Are there any remote work vacation rentals in Chesterton?
In Chesterton, Indiana, there are numerous vacation rentals suitable for remote work, with around 44 options available. The town offers a blend of residential charm and convenient access to the natural beauty of the Indiana Dunes National Park. Many of these properties come equipped with essential amenities such as high-speed Wi-Fi, dedicated workspaces, and comfortable living areas, allowing for productive work environments.

Travelers can expect a variety of accommodations, from cozy cottages to spacious homes, often featuring full kitchens for meal preparation and outdoor spaces for relaxation after work hours. The proximity to parks and local attractions, including unique shops and restaurants, makes Chesterton an appealing destination for those looking to balance work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Chesterton vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Chesterton with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Chesterton?
In Chesterton, popular vacation rental amenities typically include kitchens, which allow guests to prepare their own meals and enjoy a home-cooked experience. Many rentals also feature outdoor spaces like decks or patios, great for relaxing and taking in the fresh air. Onsite parking is another common amenity, providing convenience for travelers with vehicles. Additionally, most rentals come equipped with coffee and tea makers, ensuring guests can start their mornings with a warm beverage.
When is the best time to visit Chesterton for a vacation rental?
The peak travel season in Chesterton occurs between June and August, with July being the most popular month for visitors. This vibrant period is ideal for those looking to immerse themselves in outdoor activities, as the warm summer weather, typically ranging from the mid-70s to mid-80s Fahrenheit, invites exploration of the stunning Indiana Dunes National Park. Here, you can enjoy hiking, swimming, and picnicking, all while surrounded by picturesque landscapes.

During the summer months, Chesterton buzzes with energy, providing ample opportunities for travelers to engage in local events and festivals. Families and adventure seekers alike will appreciate the convenience of nearby attractions, including charming shops and delicious dining options that celebrate the region's culinary scene.

For those mindful of their budget, consider planning a trip in December, when you can enjoy a quieter atmosphere. The winter months offer a different kind of charm, with festive decorations and a chance to experience the local holiday spirit without the summer crowds.

Ultimately, your ideal time to visit Chesterton will depend on whether you seek the lively summer festivities or the peaceful, reflective ambiance of the winter season.
How early should I book a Chesterton vacation rental?
Book your Chesterton vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Chesterton, Indiana, United States of America?
In Chesterton, Indiana, visitors can explore a variety of attractions that highlight the area's natural beauty and local culture. One of the main draws is the Indiana Dunes National Park, where guests can enjoy stunning views of Lake Michigan, hike along scenic trails, and relax on the sandy beaches. The nearby Chesterton European Market, held on Saturdays, showcases local vendors offering fresh produce, artisanal goods, and handmade crafts, providing a vibrant community atmosphere.

For those interested in history, the Old Lighthouse Museum offers insights into the maritime history of the region and is located close to the waterfront. Additionally, the local parks, such as Dogwood Park and Coffee Creek Watershed Preserve, provide opportunities for outdoor activities, including walking, picnicking, and birdwatching.
Can I change or cancel my Chesterton home rental booking on Vrbo?
To find Chesterton vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Chesterton vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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