A wooden staircase ascending a sandy hill with sparse vegetation.

Chesterton Vacation Rentals

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Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Chesterton vacation rentals

Beach nearby

Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes

Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes
Chesterton
8.8 out of 10, Excellent, (122 reviews)
"Hot tub was working great, air conditioning great, quite roomy, with a full kitchen."
United States
Piotr S.
The price is ￥20,857
￥26,981 total
includes taxes & fees
Aug 2 - Aug 3
Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes
5 bedrooms, iron/ironing board, travel crib, 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, (94 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 ￥75,505
￥152,471 total
includes taxes & fees
Jul 14 - Jul 15
1:00 pm Check-In & Out! - 1 mile to Dunes - Roomy-Sleeps 16 - 🎮Game Room Loft🏓
Beach

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, (43 reviews)
"We loved the house. It was in a great location to all the dog friendly activities we did! Would definitely recommend staying here. "
United States
Raylynn K.
The price is ￥43,880
￥49,494 total
includes taxes & fees
Aug 5 - Aug 6
Blue Birdhouse - No Cleaning Fee - Pet Friendly - Dunes National Park
Smart TV, fireplace, foosball, 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, (21 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 ￥44,003
￥112,119 total
includes taxes & fees
Jul 15 - Jul 16
Roomy Retreat–Family&Friends|2 King Beds|Game Room | Valpo University | Dunes
Beach nearby

The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes

The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes
Porter
9.0 out of 10, Wonderful, (18 reviews)
"Awesome place to stay and plenty to do"
United States
Cody
The price is ￥36,378
￥45,270 total
includes taxes & fees
Aug 5 - Aug 6
The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes
Smart TV, fireplace, 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
9.6 out of 10, Exceptional, (71 reviews)
"Host was welcoming and very responsive "
United States
Shannon B.
The price is ￥26,018
￥71,513 total
includes taxes & fees
Jul 27 - Jul 28
Dunes Home 3 Bedroom I 2 BHR I 2 Living rooms Home | Valpo University | Dunes
Exterior

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, (4 reviews)
"We enjoyed our stay. Very inviting and comfortable accommodations. Would stay again and would recommend!"
United States
Amanda E.
The price is ￥25,869
￥50,884 total
includes taxes & fees
Jul 19 - Jul 20
The Porter Nook! 5 minutes to Indiana Dunes, Pet Friendly
House (4 Bedrooms) | Interior

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

Sugar Shores ~ 3 Mi to Indiana Dunes Nat'l Park
3.0 star property
Chesterton
The price is ￥48,019
￥98,085 total
includes taxes & fees
Aug 5 - Aug 6
Sugar Shores ~ 3 Mi to Indiana Dunes Nat'l Park
Living area

Pleasant Townhome/Chesterton/Indiana Dunes/close to Chicago

Pleasant Townhome/Chesterton/Indiana Dunes/close to Chicago
Chesterton
The price is ￥52,546
￥99,957 total
includes taxes & fees
Jul 14 - Jul 15
Pleasant Townhome/Chesterton/Indiana Dunes/close to Chicago
Beach nearby

The "Pool Barn Camper" w/Hot Tub near Indiana Dunes

The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
Porter
8.8 out of 10, Excellent, (16 reviews)
"Great Stay!"
United States
Erin
The price is ￥27,324
￥34,225 total
includes taxes & fees
Aug 11 - Aug 12
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
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)
The price is ￥25,707
￥63,197 total
includes taxes & fees
Jul 14 - Jul 15
NEW! Beautiful Riverfront Home on 10 Acres!
TV, fireplace, DVD player, foosball

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, (23 reviews)
"Great Property. Very helpful hosts! "
United States
Toni L.
The price is ￥38,965
￥94,525 total
includes taxes & fees
Aug 5 - Aug 6
Sugar Shores ~ 3 Mi to Indiana Dunes Nat'l Park
Spa

Adorable Cottage New Buffalo, Mi. Near Grand Beach.1 Bedroom, Sleeps 5

Adorable Cottage New Buffalo, Mi. Near Grand Beach.1 Bedroom, Sleeps 5
New Buffalo
9.8 out of 10, Exceptional, (204 reviews)
"Very relaxing cottage, and the hosts are terrific. We have stayed here many times and we always enjoy it! Lots of personal touches and awesome landscaping, with a nice fireplace indoors and big fire ring out back."
United States
Steve P.
Adorable Cottage New Buffalo, Mi. Near Grand Beach.1 Bedroom, Sleeps 5
Beach nearby, sun loungers, beach towels

Fun w/Loft! Beach ~Nature Trails ~Grill~ Firepit ~Indiana Dunes National Park

Fun w/Loft! Beach ~Nature Trails ~Grill~ Firepit ~Indiana Dunes National Park
Miller Beach
10.0 out of 10, Exceptional, (52 reviews)
"Had a great stay and robin was super helpful and friendly! Great location close to lake"
United States
Weylin W.
The price is ￥112,893
￥185,835 total
includes taxes & fees
Jul 31 - Aug 1
Fun w/Loft! Beach ~Nature Trails ~Grill~ Firepit ~Indiana Dunes National Park
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, (33 reviews)
"Very nice place and all as advertised. Would stay here again"
United States
Murray
The price is ￥50,444
￥102,298 total
includes taxes & fees
Aug 10 - Aug 11
Eagles Beach Nest 2:Pet-Friendly*Fenced*Walk2Beach
Property grounds

BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.

BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.
Michigan City
9.2 out of 10, Wonderful, (133 reviews)
"Great spot. So close to the beach and the hot tub was amazing!"
United States
Sean B.
The price is ￥24,252
￥47,624 total
includes taxes & fees
Aug 5 - Aug 6
BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.
Interior

Beautiful Rustic Cabin for Two!

Beautiful Rustic Cabin for Two!
Griffith
8.6 out of 10, Excellent, (30 reviews)
"Easy to find little cabin in Griffith"
United States
Allison R.
The price is ￥13,904
￥19,194 total
includes taxes & fees
Jul 19 - Jul 20
Beautiful Rustic Cabin for Two!
Outdoor dining

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, (94 reviews)
"Great place Awesome host"
United States
Kevin K.
The price is ￥80,840
￥124,222 total
includes taxes & fees
Jul 27 - Jul 28
Lakehouse with Pontoon, Deck, Firepit, Paddle Boards, Grill & more INCLUDED!!
Beach nearby

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, (23 reviews)
"Cutest, coziest place! Super clean. Great communication with owner. Worked perfect for stay. We'll be back!"
United States
Nancy R.
Cozy House: 5 min drive to beach-zoo-restaurants-casino-brewery-train to Chicago
Exterior

Uptown Penthouse on Pine: By Lake Michigan, Shopping & Casino!

Uptown Penthouse on Pine: By Lake Michigan, Shopping & Casino!
Michigan City
9.8 out of 10, Exceptional, (40 reviews)
"Lovely place for family stay! Everything was nice, clean and neat! Very home comforting! Couldn’t have had a better place! Close to all the beach, zoo, outlets, and casino! Just a wonderful experience!"
United States
Patricia
The price is ￥36,232
￥72,995 total
includes taxes & fees
Jul 16 - Jul 17
Uptown Penthouse on Pine: By Lake Michigan, Shopping & Casino!
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
"The staff were so kind and helpful. The shows were great. The food was delicious. We had a great weekend."
Stephanie 2-night trip
Posted 9 hours ago
Four Winds Casino Resort – New Buffalo

Find out more about Chesterton

Search for holiday rentals in Chesterton on Expedia! You can easily find your home rentals, villas, holiday apartments in Chesterton using one of the methods below:

  • View our selection of featured holiday rentals in Chesterton
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  • Enter your travel dates to view the best deals on holiday rentals in Chesterton while they last

Look no further and take a look at our great range of rental properties in Chesterton!

Frequently asked questions

Are there vacation rentals in Chesterton?

Yes, we give you a choice of vacation rentals close to the most popular local attractions in Chesterton, or you can choose a more secluded option if you're looking for relaxation. Discover why Chesterton is known for its shops and beaches. While you're here, grab a bite or have a drink at the restaurants.

What's the top vacation rental that Chesterton has to offer?

Blue Birdhouse - No Cleaning Fee - Pet Friendly - Dunes National Park: This highly rated vacation home rental in Chesterton offers a patio, a private yard, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. You and your friends and family can relax into your vacation with amenities like a selection of books.

How many vacation rentals are there in Chesterton?

Choose from 36 Expedia vacation rentals in Chesterton for a memorable vacation.

What can I see and do in Chesterton?

Indiana Dunes National Park and Lake Michigan are a couple of scenic spots to enjoy the outdoors, whereas Chesterton Art Center is one of the cultural attractions. Other places in town to visit include Indiana Dunes State Park and Lustron House.

What are vacation rentals like in Chesterton?

Vacation rentals are private properties you can reserve for a couple days or more in Chesterton. Vacation rentals feature extras such as kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about a clean environment, vacation rentals can provide a sense of privacy away from shared hotel elevators and lobbies packed with people while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a popular option for a family getaway.