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Check prices for these dates

In two weeks
4 Sep - 6 Sep
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Chesterton vacation 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 AED 393
AED 1,394 total
includes taxes & fees
3 Sep - 4 Sep
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
9.0 out of 10, Wonderful, (6 reviews)
"Jessica was a great host to my family and me. We spent two nights there and she was very accommodating of our needs and special requests."
United States
Jess K.
The price is AED 404
AED 930 total
includes taxes & fees
15 Sep - 16 Sep
The Porter Nook! 5 minutes to Indiana Dunes, Pet Friendly
Beach

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, (46 reviews)
"Fantastic stay!"
United States
Steven F.
The price is AED 1,064
AED 1,237 total
includes taxes & fees
27 Aug - 28 Aug
Blue Birdhouse - No Cleaning Fee - Pet Friendly - Dunes National Park
Smart TV, fireplace, foosball, 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 AED 972
AED 2,512 total
includes taxes & fees
19 Aug - 20 Aug
Roomy Retreat–Family&Friends|2 King Beds|Game Room | Valpo University | Dunes
Interior

5. NEW! Beautiful Riverfront Home on 10 Acres!

NEW! Beautiful Riverfront Home on 10 Acres!
Chesterton
8.2 out of 10, Very Good, (12 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 AED 731
AED 1,641 total
includes taxes & fees
1 Sep - 2 Sep
NEW! Beautiful Riverfront Home on 10 Acres!
Property grounds

6. Heart of Indiana Dunes National Park with Hot Tub

Heart of Indiana Dunes National Park with Hot Tub
Chesterton
10.0 out of 10, Exceptional, (8 reviews)
"The house was beautiful and had so much charm. The amount of activities available was great. Highly recommend and we will definitely be back!"
United States
Becky G.
Heart of Indiana Dunes National Park with Hot Tub
6 bedrooms, desk, WiFi (free)

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.
The price is AED 6,545
AED 8,375 total
includes taxes & fees
25 Aug - 26 Aug
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, (9 reviews)
"Nice place close to the beach."
United States
Zdenek M.
The price is AED 364
AED 868 total
includes taxes & fees
23 Aug - 24 Aug
Charming 1-bedroom apt in house by creek with AC, in delightful Portage
Coffee/tea maker, fridge, microwave, oven

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, (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 AED 768
AED 983 total
includes taxes & fees
19 Aug - 20 Aug
No Cleaning Fee! Cozy Cottage in Dunes National Park, Beverly Shores Indiana.
Beach nearby

10. The Boutique at Midtown Central / Hot Tub / Pet Friendly

The Boutique at Midtown Central / Hot Tub / Pet Friendly
Michigan City
9.8 out of 10, Exceptional, (18 reviews)
"Cute and cozy"
United States
angel R.
The price is AED 564
AED 1,255 total
includes taxes & fees
19 Aug - 20 Aug
The Boutique at Midtown Central / Hot Tub / Pet Friendly
Beach nearby

11. 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, (27 reviews)
"It was a cute little place to stay"
United States
Janielle K.
The price is AED 496
AED 917 total
includes taxes & fees
26 Aug - 27 Aug
Cozy House: 5 min drive to beach-zoo-restaurants-casino-brewery-train to Chicago
Coffee/tea maker, fridge, microwave, oven

12. Newly Renovated / Dog Friendly / Sleeps 6

Newly Renovated / Dog Friendly / Sleeps 6
Michigan City
10.0 out of 10, Exceptional, (4 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 AED 533
AED 1,105 total
includes taxes & fees
1 Sep - 2 Sep
Newly Renovated / Dog Friendly / Sleeps 6
TV

13. 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 AED 639
AED 1,380 total
includes taxes & fees
19 Aug - 20 Aug
Cozy 2 Bedroom Home Near Lake Michigan & Downtown
Outdoor dining

14. 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 AED 1,653
AED 2,587 total
includes taxes & fees
19 Aug - 20 Aug
Lakehouse with Pontoon, Deck, Firepit, Paddle Boards, Grill & more INCLUDED!!
Interior

15. 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 AED 559
AED 1,848 total
includes taxes & fees
26 Aug - 27 Aug
Campus To Dunes Escape | 2 King Beds | Game Area + Fire Pit + Deck Lounge
Dining

16. ✨ 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 AED 579
AED 1,759 total
includes taxes & fees
14 Sep - 15 Sep
✨ Valpo Glow & Dunes Flow | Sleeps 12 | Firepit + Gazebo | Game Area | Valpo University | Indiana Dunes National Park
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.
Game room / Hot Tub / Pet Friendly / Duplex
Smart TV, fireplace, foosball, books

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, (38 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 AED 956
AED 2,239 total
includes taxes & fees
19 Aug - 20 Aug
Sand & Sun Getaway | Drive to Beach Game Room + 2 Living Areas |Game Room | Minutes to Beach
TV

19. Near Indiana Dunes & Beaches, House sleeps 8, Yes to Pets, Private backyard

Near Indiana Dunes & Beaches, House sleeps 8, Yes to Pets, Private backyard
Michigan City
10.0 out of 10, Exceptional, (1 review)
"We really enjoyed our stay in this beautiful, newly restored home in Michigan City! There was plenty of room for our family, and the open, clean spaces felt very welcoming. Check-in and check-out were super easy, and the host had great communication throughout our stay. The house had a warm and positive vibe that made us feel right at home.I really loved the open layout, but the home overall wasn’t very baby-proofed due to the staircases and some decorative items, which made it a bit tricky with...
United States
Kelsi J.
The price is AED 992
AED 1,835 total
includes taxes & fees
25 Aug - 26 Aug
Near Indiana Dunes & Beaches, House sleeps 8, Yes to Pets, Private backyard
Terrace/patio

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

Hot Tub / Pet Friendly / Close to the Beach
Michigan City
10.0 out of 10, Exceptional, (6 reviews)
"This place was very nice and clean & decorated with nice up to date modern decor. The beds were very comfortable. Would definitely recommend to others."
United States
Loretta M.
The price is AED 787
AED 1,430 total
includes taxes & fees
19 Aug - 20 Aug
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

Four Winds Casino Resort – New Buffalo

Four Winds Casino Resort – New Buffalo

10/10 Excellent
"We're not casino people but we already planned another trip just to stay at Four Winds for a long weekend. We were very impressed. It's clean and luxurious. The staff was great. Loved the Copper Rock Steakhouse! 😍 I highly recommend."
William 1-night trip
Posted 3 hours ago
Four Winds Casino Resort – New Buffalo