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
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Chesterton holiday homes

Exterior

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, (8 reviews)
"We enjoyed our stay. Very inviting and comfortable accommodations. Would stay again and would recommend!"
United States
Amanda E.
The price is €222
includes taxes & fees
22 Sept - 23 Sept
The Porter Nook! 5 minutes to Indiana Dunes, Pet Friendly
Living area

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, (74 reviews)
"Very nice space, with plenty of room and a great location. "
United States
Briana R.
The price is €343
includes taxes & fees
7 Sept - 8 Sept
Dunes Home – Walk to Town, Fenced Yard, Near Dunes | Valpo University | Dunes
Beach

3. Tower Haus w/Private Hot Tub

Tower Haus w/Private Hot Tub
Chesterton
9.8 out of 10, Exceptional, (34 reviews)
"This is a great setup for visiting the Dunes and also Chicago via South Shore. Host was great and place was very clean and new."
United States
Kevin J.
The price is €348
includes taxes & fees
7 Sept - 8 Sept
Tower Haus w/Private Hot Tub
Living area

4. 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)
"This place was so roomy, clean, and comfortable. Plenty of room to relax and enjoy family company. "
United States
Kile B.
Sugar Shores ~ 3 Mi to Indiana Dunes Nat'l Park
Interior

5. 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 €375
includes taxes & fees
1 Oct - 2 Oct
NEW! Beautiful Riverfront Home on 10 Acres!
Beach

6. 1:00 pm Check-In & Out! - 1 mile to Dunes - Roomy-Sleeps 16 - 🎮Game Room Loft🏓

1:00 pm Check-In & Out! - 1 mile to Dunes - Roomy-Sleeps 16 - 🎮Game Room Loft🏓
Porter
10.0 out of 10, Exceptional, (99 reviews)
"Our family enjoyed our stay very much, especially with having the clean well-kept accommodations and so close to our favorite Lake Michigan beaches. This is a very comfortable home for family to relax and enjoy their home away from home."
United States
Aleta F.
The price is €743
includes taxes & fees
8 Sept - 9 Sept
1:00 pm Check-In & Out! - 1 mile to Dunes - Roomy-Sleeps 16 - 🎮Game Room Loft🏓
Room

7. 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.
Full House booking of a history building close to the Dunes
Terrace/patio

8. 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 €223
includes taxes & fees
17 Sept - 18 Sept
Charming 1-bedroom apt in house by creek with AC, in delightful Portage
Private kitchen

9. 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, (39 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.
No Cleaning Fee! Cozy Cottage in Dunes National Park, Beverly Shores Indiana.
Beach

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)
"Cute and cozy"
United States
angel R.
The Boutique at Midtown Central / Hot Tub / Pet Friendly
Exterior

11. Dune Haus + Indiana National Dunes Park

Dune Haus + Indiana National Dunes Park
Portage
10.0 out of 10, Exceptional, (1 review)
"Very great stay all around"
United States
Devan G.
The price is €305
includes taxes & fees
7 Sept - 8 Sept
Dune Haus + Indiana National Dunes Park
Beach

12. Cozy House: 5 min drive to beach-zoo-restaurants-casino-brewery-train to Chicago

Cozy House: 5 min drive to beach-zoo-restaurants-casino-brewery-train to Chicago
Michigan City
9.8 out of 10, Exceptional, (30 reviews)
"It was a cute little place to stay"
United States
Janielle K.
The price is €194
includes taxes & fees
15 Sept - 16 Sept
Cozy House: 5 min drive to beach-zoo-restaurants-casino-brewery-train to Chicago
Outdoor dining

13. 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 €541
includes taxes & fees
8 Sept - 9 Sept
Lakehouse with Pontoon, Deck, Firepit, Paddle Boards, Grill & more INCLUDED!!
Private kitchen

14. 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 €237
includes taxes & fees
5 Oct - 6 Oct
Newly Renovated / Dog Friendly / Sleeps 6
Dining

15. ✨ 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 €379
includes taxes & fees
23 Sept - 24 Sept
✨ Valpo Glow & Dunes Flow | Sleeps 12 | Firepit + Gazebo | Game Area | Valpo University | Indiana Dunes National Park
Interior

16. 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 €411
includes taxes & fees
15 Sept - 16 Sept
Campus To Dunes Escape | 2 King Beds | Game Area + Fire Pit + Deck Lounge
Terrace/patio

17. 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 €283
includes taxes & fees
1 Oct - 2 Oct
Game room / Hot Tub / Pet Friendly / Duplex
Living area

18. 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.
Sand & Sun Getaway | Drive to Beach Game Room + 2 Living Areas |Game Room | Minutes to Beach
Living area

19. 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 €321
includes taxes & fees
7 Sept - 8 Sept
Cozy 2 Bedroom Home Near Lake Michigan & Downtown
Beach

20. 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 €210
includes taxes & fees
7 Sept - 8 Sept
Duplex | Firepit | Game Room | Hot Tub-all year
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

Spring House Inn

Spring House Inn

10/10 Excellent
"Location so close to Indiana Dunes was perfect. Breakfast didn’t look as well displayed as some hotels but quality was good - some things eg apples, yoghurt and milk hiding in fridge. Pastries were good quality."
Antonia 1-night trip
Posted 3 hours ago
Spring House Inn

Find out more about Chesterton

Chesterton Holiday Homes information

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