Chesterton Vacation Rentals

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Tonight
Nov 18 - Nov 19
Tomorrow
Nov 19 - Nov 20
This weekend
Nov 21 - Nov 23
Next weekend
Nov 28 - Nov 30

Vacation 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 ￥9,041
￥13,589 total
includes taxes & fees
Nov 20 - Nov 21
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)
"The house was very clean and served us well. It was in a great walkable small town with plenty of good restaurants, and only a short drive to the dunes"
United States
Sue
The price is ￥10,819
￥47,948 total
includes taxes & fees
Nov 19 - Nov 20
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 ￥27,124
￥50,633 total
includes taxes & fees
Nov 24 - Nov 25
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)
"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 ￥13,214
￥45,959 total
includes taxes & fees
Nov 23 - Nov 24
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 ￥17,943
￥23,559 total
includes taxes & fees
Nov 23 - Nov 24
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)
"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 ￥12,437
￥17,409 total
includes taxes & fees
Nov 19 - Nov 20
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)
"This was a perfect getaway with the pups. The house is clean with everything needed for the stay, and the property manager quickly replied to a few questions. "
United States
Lesley R.
The price is ￥29,674
￥33,828 total
includes taxes & fees
Nov 21 - Nov 22
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)
"This is a beautiful place. It has everything that you could possibly need. "
United States
George N.
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 ￥39,101
￥89,835 total
includes taxes & fees
Nov 19 - Nov 20
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.
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, (12)
"Jessica has done a truly outstanding job in providing all the little things for making a great stay. The finishes, kitchen & equipment, towels & bedding and snacks/coffee/spices are all best I have seen through many short-term stays. The unit is in a very central location with access to Chesterton, Valpo, the dunes and all transportation. Thanks Jessica!"
United States
KEVIN M.
The price is ￥20,092
￥45,005 total
includes taxes & fees
Dec 8 - Dec 9
Cozy Retreat w/Hot tub Indiana dunes Beaches Trails
Outdoor dining
Indiana Dunes National Park

Indiana Dunes National Park

Porter
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 ￥174,679
￥243,290 total
includes taxes & fees
Nov 19 - Nov 20
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 ￥34,078
￥43,708 total
includes taxes & fees
Nov 19 - Nov 20
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 ￥15,455
￥41,648 total
includes taxes & fees
Nov 19 - Nov 20
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 ￥11,576
￥32,402 total
includes taxes & fees
Nov 19 - Nov 20
Heart of Historical Dist.*Parking*Claw Tub*A/C #4
Smart TV, fireplace, foosball, 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 ￥13,910
￥57,468 total
includes taxes & fees
Nov 23 - Nov 24
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)
"Our stay was comfortable and the host was very communicative through the entire process. "
United States
Elizabeth G.
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)
"It was very cozy and perfect! "
United States
Tommy W.
The price is ￥12,364
￥23,368 total
includes taxes & fees
Nov 24 - Nov 25
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)
"Was as described great stay"
United States
Amber C.
The price is ￥13,755
￥30,984 total
includes taxes & fees
Nov 19 - Nov 20
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

Four Winds Casino Resort – New Buffalo

Four Winds Casino Resort – New Buffalo

10/10 Excellent
"Clean room..nice stay"
Etonia 2-night trip
Posted 2 days 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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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?

Big Family House 5 Minutes from Lake Michigan/Blue Chip Casino/Brewery/Wineries!: You might want to consider this vacation home rental near Chesterton, which is located on a lake and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Chesterton?

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

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 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.