Book Chesterton Bed & Breakfast

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    one key illustration
    Treat yourself
    Save instantly and earn perks with One Key
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Compare 1 B&B in Chesterton with updated reviews, rates, and availability.

Valparaiso Inn Bed & Breakfast

3.5 star property
10.0 out of 10, Exceptional, (26)
"Wonderful host!"
Valparaiso Inn Bed & Breakfast
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.
Don't see what you're looking for?
See all available properties in Chesterton
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Chesterton

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

9.0 out of 10, Wonderful, (54)
"Donnie was so kind, and was very prompt with responding. It was a very cute space with plenty of amenities. Would definitely recommend to others. "
The price is $88
includes taxes & fees
$79 per night
May 1 - May 2
Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes

Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly

10.0 out of 10, Exceptional, (95)
"This house is in a beautiful and amazing location. The view of Lake Michigan is incredible and the house is cozy and welcoming. The little touches like board games and a pretty well equipped kitchen made it feel inviting and we hope to come back again sometime!"
Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly

The Neighborhood Hotel - Grand Beach

4.0 star property
9.6 out of 10, Exceptional, (46)
"Great hotel. Firepits, common area, s’mores bar and a great patio too. Within walking distance of the beach and you’ll get to see deer too. "
The Neighborhood Hotel - 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.

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 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.