A wooden staircase ascending a sandy hill with sparse vegetation.

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Check prices for these dates

Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10
No exact matches found, but these alternatives could be just right

Recommended hotels in Chesterton

A wooden deck with a railing overlooking a calm lake at sunset.

1. Best Western Indian Oak

Best Western Indian Oak
2.5 star property
Chesterton
8.6 out of 10, Excellent, (1,003 reviews)
"The staff was friendly and room was clean."
United States
Alyssa
$89 nightly
The price is $100
Nov 22 - Nov 23
Total with taxes and fees
Best Western Indian Oak
A spacious room with wooden floors, a large chandelier, and a cozy seating area with sofas and chairs.

2. Spring House Inn

Spring House Inn
2.5 star property
Chesterton
8.8 out of 10, Excellent, (1,004 reviews)
"Good breakfast, staff was very helpful, there was a good restaurant on site."
United States
Michael
$95 nightly
The price is $107
Nov 30 - Dec 1
Total with taxes and fees
Spring House Inn
A spacious lobby with high ceilings, modern lighting fixtures, and potted plants.

3. Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton
3.0 star property
Chesterton
8.8 out of 10, Excellent, (1,000 reviews)
"Excellent hotel, friendly staff"
United States
Cheryl
$126 nightly
The price is $141
Dec 4 - Dec 5
Total with taxes and fees
Hilton Garden Inn Chesterton
A modern building with a stone facade and a sign for 'Waterbird Lakeside Inn'.

4. Waterbird Lakeside Inn

Waterbird Lakeside Inn
2.0 star property
Chesterton
8.2 out of 10, Very good, (1,000 reviews)
"Loved the balcony overlooking the lake."
United States
Marsha
$95 nightly
The price is $106
Nov 15 - Nov 16
Total with taxes and fees
Waterbird Lakeside Inn
A hotel room with a bed, a chair, a nightstand, and a lamp.

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, (875 reviews)
"Had a great weekend. Staff was great, room was clean, facility was great for a budget."
United States
Albie
$76 nightly
The price is $85
Dec 14 - Dec 15
Total with taxes and fees
Quality Inn Chesterton near Indiana Dunes National Park I-94
A reception area with a counter, a vending machine, and a view of the outside through glass doors.

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
$80 nightly
The price is $90
Dec 13 - Dec 14
Total with taxes and fees
Comfort Inn & Suites Porter near Indiana Dunes
A dining area with a round table and four striped chairs, a window with blinds, and an air conditioning unit on the wall.

7. Furness Mansion

Furness Mansion
2.0 star property
Chesterton
9.0 out of 10, Wonderful, (119 reviews)
"Very unique stay! Easy check-in, and staff was easily accessible via text. Would definitely stay here again due to its closeness to the Dunes and restaurants!"
United States
Noelle
$127 nightly
The price is $142
Nov 16 - Nov 17
Total with taxes and fees
Furness Mansion
A patio with a table and chairs, a bicycle, and a string of lights against a twilight sky.

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

The Porter Nook! 5 minutes to Indiana Dunes, Pet Friendly
Porter
9.4 out of 10, Exceptional, (11 reviews)
"We enjoyed our stay. Very inviting and comfortable accommodations. Would stay again and would recommend!"
United States
Amanda E.
$218 nightly
The price is $244
Dec 1 - Dec 2
Total with taxes and fees
The Porter Nook! 5 minutes to Indiana Dunes, Pet Friendly
A beach with a parking lot and buildings in the background.

9. 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, (141 reviews)
"Perfect for location to walk to local winery or brewery for a little fancy and fancy-free!We’d recommend"
United States
Laura H.
$131 nightly
The price is $147
Nov 15 - Nov 16
Total with taxes and fees
Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes
A hotel lobby with a red carpet, a bookshelf with books, a potted plant, a table with chairs, a small table with a vase, and a door with a red mat.

10. Fairbridge Inn Express Chesterton

Fairbridge Inn Express Chesterton
2.0 star property
Chesterton
6.8 out of 10, (399 reviews)
"Stayed here several times over the years. Always clean so we keep coming back. Recently updated furniture is an improvement."
United States
Daniel
$88 nightly
The price is $99
Dec 15 - Dec 16
Total with taxes and fees
Fairbridge Inn Express Chesterton
A beach with sand dunes and grass.

11. 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, (22 reviews)
"Awesome place to stay and plenty to do"
United States
Cody
$215 nightly
The price is $241
Nov 15 - Nov 16
Total with taxes and fees
The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes
A beach with a sunset, waves, and sparse vegetation.

12. Tower Haus w/Private Hot Tub

Tower Haus w/Private Hot Tub
Chesterton
9.8 out of 10, Exceptional, (40 reviews)
"Super clean, new and well-stocked house. Great for our family of five."
United States
john
$262 nightly
The price is $294
Dec 1 - Dec 2
Total with taxes and fees
Tower Haus w/Private Hot Tub
A fire pit surrounded by six Adirondack chairs in various colors.

13. 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, (77 reviews)
"Great location, walking distance to downtown Chesterton which had an excellent ice cream shop and other restaurants. Easy driving distance to different parts of Indiana Dunes National Park. Host had great communication before and throughout the visit and the house had all the amenities we needed."
United States
Ammari Capito F.
$329 nightly
The price is $369
Nov 24 - Nov 25
Total with taxes and fees
Dunes Home – Walk to Town, Fenced Yard, Near Dunes | Valpo University | Dunes
A backyard with a barbecue grill, a picnic table, and chairs.

14. Dunes Homestead - Near Dunes + Lake + Dog Friendly

Dunes Homestead - Near Dunes + Lake + Dog Friendly
Porter
9.8 out of 10, Exceptional, (37 reviews)
"Everything was as described, and had everything we needed!"
United States
Chrissy B.
$311 nightly
The price is $348
Nov 28 - Nov 29
Total with taxes and fees
Dunes Homestead - Near Dunes + Lake + Dog Friendly
A modern kitchen with a central island, stainless steel appliances, and a clock on the wall.

15. NEW! Beautiful Riverfront Home on 10 Acres!

NEW! Beautiful Riverfront Home on 10 Acres!
Chesterton
7.8 out of 10, Good, (13 reviews)
"The host was responsive and super friendly. We loved staying here - Chesterton was beautiful and the downtown area was incredible. We fell in love."
United States
Amanda H.
$320 nightly
The price is $358
Nov 26 - Nov 27
Total with taxes and fees
NEW! Beautiful Riverfront Home on 10 Acres!
A beach with sand dunes and grass.

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

The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
Porter
8.6 out of 10, Excellent, (23 reviews)
"Camper is small, but cozy and worked well for my son and I to spend a few days relaxing! Hosts are very friendly, responsive, and helpful and we loved spending time in the pool."
United States
Melissa P.
$141 nightly
The price is $158
Nov 23 - Nov 24
Total with taxes and fees
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
A bedroom with a bed, a ceiling fan, a window, a desk, and a chair.

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)
"We are happy with the property. clean property, quite spacious and large enough to accommodate large group, quite close to Dunes."
United States
Mahesh K.
$1,934 nightly
The price is $2,166
Nov 16 - Nov 17
Total with taxes and fees
Full House booking of a history building close to the Dunes
A spacious living area with a fireplace, a staircase, and a cozy seating arrangement.

18. 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
$141 nightly
The price is $158
Dec 10 - Dec 11
Total with taxes and fees
Country Inn & Suites by Radisson, Portage, IN
A spacious interior with a central staircase, multiple doors, and a chandelier.

19. Quality Inn & Suites Portage Central

Quality Inn & Suites Portage Central
2.5 star property
Portage
6.8 out of 10, (952 reviews)
"Clean room, staff very helpful."
United States
robert
$70 nightly
The price is $79
Dec 6 - Dec 7
Total with taxes and fees
Quality Inn & Suites Portage Central
A two-story brick house with a gabled roof, surrounded by a well-maintained garden with various plants and a lawn.

20. The Brewery Lodge Hotel

The Brewery Lodge Hotel
3.5 star property
Michigan City
9.0 out of 10, Wonderful, (928 reviews)
"Was a great stay. Would highly recommend."
United States
Andrew
$99 nightly
The price is $111
Nov 29 - Nov 30
Total with taxes and fees
The Brewery Lodge Hotel
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

Best Western Indian Oak

Best Western Indian Oak

10/10 Excellent
"Room was clean with a beautiful view though it was too cold to sit outside and enjoy it. Breakfast was average. Make your own waffles, scrambled eggs and sausage links or patties every day and then the norm toast,bagels muffins, fruit, juice and coffee. Hotel was great and workers were amazing."
Wretha 3-night trip
Posted 1 day ago
Best Western Indian Oak

Find out more about Chesterton

Chesterton B&B information

Number of reviews
5,244
Accommodation
1 B&B
Lowest Price
$79
Highest Price
$2,166

Frequently asked questions

What is the nightly rate for a B&B in Chesterton?
Prices for B&Bs in Chesterton often vary, but you can find a great deal from $79 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Chesterton B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a Bed and Breakfast in Chesterton?
The best time to book a B&B in Chesterton is during the late spring and early summer months, particularly from May to June. This period showcases the picturesque landscapes and vibrant flora of the Indiana Dunes National Park, making it an ideal time for outdoor enthusiasts and families looking for adventure. The pleasant temperatures, typically ranging from the low 50s to mid-70s Fahrenheit, create a comfortable environment for hiking, biking, and enjoying the stunning beaches along Lake Michigan.

As the summer progresses, July attracts a higher volume of visitors, drawn to the area's many festivals and events. This lively atmosphere is great for those who thrive on socializings and community celebrations. However, if you prefer a more tranquil experience while still enjoying lovely weather, consider booking your stay in late May or early June, when the crowds are lighter, yet the natural beauty is at its peak.

For travelers seeking budget-friendly options, October presents a fantastic opportunity to appreciate the fall foliage and enjoy a quieter, more reflective ambiance. The crisp air and stunning autumn colors along the trails provide a great backdrop for leisurely strolls and scenic drives.
What is the difference between a Chesterton Bed & Breakfast and a hotel?
Every Chesterton B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Chesterton B&Bs.

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