Holiday Homes in Chesterton

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Check prices for these dates

In two weeks
15 May - 17 May
In two months
26 Jun - 28 Jun
In three months
24 Jul - 26 Jul
In four months
21 Aug - 23 Aug

Our top choices for Chesterton holiday homes

Property grounds

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 NZ$541
includes taxes & fees
1 May - 2 May
Balcony/Patio/ Separate Fenced Yard + Beach, Park & Downtown+close to Chicago
Smart TV, books

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 NZ$683
includes taxes & fees
1 May - 2 May
Dunes Home 3 Bedroom I 2 BHR I 2 Living rooms Home | Valpo University | Dunes
Exterior

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

Dune trail retreat! 5 minutes to Indiana Dunes, Pet Friendly
Porter
8.0 out of 10, Very good, (1 review)
"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 NZ$384
includes taxes & fees
1 May - 2 May
Dune trail retreat! 5 minutes to Indiana Dunes, Pet Friendly
Fridge, microwave, oven, stovetop

Cozy Modern Townhome in Unbeatable Chesterton Location

Cozy Modern Townhome in Unbeatable Chesterton Location
Chesterton
The price is NZ$582
includes taxes & fees
18 May - 19 May
Cozy Modern Townhome in Unbeatable Chesterton Location
Smart TV, fireplace, table football, books

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 NZ$1,006
includes taxes & fees
5 May - 6 May
Roomy Retreat–Family&Friends|2 King Beds|Game Room | Valpo University | Dunes
Interior

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 NZ$790
includes taxes & fees
26 May - 27 May
Modern Comfort 3-bedroom house in lovely Chesterton with cool breeze and charm
Interior

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 NZ$594
includes taxes & fees
3 May - 4 May
NEW! Beautiful Riverfront Home on 10 Acres!
Outdoor dining

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.
The price is NZ$426
includes taxes & fees
4 May - 5 May
Indiana Dunes National Park
5 bedrooms, iron/ironing board, travel cot, free WiFi

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, (90 reviews)
"Always such a wonderful time at The Nook! With the beach close and all the activities at the house, our family stays entertained for the whole stay. We look forward to coming here again!!"
United States
Abby B.
The price is NZ$1,481
includes taxes & fees
27 May - 28 May
1:00 pm Check-In & Out! - 1 mile to Dunes - Roomy-Sleeps 16 - 🎮Game Room Loft🏓
Exterior

3 Bed 3 Ba Screenporch/Sunset Lake Views

3 Bed 3 Ba Screenporch/Sunset Lake Views
LaPorte, Indiana, US
10.0 out of 10, Exceptional, (68 reviews)
"This property was very comfortable and worked great for our family!"
United States
Rolf B.
The price is NZ$916
includes taxes & fees
6 May - 7 May
3 Bed 3 Ba Screenporch/Sunset Lake Views
Exterior

UncleLarry's LakePlace, Hot Tub

UncleLarry's LakePlace, Hot Tub
La Porte
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful lake house stay, very refreshing! Lovely views of the lake and quiet area when we were there in November. Super comfy beds, great hot tub, and amazing view. Would definitely stay here again!"
United States
Jessica E.
The price is NZ$1,093
includes taxes & fees
7 May - 8 May
UncleLarry's LakePlace, Hot Tub
Fridge, microwave, oven, stovetop

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, (19 reviews)
"The backyard/garage area was awesome! So much to do. The house was very clean and the beds were super comfortable! The host was also extremely response!"
United States
Franny
The price is NZ$951
includes taxes & fees
5 May - 6 May
Sq Toe`s Last Resort:Pet-Friendly*Fenced* GameRoom
Fridge, microwave, oven, stovetop

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)
"Very nice place and all as advertised. Would stay here again"
United States
Murray
The price is NZ$701
includes taxes & fees
5 May - 6 May
Eagles Beach Nest 2:Pet-Friendly*Fenced*Walk2Beach
Beach nearby

(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 NZ$988
includes taxes & fees
3 May - 4 May
(4 bedrooms and 2 full baths; sleeps 11)
Exterior detail

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, (86 reviews)
"We enjoyed our stay."
United States
Ramona M.
The price is NZ$481
includes taxes & fees
3 May - 4 May
Restored 1870 Victorian Home in Historic LaPorte, IN all for you..
Terrace/patio

Game room/ Hot Tub / Pet Friendly / Duplex

Game room/ Hot Tub / Pet Friendly / Duplex
Michigan City
10.0 out of 10, Exceptional, (5 reviews)
"The house was perfect for and we enjoyed the hot tub."
United States
Mistre S.
The price is NZ$583
includes taxes & fees
3 May - 4 May
Game room/ Hot Tub / Pet Friendly / Duplex
Fridge, microwave, oven, stovetop

Newly Renovated / Dog Friendly / Sleeps 6

Newly Renovated / Dog Friendly / Sleeps 6
Michigan City
The price is NZ$449
includes taxes & fees
3 May - 4 May
Newly Renovated / Dog Friendly / Sleeps 6
Beach nearby

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, (14 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 NZ$503
includes taxes & fees
3 May - 4 May
The Boutique at Midtown Central / Hot Tub / Pet Friendly
Beach nearby

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 NZ$1,313
includes taxes & fees
3 May - 4 May
View of the lake from 2 decks in this 6BR Lake Shore Dr home, steps to the beach
Smart TV, fireplace, table football, books

Sand & Sun Getaway | 4BR w/ Game Room + 2 Living Areas |Game Room | Minutes to Beach

Sand & Sun Getaway | 4BR w/ Game Room + 2 Living Areas |Game Room | Minutes to Beach
Michigan City
9.4 out of 10, Exceptional, (34 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 NZ$680
includes taxes & fees
4 May - 5 May
Sand & Sun Getaway | 4BR w/ Game Room + 2 Living Areas |Game Room | Minutes to 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
"Four Winds is a beautiful casino with very clean rooms, clean casino floor and grounds. We really enjoyed our stay at Four Winds on New Buffalo, MI. We plan to go there again soon."
Barbara 1-night trip
Posted 3 hours ago
Four Winds Casino Resort – New Buffalo

Find out more about Chesterton

Chesterton Holiday Homes information

Number of reviews
493
Accommodation
727 Holiday Homes
Lowest Price
NZ$384
Highest Price
NZ$1,481