A wooden staircase ascending a sandy hill with sparse vegetation.

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Our top choices for Chesterton hotels

1. Best Western Indian Oak

Best Western Indian Oak
2.5 star property
Chesterton
8.6 out of 10, Excellent, (1,004 reviews)
"The staff was friendly and room was clean."
United States
Alyssa
The price is AED 328
AED 367 total
includes taxes & fees
16 Nov - 17 Nov
Best Western Indian Oak

2. Spring House Inn

Spring House Inn
2.5 star property
Chesterton
8.8 out of 10, Excellent, (1,009 reviews)
"Good breakfast, staff was very helpful, there was a good restaurant on site."
United States
Michael
The price is AED 333
AED 392 total
includes taxes & fees
9 Nov - 10 Nov
Spring House Inn

3. Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton
3.0 star property
Chesterton
8.8 out of 10, Excellent, (1,006 reviews)
"Excellent hotel, friendly staff"
United States
Cheryl
The price is AED 462
AED 518 total
includes taxes & fees
5 Dec - 6 Dec
Hilton Garden Inn Chesterton

4. Waterbird Lakeside Inn

Waterbird Lakeside Inn
2.0 star property
Chesterton
8.2 out of 10, Very good, (1,001 reviews)
"Loved the balcony overlooking the lake."
United States
Marsha
The price is AED 345
AED 387 total
includes taxes & fees
8 Nov - 9 Nov
Waterbird Lakeside Inn

5. Quality Inn Chesterton near Indiana Dunes National Park I-94

Quality Inn Chesterton near Indiana Dunes National Park I-94
2.5 star property
Chesterton
7.8 out of 10, Good, (874 reviews)
"Had a great weekend. Staff was great, room was clean, facility was great for a budget."
United States
Albie
The price is AED 278
AED 311 total
includes taxes & fees
6 Dec - 7 Dec
Quality Inn Chesterton near Indiana Dunes National Park I-94

6. Comfort Inn & Suites Porter near Indiana Dunes

Comfort Inn & Suites Porter near Indiana Dunes
2.5 star property
Chesterton
7.8 out of 10, Good, (1,002 reviews)
"Good one night stay. Nice to have breakfast there before we headed out."
United States
Julie Van
The price is AED 299
AED 334 total
includes taxes & fees
1 Dec - 2 Dec
Comfort Inn & Suites Porter near Indiana Dunes

7. Furness Mansion

Furness Mansion
2.0 star property
Chesterton
9.0 out of 10, Wonderful, (117 reviews)
"Staff was extremely helpful and responded promptly. The room was very clean, and inviting. Great location for the beaches or short trips to Michigan."
United States
Bryan
The price is AED 478
AED 535 total
includes taxes & fees
9 Nov - 10 Nov
Furness Mansion

8. Fairbridge Inn Express Chesterton

Fairbridge Inn Express Chesterton
2.0 star property
Chesterton
6.8 out of 10, (397 reviews)
"Stayed here several times over the years. Always clean so we keep coming back. Recently updated furniture is an improvement."
United States
Daniel
The price is AED 286
AED 320 total
includes taxes & fees
8 Dec - 9 Dec
Fairbridge Inn Express Chesterton

9. Country Inn & Suites by Radisson, Portage, IN

Country Inn & Suites by Radisson, Portage, IN
3.0 star property
Portage
8.4 out of 10, Very good, (1,000 reviews)
"Nice breakfast, and a wonderful, kid-friendly pool that is particularly good for very young children."
United States
Rachel
The price is AED 494
AED 553 total
includes taxes & fees
6 Dec - 7 Dec
Country Inn & Suites by Radisson, Portage, IN

10. Hampton Inn Portage

Hampton Inn Portage
2.5 star property
Portage
8.6 out of 10, Excellent, (96 reviews)
"Staff was friendly and hotel was well maintained."
Canada
Allan
The price is AED 403
AED 451 total
includes taxes & fees
27 Nov - 28 Nov
Hampton Inn Portage

11. Home2 Suites by Hilton Michigan City

Home2 Suites by Hilton Michigan City
3.0 star property
Michigan City
9.0 out of 10, Wonderful, (24 reviews)
"Excellent service and clean."
United States
Melina
The price is AED 509
AED 570 total
includes taxes & fees
25 Nov - 26 Nov
Home2 Suites by Hilton Michigan City

12. Tru By Hilton Valparaiso

Tru By Hilton Valparaiso
2.5 star property
Valparaiso
9.0 out of 10, Wonderful, (65 reviews)
"Staff were really friendly, breakfast was great. Even liked that this hotel has actual hand soap that’s a pump in the bathrooms (in the rooms)."
United States
Phillip
The price is AED 389
AED 435 total
includes taxes & fees
22 Nov - 23 Nov
Tru By Hilton Valparaiso

13. Quality Inn & Suites Portage Central

Quality Inn & Suites Portage Central
2.5 star property
Portage
6.8 out of 10, (947 reviews)
"The cleaning quality of the room could’ve been better as far as the smell."
United States
Parrish
The price is AED 261
AED 292 total
includes taxes & fees
6 Dec - 7 Dec
Quality Inn & Suites Portage Central

14. Holiday Inn Express & Suites Michigan City by IHG

Holiday Inn Express & Suites Michigan City by IHG
2.5 star property
Michigan City
9.0 out of 10, Wonderful, (895 reviews)
"Great staff"
United States
Edward
The price is AED 433
AED 505 total
includes taxes & fees
15 Nov - 16 Nov
Holiday Inn Express & Suites Michigan City by IHG

15. OYO Hotel Portage I-94

OYO Hotel Portage I-94
2.0 star property
Portage
6.4 out of 10, (876 reviews)
"It was quite n relaxing"
United States
Rebecca
The price is AED 241
AED 294 total
includes taxes & fees
8 Nov - 9 Nov
OYO Hotel Portage I-94

16. Baymont by Wyndham Portage Indiana Dunes

Baymont by Wyndham Portage Indiana Dunes
2.5 star property
Portage
7.0 out of 10, Good, (1,002 reviews)
"Breakfast can improve a bit. Overall I will come again"
United States
Ibrahim
The price is AED 238
AED 266 total
includes taxes & fees
8 Dec - 9 Dec
Baymont by Wyndham Portage Indiana Dunes

17. Four Winds Casino Resort – New Buffalo

Four Winds Casino Resort – New Buffalo
3.5 star property
New Buffalo
9.4 out of 10, Exceptional, (2,347 reviews)
"Great stay, friendly staff, clean building!"
United States
thomas
The price is AED 327
AED 380 total
includes taxes & fees
8 Nov - 9 Nov
Four Winds Casino Resort – New Buffalo

18. Best Western University Inn At Valparaiso

Best Western University Inn At Valparaiso
2.5 star property
Valparaiso
8.0 out of 10, Very good, (1,004 reviews)
"Nice hotel, easy to access, kind staff"
United States
Karen
The price is AED 371
AED 415 total
includes taxes & fees
6 Dec - 7 Dec
Best Western University Inn At Valparaiso

19. Country Inn & Suites by Radisson, Valparaiso, IN

Country Inn & Suites by Radisson, Valparaiso, IN
3.0 star property
Valparaiso
8.6 out of 10, Excellent, (1,001 reviews)
"great staff, comfortable beds, clean rooms"
United States
Christopher
The price is AED 438
AED 490 total
includes taxes & fees
28 Nov - 29 Nov
Country Inn & Suites by Radisson, Valparaiso, IN

20. Hampton Inn & Suites Valparaiso

Hampton Inn & Suites Valparaiso
2.5 star property
Valparaiso
8.8 out of 10, Excellent, (878 reviews)
"Nice clean room, staff very friendly, accommodating our needs with a large party."
United States
William
The price is AED 419
AED 469 total
includes taxes & fees
15 Nov - 16 Nov
Hampton Inn & Suites Valparaiso
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotels recommended for families in Chesterton

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Where to stay in Chesterton

Find the best Chesterton areas and neighborhoods for the activities you enjoy most.

Porter Beach

While visiting Porter Beach, you might make a stop by sights like Lake Michigan and Waverly Beach.

Stay near popular Chesterton attractions

Learn more about Chesterton

Nestled along Lake Michigan's shore, this small town offers scenic trails through Indiana Dunes National Park for hiking and birdwatching. Coffee shops and local restaurants line the historic downtown, while nearby beaches provide perfect spots for summer swimming and sunset views.

A wooden staircase leading up a sandy hill with dense green forest in the background.
Photo by Susan Ross
Open Photo by Susan Ross

Top Chesterton Hotel Reviews

More cheap stays in Chesterton

Find out more about Chesterton

Top reasons to visit Chesterton

  • Scenic Outdoor Adventures: Chesterton is perfect for nature lovers, with beautiful beaches, parks, and scenic trails for exploration.
  • Charming Downtown: Stroll through the quaint downtown area, featuring unique shops and local eateries.
  • Family-Friendly Activities: Enjoy recreational areas, playgrounds, and activities suitable for all ages.
  • Local Wineries: Discover nearby wineries offering tastings and tours for a delightful experience.
  • Diverse Accommodations: Choose from cozy B&Bs to well-equipped hotels that cater to all types of travelers.

Find great hotels near Chesterton

Chesterton, Indiana offers a diverse selection of accommodations, from cozy bed and breakfasts to well-equipped hotels, catering to both business travelers and families. Whether you're seeking pet-friendly options or a place to unwind after a day of exploring, you'll discover a variety of local hotels with excellent amenities. Be sure to check out hotel reviews to find the best fit for your stay in this charming Midwestern town.

  • Baymont by Wyndham Michigan City: Located 16.1km from Chesterton, Baymont by Wyndham Michigan City is an ideal choice for travelers seeking a blend of comfort and convenience. This pet-friendly hotel is perfect for families and business travelers alike, with amenities catered to children, including complimentary cribs. Guests will appreciate the welcoming atmosphere, making it an excellent option for a family vacation. With a strong commitment to hospitality, the hotel also allows pets, ensuring all members of your family can enjoy the stay.
  • Microtel Inn & Suites by Wyndham Michigan City: Just 16.1km from Chesterton, Microtel Inn & Suites by Wyndham Michigan City stands out as a welcoming haven for LGBTQIA travelers. This hotel embraces inclusivity, making it a great choice for those looking for a supportive environment during their stay. With modern amenities and a focus on comfort, guests can enjoy a pleasant and professional atmosphere ideal for business trips or leisure. Its affiliation with LGBTQI travel guides ensures a friendly and affirming experience.
  • Days Inn by Wyndham Portage/Indiana Dunes National Park: Situated only 9.7km from Chesterton, Days Inn by Wyndham Portage/Indiana Dunes National Park offers a nature-themed retreat for outdoor enthusiasts. This hotel serves as a perfect base for exploring the stunning natural beauty of the Indiana Dunes National Park. With comfortable accommodations and essential amenities, guests can relax after a day of hiking or enjoying the beach. The serene surroundings make it an excellent choice for those looking to connect with nature during their vacation.

Where to stay in and around Chesterton

Chesterton, Indiana, is a delightful destination for travelers seeking scenic outdoor adventures and a relaxing atmosphere. Explore the charming downtown area, discover local wineries, and enjoy various recreational opportunities that cater to families and couples alike. With its close proximity to stunning natural landscapes, Chesterton offers a perfect blend of family-friendly vibes and romantic getaways, making it an ideal spot for your vacation.

  • Michigan City: Located 17.7km from Chesterton, Michigan City offers a delightful blend of natural beauty and outdoor adventure. This city experiences a moderate seasonal influx of visitors, peaking in the summer months. Travelers flock here for its scenic landscapes and numerous recreational opportunities. Explore the vast Indiana Dunes National Park, where you can hike, swim, or simply enjoy breathtaking views. Families can visit the local playgrounds or indulge in body treatments at nearby wellness centers. Michigan City is a perfect getaway for those seeking both adventure and relaxation.
  • Portage: Just 9.7km from Chesterton, Portage is a vibrant city that welcomes visitors year-round. While summer sees a spike in travelers, the charm of Portage remains consistent throughout all seasons. Known for its scenic outdoor spaces, Portage boasts various recreational areas and fairgrounds, where you can catch exciting shows and events. The nearby national and state parks provide ample opportunities for exploration and adventure, making it an ideal spot for nature enthusiasts. Portage is a fantastic destination for those looking to soak up the local culture and outdoor fun.
  • Porter: Nestled right in the vicinity of Chesterton, Porter is a quaint village that attracts visitors with its charming ambiance and outdoor activities. Similar to its neighbors, Porter sees a moderate seasonal flow of tourists, particularly in the summer months. The village features lovely recreational areas and playgrounds, making it a family-friendly destination. Nature lovers will appreciate its proximity to the Indiana Dunes National Park, where they can hike along scenic trails or relax on the beach. Porter is the perfect spot for those looking for a peaceful yet adventurous escape.

Things to do in and around Chesterton

Chesterton, Indiana, offers a perfect blend of outdoor and recreational activities for tourists. Enjoy scenic nature walks, hit the links at local golf courses, and explore nearby wineries. For a more relaxed experience, unwind at a body treatment center or visit local dive bars for a taste of the nightlife. Families can also take advantage of the recreational areas and playgrounds, ensuring a fun-filled vacation for everyone.

Shopping

For a delightful shopping experience in Chesterton, visit Lighthouse Place Premium Outlets, located 17.7km away, offering various brands and family-friendly vibes. If you're up for a drive, check out Westfield Southlake Mall, 25.7km away, featuring diverse shops and entertainment options.

Recreation

At Marquette Park, enjoy serene walks along beautiful trails and relax by the lake, soaking in the peaceful ambiance. The Course at Aberdeen offers a scenic golfing experience surrounded by nature, perfect for outdoor enthusiasts. Meanwhile, the Disk Golf Course provides a fun and active way to enjoy the outdoors.

Adventure

Experience thrill at Deep River Water Park, located 20.9km from Chesterton, where you can enjoy various water slides and activities perfect for families and adventure seekers. For a scenic hike, explore Cowles Bog Trailhead in Chesterton, where nature trails offer stunning views and a chance to connect with the outdoors.

Nightlife

Experience a vibrant nightlife in Chesterton with a visit to the Chicago Street Theatre for captivating performances, or catch a film at Cinemark Valparaiso for a family-friendly outing. For a live show, head to the Guy Foreman Bicentennial Amphitheater, where romance and culture come alive.

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

Booking tips and Expedia advantages for Chesterton

Chesterton, Indiana, provides numerous budget-friendly options for travelers. Enjoy free access to scenic spots like Lake View Beach and Dune Acres Beach. For transportation, consider using bicycles or renting a car for convenience. The most economical months to visit are January, February, and November, with Mondays being the cheapest days to stay. To save even more, book an Expedia package that combines your hotel, flights, and activities. Always check for exclusive discounts and last-minute deals to maximize savings on your trip.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Chesterton are January to February and November, where the prices are slightly lower. This is in comparison to June to August, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Chesterton is Monday. The most expensive day to stay in Chesterton is Saturday.
  • Find cheap hotels on Expedia: Utilize Expedia's search tool to refine your preferences, such as your budget, preferred location, and the type of hotel you desire. To discover the best prices and deals, simply arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by booking an Expedia package that combines your Chesterton hotel stay with your flights and activities.

Find the best attractions in and around Chesterton

Chesterton, Indiana, is a great destination for outdoor enthusiasts and families alike, boasting beautiful beaches, national and state parks, and urban parks. Visitors can enjoy a variety of activities, from relaxing by the shores to exploring scenic trails, making it an ideal spot for those seeking adventure and memorable experiences in nature. Whether you're looking for a family-friendly outing or a peaceful retreat, Chesterton has something for everyone.

  • Indiana Dunes National Park: Experience the stunning beauty of diverse landscapes at Indiana Dunes National Park, located 4.8km from Chesterton. Explore sandy beaches, towering dunes, and lush forests while enjoying outdoor activities like hiking, birdwatching, and swimming in Lake Michigan.
  • Indiana Dunes Visitor Center: Situated within Chesterton, this visitor center is the perfect starting point for families. Engage with interactive exhibits, attend educational programs, and receive expert advice on outdoor adventures in the park.
  • Bailly Homestead - American Indians and Fur Traders: Immerse yourself in local history at this historic site in Chesterton. Discover the cultural significance of the homestead, learn about early American Indian life, and explore the fur trading era that shaped the region.

The nearest major airports for your trip to Chesterton

When visiting Chesterton, Indiana, travelers can fly into several major airports. Chicago O'Hare International Airport (ORD) is located 80.5km away, with nearby hotels such as the 4.5-star Loews Chicago O'Hare Hotel and Hyatt Regency O'Hare, both just 3.2km from the airport. Midway International Airport (MDW) is 59.5km away, offering luxurious options like The Langham, Chicago and Nobu Hotel, both within 14.5km. South Bend International Airport (SBN) is 314.5km from Chesterton, with hotels like the 4-star Doubletree Hotel South Bend, located 6.4km away, providing convenient airport transportation services. Each airport offers a variety of accommodations for a comfortable stay.

Frequently asked questions

Where is the best place for a stay in Chesterton?
Based on our traveler data, Spring House Inn is one of the top choices for your stay. This hotel is a short 10-minute walk from Indiana Dunes National Park, and it offers free breakfast and an indoor pool. Other good options for your trip include Best Western Indian Oak and Quality Inn Chesterton near Indiana Dunes National Park I-94. See all available top hotels, or vacation rentals in Chesterton.
What are some of the best vacation home rentals that Chesterton has to offer?
Blue Birdhouse - No Cleaning Fee - Pet Friendly - Dunes National Park: Visitors like this Chesterton vacation home rental. It offers a patio, a private yard, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. You and your friends and family can relax into your vacation with amenities like a selection of books. See all vacation rentals in Chesterton.
If I need to cancel my hotel reservation in Chesterton, will I receive a refund?
Yes! Most hotel reservations are fully refundable as long as you cancel prior to the accommodation's cancellation deadline, which in most cases is within 24 or 48 hours of your scheduled arrival. If you have a reservation that's non-refundable, it might still be possible to cancel it and get a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Chesterton.
Where can I learn more about changing or cancelling my trip to Chesterton?
For additional details about picking new dates or cancelling your trip to Chesterton, head over to our customer service page.
What's the best accommodation for a family vacation to Chesterton?
Best Western Indian Oak is a hotel with an indoor pool and free parking, and it's a top choice on Expedia for families. Other choices to stay with the kids include Hilton Garden Inn Chesterton and Quality Inn Chesterton near Indiana Dunes National Park I-94. Attractions in the area like Washington Park Zoo and Deep River Water Park are also fun for kids of all ages. Find more child-friendly accommodations in Chesterton.
What is the top LGBTQ-friendly hotel in Chesterton?
Hilton Garden Inn Chesterton is a top LGBTQ-friendly hotel that features free parking and a 24-hour fitness center. Quality Inn Chesterton near Indiana Dunes National Park I-94 is another good option for your stay.
What's the best pet-friendly place to stay in Chesterton?
Furness Mansion is a top dog-friendly hotel, and offers free use of bicycles along with in-room kitchenettes for its human guests. Two other good options for you and your pet include Hilton Garden Inn Chesterton and Fairbridge Inn Express Chesterton. See more pet-friendly hotel accommodations in Chesterton.
Where is the best hotel to stay with easy access to Coffee Creek Watershed Conservancy Preserve?
Hilton Garden Inn Chesterton is one of the top choices for your stay based on our traveler data, and this 3-star hotel offers a restaurant and an indoor pool. It's located just a short 0.9 mi (1.4 km) from Coffee Creek Watershed Conservancy Preserve. Other good options within a few miles include Best Western Indian Oak and Quality Inn Chesterton near Indiana Dunes National Park I-94.
What are some accommodations with pools in Chesterton?
Spring House Inn: Hotel, 10-minute walk from Indiana Dunes National Park. Features a sauna, an indoor pool, and daily. Best Western Indian Oak and Comfort Inn & Suites Porter near Indiana Dunes are a couple of other choices with an onsite pool. View all hotels with pools in Chesterton.
What is the best spa hotel in Chesterton?
Furness Mansion is a top spa hotel with 5 rooms, barbecue grills, and laundry facilities. Spend an afternoon at the spa where you'll find Swedish massages, Thai massages, and hot stone massages. In-room massages are also available. See all spa hotels in Chesterton.
What is the best accommodation for staying close to O'Hare International Airport (ORD)?
Hilton Chicago O'Hare Airport is a popular 4-star hotel featuring 2 restaurants and 2 bars. It's located a short 0.1 mi (0.1 km) from O'Hare Intl. Airport. Other good options close to the airport are Edward Hotel Chicago and Best Western At O'Hare.
What's it like to stay in Chesterton?
Visitors to Chesterton are sure to enjoy the shopping, beaches, and restaurants. Tourists can also enjoy so much more including its coffeehouses. A top sight in the city is Lake Michigan. In Chesterton, there are 62 hotels and other accommodations to choose from. Find out more about Chesterton.
What should I do while I'm visiting Chesterton?
Landmarks like Lustron House, Bailly Homestead - American Indians and Fur Traders, and Chellberg Farm might be worth a visit. Natural beauty is on display at Lake Michigan, Indiana Dunes Visitor Center, and Indiana Dunes National Park. A couple of additional sights to add to your agenda are Indiana Dunes State Park and Dune Acres Beach. Check out what more to see and do in Expedia's Chesterton guide.
What's the seasonal weather like in Chesterton?
The hottest months are usually July and August with an average temp of 70°F, while the coldest months are January and February with an average of 31°F. The snowiest months in Chesterton are January, December, November, and February, with each month seeing an average of 6 inches of snowfall.