Holiday Homes in Chesterton

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Our top choices for Chesterton holiday homes

Balcony/Patio/ Separate Fenced Yard + Beach, Park & Downtown+close to Chicago

Balcony/Patio/ Separate Fenced Yard + Beach, Park & Downtown+close to Chicago
Chesterton
9.0 out of 10, Wonderful, (10 reviews)
"Thank you for a great stay for both the humans and fur babies! Very responsive hosts and easy check-in."
United States
Kara K.
The price is AU$450
includes taxes & fees
21 Apr - 22 Apr
Balcony/Patio/ Separate Fenced Yard + Beach, Park & Downtown+close to Chicago

Dunes Home 3 Bedroom I 2 BHR I 2 Living rooms Home | Valpo University | Dunes

Dunes Home 3 Bedroom I 2 BHR I 2 Living rooms Home | Valpo University | Dunes
Chesterton
9.8 out of 10, Exceptional, (66 reviews)
"Host was very accommodating. We stayed at the Dunes House in December. The blankets were cozy and the accommodations were comfortable."
United States
marjorie b.
The price is AU$484
includes taxes & fees
19 Apr - 20 Apr
Dunes Home 3 Bedroom I 2 BHR I 2 Living rooms Home | Valpo University | Dunes

Cozy Modern Townhome in Unbeatable Chesterton Location

Cozy Modern Townhome in Unbeatable Chesterton Location
Chesterton
The price is AU$447
includes taxes & fees
17 Apr - 18 Apr
Cozy Modern Townhome in Unbeatable Chesterton Location

Modern Comfort 3-bedroom house in lovely Chesterton with cool breeze and charm

Modern Comfort 3-bedroom house in lovely Chesterton with cool breeze and charm
Chesterton
The price is AU$620
includes taxes & fees
16 Apr - 17 Apr
Modern Comfort 3-bedroom house in lovely Chesterton with cool breeze and charm

Dunes Retreat w/Private Hot Tub

Dunes Retreat w/Private Hot Tub
Chesterton
9.8 out of 10, Exceptional, (20 reviews)
"We love staying here, by far our favorite hosts! Incredibly clean and all the little extras to make the stay feel like home. Great communication and easy check-in.Thanks again!"
United States
Kara K.
The price is AU$498
includes taxes & fees
16 Apr - 17 Apr
Dunes Retreat w/Private Hot Tub

NEW! Beautiful Riverfront Home on 10 Acres!

NEW! Beautiful Riverfront Home on 10 Acres!
Chesterton
8.0 out of 10, Very good, (9 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$542
includes taxes & fees
16 Apr - 17 Apr
NEW! Beautiful Riverfront Home on 10 Acres!

Dune trail retreat! 5 minutes to Indiana Dunes, Pet Friendly

Dune trail retreat! 5 minutes to Indiana Dunes, Pet Friendly
Porter
The price is AU$321
includes taxes & fees
22 Apr - 23 Apr
Dune trail retreat! 5 minutes to Indiana Dunes, Pet Friendly

Indiana Dunes National Park

Indiana Dunes National Park
Porter
9.0 out of 10, Wonderful, (2 reviews)
"Clean accommodations, everything was as advertised for our 1 night stay. The album collection was a bonus."
United States
Heather F.
Indiana Dunes National Park

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, (20 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$773
includes taxes & fees
20 Apr - 21 Apr
Roomy Retreat–Family&Friends|2 King Beds|Game Room | Valpo University | Dunes

(4 bedrooms and 2 full baths; sleeps 11)

(4 bedrooms and 2 full baths; sleeps 11)
Michiana Shores
9.2 out of 10, Wonderful, (32 reviews)
"The house was perfect for my family and I. Very nice area and easy short drive to Buffalo. We really enjoyed our stay.."
United States
David C.
The price is AU$830
includes taxes & fees
16 Apr - 17 Apr
(4 bedrooms and 2 full baths; sleeps 11)

Sq Toe`s Last Resort:Pet-Friendly*Fenced* GameRoom

Sq Toe`s Last Resort:Pet-Friendly*Fenced* GameRoom
New Buffalo
9.8 out of 10, Exceptional, (17 reviews)
"Great cozy place with great yard and activity space"
United States
Derek E.
The price is AU$772
includes taxes & fees
20 Apr - 21 Apr
Sq Toe`s Last Resort:Pet-Friendly*Fenced* GameRoom

Eagles Beach Nest 2:Pet-Friendly*Fenced*Walk2Beach

Eagles Beach Nest 2:Pet-Friendly*Fenced*Walk2Beach
Downtown New Buffalo
10.0 out of 10, Exceptional, (31 reviews)
"Highly recommend very clean, beautiful kitchen my family enjoyed staying there and my dog enjoyed the fenced in backyard"
United States
Mary B.
The price is AU$551
includes taxes & fees
21 Apr - 22 Apr
Eagles Beach Nest 2:Pet-Friendly*Fenced*Walk2Beach

View of the lake from 2 decks in this 6BR Lake Shore Dr home, steps to the beach

View of the lake from 2 decks in this 6BR Lake Shore Dr home, steps to the beach
Michigan City
8.4 out of 10, Very good, (90 reviews)
"nice location near the dunes had a beautiful view of the sunset"
United States
ron m.
The price is AU$1,103
includes taxes & fees
16 Apr - 17 Apr
View of the lake from 2 decks in this 6BR Lake Shore Dr home, steps to the beach

Game room/ Hot Tub / Pet Friendly/ Big Groups 20+

Game room/ Hot Tub / Pet Friendly/ Big Groups 20+
Michigan City
10.0 out of 10, Exceptional, (5 reviews)
"Our friend group had a great stay at this property. It is very well equipped, clean and great for a large group to stay. Jacuzzi is very nice. "
United States
Zhiling C.
The price is AU$921
includes taxes & fees
19 Apr - 20 Apr
Game room/ Hot Tub / Pet Friendly/ Big Groups 20+

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, (13 reviews)
"We loved staying here. Jason was a great communicator and made sure our needs were met. Plenty of beds for our family of 8 adults. 10 minutes to the national park and its pristine beaches. "
United States
Cindy W.
The price is AU$419
includes taxes & fees
16 Apr - 17 Apr
The Boutique at Midtown Central / Hot Tub / Pet Friendly

Newly Renovated / Dog Friendly / Sleeps 6

Newly Renovated / Dog Friendly / Sleeps 6
Michigan City
The price is AU$355
includes taxes & fees
16 Apr - 17 Apr
Newly Renovated / Dog Friendly / Sleeps 6

Restored 1870 Victorian Home in Historic LaPorte, IN all for you..

Restored 1870 Victorian Home in Historic LaPorte, IN all for you..
La Porte
9.8 out of 10, Exceptional, (85 reviews)
"We enjoyed our stay."
United States
Ramona M.
The price is AU$401
includes taxes & fees
16 Apr - 17 Apr
Restored 1870 Victorian Home in Historic LaPorte, IN all for you..

Rustic Getaway by Lake Michigan!

Rustic Getaway by Lake Michigan!
Michigan City
9.8 out of 10, Exceptional, (6 reviews)
"Very Nice! Has a very cozy feel and very well decored. Had great time! Lot of activites to do with the families. I would definetley recommend staying here. "
United States
Mohammed
The price is AU$1,230
includes taxes & fees
16 Apr - 17 Apr
Rustic Getaway by Lake Michigan!

Lake Life Escape. 5 Minutes to the beach, zoo, & casino

Lake Life Escape. 5 Minutes to the beach, zoo, & casino
Michigan City
7.8 out of 10, Good, (14 reviews)
"Great stay. Property was easy to access and very clean! "
United States
Riley C.
The price is AU$598
includes taxes & fees
16 Apr - 17 Apr
Lake Life Escape. 5 Minutes to the beach, zoo, & casino

Hilltop Cove- Charming 2 bed/2 bath in Beachwalk Resort with Golf Cart!

Hilltop Cove- Charming 2 bed/2 bath in Beachwalk Resort with Golf Cart!
Michigan City
9.8 out of 10, Exceptional, (16 reviews)
"Our family thoroughly enjoyed our stay at Hilltop Cove! We will definitely visit again!"
United States
Rebecca
The price is AU$1,094
includes taxes & fees
19 Apr - 20 Apr
Hilltop Cove- Charming 2 bed/2 bath in Beachwalk Resort with Golf Cart!
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
393
Accommodation
727 Holiday Homes
Lowest Price
AU$321
Highest Price
AU$1,230