Book Hotels in Chesterton, Indiana

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Oct 1 - Oct 2

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Oct 2 - Oct 3

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Oct 6 - Oct 8

Most frequently booked Chesterton hotels

Best Western Indian Oak

558 Indian Boundary Road, Chesterton, IN

Free Cancellation

Reserve now, pay when you stay

1.16 mi from city center

$90

per night

Nov 1 - Nov 2

This hotel features an indoor pool and a 24-hour gym. Enjoy the sauna and perks like free self parking and free WiFi. There's a bar/lounge on site, and laundry facilities and free newspapers are also provided.

Hilton Garden Inn Chesterton

501 Gateway Boulevard, Chesterton, IN

Free Cancellation

Reserve now, pay when you stay

2.64 mi from city center

$136

per night

Oct 23 - Oct 24

This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the 4 conference rooms, 24-hour business center, and express check-in. Enjoy the spa tub and perks like free self parking.

Waterbird Lakeside Inn

556 Indian Boundary Road, Chesterton, IN

Free Cancellation

Reserve now, pay when you stay

1.08 mi from city center

$99

per night

Oct 2 - Oct 3

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Express check-out and laundry facilities are also provided.

Fairbridge Inn Express Chesterton

713 Plaza Dr., Chesterton, IN

Free Cancellation

Reserve now, pay when you stay

1.18 mi from city center

$82

per night

Oct 2 - Oct 3

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. The front desk is staffed around-the-clock and laundry facilities are on offer.

Blue Chip Casino Hotel and Spa

777 Blue Chip Drive, Michigan City, IN

Free Cancellation

Reserve now, pay when you stay

11.63 mi from city center

$112

per night

Oct 2 - Oct 3

This hotel features a casino, a full-service spa, and 3 restaurants. Traveling for business? Take advantage of the free WiFi in public areas, laundry service, and conference space. You'll appreciate the indoor pool, bar/lounge, and coffee shop.

Baymont by Wyndham New Buffalo

18800 Harbor Country Drive, New Buffalo, MI

Free Cancellation

Reserve now, pay when you stay

20.63 mi from city center

$67

per night

Oct 8 - Oct 9

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the outdoor tennis court and free perks like continental breakfast and free self parking.

Four Winds Casino Resort – New Buffalo

11111 Wilson Road, New Buffalo, MI

Free Cancellation

20.74 mi from city center

$149

per night

Oct 31 - Nov 1

A casino, 5 restaurants, and 2 spa tubs are all featured at this hotel. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and free valet parking. Unwind with a drink at one of the 3 bars/lounges and enjoy free perks like free self parking and an area shuttle.

Microtel Inn & Suites by Wyndham Michigan City

9834 W 400 N, Michigan City, IN

Free Cancellation

Reserve now, pay when you stay

9.71 mi from city center

$65

per night

Nov 1 - Nov 2

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Country Inn & Suites by Radisson, Merrillville, IN

8311 Ohio, Merrillville, IN

Free Cancellation

16.63 mi from city center

$84

per night

Oct 8 - Oct 9

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like on-the-go breakfast and free self parking.

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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.

Top hotels in Chesterton where Kids stay FREE

Fairbridge Inn Express Chesterton

713 Plaza Dr., Chesterton, IN

$82

per night

Oct 2 - Oct 3

6.2/10 (196 reviews)

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.

Top family friendly Chesterton hotel deals

Fairbridge Inn Express Chesterton

713 Plaza Dr., Chesterton, IN

$82

per night

Oct 2 - Oct 3

6.2/10 (196 reviews)

Top cheap Chesterton hotel deals

Fairbridge Inn Express Chesterton

713 Plaza Dr., Chesterton, IN

$82

per night

Oct 2 - Oct 3

6.2/10 (196 reviews)

Top hotels in Chesterton for Extended Stay

The Neighborhood Hotel Grand Beach Suite 8 - Studio

Grand Beach

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.

Chesterton Hotel & Travel Guide\n

Planning to spend some time in Northwest Indiana? Need to reserve a hotel in Chesterton? Within a 6-mile (10-kilometer) distance from the center of Chesterton, you will find 8 suitable hotel options.

Hoping to come across somewhere to base yourself within strolling distance of the middle of Chesterton? Hilton Garden Inn Chesterton and Best Western Indian Oak is sure to suit your needs.

The Blue Chip Casino Hotel and Spa is about 12 miles (19 kilometers) from the main part of Chesterton. Or, alternatively, the Inn at Aberdeen can be found approximately 11 miles (18 kilometers) away. Another possibility is to book a bed at the Holiday Inn Express Valparaiso or the Hampton Inn Merrillville.

Planning on checking out more of the rural landscapes common to this area? How about you spend some time in some of the other pockets of Northern Indiana? Enlightened visitors should meet locals at the region's diverse sights or try your luck at hiking before you check in to a close Travelocity-registered hotel to stay the night.

Schererville is found 11 miles (18 kilometers) to the northeast of Chesterton. During your stay, take the chance to see the Lighthouse Place Premium Outlets. Michigan City features some comfortable Travelocity-listed places to spend the night. While exploring the region, you might like to visit Schererville, where you can explore the Hoosier Prairie. Schererville is located 20 miles (35 kilometers) west of Chesterton. Travelocity-registered room options in Schererville include the Holiday Inn Express & Suites Schererville and Hampton Inn & Suites Schererville.

If you think of sport as your life and enjoy attending local clashes you should definitely spend the day at Wrigley Field, situated 40 miles (63 kilometers) to the northwest of Chesterton. Book a Travelocity-listed hotel close to the action at the Roscoe Village Guesthouse or the Best Western Plus Hawthorne Terrace Hotel.

If you're traveling through Midway International Airport and would like to book a Travelocity-listed hotel in the area, try Chicago Marriott Midway or Residence Inn Marriott Chicago Midway.

Chesterton hotels essential information

Accommodation	1,071 hotels
Lowest Price	$65
Highest Price	$149
Popular hotels	Best Western Indian Oak, Hilton Garden Inn Chesterton, Waterbird Lakeside Inn, Fairbridge Inn Express Chesterton, Blue Chip Casino Hotel and Spa, Baymont by Wyndham New Buffalo, Four Winds Casino Resort – New Buffalo, Microtel Inn & Suites by Wyndham Michigan City, Country Inn & Suites by Radisson, Merrillville, IN

Frequently asked questions

What are the top kid-friendly hotels in Chesterton?

Take some of the troubles out of traveling with kids by choosing a family-friendly hotel in Chesterton. From well-thought-out amenities to extra-helpful services, these stays come with perks that’ll help make your getaway run like a dream: The entire crew will enjoy staying at Rileys Railhouse Bed & Breakfast. Pet-friendly facilities and free WiFi are just a few of the things that help make this property a sought-after option. Sweet Home in Chesterton Dog Friendly is another great choice. After an exciting day of exploring Chesterton, come home to your comfy room and amenities like a nearby beach and animal viewing activities.

Where can I find cheap hotels in Chesterton?

At Travelocity you’ll find really nice hotels in Chesterton at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Chesterton rather than in Chesterton. We may find you even better rates, too.

How do I find the best Chesterton hotel deals?

Simple! On Travelocity, look through the fantastic offers we’ve already found in Chesterton then use our filters to find a great deal that’s perfect for you. Enter your travel dates, select the number of rooms you need, and we’ll do the rest. You can get great discounts on flights and car hire, too, when you bundle.

How much does it cost to stay in a hotel in Chesterton?

The cheapest hotel in Chesterton is $65. This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel’s location. Prices and availability are subject to change. Additional terms apply.

How many hotels are in Chesterton?

There are 1,071 hotels in Chesterton on Travelocity.

What are the best hotels in Chesterton?

Chesterton has so many great hotels to choose from at Travelocity — and it’s so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Chesterton for you!

When is the best time to visit Chesterton?

If you want the joy of a fun-filled trip in peak season, visit Chesterton during May, June and July. If you’d prefer the peace of off-season, book a stay during quieter months, such as December, January and February.

When is the cheapest time to stay in Chesterton?

Based on historic data is usually the cheapest month to visit Chesterton. However, we have incredible deals all year round, so we’re confident you’ll find a room in your budget whenever you choose to travel.

Are there any great family-friendly hotels in Chesterton?

There are multiple hotels in Chesterton that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We’ve got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Chesterton. We have plenty of kid-friendly hotels in Chesterton to choose from on Travelocity!

Why book a hotel in Chesterton through Travelocity?

Because we have the top hotels in Chesterton! We want to help you travel more and worry less. That’s why we’ve put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you’re getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!

How do I cancel my hotel booking in Chesterton on Travelocity?

Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Chesterton hotel reviews by fellow wanderers

Best Western Indian Oak

5 out of 5

Posted 2 days ago

Travelocity Verified Review

"The staff was welcoming, friendly, and helpful. The room was clean and accommodating. The bathroom was immaculate, and the amenities were good. The bed was comfortable, and our stay was pleasant and quiet. The breakfast was wonderful with lots of options in a nice room. We would definitely stay here again."

A verified traveler stayed at Best Western Indian Oak