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
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 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 €230
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 €361
includes taxes & fees
5 Nov - 6 Nov
Dunes Home – Walk to Town, Fenced Yard, Near Dunes | Valpo University | Dunes
A living room with a grey sofa, two armchairs, a coffee table, and a rug. There are two lamps, a framed picture on the wall, and a window with curtains.

3. Blue Birdhouse - No Cleaning Fee - Pet Friendly - Dunes National Park

Blue Birdhouse - No Cleaning Fee - Pet Friendly - Dunes National Park
Chesterton
9.4 out of 10, Exceptional, (50 reviews)
"Fantastic stay!"
United States
Steven F.
The price is €200
includes taxes & fees
8 Nov - 9 Nov
Blue Birdhouse - No Cleaning Fee - Pet Friendly - Dunes National Park
A modern kitchen with wooden cabinets, stainless steel appliances, and a central island.

4. Tower Haus w/Private Hot Tub

Tower Haus w/Private Hot Tub
Chesterton
9.8 out of 10, Exceptional, (38 reviews)
"Great place to stay! It was really clean! Highly recommend!"
United States
Joshua N.
The price is €265
includes taxes & fees
16 Nov - 17 Nov
Tower Haus w/Private Hot Tub
A modern kitchen with a central island, wooden dining table, and chairs. There is a ceiling fan, a microwave, and a refrigerator.

5. 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 €354
includes taxes & fees
1 Nov - 2 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.

6. 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 €1,988
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.

7. 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 €256
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.

8. 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, (51 reviews)
"Very cute house in a great location. Very convenient to The Dunes beaches and hiking."
United States
Crystal K.
The price is €231
includes taxes & fees
26 Oct - 27 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.

9. 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 €207
includes taxes & fees
26 Oct - 27 Oct
Newly Renovated / Dog Friendly / Sleeps 6
A modern hotel with a curved glass facade, a prominent 'Blue Chip' sign, and a landscaped courtyard.

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 €257
includes taxes & fees
25 Oct - 26 Oct
The Boutique at Midtown Central / Hot Tub / Pet Friendly
A modern hotel with a curved glass facade, a prominent Blue Chip sign, and a landscaped entrance area.

11. 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 €189
includes taxes & fees
25 Oct - 26 Oct
Duplex | Firepit | Game Room | Hot Tub-all year
A modern kitchen with dark cabinets, a wooden dining table, and a light wood floor.

12. ✨ 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)
"We stayed for 8 nights and the location was perfect. Rooms were as described and plenty of space for our family. Eddi was very responsive for any questions that arose during the trip."
United States
Alexis U.
The price is €381
includes taxes & fees
27 Oct - 28 Oct
✨ Valpo Glow & Dunes Flow | Sleeps 12 | Firepit + Gazebo | Game Area | Valpo University | Indiana Dunes National Park
A modern outdoor patio with a hot tub, two barbecue grills, and a white brick wall.

13. 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 €238
includes taxes & fees
26 Oct - 27 Oct
Game room / Hot Tub / Pet Friendly / Duplex
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 €449
includes taxes & fees
25 Oct - 26 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 €191
includes taxes & fees
27 Oct - 28 Oct
Cozy Duplex Retreat | Hot Tub + Full Kitchen
A modern living room with a sofa, coffee table, and floor lamp.

16. 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, (34 reviews)
"Great place to stay close to everything!"
United States
Anonymous traveller
The price is €217
includes taxes & fees
28 Oct - 29 Oct
Cozy House Retreat: Exclusive Full Yard & Porch-2 Miles to Beach and Mt Baldy
A modern kitchen with grey cabinets, a central island with stools, a microwave, and a dishwasher.

17. 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)
"Great location "
United States
Tracy
The price is €520
includes taxes & fees
1 Nov - 2 Nov
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.

18. 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 €337
includes taxes & fees
24 Oct - 25 Oct
Cozy 2 Bedroom Home Near Lake Michigan & Downtown
A modern kitchen with wooden cabinets, stainless steel appliances, and a white countertop island.

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

Modern 3BR w/Deck · Minutes from I-65. Fenced Yard
Merrilville
8.6 out of 10, Excellent, (4 reviews)
"Great pet friendly home and yard. Host was responsive great communication. Excellent, easy to access location."
United States
Lynda L.
The price is €420
includes taxes & fees
1 Nov - 2 Nov
Modern 3BR w/Deck · Minutes from I-65. Fenced Yard
A spacious kitchen with a central island, bar stools, a brick accent wall, and a welcoming tree decoration.

20. Hot Tub + Fire Pit + Dog-Friendly Retreat Beach

Hot Tub + Fire Pit + Dog-Friendly Retreat Beach
Michigan City
8.8 out of 10, Excellent, (13 reviews)
"Had a great time at this rental. Holiday get together with family in a central location. Lots of beds for a large group. "
United States
Anonymous traveller
The price is €335
includes taxes & fees
25 Oct - 26 Oct
Hot Tub + Fire Pit + Dog-Friendly Retreat 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

Ameristar Casino Hotel East Chicago

Ameristar Casino Hotel East Chicago

10/10 Excellent
"Nice people had. Fun I will be back soon thanks so much"
Carnell 1-night trip
Posted 3 hours ago
Ameristar Casino Hotel East Chicago

Find out more about Chesterton

Chesterton Holiday Homes information

Number of reviews
376
Accommodation
723 Holiday Homes
Lowest Price
€189
Highest Price
€1,988