A wooden staircase ascending a sandy hill with sparse vegetation.

Holiday Homes in Chesterton

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Our top choices for Chesterton holiday homes

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 NZ$384
includes taxes & fees
4 Nov - 5 Nov
The Porter Nook! 5 minutes to Indiana Dunes, Pet Friendly

2. 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 NZ$498
includes taxes & fees
3 Nov - 4 Nov
Tower Haus w/Private Hot Tub

3. 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, (76 reviews)
"Great location, walking distance to downtown Chesterton which had an excellent ice cream shop and other restaurants. Easy driving distance to different parts of Indiana Dunes National Park. Host had great communication before and throughout the visit and the house had all the amenities we needed."
United States
Ammari Capito F.
The price is NZ$745
includes taxes & fees
24 Nov - 25 Nov
Dunes Home – Walk to Town, Fenced Yard, Near Dunes | Valpo University | Dunes

4. NEW! Beautiful Riverfront Home on 10 Acres!

NEW! Beautiful Riverfront Home on 10 Acres!
Chesterton
7.8 out of 10, Good, (13 reviews)
"The host was responsive and super friendly. We loved staying here - Chesterton was beautiful and the downtown area was incredible. We fell in love."
United States
Amanda H.
The price is NZ$650
includes taxes & fees
3 Nov - 4 Nov
NEW! Beautiful Riverfront Home on 10 Acres!

5. 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)
"We are happy with the property. clean property, quite spacious and large enough to accommodate large group, quite close to Dunes."
United States
Mahesh K.
The price is NZ$3,677
includes taxes & fees
16 Nov - 17 Nov
Full House booking of a history building close to the Dunes

6. 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 NZ$446
includes taxes & fees
30 Nov - 1 Dec
Charming 1-bedroom apt in house by creek with AC, in delightful Portage

7. 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, (52 reviews)
"Very cute house in a great location. Very convenient to The Dunes beaches and hiking."
United States
Crystal K.
The price is NZ$461
includes taxes & fees
3 Nov - 4 Nov
No Cleaning Fee! Cozy Cottage in Dunes National Park, Beverly Shores Indiana.

8. 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 NZ$376
includes taxes & fees
5 Nov - 6 Nov
Newly Renovated / Dog Friendly / Sleeps 6

9. Three Waters Escape | 2 Kings | Game Lounge

Three Waters Escape | 2 Kings | Game Lounge
Valparaiso
10.0 out of 10, Exceptional, (5 reviews)
"Great property. I will definitely stay there again when I'm in town."
United States
anthony h.
The price is NZ$940
includes taxes & fees
9 Nov - 10 Nov
Three Waters Escape | 2 Kings | Game Lounge

10. 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 NZ$341
includes taxes & fees
4 Nov - 5 Nov
Duplex | Firepit | Game Room | Hot Tub-all year

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 NZ$414
includes taxes & fees
5 Nov - 6 Nov
Cozy Duplex Retreat | Hot Tub + Full Kitchen

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 NZ$792
includes taxes & fees
17 Nov - 18 Nov
Campus To Dunes Escape | 2 King Beds | Game Area + Fire Pit + Deck Lounge

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

Game room / Hot Tub / Pet Friendly / Duplex
Michigan City
9.8 out of 10, Exceptional, (9 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 NZ$489
includes taxes & fees
3 Nov - 4 Nov
Game room / Hot Tub / Pet Friendly / Duplex

14. 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 NZ$534
includes taxes & fees
3 Nov - 4 Nov
The Boutique at Midtown Central / Hot Tub / Pet Friendly

15. 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 NZ$438
includes taxes & fees
3 Nov - 4 Nov
Cozy House Retreat: Exclusive Full Yard & Porch-2 Miles to Beach and Mt Baldy

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)
"Extremely clean. Kitchen needs more/newer cookware/bakeware to match how nice the house is. Hot tub was a wonderful addition along with the extra room on the back of the house. Overall we enjoyed our stay."
United States
Julie R.
The price is NZ$1,004
includes taxes & fees
3 Nov - 4 Nov
An Escape to a Dream of Green and relaxation.

17. ✨ 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, (14 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 NZ$818
includes taxes & fees
9 Nov - 10 Nov
✨ Valpo Glow & Dunes Flow | Sleeps 12 | Firepit + Gazebo | Game Area | Valpo University | Indiana Dunes National Park

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 NZ$1,723
includes taxes & fees
3 Nov - 4 Nov
Dunes & Beach Getaway - Sleeps 10 - Room for the Whole Crew

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 NZ$696
includes taxes & fees
9 Nov - 10 Nov
Sand & Sun Getaway | Drive to Beach Game Room + 2 Living Areas |Game Room | Minutes to Beach

20. 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 NZ$687
includes taxes & fees
3 Nov - 4 Nov
Cozy 2 Bedroom Home Near Lake Michigan & Downtown
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

Find out more about Chesterton

Chesterton Holiday Homes information

Number of reviews
372
Accommodation
726 Holiday Homes
Lowest Price
NZ$341
Highest Price
NZ$3,677