A wooden staircase ascending a sandy hill with sparse vegetation.

Best Resorts in Chesterton

Check prices for these dates

Next weekend
Aug 28 - Aug 30
In two weeks
Sep 4 - Sep 6
In one month
Sep 18 - Sep 20
In two months
Oct 16 - Oct 18
No exact matches found, but these alternatives could be just right

Recommended hotels in Chesterton

Exterior

1. Best Western Indian Oak

Best Western Indian Oak
2.5 star property
Chesterton
8.6 out of 10, Excellent, (1,005 reviews)
"Everything was lovely and a very quiet hotel. Has a great stay!"
United States
Catherine
$110 nightly
The price is $124
Sep 1 - Sep 2
Total with taxes and fees
Best Western Indian Oak
Property entrance

2. Spring House Inn

Spring House Inn
2.5 star property
Chesterton
8.8 out of 10, Excellent, (1,020 reviews)
"Beautiful scenery and very helpful staff"
United States
Amanda
$123 nightly
The price is $138
Sep 1 - Sep 2
Total with taxes and fees
Spring House Inn
Exterior

3. Furness Mansion

Furness Mansion
2.0 star property
Chesterton
9.0 out of 10, Wonderful, (93 reviews)
"Charming venue. We’re glad we stayed!"
United States
Margaret
$127 nightly
The price is $142
Aug 25 - Aug 26
Total with taxes and fees
Furness Mansion
Lobby

4. 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
8.0 out of 10, Very Good, (808 reviews)
"We enjoyed our stay there. Location is near Indiana dunes national park."
United States
Guay
$91 nightly
The price is $102
Sep 17 - Sep 18
Total with taxes and fees
Quality Inn Chesterton near Indiana Dunes National Park I-94
Room, 1 King Bed, Lake View | Iron/ironing board, WiFi (free), bed sheets

5. Waterbird Lakeside Inn

Waterbird Lakeside Inn
2.0 star property
Chesterton
8.2 out of 10, Very Good, (1,007 reviews)
"Enjoyed my stay"
United States
Ashley
$114 nightly
The price is $128
Aug 23 - Aug 24
Total with taxes and fees
Waterbird Lakeside Inn
Lobby

6. Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton
3.0 star property
Chesterton
8.8 out of 10, Excellent, (1,012 reviews)
"Great place to stay"
United States
Lynette
$153 nightly
The price is $171
Aug 31 - Sep 1
Total with taxes and fees
Hilton Garden Inn Chesterton
Beach nearby

7. Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes

Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes
Chesterton
8.8 out of 10, Excellent, (131 reviews)
"Very cozy, comfortable, and relaxing we’ll stay there again"
United States
Vanski M.
$149 nightly
The price is $167
Aug 19 - Aug 20
Total with taxes and fees
Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes
Restaurant

8. Fairbridge Inn Express Chesterton

Fairbridge Inn Express Chesterton
2.0 star property
Chesterton
6.8 out of 10, (376 reviews)
"Friendly staff great locatikn"
United States
Kayla
$96 nightly
The price is $107
Sep 4 - Sep 5
Total with taxes and fees
Fairbridge Inn Express Chesterton
Beach nearby

9. The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes

The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes
Porter
9.0 out of 10, Wonderful, (20 reviews)
"Awesome place to stay and plenty to do"
United States
Cody
$257 nightly
The price is $288
Aug 23 - Aug 24
Total with taxes and fees
The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes
Smart TV, fireplace, books

10. Dunes Home – Walk to Town, Fenced Yard, Near Dunes | Valpo University | Dunes

Dunes Home – Walk to Town, Fenced Yard, Near Dunes | Valpo University | Dunes
Chesterton
9.6 out of 10, Exceptional, (74 reviews)
"Very nice space, with plenty of room and a great location. "
United States
Briana R.
$339 nightly
The price is $380
Sep 3 - Sep 4
Total with taxes and fees
Dunes Home – Walk to Town, Fenced Yard, Near Dunes | Valpo University | Dunes
Exterior

11. The Porter Nook! 5 minutes to Indiana Dunes, Pet Friendly

The Porter Nook! 5 minutes to Indiana Dunes, Pet Friendly
Porter
9.0 out of 10, Wonderful, (6 reviews)
"Jessica was a great host to my family and me. We spent two nights there and she was very accommodating of our needs and special requests."
United States
Jess K.
$233 nightly
The price is $261
Sep 15 - Sep 16
Total with taxes and fees
The Porter Nook! 5 minutes to Indiana Dunes, Pet Friendly
Beach nearby

12. The "Pool Barn Camper" w/Hot Tub near Indiana Dunes

The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
Porter
8.4 out of 10, Very Good, (22 reviews)
"Great Stay!"
United States
Erin
$193 nightly
The price is $216
Aug 23 - Aug 24
Total with taxes and fees
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
Smart TV, fireplace, foosball, books

13. Roomy Retreat–Family&Friends|2 King Beds|Game Room | Valpo University | Dunes

Roomy Retreat–Family&Friends|2 King Beds|Game Room | Valpo University | Dunes
Chesterton
9.2 out of 10, Wonderful, (22 reviews)
"I really enjoyed my stay even though I did not venture out but the house was like a dreamy oasis. "
United States
Kendall C.
Roomy Retreat–Family&Friends|2 King Beds|Game Room | Valpo University | Dunes
House (4 Bedrooms) | Front of property

14. Sugar Shores ~ 3 Mi to Indiana Dunes Nat'l Park

Sugar Shores ~ 3 Mi to Indiana Dunes Nat'l Park
3.0 star property
Chesterton
$542 nightly
The price is $607
Sep 3 - Sep 4
Total with taxes and fees
Sugar Shores ~ 3 Mi to Indiana Dunes Nat'l Park
Lobby

15. 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, (1,007 reviews)
"Was easy to check in and out. Good location, felt safe. Was kept clean"
United States
Christopher
$114 nightly
The price is $128
Sep 8 - Sep 9
Total with taxes and fees
Comfort Inn & Suites Porter near Indiana Dunes
Interior

16. NEW! Beautiful Riverfront Home on 10 Acres!

NEW! Beautiful Riverfront Home on 10 Acres!
Chesterton
8.2 out of 10, Very Good, (12 reviews)
"Very tranquil and private stay. The house was clean and comfortable, the fire pit was very nice,. CLose to town, and close to the beach. We loved it."
United States
Jeff S.
$548 nightly
The price is $614
Sep 1 - Sep 2
Total with taxes and fees
NEW! Beautiful Riverfront Home on 10 Acres!
6 bedrooms, desk, WiFi (free)

17. Full House booking of a history building close to the Dunes

Full House booking of a history building close to the Dunes
Chesterton
9.4 out of 10, Exceptional, (6 reviews)
"Beautiful historic building. "
United States
Deborah S.
$2,036 nightly
The price is $2,280
Aug 25 - Aug 26
Total with taxes and fees
Full House booking of a history building close to the Dunes
WiFi (free)

18. Home2 Suites by Hilton Michigan City

Home2 Suites by Hilton Michigan City
3.0 star property
Michigan City
9.0 out of 10, Wonderful, (18 reviews)
"New property and kept very clean. Suites are spacious. The staff is friendly and helpful. Hot breakfast and hot tea available at night. Would highly recommend"
United States
Preksha
$139 nightly
The price is $155
Aug 30 - Aug 31
Total with taxes and fees
Home2 Suites by Hilton Michigan City
Exterior

19. Tru By Hilton Valparaiso

Tru By Hilton Valparaiso
2.5 star property
Valparaiso
9.4 out of 10, Exceptional, (26 reviews)
"Nice new property, clean rooms, welcoming staff, great breakfast. "
United States
Amy
$114 nightly
The price is $128
Sep 6 - Sep 7
Total with taxes and fees
Tru By Hilton Valparaiso
Indoor pool

20. 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, (1,001 reviews)
"Clean and convenient location. Good option for families."
United States
Randal
$148 nightly
The price is $166
Aug 27 - Aug 28
Total with taxes and fees
Country Inn & Suites by Radisson, Portage, IN
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.
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Top Chesterton Hotel Reviews

Waterbird Lakeside Inn

Waterbird Lakeside Inn

10/10 Excellent
"Room and bathroom were clean. Everything worked inclueding the iron. Stores and food places very close. Attended a wedding at the very nice venue right next door, can't remember the name, sorry. Nice view of the lake, balcony over hangs the water pretty cool. AC worked great, I had a very comfortable stay very convenient for the wedding I attended."
Tim 2-night trip
Posted 6 hours ago
Waterbird Lakeside Inn

Find out more about Chesterton

Chesterton Resorts information

Number of reviews
9,619
Accommodation
0 Resorts
Lowest Price
$59
Highest Price
$607

Frequently asked questions

What is Chesterton like for a resort vacation?
Expedia can help you find resorts and other lodging options that offer similar amenities and comforts. If you have trouble finding a resort in Chesterton that works for you, try using the search page filters to look for hotels, or search for properties that offer amenities like pools or all-inclusive rates. We make it easy to book great accommodations so you can focus on planning your trip itinerary.
What can I do in Chesterton?
Travelers enjoy exploring the beaches, and have good things to say about the shopping and other activities. Dune Acres Beach and Kemil Beach are great places to spend time by the water, while other big draws include Indiana Dunes National Park and Indiana Dunes State Park. Additional attractions in the area include Lake Michigan and Lustron House.
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.
What's the best way to get to and around Chesterton?
Fly into Chicago Midway Airport (MDW), which is located 37 mi (59.6 km) from the heart of the city. You can also search for flights into Chicago O'Hare Intl. Airport (ORD), which is 50.2 mi (80.7 km) away. If you'd like to explore around the area, you may want to rent a car for your trip.

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