Chesterton, IN Cottages from AED 459

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Our top choices for Chesterton cottages

A covered outdoor seating area with a sofa, two chairs, and a coffee table.

1. Treehouse Bungalow- Quaint and Cozy Getaway!

Michigan City

Unspecified U.

AED 1,095 total

includes taxes & fees

8 Nov - 9 Nov

Ceiling fans keep air flow and also Central Air and Heat.

2. 3BR 2b New Buff cottage dogs ok, steps to dwntn restaurants&shops, walk to beach

Downtown New Buffalo

christian s.

AED 1,724 total

includes taxes & fees

8 Nov - 9 Nov

A wooden deck with a bench and two chairs, overlooking a body of water and trees.

3. Private Beach Steps to the Lake.

Union Pier

Jalen W.

AED 4,026 total

includes taxes & fees

8 Nov - 9 Nov

A wooden deck with a black sofa, a table with a plant, and a pergola with lights.

4. Secluded Retreat, Hot Tub, Fire Pit, Wildlife Views, Near New Buffalo Beach!

New Buffalo

Citlaly D.

AED 2,385 total

includes taxes & fees

8 Nov - 9 Nov

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Learn more about Chesterton

Nestled along Lake Michigan's shore, this small town offers scenic trails through Indiana Dunes National Park for hiking and birdwatching. Coffee shops and local restaurants line the historic downtown, while nearby beaches provide perfect spots for summer swimming and sunset views.

See all hotels in Chesterton

A wooden staircase leading up a sandy hill with dense green forest in the background.

Top reviews in Chesterton

A hotel with a modern design, featuring a mix of white and orange buildings, a parking lot, and a flagpole with an American flag.

Hilton Garden Inn Chesterton

Chesterton

10/10 Excellent

anne

A modern building with large windows and balconies, a wooden deck, and a calm lake.

Best Western Indian Oak

Chesterton

10/10 Excellent

Great location with plenty to do in the area. The purpose of our trip was to visit Indiana Dunes NP, which is very close to the hotel. The hotel is located on a lake which added to its appeal. The general areas of the property were well kept and clean as was our room and bathroom. The breakfast was a typical hotel breakfast. I would definitely recommend this hotel when traveling to the area, and I would stay here again.

Edward

Waterbird Lakeside Inn

Chesterton

10/10 Excellent

Philip

A two-story building with a brick facade and a flat roof.

Quality Inn Chesterton near Indiana Dunes National Park I-94

Chesterton

10/10 Excellent

Jerry

A hotel with a covered entrance, multiple windows, and a parking lot.

Comfort Inn & Suites Porter near Indiana Dunes

Chesterton

10/10 Excellent

Anonymous traveler

A hotel with a large parking lot, a central courtyard, and a building with a distinctive curved roof.

Four Winds Casino Resort – New Buffalo

New Buffalo

10/10 Excellent

Angela

A dock with a boat, a rusty bridge, and greenery in the background.

Bridge Inn

Michigan City

10/10 Excellent

We stayed in suite 23. Its an upper level room but the stairs were quite manageable. We received a text when our room was ready which was before check in time. The room was very cozy and clean. This suite has a jetted tub 😀. The property manager Pete was very nice. We were only in the area 1 night but I waa amazed at all the things to do in the area. We definitely want to go back for a longer visit in the summer. They have a website that you can contact separately that will save you money on...

Joyce

A Holiday Inn Express & Suites building with a covered entrance, multiple floors, and a parking lot.

Holiday Inn Express & Suites Michigan City by IHG

Michigan City

10/10 Excellent

Anonymous traveler

A two-story brick house with a gabled roof, surrounded by a well-maintained garden with various plants and a lawn.

The Brewery Lodge Hotel

Michigan City

10/10 Excellent

Our stay was just great, and the facility was wonderful. However we had serious problems with the Hotels.com website. The website and booking process were deceptive and difficult. Our efforts to communicate with hotels.com did not get results and we were not able to find out why our credit card was charged more than advertised. We will go to the Brewery Lodge Hotel again but we won't be booking through Hotels.com. Final score 5+ for the Brewery Lodge Hotel 0 minus for Hotels.com.

Anonymous traveler

A modern Hampton Inn & Suites building with a well-lit entrance and a large tree in front.

Hampton Inn & Suites Valparaiso

Valparaiso

10/10 Excellent

Eight 1981 VHS grads used Hampton Inn & Suites as our home base for a reunion weekend. The staff was very pleasant and accommodating, the breakfast was very good and plentiful, and the rooms were exceptionally quiet and comfortable. The beds and pillows were so nice that my body was convinced that it rested at home. It was a lovely weekend. Thank you for the “Vail of Paradise” hospitality.

Susan

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Change your mind

Treat yourself

Be picky

Find vacation rentals that suit your style

Check prices for these dates

Our top choices for Chesterton cottages

1. Treehouse Bungalow- Quaint and Cozy Getaway!

2. 3BR 2b New Buff cottage dogs ok, steps to dwntn restaurants&shops, walk to beach

3. Private Beach Steps to the Lake.

4. Secluded Retreat, Hot Tub, Fire Pit, Wildlife Views, Near New Buffalo Beach!

Learn more about Chesterton

Top reviews in Chesterton

Hilton Garden Inn Chesterton

10/10 Excellent

Frequently Asked Questions

Why book your cottage in Chesterton with Expedia?

How can I find cheap cottages in Chesterton?