Title: Chesterton Vacation Home Rentals from CA $223: Search Top Private Vacation Homes for Rent | Expedia.ca

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Photo by Eva Johnson

# Chesterton Vacation Rentals

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## Check prices for these dates

Next weekend

[Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2026-01-23&endDate=2026-01-25&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Chesterton vacation homes

![Smart TV, books](https://images.trvl-media.com/lodging/90000000/89020000/89011100/89011067/w1440h955x0y0-2001df05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/90000000/89020000/89011100/89011067/w1435h950x0y4-962b42a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/90000000/89020000/89011100/89011067/w1440h955x0y5-c37c59a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/90000000/89020000/89011100/89011067/w1435h955x2y2-baabc10c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Chesterton-Hotels-Relaxing-3-Bedroom-I-2-Baths-I-2-Living-Rooms-Home.h89011067.Hotel-Information)

Chesterton

9.8/10

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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Christine C.

CA $127

CA $464 total

includes taxes & fees

Jan 6 - Jan 7, 2026

[](https://www.expedia.ca/Chesterton-Hotels-Relaxing-3-Bedroom-I-2-Baths-I-2-Living-Rooms-Home.h89011067.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/96000000/95050000/95044300/95044250/a5e3e3f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, WiFi, bed sheets](https://images.trvl-media.com/lodging/96000000/95050000/95044300/95044250/37fd4a15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, offices](https://images.trvl-media.com/lodging/96000000/95050000/95044300/95044250/ecb842fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/96000000/95050000/95044300/95044250/d82a9d62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Chesterton-Hotels-BalconyPatio-Separate-Fenced-Yard-Beach.h95044250.Hotel-Information)

Chesterton

9.0/10

Wonderful

(9)

"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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Nick R.

CA $142

CA $441 total

includes taxes & fees

Dec 28 - Dec 29

[](https://www.expedia.ca/Chesterton-Hotels-BalconyPatio-Separate-Fenced-Yard-Beach.h95044250.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/96000000/95040000/95038900/95038818/8f20fe7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/96000000/95040000/95038900/95038818/cacec885.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95040000/95038900/95038818/046bf033.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, offices](https://images.trvl-media.com/lodging/96000000/95040000/95038900/95038818/c15b3e2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Chesterton-Hotels-BalconyPatio-Fenced-Yard-Attached-Garagenear-Beach.h95038818.Hotel-Information)

Chesterton

9.4/10

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](https://a.travel-assets.com/egds/marks/flags/us.svg)

T J.

CA $147

CA $534 total

includes taxes & fees

Dec 27 - Dec 28

[](https://www.expedia.ca/Chesterton-Hotels-BalconyPatio-Fenced-Yard-Attached-Garagenear-Beach.h95038818.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/75000000/74520000/74510800/74510787/w1024h569x0y58-4410e30f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/75000000/74520000/74510800/74510787/w905h683x60y0-5b7990bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/75000000/74520000/74510800/74510787/w1024h570x0y56-96756eb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms](https://images.trvl-media.com/lodging/75000000/74520000/74510800/74510787/w905h683x60y0-3917a528.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### NEW! Beautiful Riverfront Home on 10 Acres!

[](https://www.expedia.ca/NEW-Beautiful-Riverfront-Home-On-10-Acres.h74510787.Hotel-Information)

Chesterton

8.0/10

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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jeff S.

CA $219

CA $537 total

includes taxes & fees

Dec 28 - Dec 29

[](https://www.expedia.ca/NEW-Beautiful-Riverfront-Home-On-10-Acres.h74510787.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/120000000/119050000/119048700/119048616/bf2ce6c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/120000000/119050000/119048700/119048616/deae7b79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/120000000/119050000/119048700/119048616/bda4219b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119050000/119048700/119048616/a1727f43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Retreat w/Hot tub Indiana dunes Beaches Trails

[](https://www.expedia.ca/Chesterton-Hotels-Moody-Modern-Dunes-Hot-Tub-Beaches-Trails.h119048616.Hotel-Information)

Chesterton

10/10

Exceptional

(12)

"This rental was amazing!!! So very clean, amazingly comfortable bed, and every amenity thought off. You will not be sorry that you stayed here. We hope to stay again. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Leiann N.

CA $210

CA $440 total

includes taxes & fees

Dec 29 - Dec 30

[](https://www.expedia.ca/Chesterton-Hotels-Moody-Modern-Dunes-Hot-Tub-Beaches-Trails.h119048616.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/124000000/123050000/123045700/123045662/02685887.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/124000000/123050000/123045700/123045662/67c0f374.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/124000000/123050000/123045700/123045662/c5da5238.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/124000000/123050000/123045700/123045662/d1dd0074.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Chesterton-Hotels-Modern-Comfort-3-Bedroom-House-In-Lovely-Chesterton-With-Cool-Breeze-And-Charm.h123045662.Hotel-Information)

Chesterton

CA $210

CA $622 total

includes taxes & fees

Dec 29 - Dec 30

[](https://www.expedia.ca/Chesterton-Hotels-Modern-Comfort-3-Bedroom-House-In-Lovely-Chesterton-With-Cool-Breeze-And-Charm.h123045662.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/107000000/106620000/106616300/106616253/957448f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/107000000/106620000/106616300/106616253/8ae6adcf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/107000000/106620000/106616300/106616253/w2100h1399x0y1-911a8bb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/107000000/106620000/106616300/106616253/c64fb80f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Michigan-City-Hotels-Grand-Reunion-House-2-Hot-Tub-Pet-Friendly-Duplex.h106616253.Hotel-Information)

Michigan City

10/10

Exceptional

(5)

"Great option for a quick weekend trip to the Dunes. Clean, comfy and good communication from the host."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Dillon K.

CA $142

CA $375 total

includes taxes & fees

Dec 28 - Dec 29

[](https://www.expedia.ca/Michigan-City-Hotels-Grand-Reunion-House-2-Hot-Tub-Pet-Friendly-Duplex.h106616253.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101340000/101338400/101338315/2070fc73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, books, stereo, offices](https://images.trvl-media.com/lodging/102000000/101340000/101338400/101338315/1f1e512c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/102000000/101340000/101338400/101338315/dd180752.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/102000000/101340000/101338400/101338315/8fcd0ce4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Eagles Beach Nest 2:Pet-Friendly\*Fenced\*Walk2Beach

[](https://www.expedia.ca/New-Buffalo-Hotels-Eagles-Beach-Nest-II.h101338315.Hotel-Information)

Downtown New Buffalo

10/10

Exceptional

(29)

"It was a lovely stay! Very clean and it was awesome I could take my dog with me :)"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Roxie

CA $138

CA $416 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/New-Buffalo-Hotels-Eagles-Beach-Nest-II.h101338315.Hotel-Information)

![Beach nearby](https://images.trvl-media.com/lodging/103000000/102860000/102853200/102853153/4d6f849b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/103000000/102860000/102853200/102853153/66d18154.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/103000000/102860000/102853200/102853153/9e42e19a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/103000000/102860000/102853200/102853153/db28a9c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Michigan-City-Hotels-New-Cozy-House-5-Min-To-Beach-Zoo-Restaurants-Casino-Brewery-Train-To-Chicago.h102853153.Hotel-Information)

Michigan City

9.8/10

Exceptional

(14)

"It was very cozy and perfect! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Tommy W.

CA $124

CA $223 total

includes taxes & fees

Dec 28 - Dec 29

[](https://www.expedia.ca/Michigan-City-Hotels-New-Cozy-House-5-Min-To-Beach-Zoo-Restaurants-Casino-Brewery-Train-To-Chicago.h102853153.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101340000/101338400/101338318/30768e3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101340000/101338400/101338318/b103ffa0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101340000/101338400/101338318/29b2fe90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/102000000/101340000/101338400/101338318/7b3243b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sq Toe\`s Last Resort:Pet-Friendly\*Fenced\* GameRoom

[](https://www.expedia.ca/New-Buffalo-Hotels-Sq-Toes-Last-ResortPet-FriendlyFenced-GameRoom.h101338318.Hotel-Information)

New Buffalo

10/10

Exceptional

(16)

"Cozy house close to New Buffalo. Yard was great and game room was great additional space to hang out in. Would definitely go back!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Liz W.

CA $141

CA $426 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/New-Buffalo-Hotels-Sq-Toes-Last-ResortPet-FriendlyFenced-GameRoom.h101338318.Hotel-Information)

![Beach nearby](https://images.trvl-media.com/lodging/35000000/34340000/34331200/34331150/07208029.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/35000000/34340000/34331200/34331150/b42e50fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/35000000/34340000/34331200/34331150/ce8f5d86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/35000000/34340000/34331200/34331150/0f71f5e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### View of the lake from 2 decks in this 6BR Lake Shore Dr home, steps to the beach

[](https://www.expedia.ca/Michigan-City-Hotels-View-Of-The-Lake-From-2-Decks-In-This-6BR-Lake-Shore-Dr-Home.h34331150.Hotel-Information)

Michigan City

8.6/10

Excellent

(88)

"nice location near the dunes had a beautiful view of the sunset"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

ron m.

CA $158

CA $605 total

includes taxes & fees

Dec 24 - Dec 25

[](https://www.expedia.ca/Michigan-City-Hotels-View-Of-The-Lake-From-2-Decks-In-This-6BR-Lake-Shore-Dr-Home.h34331150.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/98000000/97510000/97500100/97500047/9ea02ae0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, table tennis, stereo](https://images.trvl-media.com/lodging/98000000/97510000/97500100/97500047/85e9761b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, table tennis, stereo](https://images.trvl-media.com/lodging/98000000/97510000/97500100/97500047/ee54bd91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/98000000/97510000/97500100/97500047/d5a902a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### UncleLarry's LakePlace, Hot Tub

[](https://www.expedia.ca/Unclelarrys-Lakeplace.h97500047.Hotel-Information)

La Porte

10/10

Exceptional

(5)

"This place was wonderful! The views of the lake were amazing. The beds were extremely comfortable. All of the amenities you could want and more. It was a great locale for our family stay. We hope to visit again!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Meredith C.

CA $252

CA $725 total

includes taxes & fees

Jan 7 - Jan 8, 2026

[](https://www.expedia.ca/Unclelarrys-Lakeplace.h97500047.Hotel-Information)

![Beach nearby](https://images.trvl-media.com/lodging/83000000/82500000/82495900/82495809/20ddc9f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/83000000/82500000/82495900/82495809/f7f8c3f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/83000000/82500000/82495900/82495809/26d5ff9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/83000000/82500000/82495900/82495809/428b4b70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Duplex | Firepit | Game Room | Hot Tub-all year

[](https://www.expedia.ca/Michigan-City-Hotels-Family-Beach-Fun-Spot-Firepit-Games-FireTV.h82495809.Hotel-Information)

Michigan City

8.6/10

Excellent

(17)

"Nice rental with lots of fun extras. Had a great time in the game room, hot tub and fire pit. Great neighborhood. The property condition was ok. Not very clean. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Andrea

CA $99

CA $281 total

includes taxes & fees

Dec 28 - Dec 29

[](https://www.expedia.ca/Michigan-City-Hotels-Family-Beach-Fun-Spot-Firepit-Games-FireTV.h82495809.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/114000000/113300000/113298900/113298890/1ff3a399.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/114000000/113300000/113298900/113298890/32054cb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/114000000/113300000/113298900/113298890/4537694a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113300000/113298900/113298890/5bde82d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 3-bedroom house in charming La Porte three minute walk to beautiful Stone Lake

[](https://www.expedia.ca/La-Porte-Hotels-3-Bedroom-House-In-Charming-La-Porte-Three-Minute-Walk-To-Beautiful-Stone-Lake.h113298890.Hotel-Information)

La Porte

9.8/10

Exceptional

(6)

"Nice layout of the home for our group. Good location. We had a very nice time. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Lisa C.

CA $260

CA $433 total

includes taxes & fees

Dec 24 - Dec 25

[](https://www.expedia.ca/La-Porte-Hotels-3-Bedroom-House-In-Charming-La-Porte-Three-Minute-Walk-To-Beautiful-Stone-Lake.h113298890.Hotel-Information)

![Smart TV, fireplace, foosball, books](https://images.trvl-media.com/lodging/101000000/100110000/100107800/100107758/57e5f713.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100110000/100107800/100107758/e5af2c80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/101000000/100110000/100107800/100107758/21e72259.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100110000/100107800/100107758/207e9881.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sand & Sun Getaway | 4BR w/ Game Room + 2 Living Areas |Game Room | Minutes to Beach

[](https://www.expedia.ca/Michigan-City-Hotels-Sand-Sun-Retreat.h100107758.Hotel-Information)

Michigan City

9.4/10

Exceptional

(33)

"Nice"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Maryellen W.

CA $136

CA $527 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/Michigan-City-Hotels-Sand-Sun-Retreat.h100107758.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/102000000/101950000/101944500/101944488/86903aff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/102000000/101950000/101944500/101944488/w1439h959x1y1-fc54c922.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/102000000/101950000/101944500/101944488/56fb79e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/102000000/101950000/101944500/101944488/6e8eefad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Singing Sands Trl | Hot Tub Retreat | Dogs OK

[](https://www.expedia.ca/Michigan-City-Hotels-SingingSands-Trl-Hottub-Retreat.h101944488.Hotel-Information)

Michigan City

9.8/10

Exceptional

(23)

"Property was as described in listing. Overall great stay. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Maria L.

CA $166

CA $365 total

includes taxes & fees

Dec 28 - Dec 29

[](https://www.expedia.ca/Michigan-City-Hotels-SingingSands-Trl-Hottub-Retreat.h101944488.Hotel-Information)

![TV, books](https://images.trvl-media.com/lodging/102000000/101340000/101338400/101338321/cf7a83ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/102000000/101340000/101338400/101338321/fb1212f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101340000/101338400/101338321/a0cb6d5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, books](https://images.trvl-media.com/lodging/102000000/101340000/101338400/101338321/b6c04b84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Eagle\`s Beach Nest: Pet-Friendly\*Fenced\*Walk2Beach

[](https://www.expedia.ca/New-Buffalo-Hotels-Eagles-Beach-Nest-Pet-FriendlyFencedWalk2Beach.h101338321.Hotel-Information)

Downtown New Buffalo

10/10

Exceptional

(19)

"Great stay, loved the place!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ryan J.

CA $154

CA $518 total

includes taxes & fees

Jan 12 - Jan 13, 2026

[](https://www.expedia.ca/New-Buffalo-Hotels-Eagles-Beach-Nest-Pet-FriendlyFencedWalk2Beach.h101338321.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/120000000/119850000/119840200/119840147/93b14677.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/120000000/119850000/119840200/119840147/225a8b36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/120000000/119850000/119840200/119840147/9d9fd242.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby](https://images.trvl-media.com/lodging/120000000/119850000/119840200/119840147/98eed46a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 5BR 3.5BA Dune Side Home w/ Short Walk to the BEACH! NEW LISTING - Built in 2022

[](https://www.expedia.ca/Michigan-City-Hotels-5BR-35BA-Dune-Side-Home-W-Short-Walk-To-The-BEACH-NEW-LISTING-Built-In-2022.h119840147.Hotel-Information)

Michigan City

8.6/10

Excellent

(4)

"Good house and good location. Lots of space"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Todd K.

CA $123

CA $598 total

includes taxes & fees

Dec 28 - Dec 29

[](https://www.expedia.ca/Michigan-City-Hotels-5BR-35BA-Dune-Side-Home-W-Short-Walk-To-The-BEACH-NEW-LISTING-Built-In-2022.h119840147.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/115000000/114350000/114343600/114343521/36c85222.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/115000000/114350000/114343600/114343521/542324cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/115000000/114350000/114343600/114343521/f433576a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/115000000/114350000/114343600/114343521/a6829a78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Downtown 2 BR Cottage w/ King Bed

[](https://www.expedia.ca/Valparaiso-Hotels-Charming-Renovated-2-Bedroom-House-Close-To-Downtown-Valparaiso.h114343521.Hotel-Information)

Valparaiso

9.8/10

Exceptional

(9)

"Great stay"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Bernie H.

CA $172

CA $391 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/Valparaiso-Hotels-Charming-Renovated-2-Bedroom-House-Close-To-Downtown-Valparaiso.h114343521.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/119000000/118080000/118071600/118071536/b4cd1c35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/119000000/118080000/118071600/118071536/5368334c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118080000/118071600/118071536/be38d932.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/119000000/118080000/118071600/118071536/60b1d642.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sheridan Blue - Michigan City, IN

[](https://www.expedia.ca/Michigan-City-Hotels-Sheridan-Blue-Michigan-City.h118071536.Hotel-Information)

Michigan City

10/10

Exceptional

(3)

"This place was very nice and clean & decorated with nice up to date modern decor. The beds were very comfortable. Would definitely recommend to others."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Loretta M.

[](https://www.expedia.ca/Michigan-City-Hotels-Sheridan-Blue-Michigan-City.h118071536.Hotel-Information)

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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2026-01-06&endDate=2026-01-07&regionId=7214&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Private vacation homes

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Apartments

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Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Chesterton%2C+Indiana%2C+United+States+of+America&regionId=7214&latLong=41.610592%2C-87.064201&adults=2&startDate=2026-03-23&d1=2026-03-23&endDate=2026-03-26&d2=2026-03-26&lodging=CABIN)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Chesterton%2C+Indiana%2C+United+States+of+America&regionId=7214&latLong=41.610592%2C-87.064201&adults=2&startDate=2026-03-23&d1=2026-03-23&endDate=2026-03-26&d2=2026-03-26&lodging=COTTAGE)

Aparthotels

[](https://www.expedia.ca/Hotel-Search?destination=Chesterton%2C+Indiana%2C+United+States+of+America&regionId=7214&latLong=41.610592%2C-87.064201&adults=2&startDate=2026-03-23&d1=2026-03-23&endDate=2026-03-26&d2=2026-03-26&lodging=APART_HOTEL)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Chesterton%2C+Indiana%2C+United+States+of+America&regionId=7214&latLong=41.610592%2C-87.064201&adults=2&startDate=2026-03-23&d1=2026-03-23&endDate=2026-03-26&d2=2026-03-26&lodging=CONDO)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Chesterton%2C+Indiana%2C+United+States+of+America&regionId=7214&latLong=41.610592%2C-87.064201&adults=2&startDate=2026-03-23&d1=2026-03-23&endDate=2026-03-26&d2=2026-03-26&lodging=VILLA)

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## Top Chesterton Hotel Reviews

![FairBridge Inn Express Merrillville](https://images.trvl-media.com/lodging/1000000/130000/123900/123860/39572dda_y.jpg)

### FairBridge Inn Express Merrillville

10/10 Excellent

"All depends who is working up front. On your experience. "

[](https://expedia.ca/Merrillville-Hotels-FairBridge-Inn-Express-Merrillville.h123860.Hotel-Information)

![Quality Inn Chesterton near Indiana Dunes National Park I-94](https://images.trvl-media.com/lodging/1000000/440000/439900/439829/be1c7179_y.jpg)

### Quality Inn Chesterton near Indiana Dunes National Park I-94

10/10 Excellent

"Good stay"

[](https://expedia.ca/Chesterton-Hotels-Quality-Inn.h439829.Hotel-Information)

![Fairfield Inn and Suites By Marriott Merrillville](https://images.trvl-media.com/lodging/1000000/10000/5300/5258/b28d063e_y.jpg)

### Fairfield Inn and Suites By Marriott Merrillville

10/10 Excellent

"Everything went smoothly. Nice but small workout facility, decent breakfast, nice little extras like hot chocolate bar in the winter."

[](https://expedia.ca/Merrillville-Hotels-Fairfield-Inn-And-Suites-By-Marriott-Merrillville.h5258.Hotel-Information)

![Country Inn & Suites by Radisson, Merrillville, IN](https://images.trvl-media.com/lodging/2000000/1360000/1353900/1353808/4d6bf4d2_y.jpg)

### Country Inn & Suites by Radisson, Merrillville, IN

10/10 Excellent

"The room was clean and Keisha was awesome accommodating me at check in."

[](https://expedia.ca/Merrillville-Hotels-Country-Inn-Suites-By-Radisson.h1353808.Hotel-Information)

![Blue Chip Casino Hotel and Spa](https://images.trvl-media.com/lodging/3000000/3000000/2991300/2991209/21bfd0c8_y.jpg)

### Blue Chip Casino Hotel and Spa

10/10 Excellent

"Yes"

[](https://expedia.ca/Michigan-City-Hotels-Blue-Chip-Casino-Hotel-And-Spa.h2991209.Hotel-Information)

![Four Winds Casino Resort – New Buffalo](https://images.trvl-media.com/lodging/14000000/13280000/13278700/13278629/69fa9139_y.jpg)

### Four Winds Casino Resort – New Buffalo

10/10 Excellent

"Lovely and clean rooms. Great casino games variety and food options. "

[](https://expedia.ca/Benton-Harbor-Hotels-Four-Winds-Casino-Resort-New-Buffalo.h13278629.Hotel-Information)

![Quality Inn Near Interstate I94](https://images.trvl-media.com/lodging/2000000/1330000/1320800/1320708/531382df_y.jpg)

### Quality Inn Near Interstate I94

10/10 Excellent

"Not exactly spotless. There were stains on the bedding. "

[](https://expedia.ca/Benton-Harbor-Hotels-Quality-Inn-Near-Interstate-I94.h1320708.Hotel-Information)

![Waterbird Lakeside Inn](https://images.trvl-media.com/lodging/3000000/2450000/2450000/2449990/eb33670e_y.jpg)

### Waterbird Lakeside Inn

10/10 Excellent

"We had a plumbing problem and it was immediately fixed. We were swapped rooms so that it wouldnt interfere with our plans. Comfortable beds and a beautiful view of the lake. "

[](https://expedia.ca/Chesterton-Hotels-Waterbird-Lakeside-Inn.h2449990.Hotel-Information)

![Spring House Inn](https://images.trvl-media.com/lodging/1000000/810000/809000/808936/51a347fe_y.jpg)

### Spring House Inn

10/10 Excellent

"Spring House Inn has great ambiance, friendly staff, and clean rooms. I wish I could have stayed longer than one night and had been able to enjoy the sauna, pool and fitness room. I would definitely recommend, and hope to return someday. "

[](https://expedia.ca/Porter-Hotels-Spring-House-Inn.h808936.Hotel-Information)

## Find out more about Chesterton

## Chesterton Vacation Homes information

| Number of reviews | 340                |
| ----------------- | ------------------ |
| Accommodation     | 723 Vacation Homes |
| Lowest Price      | CA $223            |
| Highest Price     | CA $725            |

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- [Things to do in Westville ](https://www.expedia.ca/Things-To-Do-In-Westville.d3000436744.Travel-Guide-Activities)

- [Book Vacation Homes in Chesterton on Expedia.com ](https://www.expedia.com/Chesterton-Private-Vacation-Homes.d7214-aaPrivateVacationHomes.Travel-Guide-Accommodation)