Chesterton Holiday Rentals

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Check prices for these dates

In two weeks
28 Nov - 30 Nov
In two months
9 Jan - 11 Jan
In three months
6 Feb - 8 Feb
In four months
6 Mar - 8 Mar

Holiday Rentals in Chesterton

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

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

Porter
9.0 out of 10, Wonderful, (12)
"Great pool hostess was very helpful"
United States
regina
The price is HK$455
HK$684 total
includes taxes & fees
16 Nov - 17 Nov
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
Fridge, microwave, oven, stovetop
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, (63)
"Beautiful stay, close to a lot of enjoyable places to go"
United States
Alejandra P.
The price is HK$560
HK$2,429 total
includes taxes & fees
18 Nov - 19 Nov
Dunes Home 3 Bedroom I 2 BHR I 2 Living rooms Home | Valpo University | Dunes
Living area
That 70’s Loft- Peace, Love and a Funky Stay!

That 70’s Loft- Peace, Love and a Funky Stay!

2.0 star property
Chesterton
10.0 out of 10, Exceptional, (6)
"Absolutely lovely stay! Space was cozy and host was phenomenal!Amenities were on point, and the location was convenient for traveling to various points on the Dunes and trails! Would recommend anyone spend time at this rental, and would love to come back again!"
United States
Christopher B.
The price is HK$1,364
HK$2,547 total
includes taxes & fees
16 Nov - 17 Nov
That 70’s Loft- Peace, Love and a Funky Stay!
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
8.6 out of 10, Excellent, (7)
"My adult daughter & I stayed for 3 nights while visiting Indian Dunes. The duplex looks newly remodeled and it was clean and comfortable. Vic&Ari were easy to communicate with and responded to our questions in a timely manner. They even recommended a great restaurant!"
United States
Linda F.
The price is HK$664
HK$2,311 total
includes taxes & fees
26 Nov - 27 Nov
Balcony/Patio/ Separate Fenced Yard + Beach, Park & Downtown+close to Chicago
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
8.8 out of 10, Excellent, (16)
"Great place to stay with kids."
United States
Jane H.
The price is HK$902
HK$1,185 total
includes taxes & fees
24 Nov - 25 Nov
The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes
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, (90)
"I stayed one night in this apartment and had a great experience. The town is cute, the location is perfect, just a short drive from the Indiana Dunes, and the place was clean and convenient for a quick trip. The host communicated clearly and promptly, which made everything easy. Highly recommend!"
United States
Megan M.
The price is HK$623
HK$872 total
includes taxes & fees
16 Nov - 17 Nov
Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes
Property grounds
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, (31)
"Our family had a wonderful time staying and making memories at the bluebird house. The house was very inviting and precious. Would def visit again."
United States
Violeta g.
The price is HK$1,138
HK$1,312 total
includes taxes & fees
16 Nov - 17 Nov
Blue Birdhouse - No Cleaning Fee - Pet Friendly - Dunes National Park
Outdoor dining
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, (19)
"The house was very clean, accommodated a large crew, and the host was very responsive. The overall stay was exceptional, and we will use again in the future."
United States
Alpine T.
The price is HK$1,057
HK$3,796 total
includes taxes & fees
17 Nov - 18 Nov
Roomy Retreat–Family&Friends|2 King Beds|Game Room | Valpo University | Dunes
Beach
After-Dune Delight! Large Home with Pool and Fun for All

After-Dune Delight! Large Home with Pool and Fun for All

Porter
10.0 out of 10, Exceptional, (1)
"The property was clean and well maintained. The host was responsive and nice. We had a wonderful stay here."
United States
Jason B.
The price is HK$1,967
HK$4,518 total
includes taxes & fees
16 Nov - 17 Nov
After-Dune Delight! Large Home with Pool and Fun for All
Interior
NEW! Beautiful Riverfront Home on 10 Acres!

NEW! Beautiful Riverfront Home on 10 Acres!

Chesterton
8.0 out of 10, Very good, (9)
"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 HK$1,236
HK$3,037 total
includes taxes & fees
23 Nov - 24 Nov
NEW! Beautiful Riverfront Home on 10 Acres!
Beach
Cozy Retreat w/Hot tub Indiana dunes Beaches Trails

Cozy Retreat w/Hot tub Indiana dunes Beaches Trails

Chesterton
10.0 out of 10, Exceptional, (11)
"This was one of the nicest, cleanest VRBO we have stated in. Don’t let the neighborhood detour you from staying. We felt safe and slept amazing in the VERY comfy king bed !! The master shower drain wasn’t working during our stay but the owner was very responsive and apologized for the inconvenience. "
United States
Dot Dot Smile Nichole W.
The price is HK$1,011
HK$2,264 total
includes taxes & fees
8 Dec - 9 Dec
Cozy Retreat w/Hot tub Indiana dunes Beaches Trails
Outdoor dining
Indiana Dunes National Park

Indiana Dunes National Park

Porter
The price is HK$1,064
HK$1,627 total
includes taxes & fees
17 Nov - 18 Nov
Indiana Dunes National Park
Interior
2 miles from Dunes National Park. A Unique Boutique Hotel.

2 miles from Dunes National Park. A Unique Boutique Hotel.

Chesterton
9.0 out of 10, Wonderful, (4)
"Great Vrbo! Very nice, very clean, enough room for everyone! We loved it!"
United States
Val S.
The price is HK$8,742
HK$12,132 total
includes taxes & fees
26 Nov - 27 Nov
2 miles from Dunes National Park. A Unique Boutique Hotel.
Property grounds
Renovated 1971 Airstream on an 80 acre animal rescue farm in Westville IN

Renovated 1971 Airstream on an 80 acre animal rescue farm in Westville IN

Westville
10.0 out of 10, Exceptional, (1)
"What a unique and lovely stay! The airstream was thoughtfully renovated and the property was beautiful. Lots of trails to walk and animals to talk to. "
United States
Stef K.
The price is HK$1,714
HK$2,198 total
includes taxes & fees
26 Nov - 27 Nov
Renovated 1971 Airstream on an 80 acre animal rescue farm in Westville IN
Fridge, microwave, oven, stovetop
Grand Reunion House 2 / Hot Tub / Pet Friendly / Duplex

Grand Reunion House 2 / Hot Tub / Pet Friendly / Duplex

2.0 star property
Michigan City
10.0 out of 10, Exceptional, (4)
"Great option for a quick weekend trip to the Dunes. Clean, comfy and good communication from the host."
United States
Dillon K.
The price is HK$777
HK$2,095 total
includes taxes & fees
16 Nov - 17 Nov
Grand Reunion House 2 / Hot Tub / Pet Friendly / Duplex
Fridge, microwave, oven, stovetop
Heart of Historical Dist.*Parking*Claw Tub*A/C #4

Heart of Historical Dist.*Parking*Claw Tub*A/C #4

Michigan City
10.0 out of 10, Exceptional, (7)
"Very clean and well cared for!"
United States
Savannah P.
The price is HK$582
HK$1,647 total
includes taxes & fees
16 Nov - 17 Nov
Heart of Historical Dist.*Parking*Claw Tub*A/C #4
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, (31)
"Nice"
United States
Maryellen W.
The price is HK$567
HK$2,716 total
includes taxes & fees
17 Nov - 18 Nov
Sand & Sun Getaway | 4BR w/ Game Room + 2 Living Areas |Game Room | Minutes to Beach
Exterior
Black Cabin Getaway in Beautiful Woods I Valpo University | Flint Lake | Dunes

Black Cabin Getaway in Beautiful Woods I Valpo University | Flint Lake | Dunes

Valparaiso
9.0 out of 10, Wonderful, (44)
"perfect location for me. a little quirky, hosts very responsive."
United States
elizabeth s.
The price is HK$529
HK$1,898 total
includes taxes & fees
16 Nov - 17 Nov
Black Cabin Getaway in Beautiful Woods I Valpo University | Flint Lake | Dunes
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, (13)
"Very cozy land beautiful home"
United States
Stanley H.
The price is HK$622
HK$1,175 total
includes taxes & fees
24 Nov - 25 Nov
Cozy House: 5 min drive to beach-zoo-restaurants-casino-brewery-train to Chicago
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
9.4 out of 10, Exceptional, (125)
"The location was PERFECT. Just a 5 minute walk down a sandy path to a beautiful beach and Lake Michigan! The tiny cottage was perfect for two people. The bed however is very very hard. If you’re young you’d be okay, but us older folks don’t do well on firm beds lolOther than that our weekend stay was perfect!"
United States
Natasha W.
The price is HK$692
HK$1,567 total
includes taxes & fees
16 Nov - 17 Nov
BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.
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

Blue Chip Casino Hotel and Spa

Blue Chip Casino Hotel and Spa

10/10 Excellent
"Yes"
Justin 1-night trip
Posted 23 hours ago
Blue Chip Casino Hotel and Spa

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
  • Use the map to find apartments and other holiday homes in the Chesterton neighbourhood you prefer
  • 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 holiday rentals in Chesterton?

Yes, there are holiday rentals close to the most popular sights in Chesterton, or you can select a more secluded option if you're looking for a relaxing stay. 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 are some of the best holiday rentals that Chesterton has to offer?

Big Family House 5 Minutes from Lake Michigan/Blue Chip Casino/Brewery/Wineries!: This holiday home rental outside of Chesterton is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Chesterton?

Choose from 29 Expedia holiday rentals in Chesterton for a memorable holiday.

What can I see and do in Chesterton?

Lake Michigan and Indiana Dunes Visitor Center 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 Lustron House and Chellberg Farm.

What are holiday rentals like in Chesterton?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chesterton. Holiday rentals offer amenities such as patios, hot tubs and fire pits so you'll be comfy for your stay. If you're concerned about a clean environment, a holiday rental can provide a sense of security away from shared hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for family gatherings.