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
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Chesterton holiday homes

Smart TV, fireplace, books

1. 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, (74 reviews)
"Very nice space, with plenty of room and a great location. "
United States
Briana R.
The price is AU$527
includes taxes & fees
3 Sept - 4 Sept
Dunes Home – Walk to Town, Fenced Yard, Near Dunes | Valpo University | Dunes
Exterior

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

The Porter Nook! 5 minutes to Indiana Dunes, Pet Friendly
Porter
9.2 out of 10, Wonderful, (7 reviews)
"We enjoyed our stay. Very inviting and comfortable accommodations. Would stay again and would recommend!"
United States
Amanda E.
The price is AU$374
includes taxes & fees
22 Sept - 23 Sept
The Porter Nook! 5 minutes to Indiana Dunes, Pet Friendly
Interior

3. NEW! Beautiful Riverfront Home on 10 Acres!

NEW! Beautiful Riverfront Home on 10 Acres!
Chesterton
7.8 out of 10, Good, (13 reviews)
"Very tranquil and private stay. The house was clean and comfortable, the fire pit was very nice,. CLose to town, and close to the beach. We loved it."
United States
Jeff S.
The price is AU$536
includes taxes & fees
1 Sept - 2 Sept
NEW! Beautiful Riverfront Home on 10 Acres!
Smart TV, fireplace, table football, books

4. Roomy Retreat–Family&Friends|2 King Beds|Game Room | Valpo University | Dunes

Roomy Retreat–Family&Friends|2 King Beds|Game Room | Valpo University | Dunes
Chesterton
9.2 out of 10, Wonderful, (22 reviews)
"I really enjoyed my stay even though I did not venture out but the house was like a dreamy oasis. "
United States
Kendall C.
The price is AU$953
includes taxes & fees
1 Sept - 2 Sept
Roomy Retreat–Family&Friends|2 King Beds|Game Room | Valpo University | Dunes
TV, fireplace, DVD player, table football

5. Sugar Shores ~ 3 Mi to Indiana Dunes Nat'l Park

Sugar Shores ~ 3 Mi to Indiana Dunes Nat'l Park
Chesterton
9.4 out of 10, Exceptional, (26 reviews)
"Great Property. Very helpful hosts! "
United States
Toni L.
The price is AU$837
includes taxes & fees
27 Sept - 28 Sept
Sugar Shores ~ 3 Mi to Indiana Dunes Nat'l Park
Terrace/patio

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
9.6 out of 10, Exceptional, (10 reviews)
"Nice place close to the beach."
United States
Zdenek M.
The price is AU$347
includes taxes & fees
3 Sept - 4 Sept
Charming 1-bedroom apt in house by creek with AC, in delightful Portage
Coffee/tea maker, fridge, microwave, oven

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, (38 reviews)
"The home is beautiful and very clean. It is in an excellent location, close to IN Dunes National Park. We had a very nice stay and will definitely stay here again if we are in the area."
United States
Judy H.
The price is AU$321
includes taxes & fees
30 Sept - 1 Oct
No Cleaning Fee! Cozy Cottage in Dunes National Park, Beverly Shores Indiana.
Private kitchen

8. Dune Haus + Indiana National Dunes Park

Dune Haus + Indiana National Dunes Park
Portage
The price is AU$429
includes taxes & fees
9 Sept - 10 Sept
Dune Haus + Indiana National Dunes Park
Beach nearby

9. 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 price is AU$420
includes taxes & fees
31 Aug - 1 Sept
The Boutique at Midtown Central / Hot Tub / Pet Friendly
Outdoor dining

10. Lakehouse with Pontoon, Deck, Firepit, Paddle Boards, Grill & more INCLUDED!!

Lakehouse with Pontoon, Deck, Firepit, Paddle Boards, Grill & more INCLUDED!!
Valparaiso
9.8 out of 10, Exceptional, (97 reviews)
"Our stay was great. We spent a lot of time on the pontoon boat that comes with the reservation. We used the paddleboards and kayaks. We took a short drive to the Indiana Dunes beach. The host was extremely kind and responsive."
United States
Heather
The price is AU$891
includes taxes & fees
1 Sept - 2 Sept
Lakehouse with Pontoon, Deck, Firepit, Paddle Boards, Grill & more INCLUDED!!
Coffee/tea maker, fridge, microwave, oven

11. Newly Renovated / Dog Friendly / Sleeps 6

Newly Renovated / Dog Friendly / Sleeps 6
Michigan City
10.0 out of 10, Exceptional, (5 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$410
includes taxes & fees
28 Sept - 29 Sept
Newly Renovated / Dog Friendly / Sleeps 6
Interior

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 had absolutely everything we needed for a fun, family vacation! "
United States
RuthAnn A.
The price is AU$718
includes taxes & fees
8 Sept - 9 Sept
Campus To Dunes Escape | 2 King Beds | Game Area + Fire Pit + Deck Lounge
Dining

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 AU$635
includes taxes & fees
28 Sept - 29 Sept
✨ Valpo Glow & Dunes Flow | Sleeps 12 | Firepit + Gazebo | Game Area | Valpo University | Indiana Dunes National Park
Terrace/patio

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

Game room/ Hot Tub / Pet Friendly / Duplex
Michigan City
8.8 out of 10, Excellent, (6 reviews)
The price is AU$741
includes taxes & fees
18 Sept - 19 Sept
Game room/ Hot Tub / Pet Friendly / Duplex
TV

15. Cozy 2 Bedroom Home Near Lake Michigan & Downtown

Cozy 2 Bedroom Home Near Lake Michigan & Downtown
Michigan City
8.0 out of 10, Very good, (2 reviews)
"Convenient location, quiet neighborhood, very close to commuter train. People do tend to drive way too fast on the street (posted 20mph and most drive 40mph). Communication with the host was excellent. Super helpful!"
United States
Jennifer K.
The price is AU$515
includes taxes & fees
31 Aug - 1 Sept
Cozy 2 Bedroom Home Near Lake Michigan & Downtown
Smart TV, fireplace, table football, books

16. 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, (39 reviews)
"Enjoyed our stay. Lots of room, easy to find, close to Lake Michigan, and received clear and helpful communication from the property manager/owner before and during our stay. "
United States
Daniel A.
The price is AU$629
includes taxes & fees
13 Sept - 14 Sept
Sand & Sun Getaway | Drive to Beach Game Room + 2 Living Areas |Game Room | Minutes to Beach
Beach nearby

17. 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$361
includes taxes & fees
1 Sept - 2 Sept
Duplex | Firepit | Game Room | Hot Tub-all year
Beach

18. Singing Sands Trl | Hot Tub Retreat | Dogs OK

Singing Sands Trl | Hot Tub Retreat | Dogs OK
Michigan City
9.8 out of 10, Exceptional, (32 reviews)
Singing Sands Trl | Hot Tub Retreat | Dogs OK
Outdoor dining

19. Michigan City Getaway: Walk to Beach, Zoo & Marina

Michigan City Getaway: Walk to Beach, Zoo & Marina
Michigan City
10.0 out of 10, Exceptional, (3 reviews)
"We really enjoyed being so close to the lake and enjoyed our stay there. Neighborhood was quiet."
United States
Pamm C.
Michigan City Getaway: Walk to Beach, Zoo & Marina
Terrace/patio

20. Cozy home near Lake Michigan with Smart TVs, fast Wi-Fi, and rustic charm.

Cozy home near Lake Michigan with Smart TVs, fast Wi-Fi, and rustic charm.
Michigan City
9.8 out of 10, Exceptional, (9 reviews)
"Beautiful home and comfortable beds! Easy to access and communication was great! We will definitely stay here again next time we are in Michigan City!"
United States
Holly F.
The price is AU$418
includes taxes & fees
1 Sept - 2 Sept
Cozy home near Lake Michigan with Smart TVs, fast Wi-Fi, and rustic charm.
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

Quality Inn Near Interstate I94

Quality Inn Near Interstate I94

8/10 Good
"This website is bogus. I click on three stars and it registers 4 stars. Motel was OK. There were a couple of annoying problems. Bathroom drain was slow to drain. AC was very loud. Breakfast was Good!"
Jim 1-night trip
Posted less than an hour ago
Quality Inn Near Interstate I94

Find out more about Chesterton

Chesterton Holiday Homes information

Number of reviews
405
Accommodation
739 Holiday Homes
Lowest Price
AU$321
Highest Price
AU$953