A wooden staircase ascending a sandy hill with sparse vegetation.

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Chesterton vacation 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, (9 reviews)
"We enjoyed our stay. Very inviting and comfortable accommodations. Would stay again and would recommend!"
United States
Amanda E.
The price is ￥14,931
￥37,075 total
includes taxes & fees
Nov 4 - Nov 5
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 ￥18,108
￥60,673 total
includes taxes & fees
Oct 20 - Oct 21
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 ￥25,151
￥61,830 total
includes taxes & fees
Nov 3 - Nov 4
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 ￥341,669
￥432,452 total
includes taxes & fees
Nov 6 - Nov 7
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)
"Nice place close to the beach."
United States
Zdenek M.
The price is ￥23,727
￥47,479 total
includes taxes & fees
Oct 31 - Nov 1
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, (46 reviews)
"The house/bathroom was clean. We had everything we needed for a great stay."
United States
Kim H.
The price is ￥31,442
￥38,754 total
includes taxes & fees
Oct 21 - Oct 22
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 ￥16,130
￥38,686 total
includes taxes & fees
Oct 14 - Oct 15
Newly Renovated / Dog Friendly / Sleeps 6
A beach with a pier extending into the water, a lighthouse in the distance, and the sun setting over the horizon.

8. 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)
"Cute and cozy"
United States
angel R.
The Boutique at Midtown Central / Hot Tub / Pet Friendly
A beach with a pier extending into the water, a lighthouse in the distance, and the sun setting over the horizon.

9. 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 ￥11,405
￥32,864 total
includes taxes & fees
Oct 21 - Oct 22
Duplex | Firepit | Game Room | Hot Tub-all year
A modern outdoor patio with a hot tub, two barbecue grills, and a white brick wall.

10. 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.
Game room / Hot Tub / Pet Friendly / Duplex
A kitchen with granite countertops, white cabinets, a ceiling fan, and pendant lighting.

11. 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 ￥15,967
￥38,504 total
includes taxes & fees
Oct 14 - Oct 15
Cozy Duplex Retreat | Hot Tub + Full Kitchen
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.

12. 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 ￥19,817
￥74,103 total
includes taxes & fees
Oct 19 - Oct 20
Campus To Dunes Escape | 2 King Beds | Game Area + Fire Pit + Deck Lounge
A modern kitchen with dark cabinets, a wooden dining table, and a light wood floor.

13. ✨ 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 ￥20,671
￥66,733 total
includes taxes & fees
Oct 14 - Oct 15
✨ Valpo Glow & Dunes Flow | Sleeps 12 | Firepit + Gazebo | Game Area | Valpo University | Indiana Dunes National Park
A sunset over a beach with people standing on the shore.

14. 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, (32 reviews)
"Great place to stay close to everything!"
United States
Anonymous traveler
The price is ￥19,908
￥37,692 total
includes taxes & fees
Oct 28 - Oct 29
Cozy House Retreat: Exclusive Full Yard & Porch-2 Miles to Beach and Mt Baldy
A hallway with a wooden door, a framed inspirational quote, a metal towel rack with a sign, and a patterned rug.

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

Dunes & Beach Getaway - Sleeps 10 - Room for the Whole Crew
Portage
The price is ￥58,511
￥131,260 total
includes taxes & fees
Oct 12 - Oct 13
Dunes & Beach Getaway - Sleeps 10 - Room for the Whole Crew
A modern living room with a brown leather sofa, a dining table with chairs, a kitchen area, and a TV mounted on the wall.

16. 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 ￥28,472
￥60,690 total
includes taxes & fees
Oct 18 - Oct 19
Cozy 2 Bedroom Home Near Lake Michigan & Downtown
A pathway leading to a house with a deck and a covered outdoor seating area.

17. Beachfront Hot Tub All Year | Outdoor Grill | Waves on Lake Michigan

Beachfront Hot Tub All Year | Outdoor Grill | Waves on Lake Michigan
Michigan City
10.0 out of 10, Exceptional, (11 reviews)
"Clean and lovely stay on the beach. We will be coming back for sure."
United States
Brittany K.
The price is ￥20,366
￥81,071 total
includes taxes & fees
Oct 21 - Oct 22
Beachfront Hot Tub All Year | Outdoor Grill | Waves on Lake Michigan
A wooden boardwalk leading to a sandy beach with the ocean in the background.

18. Red Zen | HotTub-all yr | Firepit | Grill | DogsOK

Red Zen | HotTub-all yr | Firepit | Grill | DogsOK
Michigan City
9.8 out of 10, Exceptional, (47 reviews)
"Great place"
United States
Sebastian ?.
The price is ￥18,899
￥42,495 total
includes taxes & fees
Oct 18 - Oct 19
Red Zen | HotTub-all yr | Firepit | Grill | DogsOK
A rustic interior with wooden beams, leather sofas, a clock, and a staircase leading to another level.

19. Rustic Getaway by Lake Michigan!

Rustic Getaway by Lake Michigan!
Michigan City
9.8 out of 10, Exceptional, (7 reviews)
"Nice place for us 19 people.Wonderful location"
United States
PATRICK C.
The price is ￥86,999
￥161,926 total
includes taxes & fees
Oct 11 - Oct 12
Rustic Getaway by Lake Michigan!
A bunk bed room with a painting of dogs on the wall, a small heater, and a door leading to another room.

20. Hot Tub / Pet Friendly / Close to the Beach

Hot Tub / Pet Friendly / Close to the Beach
Michigan City
9.8 out of 10, Exceptional, (9 reviews)
"Great place! Perfect for a family and the kids will love the yard and yard games. The fire pit and hot tub were wonderful to round up the night. We will be back for sure! Thank you."
United States
Jill G.
The price is ￥20,854
￥44,863 total
includes taxes & fees
Oct 12 - Oct 13
Hot Tub / Pet Friendly / Close to the 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.
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Top Chesterton Hotel Reviews

Blue Chip Casino Hotel and Spa

Blue Chip Casino Hotel and Spa

10/10 Excellent
"Nice"
jack 1-night trip
Posted 1 hour ago
Blue Chip Casino Hotel and Spa

Find out more about Chesterton

Chesterton Vacation Homes information

Number of reviews
322
Accommodation
739 Vacation Homes
Lowest Price
￥32,864
Highest Price
￥432,452