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Find Hotels in Chesterton, IN

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Chesterton hotels and places to stay

Hampton Inn & Suites Michigan City
2.5 out of 5
3674 North Frontage Road, Michigan City, IN
Free CancellationReserve now, pay when you stay
The price is $112 per night
9.16 mi from city center
4.4/5Wonderful! (310 reviews)

"The property was new, clean and decor was pleasing to the eye"…"

Reviewed on May 26, 2020

Hampton Inn & Suites Michigan City
Waterbird Lakeside Inn
2 out of 5
556 Indian Boundary Road, Chesterton, IN
Free CancellationReserve now, pay when you stay
The price is $59 per night
0.73 mi from city center
3.8/5Good! (301 reviews)

"Had an enjoyable stay. And it has a very nice view."…"

Reviewed on Jun 1, 2020

Waterbird Lakeside Inn
Motel 6 Hammond - Chicago Area
2 out of 5
3840 179th St, Hammond, IN
Free Cancellation
The price is $50 per night
19.85 mi from city center
3.2/5 (408 reviews)

"Was clean and well maintained staff pretty friendly and plenty of parking"…"

Reviewed on Feb 27, 2020

Motel 6 Hammond - Chicago Area
Best Western Indian Oak
2.5 out of 5
558 Indian Boundary Road, Chesterton, IN
Free CancellationReserve now, pay when you stay
The price is $80 per night
0.77 mi from city center
4/5Very Good! (432 reviews)

"The front desk staff was amazing. My complaint is the bed was hard, the couch had stains, the toilet was not cleaned very well. But the lakefront view was amazing."…"

Reviewed on Jun 1, 2020

Best Western Indian Oak
Country Inn & Suites by Radisson, Merrillville, IN
3 out of 5
8311 Ohio, Merrillville, IN
Free CancellationReserve now, pay when you stay
The price is $79 per night
16.94 mi from city center
4.1/5Very Good! (358 reviews)

"This property, just what our family needed. Even though, COVID-19, has the pool & fitness center closed. We look forward to visiting again."…"

Reviewed on Apr 20, 2020

Country Inn & Suites by Radisson, Merrillville, IN
Country Inn & Suites by Radisson, Portage, IN
3 out of 5
1630 Olmsted Dr, Portage, IN
Free CancellationReserve now, pay when you stay
The price is $101 per night
6.14 mi from city center
4.4/5Excellent! (1,016 reviews)

"Every time we stay here the staff is wonderful and the rooms are always clean!"…"

Reviewed on Apr 25, 2020

Country Inn & Suites by Radisson, Portage, IN
WoodSpring Suites Merrillville
2.5 out of 5
1500 E. 83rd Ave, Merrillville, IN
Free CancellationReserve now, pay when you stay
The price is $89 per night
16.71 mi from city center
3.5/5Good! (91 reviews)

"Bring your own towels, they charge $10 to give clean"…"

Reviewed on Apr 25, 2020

WoodSpring Suites Merrillville
Your Family Adventure Awaits! Private Kayak Launch New for 2020!
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0.5 mi from city center
5/5Exceptional! (2 reviews)
Immaculate house in a serene location!

"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We loved the blue "creek" house as my kiddos call ..."…"

Reviewed on May 29, 2020

Your Family Adventure Awaits! Private Kayak Launch New for 2020!
Sweet Home in Chesterton
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0.23 mi from city center
No reviews
a good stay in chesterton

"this place was clean and spacious and the hosts were very responsive and welcoming. it was so nice to be right in downtown Chesterton, walkable to many places."…"

Reviewed on Nov 30, 2019

Sweet Home in Chesterton
Comfort Suites Merrillville
2.5 out of 5
1344 E 83rd Ave, Merrillville, IN
Free CancellationReserve now, pay when you stay
The price is $69 per night
16.83 mi from city center
4.2/5Excellent! (666 reviews)

"They are awesome always at this location. Staff is always nice and kind"…"

Reviewed on Apr 11, 2020

Comfort Suites Merrillville
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Visiting Chesterton

Visitors to Chesterton are sure to enjoy the shopping, beaches, and restaurants. Tourists can also enjoy so much more including its coffeehouses.

  • There are 6 hotels and other accommodations in Chesterton
  • The closest major airport is in Chicago, IL (MDW-Midway Intl.), 37.7 mi (60.6 km) from the city center
  • The next closest is in Chicago, IL (ORD-O'Hare Intl.), 50.9 mi (81.9 km) away

Sightseeing and Staying in Chesterton

Places to visit in the larger region include Chellberg Farm, Bailly Homestead - American Indians and Fur Traders, and Indiana Dunes National Lakeshore. Additionally, you'll find Indiana Dunes State Park and Valparaiso University in the area.

As you plan your vacation, you'll find 6 hotels and other lodging options to choose from in Chesterton. Below are top ones based on our user reviews:

  • Riley's Railhouse - Amenities at this 3-star bed & breakfast include free breakfast and free WiFi. It's a favorite with Expedia travelers for its breakfast and comfortable rooms.
  • Hilton Garden Inn Chesterton - Our customers like the dining options and comfortable rooms at this hotel. This 3-star hotel features a restaurant, an indoor pool, and free WiFi.
  • Best Western Indian Oak - With a stay at this 2.5-star hotel, guests can enjoy access to free breakfast and an indoor pool, along with free WiFi. Expedia customers like its family-friendly amenities and pool.

Dressing for Chesterton

  • Between January and March, you can expect the daytime average to be around 54°F and the nighttime average to be 17°F
  • From April to June, temperatures average about 83°F during the day and 34°F at night
  • July through September averages 83°F during the day and 48°F at night
  • In October-December, the average temperature is 69°F during the day and 18°F at night
  • Chesterton gets about 40.75 inches of rain per year
  • Hottest months are usually July and June with an average temperature of 82°F, while the coldest months are January and February with an average of 20°F

Frequently asked questions

Where is the best place for a stay in Chesterton?
Hilton Garden Inn Chesterton is ranked highly by Expedia customers. This 3-star hotel offers a restaurant and an indoor pool. Reviews from our site also recommend Best Western Indian Oak and Quality Inn as top options for your visit.
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. Add dates, click “Search”, then you can filter by “free cancellation” to view the best 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 budget-friendly stay in Chesterton?
Based on reviews, Best Western Indian Oak is a popular 2.5-star hotel for our travelers looking for an economical choice, and features free full breakfast and free WiFi. Other options to stay on the cheap include Waterbird Lakeside Inn and Fairbridge Inn Express Chesterton.
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. Attractions in the area like Washington Park Zoo and International Friendship Gardens are also fun for kids of all ages.
What's the best hotel for a romantic vacation to Chesterton?
Waterbird Lakeside Inn is a favorite hotel for couples, and features private balconies and free WiFi.
What's the best pet-friendly place to stay in Chesterton?
Fairbridge Inn Express Chesterton is a top hotel for people traveling with their pets, and offers laundry facilities and free newspapers for its human guests. Gray Goose Inn is another good option if you’re bringing your pet along.
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 choices within 5 miles include Quality Inn and Best Western Indian Oak.
What about the best place to stay near Lustron House?
One of the top choices for your stay is Best Western Indian Oak, located a short 0.6 mi (0.9 km) from Lustron House, and this hotel offers free breakfast and an indoor pool. Quality Inn and Waterbird Lakeside Inn are a couple of other good and close options.
What's the best accommodation to stay near the beach in Chesterton?
Hilton Garden Inn Chesterton is a top 3-star hotel for a beach vacation, and features an indoor pool and a restaurant. Other good choices for your beach trip include Best Western Indian Oak and Quality Inn. Head to Waverly Beach or Lake View Beach for some quality time by the water.
What are some accommodations with pools in Chesterton?
Hilton Garden Inn Chesterton is a popular 3-star hotel featuring an indoor pool, a children’s pool, and a restaurant. Best Western Indian Oak is an additional hotel that features an onsite pool.
What is the best spa hotel in Chesterton?
Hilton Garden Inn Chesterton is a top spa hotel featuring a restaurant, an indoor pool, and a fitness center. Spend the afternoon relaxing in the spa tub and sauna. Other popular spa hotels in Chesterton include Best Western Indian Oak and Waterbird Lakeside Inn.

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