Photo by Ruslian

Find Romantic Hotels in Chesterton, IN

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Chesterton Romantic Hotels

Tonight
26 Nov - 27 Nov
Tomorrow
27 Nov - 28 Nov
This weekend
28 Nov - 30 Nov
Next weekend
5 Dec - 7 Dec

Top Chesterton Romantic Hotels

4 restaurants, dinner served
Four Winds Casino Resort – New Buffalo

Four Winds Casino Resort – New Buffalo

3.5 star property
New Buffalo
9.4 out of 10, Exceptional, (1625)
"Great place to stay"
United States
Rich
The price is AED 280
AED 325 total
includes taxes & fees
1 Dec - 2 Dec
Four Winds Casino Resort – New Buffalo
Exterior
Blue Chip Casino Hotel and Spa

Blue Chip Casino Hotel and Spa

3.5 star property
Michigan City
8.2 out of 10, Very Good, (1839)
"property was nice and clean and the employees were polite and professional. Would stay again"
United States
Evelyn
The price is AED 306
AED 396 total
includes taxes & fees
2 Dec - 3 Dec
Blue Chip Casino Hotel and Spa
Terrace/patio
Home2 Suites by Hilton Merrillville

Home2 Suites by Hilton Merrillville

3.0 star property
Merrillville
9.0 out of 10, Wonderful, (999)
"The rooms are very spacious, it’s in a great location. The staff are very friendly and we would definitely stay here again."
United States
Sherrie
The price is AED 320
AED 359 total
includes taxes & fees
7 Dec - 8 Dec
Home2 Suites by Hilton Merrillville
Lobby
Ameristar Casino Hotel East Chicago

Ameristar Casino Hotel East Chicago

4.0 star property
East Chicago
8.6 out of 10, Excellent, (1023)
"We are local to the area, and were very pleased with the hotel experience!"
United States
Junetta
Ameristar Casino Hotel East Chicago
Children's pool
Rodeway Inn

Rodeway Inn

2.5 star property
Portage
7.0 out of 10, Good, (790)
"Decent place to stay. Room was comfortable. Coffee in lobby needs improving. Overall ok place to stay."
United States
Gary
The price is AED 181
AED 203 total
includes taxes & fees
25 Dec - 26 Dec
Rodeway Inn
Front of property
The Brewery Lodge Hotel

The Brewery Lodge Hotel

3.5 star property
Michigan City
9.0 out of 10, Wonderful, (785)
"Great place to stay"
United States
James
The Brewery Lodge Hotel
Indoor pool, seasonal outdoor pool, sun loungers
Pine Lake Resort and Banquets

Pine Lake Resort and Banquets

2.5 star property
La Porte
6.8 out of 10, (577)
"Great stay"
United States
Tiffany
The price is AED 290
AED 334 total
includes taxes & fees
27 Nov - 28 Nov
Pine Lake Resort and Banquets
Outdoor dining
Huge yard, Family-friendly, Hot Tub, walk to Beach, Dunes, Hiking Trails

Huge yard, Family-friendly, Hot Tub, walk to Beach, Dunes, Hiking Trails

Miller Beach
8.6 out of 10, Excellent, (45)
"Great place and great location "
United States
Travis B.
Huge yard, Family-friendly, Hot Tub, walk to Beach, Dunes, Hiking Trails
Interior entrance
Michigan City Inn

Michigan City Inn

Michigan City
4.6 out of 10, (1000)
"Good area to stay for Indiana Dunes or beach. Hotel needs some new carpet and paint and would be a great place to stay."
United States
Ryan
The price is AED 331
AED 370 total
includes taxes & fees
27 Nov - 28 Nov
Michigan City Inn
Beach
On Lake Shore Drive, Across St From Beach & Beach Stop, Lake MI Views

On Lake Shore Drive, Across St From Beach & Beach Stop, Lake MI Views

Michigan City
9.6 out of 10, Exceptional, (76)
"House was very clean and not too far from the beach. Loved sitting on the porch listening to the water. Will definitely be booking again next year. "
United States
Rebecca B.
The price is AED 1,612
AED 1,872 total
includes taxes & fees
30 Nov - 1 Dec
On Lake Shore Drive, Across St From Beach & Beach Stop, Lake MI Views
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.
View all properties

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels
Book now

Top Chesterton Hotel Reviews

Waterbird Lakeside Inn

Waterbird Lakeside Inn

10/10 Excellent
"Waterside view was wonderful"
Dana 1-night trip
Posted 4 days ago
Waterbird Lakeside Inn

Explore a world of travel with Expedia

Frequently asked questions

Searching for romantic hotels in Chesterton?
Are you looking for a romantic vacation? Our guests also enjoy Chesterton for its shopping, restaurants, and beaches. If you'd like to explore some of the area's notable sights, you might make a stop by Lake Michigan, Lustron House, or Chellberg Farm. If you'd like to stay close to a certain attraction, you can sort properties by neighborhood or distance to top sights, so you'll be able to see everything on your list.
When is the best time of year for a romantic getaway to Chesterton?
If you're looking forward to lots of outings with your partner, check out these details about year-round temperatures 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 is there to do in Chesterton?
There's nothing better than wandering around a new place with your sweetheart, so consider taking time to discover all that Chesterton has to offer. Couples looking for a little of everything will enjoy Chesterton for its beaches, lakeside setting, and restaurants. Lake Michigan, Lustron House, and Chellberg Farm are worth a stop when you're out and about.
What's the best way to get to Chesterton and around town during my romantic getaway?
These transportation options in Chesterton might help your romantic trip get off to a smooth start: To get to Chesterton, you can fly into Chicago Midway Airport (MDW), which is the closest major airport, located 37 mi (59.6 km) from the city center. If you'd like to explore around the area, you may want a rental car for your journey.