A wooden staircase ascending a sandy hill with sparse vegetation.

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Check availability on Chesterton Luxury Hotels

Tonight
Oct 19 - Oct 20
Tomorrow
Oct 20 - Oct 21
This weekend
Oct 23 - Oct 25
Next weekend
Oct 30 - Nov 1
No exact matches found, but these alternatives could be just right

Recommended hotels in Chesterton

A bedroom with two beds, a ceiling fan, a TV on a dresser, and a window with blinds.
A bedroom with a large bed, two bedside tables, a ceiling fan, and a chair.
A bedroom with a bed, a desk, a chair, a television, and a ceiling fan.
A bedroom with a bed, a ceiling fan, a fireplace, and a television.

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

Full House booking of a history building close to the Dunes
Chesterton
￥281,592
￥360,337 total
includes taxes & fees
Nov 18 - Nov 19
Full House booking of a history building close to the Dunes
A beach with sand dunes and grass.
A two-story building with a white exterior and a covered porch.
A covered outdoor grill area with a metal roof and a glass enclosure, surrounded by a wooden deck.
A large house with a swimming pool, a covered patio, and a garage with multiple doors.

2. 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
￥31,446
￥39,821 total
includes taxes & fees
Oct 21 - Oct 22
The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes
A modern kitchen with a central island, wooden dining table, and chairs. There is a ceiling fan, a microwave, and a refrigerator.
A two-story house with a porch, a garage, and a wooded backdrop.
A modern kitchen with a central island, stainless steel appliances, and a clock on the wall.
A compact kitchen with grey cabinets, a wooden countertop, and a coffee maker.

3. NEW! Beautiful Riverfront Home on 10 Acres!

NEW! Beautiful Riverfront Home on 10 Acres!
Chesterton
￥25,125
￥61,767 total
includes taxes & fees
Nov 1 - Nov 2
NEW! Beautiful Riverfront Home on 10 Acres!
A beach with a sunset, waves, and sparse vegetation.
An outdoor patio with a gray sofa set, a barbecue grill, and a hot tub.
A bedroom with a bed, pillows, a ceiling fan, and a wardrobe.
A two-story building with a dark exterior, a front porch with wooden beams, and a small front yard with a gravel path.

4. Tower Haus w/Private Hot Tub

Tower Haus w/Private Hot Tub
Chesterton
￥21,048
￥45,342 total
includes taxes & fees
Oct 21 - Oct 22
Tower Haus w/Private Hot Tub
A large house surrounded by dense forest with a beach and ocean in the background.
A bedroom with a bed, a desk, a chair, a TV, and a ceiling fan.
A living room with two wicker chairs, a small table, and a grey sofa.
A dining area with a table and chairs, a door leading to a balcony, a fireplace, and a mounted television.

5. Furness Mansion

Furness Mansion
Chesterton
￥18,879
￥21,145 total
includes taxes & fees
Oct 27 - Oct 28
Furness Mansion
A beach with sand dunes and grass.
A large house with a swimming pool, a covered patio, and a garage with multiple doors.
A wooden play structure with a slide and a small building.
A fire pit surrounded by wooden benches and chairs in an outdoor setting.

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

The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
Porter
￥20,385
￥26,371 total
includes taxes & fees
Nov 3 - Nov 4
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
A spacious lobby with high ceilings, modern lighting fixtures, and potted plants.
A spacious lobby with a stone fireplace, comfortable seating, and large windows offering a view of the outdoors.
A modern reception area with a wooden reception desk, a small seating area, and a snack bar with various packaged goods.
A hotel room with a dining area, a sofa, a TV, and a microwave.

7. Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton
Chesterton
￥16,853
￥18,875 total
includes taxes & fees
Nov 2 - Nov 3
Hilton Garden Inn Chesterton
A beach with a parking lot and buildings in the background.
A bedroom with a bed, bedside tables, a nightstand, a window, and a bathroom with a bathtub.
A dining area with a table set for four, a potted plant, and a kitchen in the background.
A living room with a sectional sofa, a flat-screen TV, a wooden clock, and a window with a plant.

8. 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
￥18,804
￥24,600 total
includes taxes & fees
Oct 22 - Oct 23
Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes
A brick building with a balcony and green shutters, surrounded by trees.
A pool area with a round table and chairs, a tiled floor, and large windows.
A spacious dining area with high ceilings and large windows, featuring wooden tables and chairs.
A traditional half-timbered house with multiple balconies, a well-maintained garden, and a clear view of the surrounding greenery.

9. Spring House Inn

Spring House Inn
Chesterton
￥15,644
￥18,311 total
includes taxes & fees
Nov 1 - Nov 2
Spring House Inn
A modern bathroom with a large mirror, a bathtub, and a sink.
A spacious lobby with a staircase, a reception desk, and a chandelier.
A modern building with a stone facade and a sign for 'Waterbird Lakeside Inn'.
A wooden deck with two white plastic chairs facing a calm lake and forested hills.

10. Waterbird Lakeside Inn

Waterbird Lakeside Inn
Chesterton
  • Lakeside luxury thrives at this Chesterton retreat where private balconies frame serene water views and wildlife encounters.
￥14,852
￥16,634 total
includes taxes & fees
Oct 21 - Oct 22
Waterbird Lakeside Inn
View all properties

Top Chesterton Hotel Reviews

Blue Chip Casino Hotel and Spa

Blue Chip Casino Hotel and Spa

10/10 Excellent
"Our second time staying at Blue Chip. Room was awesome! 18th floor. Sun came up and shined in! Huge windows, room was clean, comfortable and reasonable!!"
George 2-night trip
Posted 3 hours ago
Blue Chip Casino Hotel and Spa
Waterbird Lakeside Inn

Waterbird Lakeside Inn

10/10 Excellent
"Great stay. Reasonable price."
Sandra 2-night trip
Posted 13 hours ago
Waterbird Lakeside Inn
Best Western Indian Oak

Best Western Indian Oak

10/10 Excellent
"Very nice room. Lake view was nice. Breakfast was good."
Ruth 1-night trip
Posted 1 day ago
Best Western Indian Oak
Quality Inn Chesterton near Indiana Dunes National Park I-94

Quality Inn Chesterton near Indiana Dunes National Park I-94

8/10 Good
"We only spent one night here and slept through breakfast so our experience with anything other than the room itself (very clean and smelling good) was good."
Cathy 1-night trip
Posted 11 days ago
Quality Inn Chesterton near Indiana Dunes National Park I-94

Frequently asked questions

Are you searching for the perfect hotel for your luxury getaway to Chesterton?
Let Expedia help you arrange your flight to Chicago Midway Airport (MDW) airport or Chicago O'Hare Intl. Airport (ORD) airport, and then choose from some places to stay that will deliver the luxury you seek. Amenities are important when you plan a trip, so we make it easy to find what you need to make your stay relaxing and comfortable. If you want an upscale hotel with a spa, an indoor pool, or luxury bedding, Expedia can assist you in finding the best luxury hotel experience that Chesterton offers. Known for its restaurants, Chesterton also has some interesting things to see and do including Lake Michigan, so you may want to take in the local sights during your visit.
When can I expect good weather in Chesterton?
Planning for the weather is an important factor for making your trip to Chesterton a success, especially when you're splurging. 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 there to see and do in Chesterton?
Enjoy Chesterton and visit Lake Michigan, Lustron House, and Indiana Dunes Visitor Center. If you have extra time while you're in the area, you might want to see Bailly Homestead - American Indians and Fur Traders and Indiana Dunes National Park.

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