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Chesterton Holiday Rentals

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Check prices for these dates

Tonight
9 Jan - 10 Jan
Tomorrow
10 Jan - 11 Jan
This weekend
9 Jan - 11 Jan
Next weekend
16 Jan - 18 Jan

Our top choices for Chesterton holiday rentals

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

Mobile Home in Porter

The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
9.0 out of 10, Wonderful, (12 reviews)
"Every aspect of my booking & stay was convenient & seamless; from the reasonable price, online reservation process, host communication, beautiful grounds, to the abundant amenities offered there was nothing I or my family wanted for. Don & Kim are accommodating, professional & experienced hosts and it showed. Thank you for the wonderful experience I recommend their multiple spaces to anyone & would stay with them again without hesitation! "
United States
esther Amber C.
The price is HK$456
HK$685 total
includes taxes & fees
11 Jan - 12 Jan
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
Property grounds
Balcony/Patio/ Separate Fenced Yard + Beach, Park & Downtown+close to Chicago

Holiday Home in Chesterton

Balcony/Patio/ Separate Fenced Yard + Beach, Park & Downtown+close to Chicago
9.0 out of 10, Wonderful, (10 reviews)
"Excellent spot for several people to stay and enjoy the Dunes. Clean, quiet, centrally located to lots of Dunes hotspots. Thanks for the great stay!"
United States
Nick R.
The price is HK$806
HK$2,500 total
includes taxes & fees
11 Jan - 12 Jan
Balcony/Patio/ Separate Fenced Yard + Beach, Park & Downtown+close to Chicago
Property grounds
Balcony/Patio/ Fenced Yard/ Attached Garage/near Beach, Park /close to Chicago

Holiday Home in Chesterton

Balcony/Patio/ Fenced Yard/ Attached Garage/near Beach, Park /close to Chicago
9.4 out of 10, Exceptional, (3 reviews)
"I enjoyed my short stay and visit to The Indiana National Dunes. The Host was friendly and she put special effort into setting the place up for my stay. I 100% would rent again from this host and would recommend "
United States
T J.
The price is HK$877
HK$3,076 total
includes taxes & fees
11 Jan - 12 Jan
Balcony/Patio/ Fenced Yard/ Attached Garage/near Beach, Park /close to Chicago
Smart TV, books
Dunes Home 3 Bedroom I 2 BHR I 2 Living rooms Home | Valpo University | Dunes

Holiday Home in Chesterton

Dunes Home 3 Bedroom I 2 BHR I 2 Living rooms Home | Valpo University | Dunes
9.8 out of 10, Exceptional, (64 reviews)
"This place was great. It was very spacious, clean, and close to restaurants and grocery stores. The host was very communicative and answered any questions we had very quickly. The house was easy to find and parking was right in front of the house. The neighborhood was quiet and safe."
United States
Christine C.
The price is HK$584
HK$2,461 total
includes taxes & fees
15 Jan - 16 Jan
Dunes Home 3 Bedroom I 2 BHR I 2 Living rooms Home | Valpo University | Dunes
Smart TV, fireplace, table football, books
Roomy Retreat–Family&Friends|2 King Beds|Game Room | Valpo University | Dunes

Holiday Home in Chesterton

Roomy Retreat–Family&Friends|2 King Beds|Game Room | Valpo University | Dunes
9.2 out of 10, Wonderful, (20 reviews)
"This is a beautiful place. It has everything that you could possibly need. "
United States
George N.
The price is HK$1,013
HK$3,726 total
includes taxes & fees
11 Jan - 12 Jan
Roomy Retreat–Family&Friends|2 King Beds|Game Room | Valpo University | Dunes
On the beach, sun-loungers, beach towels
Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly

Cabin in Porter Beach

Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly
10.0 out of 10, Exceptional, (133 reviews)
"Loved the cabin, in a beautiful place.William is an excellent host."
United States
Lee Anna E.
The price is HK$1,325
HK$2,199 total
includes taxes & fees
25 Jan - 26 Jan
Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly
Outdoor dining
Indiana Dunes National Park

Holiday Home in Porter

Indiana Dunes National Park
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 HK$1,066
HK$1,639 total
includes taxes & fees
11 Jan - 12 Jan
Indiana Dunes National Park
Beach
Blue Birdhouse - No Cleaning Fee - Pet Friendly - Dunes National Park

Holiday Home in Chesterton

Blue Birdhouse - No Cleaning Fee - Pet Friendly - Dunes National Park
9.4 out of 10, Exceptional, (31 reviews)
"We stayed 2 nights at Blue Birdhouse and it was perfect for us! Bonus, big fenced back yard for the pups! "
United States
Carolyn F.
The price is HK$1,113
HK$1,287 total
includes taxes & fees
11 Jan - 12 Jan
Blue Birdhouse - No Cleaning Fee - Pet Friendly - Dunes National Park
Beach nearby
The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes

Apartment in Porter

The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes
8.8 out of 10, Excellent, (16 reviews)
"Great place to stay with kids."
United States
Jane H.
The price is HK$1,578
HK$1,994 total
includes taxes & fees
11 Jan - 12 Jan
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

Apartment in Chesterton

Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes
9.0 out of 10, Wonderful, (92 reviews)
"Great stay on every level "
United States
Tom M.
The price is HK$577
HK$820 total
includes taxes & fees
1 Feb - 2 Feb
Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes
Dining
That 70’s Loft- Peace, Love and a Funky Stay!

Apartment in Chesterton

That 70’s Loft- Peace, Love and a Funky Stay!
2.0 star property
10.0 out of 10, Exceptional, (6 reviews)
"Perfect location! The loft had everything we needed and Reina is an exceptional host. "
United States
Melissa H.
The price is HK$1,368
HK$2,518 total
includes taxes & fees
11 Jan - 12 Jan
That 70’s Loft- Peace, Love and a Funky Stay!
Beach
Cozy Retreat w/Hot tub Indiana dunes Beaches Trails

Holiday Home in Chesterton

Cozy Retreat w/Hot tub Indiana dunes Beaches Trails
10.0 out of 10, Exceptional, (13 reviews)
"Great host, everything was clean, many little extras for comfort and convenience!"
United States
Kara K.
The price is HK$1,543
HK$2,932 total
includes taxes & fees
11 Jan - 12 Jan
Cozy Retreat w/Hot tub Indiana dunes Beaches Trails
Interior
NEW! Beautiful Riverfront Home on 10 Acres!

Holiday Home in Chesterton

NEW! Beautiful Riverfront Home on 10 Acres!
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 HK$1,239
HK$3,046 total
includes taxes & fees
11 Jan - 12 Jan
NEW! Beautiful Riverfront Home on 10 Acres!
Interior
Modern Comfort 3-bedroom house in lovely Chesterton with cool breeze and charm

Holiday Home in Chesterton

Modern Comfort 3-bedroom house in lovely Chesterton with cool breeze and charm
2.0 star property
The price is HK$1,325
HK$3,692 total
includes taxes & fees
29 Jan - 30 Jan
Modern Comfort 3-bedroom house in lovely Chesterton with cool breeze and charm
Exterior detail
2 miles from Dunes National Park. A Unique Boutique Hotel.

Aparthotel in Chesterton

2 miles from Dunes National Park. A Unique Boutique Hotel.
9.0 out of 10, Wonderful, (4 reviews)
"Beautiful historic building. "
United States
Deborah S.
The price is HK$8,766
HK$12,209 total
includes taxes & fees
11 Jan - 12 Jan
2 miles from Dunes National Park. A Unique Boutique Hotel.
Property grounds
BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.

Apartment in Michigan City

BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.
9.4 out of 10, Exceptional, (126 reviews)
"Was as described great stay"
United States
Amber C.
The price is HK$616
HK$1,475 total
includes taxes & fees
14 Jan - 15 Jan
BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.
Smart TV, fireplace, table football, books
Sand & Sun Getaway | 4BR w/ Game Room + 2 Living Areas |Game Room | Minutes to Beach

Holiday Home in Michigan City

Sand & Sun Getaway | 4BR w/ Game Room + 2 Living Areas |Game Room | Minutes to Beach
9.4 out of 10, Exceptional, (33 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 HK$592
HK$2,759 total
includes taxes & fees
11 Jan - 12 Jan
Sand & Sun Getaway | 4BR w/ Game Room + 2 Living Areas |Game Room | Minutes to Beach
Fridge, microwave, oven, stovetop
Eagles Beach Nest 2:Pet-Friendly*Fenced*Walk2Beach

Holiday Home in Downtown New Buffalo

Eagles Beach Nest 2:Pet-Friendly*Fenced*Walk2Beach
10.0 out of 10, Exceptional, (29 reviews)
"It was a lovely stay! Very clean and it was awesome I could take my dog with me :)"
United States
Roxie
The price is HK$844
HK$2,414 total
includes taxes & fees
11 Jan - 12 Jan
Eagles Beach Nest 2:Pet-Friendly*Fenced*Walk2Beach
Terrace/patio
Grand Reunion House 2 / Hot Tub / Pet Friendly / Duplex

Holiday Home in Michigan City

Grand Reunion House 2 / Hot Tub / Pet Friendly / Duplex
2.0 star property
10.0 out of 10, Exceptional, (5 reviews)
"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$803
HK$2,143 total
includes taxes & fees
14 Jan - 15 Jan
Grand Reunion House 2 / Hot Tub / Pet Friendly / Duplex
TV, books
Eagle`s Beach Nest: Pet-Friendly*Fenced*Walk2Beach

Holiday Home in Downtown New Buffalo

Eagle`s Beach Nest: Pet-Friendly*Fenced*Walk2Beach
10.0 out of 10, Exceptional, (19 reviews)
"Great stay, loved the place!"
United States
Ryan J.
The price is HK$711
HK$2,733 total
includes taxes & fees
11 Jan - 12 Jan
Eagle`s Beach Nest: Pet-Friendly*Fenced*Walk2Beach
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
"Clean room. Checkin staff was pleasant and helpful. "
Karen 1-night trip
Posted 1 day 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
  • 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?

View of the lake from 2 decks in this 6BR Lake Shore Dr home, steps to the beach: This holiday home rental outside of Chesterton is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Chesterton?

Choose from 30 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.