A wooden staircase ascending a sandy hill with sparse vegetation.

Holiday Homes in Chesterton

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Chesterton holiday homes

A patio with a table and chairs, a bicycle, and a string of lights against a twilight sky.

1. The Porter Nook! 5 minutes to Indiana Dunes, Pet Friendly

The Porter Nook! 5 minutes to Indiana Dunes, Pet Friendly
Porter
9.4 out of 10, Exceptional, (10 reviews)
"We enjoyed our stay. Very inviting and comfortable accommodations. Would stay again and would recommend!"
United States
Amanda E.
The price is AU$361
includes taxes & fees
4 Nov - 5 Nov
The Porter Nook! 5 minutes to Indiana Dunes, Pet Friendly
A living room with a dark blue door, a grey sofa, a blue sofa, a coffee table, and a floor lamp.

2. Dunes Home – Walk to Town, Fenced Yard, Near Dunes | Valpo University | Dunes

Dunes Home – Walk to Town, Fenced Yard, Near Dunes | Valpo University | Dunes
Chesterton
9.6 out of 10, Exceptional, (75 reviews)
"Very nice space, with plenty of room and a great location. "
United States
Briana R.
The price is AU$511
includes taxes & fees
19 Oct - 20 Oct
Dunes Home – Walk to Town, Fenced Yard, Near Dunes | Valpo University | Dunes
A modern kitchen with a central island, wooden dining table, and chairs. There is a ceiling fan, a microwave, and a refrigerator.

3. NEW! Beautiful Riverfront Home on 10 Acres!

NEW! Beautiful Riverfront Home on 10 Acres!
Chesterton
7.8 out of 10, Good, (13 reviews)
"A nice house, everything is fine, you just have to take into account that there are many mosquitoes and flies"
United States
Maria jose S.
The price is AU$560
includes taxes & fees
8 Nov - 9 Nov
NEW! Beautiful Riverfront Home on 10 Acres!
A bedroom with two beds, a ceiling fan, a TV on a dresser, and a window with blinds.

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

Full House booking of a history building close to the Dunes
Chesterton
9.4 out of 10, Exceptional, (6 reviews)
"Beautiful historic building. "
United States
Deborah S.
The price is AU$3,157
includes taxes & fees
26 Oct - 27 Oct
Full House booking of a history building close to the Dunes
A hot tub with water, a wooden deck, and a chair.

5. Charming 1-bedroom apt in house by creek with AC, in delightful Portage

Charming 1-bedroom apt in house by creek with AC, in delightful Portage
Portage
9.8 out of 10, Exceptional, (11 reviews)
"This was a very comfortable space for our Indiana Dunes area trip. It was the perfect place to relax after busy days at the area attractions. Our host was very kind and messaged us after we arrived to make sure we had everything we needed for our stay and again a couple of days later for the same."
United States
Michael T.
The price is AU$431
includes taxes & fees
31 Oct - 1 Nov
Charming 1-bedroom apt in house by creek with AC, in delightful Portage
A modern kitchen with white cabinetry, stainless steel appliances, and a marble countertop.

6. No Cleaning Fee! Cozy Cottage in Dunes National Park, Beverly Shores Indiana.

No Cleaning Fee! Cozy Cottage in Dunes National Park, Beverly Shores Indiana.
Michigan City
9.8 out of 10, Exceptional, (50 reviews)
"Very cute house in a great location. Very convenient to The Dunes beaches and hiking."
United States
Crystal K.
The price is AU$365
includes taxes & fees
18 Oct - 19 Oct
No Cleaning Fee! Cozy Cottage in Dunes National Park, Beverly Shores Indiana.
A modern kitchen with white cabinets, a stainless steel refrigerator, granite countertops, and a brick accent wall.

7. Newly Renovated / Dog Friendly / Sleeps 6

Newly Renovated / Dog Friendly / Sleeps 6
Michigan City
10.0 out of 10, Exceptional, (6 reviews)
"Lovely place, well stocked, clean, safe, comfortable and spacious. Location close to restaurants and outlet mall. Host was wonderful."
United States
Billie Farrar f.
The price is AU$351
includes taxes & fees
19 Oct - 20 Oct
Newly Renovated / Dog Friendly / Sleeps 6
A spacious living area with a dining table, seating, a fireplace, and a view of the outdoors.

8. Three Waters Escape | 2 Kings | Game Lounge

Three Waters Escape | 2 Kings | Game Lounge
Valparaiso
10.0 out of 10, Exceptional, (4 reviews)
"Great property. I will definitely stay there again when I'm in town."
United States
anthony h.
The price is AU$778
includes taxes & fees
28 Oct - 29 Oct
Three Waters Escape | 2 Kings | Game Lounge
A modern kitchen with dark cabinets, a wooden dining table, and a light wood floor.

9. ✨ Valpo Glow & Dunes Flow | Sleeps 12 | Firepit + Gazebo | Game Area | Valpo University | Indiana Dunes National Park

✨ Valpo Glow & Dunes Flow | Sleeps 12 | Firepit + Gazebo | Game Area | Valpo University | Indiana Dunes National Park
Valparaiso
9.6 out of 10, Exceptional, (12 reviews)
"It was a great place to stay! We would definitely stay here again. "
United States
Vanessa S.
The price is AU$617
includes taxes & fees
28 Oct - 29 Oct
✨ Valpo Glow & Dunes Flow | Sleeps 12 | Firepit + Gazebo | Game Area | Valpo University | Indiana Dunes National Park
A beach with a pier extending into the water, a lighthouse in the distance, and the sun setting over the horizon.

10. The Boutique at Midtown Central / Hot Tub / Pet Friendly

The Boutique at Midtown Central / Hot Tub / Pet Friendly
Michigan City
9.6 out of 10, Exceptional, (19 reviews)
"Very clean accommoding"
United States
Linda L.
The price is AU$421
includes taxes & fees
18 Oct - 19 Oct
The Boutique at Midtown Central / Hot Tub / Pet Friendly
A sunset over a beach with people standing on the shore.

11. Cozy House Retreat: Exclusive Full Yard & Porch-2 Miles to Beach and Mt Baldy

Cozy House Retreat: Exclusive Full Yard & Porch-2 Miles to Beach and Mt Baldy
Michigan City
9.8 out of 10, Exceptional, (33 reviews)
"Great place to stay close to everything!"
United States
Anonymous traveller
The price is AU$342
includes taxes & fees
18 Oct - 19 Oct
Cozy House Retreat: Exclusive Full Yard & Porch-2 Miles to Beach and Mt Baldy
A modern outdoor patio with a hot tub, two barbecue grills, and a white brick wall.

12. Game room / Hot Tub / Pet Friendly / Duplex

Game room / Hot Tub / Pet Friendly / Duplex
Michigan City
9.8 out of 10, Exceptional, (8 reviews)
"We had a great stay! Jason was quick to respond to any messages and sent us detailed communications leading up to our stay. Space was perfect for me, my husband, and our two dogs. Location is super close to the beach, casino, and outlet shopping. Would for sure recommend!"
United States
Missy S.
The price is AU$398
includes taxes & fees
18 Oct - 19 Oct
Game room / Hot Tub / Pet Friendly / Duplex
A beach with a pier extending into the water, a lighthouse in the distance, and the sun setting over the horizon.

13. Duplex | Firepit | Game Room | Hot Tub-all year

Duplex | Firepit | Game Room | Hot Tub-all year
Michigan City
8.4 out of 10, Very good, (19 reviews)
"It’s was very clean , comfortable beds too "
United States
Donna
The price is AU$299
includes taxes & fees
21 Oct - 22 Oct
Duplex | Firepit | Game Room | Hot Tub-all year
A living room with a black leather sofa, a wooden coffee table, and a dark wooden chair. A white door with a stained glass window is visible in the background.

14. Campus To Dunes Escape | 2 King Beds | Game Area + Fire Pit + Deck Lounge

Campus To Dunes Escape | 2 King Beds | Game Area + Fire Pit + Deck Lounge
Valparaiso
9.8 out of 10, Exceptional, (6 reviews)
"The house was nice and very stocked with everything we need ."
United States
Marcia N.
The price is AU$657
includes taxes & fees
19 Oct - 20 Oct
Campus To Dunes Escape | 2 King Beds | Game Area + Fire Pit + Deck Lounge
A kitchen with granite countertops, white cabinets, a ceiling fan, and pendant lighting.

15. Cozy Duplex Retreat | Hot Tub + Full Kitchen

Cozy Duplex Retreat | Hot Tub + Full Kitchen
Michigan City
10.0 out of 10, Exceptional, (1 review)
"Very clean, beautiful home, great location! I look forward to visiting again "
United States
Josh K.
The price is AU$349
includes taxes & fees
19 Oct - 20 Oct
Cozy Duplex Retreat | Hot Tub + Full Kitchen
A modern kitchen with grey cabinets, a central island with stools, a microwave, and a dishwasher.

16. An Escape to a Dream of Green and relaxation.

An Escape to a Dream of Green and relaxation.
Miller Beach
9.6 out of 10, Exceptional, (28 reviews)
"Very clean & updated property! The hot tub water looked like it was a fresh refill.We also thoroughly enjoyed how close this property is to the "L TRAIN" stations and the DUNE NATIONAL PARK!!We will be renting this house again for sure!"
United States
Martin R.
The price is AU$834
includes taxes & fees
18 Oct - 19 Oct
An Escape to a Dream of Green and relaxation.
A modern living room with a brown leather sofa, a dining table with chairs, a kitchen area, and a TV mounted on the wall.

17. Cozy 2 Bedroom Home Near Lake Michigan & Downtown

Cozy 2 Bedroom Home Near Lake Michigan & Downtown
Michigan City
9.0 out of 10, Wonderful, (4 reviews)
"The gouse was cute and cozy. The open floor plan made it easy for all 6 of us to socialize while some were cooking and others were watching TV. The kitchen had every cooking utensil and appliance needed to prepare meals. Getting to take our dog made the trip possible. The host was super quick to respond to our need to go back to the home after check out, due to a kid losing a cell phone. Will definitely stay there agin in the future!"
United States
Suzanne R.
The price is AU$531
includes taxes & fees
16 Oct - 17 Oct
Cozy 2 Bedroom Home Near Lake Michigan & Downtown
A bedroom with bunk beds, a patterned bedspread, and a decorative rug.

18. Dunes & Beach Getaway - Sleeps 10 - Room for the Whole Crew

Dunes & Beach Getaway - Sleeps 10 - Room for the Whole Crew
Portage
The price is AU$1,469
includes taxes & fees
18 Oct - 19 Oct
Dunes & Beach Getaway - Sleeps 10 - Room for the Whole Crew
A modern living room with a sofa, coffee table, and TV. There is a dining area with a table and chairs. The room has wooden flooring and a large window with blinds.

19. Sand & Sun Getaway | Drive to Beach Game Room + 2 Living Areas |Game Room | Minutes to Beach

Sand & Sun Getaway | Drive to Beach Game Room + 2 Living Areas |Game Room | Minutes to Beach
Michigan City
9.4 out of 10, Exceptional, (40 reviews)
"Great stay, and very close to the beach!"
United States
Erin W.
The price is AU$589
includes taxes & fees
19 Oct - 20 Oct
Sand & Sun Getaway | Drive to Beach Game Room + 2 Living Areas |Game Room | Minutes to Beach
A modern kitchen with wooden cabinets, stainless steel appliances, and a white countertop island.

20. Modern 3BR w/Deck · Minutes from I-65. Fenced Yard

Modern 3BR w/Deck · Minutes from I-65. Fenced Yard
Merrilville
8.8 out of 10, Excellent, (3 reviews)
"Great pet friendly home and yard. Host was responsive great communication. Excellent, easy to access location."
United States
Lynda L.
The price is AU$643
includes taxes & fees
18 Oct - 19 Oct
Modern 3BR w/Deck · Minutes from I-65. Fenced Yard
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.
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Top Chesterton Hotel Reviews

Holiday Inn Express & Suites New Buffalo by IHG

Holiday Inn Express & Suites New Buffalo by IHG

10/10 Excellent
"The hotel is clean, comfortable, great location near I94 and good restaurants, serves a good breakfast."
Susan 1-night trip
Posted 11 hours ago
Holiday Inn Express & Suites New Buffalo by IHG

Find out more about Chesterton

Chesterton Holiday Homes information

Number of reviews
329
Accommodation
739 Holiday Homes
Lowest Price
AU$299
Highest Price
AU$3,157