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Chesterton Holiday Rentals

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Holiday Rentals in Chesterton

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 AU$137
includes taxes & fees
1 Dec - 2 Dec
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes

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

Chesterton
9.8 out of 10, Exceptional, (63)
"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 AU$449
includes taxes & fees
1 Dec - 2 Dec
Dunes Home 3 Bedroom I 2 BHR I 2 Living rooms Home | Valpo University | Dunes

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

Chesterton
8.6 out of 10, Excellent, (7)
"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 AU$459
includes taxes & fees
1 Dec - 2 Dec
Balcony/Patio/ Separate Fenced Yard + Beach, Park & Downtown+close to Chicago

Balcony/Patio/ Fenced Yard/ Attached Garage/near Beach, Park /close to Chicago

Chesterton
9.4 out of 10, Exceptional, (3)
"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 AU$614
includes taxes & fees
2 Dec - 3 Dec
Balcony/Patio/ Fenced Yard/ Attached Garage/near Beach, Park /close to Chicago

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 AU$236
includes taxes & fees
1 Dec - 2 Dec
The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes

Cozy Retreat w/Hot tub Indiana dunes Beaches Trails

Chesterton
10.0 out of 10, Exceptional, (12)
"My husband and I met up with our son from Chicago and loved your beautiful home! It was so clean and comfortable. The house was so well stocked with anything we would need! We were very impressed!"
United States
Kim L.
The price is AU$423
includes taxes & fees
8 Dec - 9 Dec
Cozy Retreat w/Hot tub Indiana dunes Beaches Trails

Roomy Retreat–Family&Friends|2 King Beds|Game Room | Valpo University | Dunes

Chesterton
9.2 out of 10, Wonderful, (19)
"This is a beautiful place. It has everything that you could possibly need. "
United States
George N.
The price is AU$746
includes taxes & fees
1 Dec - 2 Dec
Roomy Retreat–Family&Friends|2 King Beds|Game Room | Valpo University | Dunes

Indiana Dunes National Park

Porter
9.0 out of 10, Wonderful, (2)
"Clean accommodations, everything was as advertised for our 1 night stay. The album collection was a bonus."
United States
Heather F.
The price is AU$323
includes taxes & fees
1 Dec - 2 Dec
Indiana Dunes National Park

Blue Birdhouse - No Cleaning Fee - Pet Friendly - Dunes National Park

Chesterton
9.4 out of 10, Exceptional, (31)
"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 AU$255
includes taxes & fees
1 Dec - 2 Dec
Blue Birdhouse - No Cleaning Fee - Pet Friendly - Dunes National Park

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

Chesterton
8.8 out of 10, Excellent, (90)
"Great location for visiting the Dunes. Having a gas grill available was a nice perk. Was what we needed at a great value. "
United States
Brian L.
The price is AU$174
includes taxes & fees
1 Dec - 2 Dec
Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes

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

Chesterton
9.0 out of 10, Wonderful, (4)
"Beautiful historic building. "
United States
Deborah S.
The price is AU$2,419
includes taxes & fees
1 Dec - 2 Dec
2 miles from Dunes National Park. A Unique Boutique Hotel.

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 AU$506
includes taxes & fees
1 Dec - 2 Dec
That 70’s Loft- Peace, Love and a Funky Stay!

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 AU$603
includes taxes & fees
28 Dec - 29 Dec
NEW! Beautiful Riverfront Home on 10 Acres!

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

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

Cozy House: 5 min drive to beach-zoo-restaurants-casino-brewery-train to Chicago

Michigan City
9.8 out of 10, Exceptional, (13)
"It was very cozy and perfect! "
United States
Tommy W.
The price is AU$251
includes taxes & fees
2 Dec - 3 Dec
Cozy House: 5 min drive to beach-zoo-restaurants-casino-brewery-train to Chicago

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 AU$531
includes taxes & fees
2 Dec - 3 Dec
Sand & Sun Getaway | 4BR w/ Game Room + 2 Living Areas |Game Room | Minutes to Beach

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

Brand New Cottage Walkable to All Downtown Michigan City & Beach!

Michigan City
9.6 out of 10, Exceptional, (15)
"Beautiful and feels like home! Great location too! "
United States
Michelle T.
The price is AU$458
includes taxes & fees
1 Dec - 2 Dec
Brand New Cottage Walkable to All Downtown Michigan City & Beach!

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

Valparaiso
9.0 out of 10, Wonderful, (44)
"Our stay was comfortable and the host was very communicative through the entire process. "
United States
Elizabeth G.
The price is AU$392
includes taxes & fees
7 Dec - 8 Dec
Black Cabin Getaway in Beautiful Woods I Valpo University | Flint Lake | Dunes

Secluded Oasis: 4 Bedrooms, 3 Blocks to Downtown

New Buffalo
9.6 out of 10, Exceptional, (5)
"We really loved this house! Comfy beds, fun amenities (the converted garage hangout space is fabulous), great design/layout with plenty of room for everyone to spread out or all be together. The backyard was great, too! The location felt secluded, but everything is only a few minutes drive away."
United States
Jeana H.
The price is AU$740
includes taxes & fees
1 Dec - 2 Dec
Secluded Oasis: 4 Bedrooms, 3 Blocks to Downtown
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

Everything you need to know about Chesterton holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chesterton holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chesterton holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Chesterton holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesterton. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chesterton holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chesterton holiday rentals we have selected for you start as low as AU$137 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Chesterton rentals

At Expedia, we put the best Chesterton holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chesterton rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chesterton holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chesterton. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Beautiful Family Cottage in Beachwalk-Grill-AC-Free Wifi-Kids Haven.: This holiday home rental outside of Chesterton offers a balcony, a selection of games and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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.