Search Bed and Breakfasts in Chesterton

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
2 May - 4 May
In two weeks
9 May - 11 May
In one month
23 May - 25 May
In two months
20 Jun - 22 Jun

Browse Select Chesterton B&B

Valparaiso Inn Bed & Breakfast
Front of property – evening/night

Valparaiso Inn Bed & Breakfast

3.5 star property
10.0 out of 10, Exceptional, (25)
"The room was spotless, the bed was very comfortable, the gourmet breakfasts were superb, and the host was friendly and knowledgeable. It exceeded our expectations!"
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
Sign in
Sign up, it's free

Other property types in Chesterton

The Neighborhood Hotel - Grand Beach
Beach nearby, beach towels

The Neighborhood Hotel - Grand Beach

4.0 star property
9.6 out of 10, Exceptional, (46)
"This is our second trip to the Grand Beach Neighborhood. We traveled with our girls, their husbands and grandchildren and their dogs. The accommodations were perfect. The full kitchen was perfect as we brought food to prepare while we stayed. The unit was very Clean and the in unit washer and dryer came in handy with the kiddos. We loved the Saturday breakfast was delicious and Pamela was so inviting and helpful. The evening bonfires were a fun gathering area and loved the common area hangout....
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

Searching for B&Bs in Chesterton?
Whether you’re on a family holiday and want a small, cosy place to stay, or you’re travelling solo and hoping to meet fellow tourists, B&Bs can be a great choice for many types of holidaymakers. If your ideal holiday to Chesterton includes spending lots of time outside, Indiana Dunes National Park and Indiana Dunes Visitor Center are good spots to enjoy the scenery.
Are you thinking about an apartment instead of a traditional hotel?
Every B&B has its own unique feel — whether it’s a comfy common area with a fireplace or a beautiful breakfast room, the tiny details are what make bed and breakfasts a fun place to get away.
What are the best B&Bs in Chesterton?
Take a look at this B&B in the area: Valparaiso Inn Bed & Breakfast: 5 rooms. 9.7 mi (15.6 km) from the heart of Chesterton. Enjoy the free full breakfast and private garden.
When is the best time to book my B&B in Chesterton?
When you’re planning your trip to Chesterton, make sure that you take the year-round temperatures into account. The hottest months are usually July and August, with an average temperature of 21°C, while the coldest months are January and February, with an average of 0°C. The snowiest months in Chesterton are January, December, November and February, with each month seeing an average of 15 cm of snowfall.
What is there to do in Chesterton?
Travellers looking to spend some time in nature enjoy Chesterton for its beaches and lakeside setting. Spend some time exploring Indiana Dunes National Park and Lake Michigan if you’re hoping to see some of the area’s natural features. You should put Indiana Dunes Visitor Center and Bailly Homestead - American Indians and Fur Traders on your list if you want to see more of the area.
How can I get to and around Chesterton?
You can map out your trip in and around Chesterton ahead of time with these transportation options. Fly into Chicago Midway Airport (MDW), which is located 37 mi (59.6 km) away from the heart of the city. Otherwise, you can search for flights to Chicago O’Hare International Airport (ORD), which is 50.2 mi (80.7 km) away. If you’d like to explore around the area, you may want a rental car for your journey.