Title: Chesterton Vacation Rentals from $98: Search Short-Term Rentals | Expedia.com

[Chesterton Travel Guide](https://expedia.com/Chesterton.dx7214)[Hotels in Chesterton](https://expedia.com/Chesterton-Hotels.d7214.Travel-Guide-Hotels)[Flights to Chesterton](https://expedia.com/Cheap-Flights-To-Chesterton.d7214.Travel-Guide-Flights)[Things to do in Chesterton](https://expedia.com/Things-To-Do-In-Chesterton.d7214.Travel-Guide-Activities)[Car Rentals in Chesterton](https://expedia.com/Car-Rentals-In-Chesterton.d7214.Car-Rental-Guide)[Chesterton Vacation Packages](https://expedia.com/Chesterton.d7214.Destination-Travel-Guides)

![Lake Michigan. Path off Trail 9 at one place leads right to the lake. Peaceful to just stand and watch and listen to the waves as they crash to the shore. Trail 9 is the trail to hike if one wants to see the most in the shortest time. Great views throughout the trail. The trail is over 3 miles long and is considered a moderate trail. But certainly worth it. One gets to hike through forest, dunes, and other natural environments and see such a variety of sights. 
#hiking](https://images.trvl-media.com/place/6091455/985eab23-71e6-415a-af69-65e5707ce659.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by Ruslian

![](https://images.trvl-media.com/place/6091455/985eab23-71e6-415a-af69-65e5707ce659.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Mar 13 - Mar 15](https://www.expedia.com/Hotel-Search?regionId=7214&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 24 - Apr 26](https://www.expedia.com/Hotel-Search?regionId=7214&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 22 - May 24](https://www.expedia.com/Hotel-Search?regionId=7214&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 19 - Jun 21](https://www.expedia.com/Hotel-Search?regionId=7214&startDate=2026-06-19&endDate=2026-06-21&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 rentals

![Beach nearby](https://images.trvl-media.com/lodging/70000000/69390000/69386000/69385955/3c1f7b34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Children's area](https://images.trvl-media.com/lodging/70000000/69390000/69386000/69385955/w1024h495x0y94-0f476266.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/70000000/69390000/69386000/69385955/w894h683x65y0-0fccdb4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/70000000/69390000/69386000/69385955/47cadd90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.com/Chesterton-Hotels-The-Pool-Barn-Camper-WHot-Tub-Near-Indiana-Dunes.h69385955.Hotel-Information)

Porter

9.0/10

Wonderful

(12 reviews)

"Great Stay!"

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

Erin

$88 nightly

$98 total

Feb 27 - Feb 28

Total with taxes and fees

[](https://www.expedia.com/Chesterton-Hotels-The-Pool-Barn-Camper-WHot-Tub-Near-Indiana-Dunes.h69385955.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)

![Smart TV, offices](https://images.trvl-media.com/lodging/96000000/95050000/95044300/95044250/927385a9.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.com/Chesterton-Hotels-BalconyPatio-Separate-Fenced-Yard-Beach.h95044250.Hotel-Information)

Chesterton

9.0/10

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

Nick R.

$287 nightly

$321 total

Feb 27 - Feb 28

Total with taxes and fees

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

![Beach](https://images.trvl-media.com/lodging/95000000/94690000/94689100/94689032/fb8be5d0.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/95000000/94690000/94689100/94689032/da2b62d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/95000000/94690000/94689100/94689032/13dec7e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/95000000/94690000/94689100/94689032/0e64a83e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.com/Chesterton-Hotels-Blue-Birdhouse-By-The-Beach.h94689032.Hotel-Information)

Chesterton

9.4/10

Exceptional

(34 reviews)

"Great location, very relaxing atmosphere at the house. 2 miles from the National park, straight shot from house. Awesome vacation spot!"

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

Michael S.

$168 nightly

$171 total

Mar 2 - Mar 3

Total with taxes and fees

[](https://www.expedia.com/Chesterton-Hotels-Blue-Birdhouse-By-The-Beach.h94689032.Hotel-Information)

![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)

![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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89020000/89011100/89011067/5d50cb22.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.com/Chesterton-Hotels-Relaxing-3-Bedroom-I-2-Baths-I-2-Living-Rooms-Home.h89011067.Hotel-Information)

Chesterton

9.8/10

Exceptional

(65 reviews)

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

Sue

$336 nightly

$376 total

Mar 16 - Mar 17

Total with taxes and fees

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

![Beach nearby](https://images.trvl-media.com/lodging/88000000/87910000/87908400/87908321/1ab6d529.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/88000000/87910000/87908400/87908321/ae500cb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/88000000/87910000/87908400/87908321/0357983e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/88000000/87910000/87908400/87908321/c1bf66fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.com/Chesterton-Hotels-Private-Downtown-Apt.h87908321.Hotel-Information)

Chesterton

8.8/10

Excellent

(93 reviews)

"Great stay on every level "

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

Tom M.

$109 nightly

$122 total

Feb 28 - Mar 1

Total with taxes and fees

[](https://www.expedia.com/Chesterton-Hotels-Private-Downtown-Apt.h87908321.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)

![Interior](https://images.trvl-media.com/lodging/124000000/123050000/123045700/123045662/764bca2d.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.com/Chesterton-Hotels-Modern-Comfort-3-Bedroom-House-In-Lovely-Chesterton-With-Cool-Breeze-And-Charm.h123045662.Hotel-Information)

Chesterton

$399 nightly

$447 total

Feb 27 - Feb 28

Total with taxes and fees

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

![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)

![2 bedrooms, desk, WiFi, bed sheets](https://images.trvl-media.com/lodging/96000000/95040000/95038900/95038818/a2b68ac1.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.com/Chesterton-Hotels-BalconyPatio-Fenced-Yard-Attached-Garagenear-Beach.h95038818.Hotel-Information)

Chesterton

9.4/10

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

T J.

$346 nightly

$388 total

Mar 2 - Mar 3

Total with taxes and fees

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

![Exterior](https://images.trvl-media.com/lodging/120000000/119050000/119048700/119048616/bda4219b.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)

![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/120000000/119050000/119048700/119048616/26959619.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Dunes Retreat w/Private Hot Tub

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

Chesterton

10/10

Exceptional

(16 reviews)

"Great host, everything was clean, many little extras for comfort and convenience!"

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

Kara K.

$314 nightly

$352 total

Mar 3 - Mar 4

Total with taxes and fees

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

![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)

![Interior](https://images.trvl-media.com/lodging/75000000/74520000/74510800/74510787/w1008h569x0y57-d627387b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Chesterton

8.0/10

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

Jeff S.

$352 nightly

$394 total

Mar 3 - Mar 4

Total with taxes and fees

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

![Dining](https://images.trvl-media.com/lodging/110000000/109320000/109317500/109317487/536e84f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/110000000/109320000/109317500/109317487/32406705.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/110000000/109320000/109317500/109317487/31b734ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/110000000/109320000/109317500/109317487/fcc72464.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.com/Chesterton-Hotels-That-70s-Loft-Peace.h109317487.Hotel-Information)

Chesterton

10/10

Exceptional

(6 reviews)

"We had a lovely stay in this charming, little set-up"

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

Anna K.

$289 nightly

$323 total

Feb 27 - Feb 28

Total with taxes and fees

[](https://www.expedia.com/Chesterton-Hotels-That-70s-Loft-Peace.h109317487.Hotel-Information)

![Beach nearby](https://images.trvl-media.com/lodging/70000000/69390000/69385700/69385681/7cfedc54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/70000000/69390000/69385700/69385681/10372699.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Children's area](https://images.trvl-media.com/lodging/70000000/69390000/69385700/69385681/w1024h495x0y94-e2667f25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/70000000/69390000/69385700/69385681/w894h683x65y0-32f3f4aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes

[](https://www.expedia.com/Chesterton-Hotels-The-Pool-Barn-WPool.h69385681.Hotel-Information)

Porter

9.0/10

Wonderful

(17 reviews)

"Great place to stay with kids."

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

Jane H.

$201 nightly

$225 total

Mar 1 - Mar 2

Total with taxes and fees

[](https://www.expedia.com/Chesterton-Hotels-The-Pool-Barn-WPool.h69385681.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/121000000/120060000/120059900/120059833/01d03165.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, music library](https://images.trvl-media.com/lodging/121000000/120060000/120059900/120059833/acf36ecd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120060000/120059900/120059833/01642272.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/121000000/120060000/120059900/120059833/5fcfebca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Indiana Dunes National Park

[](https://www.expedia.com/Chesterton-Hotels-Indiana-Dunes-National-Park.h120059833.Hotel-Information)

Porter

9.0/10

Wonderful

(2 reviews)

"Clean accommodations, everything was as advertised for our 1 night stay. The album collection was a bonus."

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

Heather F.

$221 nightly

$224 total

Mar 2 - Mar 3

Total with taxes and fees

[](https://www.expedia.com/Chesterton-Hotels-Indiana-Dunes-National-Park.h120059833.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/108000000/107270000/107265400/107265306/84f768c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/108000000/107270000/107265400/107265306/6b8beffe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/108000000/107270000/107265400/107265306/83c86603.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107270000/107265400/107265306/6f00451f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Heart of Indiana Dunes National Park with Hot Tub

[](https://www.expedia.com/Chesterton-Hotels-Heart-Of-Indiana-Dunes-National-Park-With-Hot-Tub.h107265306.Hotel-Information)

Chesterton

10/10

Exceptional

(6 reviews)

"The house was beautiful and had so much charm. The amount of activities available was great. Highly recommend and we will definitely be back!"

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

Becky G.

$854 nightly

$956 total

Mar 25 - Mar 26

Total with taxes and fees

[](https://www.expedia.com/Chesterton-Hotels-Heart-Of-Indiana-Dunes-National-Park-With-Hot-Tub.h107265306.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/102000000/101220000/101216500/101216471/29e63479.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/102000000/101220000/101216500/101216471/bc5589af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/102000000/101220000/101216500/101216471/ee5580a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/102000000/101220000/101216500/101216471/2f70f777.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.com/Chesterton-Hotels-2-Miles-From-Dunes-National-Park-A-Unique-Boutique-Hotel.h101216471.Hotel-Information)

Chesterton

9.0/10

Wonderful

(4 reviews)

"Beautiful historic building. "

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

Deborah S.

$1,399 nightly

$1,567 total

Feb 27 - Feb 28

Total with taxes and fees

[](https://www.expedia.com/Chesterton-Hotels-2-Miles-From-Dunes-National-Park-A-Unique-Boutique-Hotel.h101216471.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/107000000/106620000/106616300/106616257/969867c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/107000000/106620000/106616300/106616257/cf47609f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/107000000/106620000/106616300/106616257/07505dcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106620000/106616300/106616257/bd8349c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.com/Michigan-City-Hotels-Grand-Reunion-House-Hot-Tub-Pet-Friendly.h106616257.Hotel-Information)

Michigan City

10/10

Exceptional

(5 reviews)

"Our friend group had a great stay at this property. It is very well equipped, clean and great for a large group to stay. Jacuzzi is very nice. "

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

Zhiling C.

$540 nightly

$575 total

Mar 1 - Mar 2

Total with taxes and fees

[](https://www.expedia.com/Michigan-City-Hotels-Grand-Reunion-House-Hot-Tub-Pet-Friendly.h106616257.Hotel-Information)

![Smart TV, table tennis, stereo](https://images.trvl-media.com/lodging/98000000/97510000/97500100/97500047/67e17a71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/98000000/97510000/97500100/97500047/dbcba1b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/98000000/97510000/97500100/97500047/6b395ece.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/98000000/97510000/97500100/97500047/5b2cba49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### UncleLarry's LakePlace, Hot Tub

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

La Porte

10/10

Exceptional

(6 reviews)

"Beautiful lake house stay, very refreshing! Lovely views of the lake and quiet area when we were there in November. Super comfy beds, great hot tub, and amazing view. Would definitely stay here again!"

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

Jessica E.

$492 nightly

$550 total

Mar 25 - Mar 26

Total with taxes and fees

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

![Terrace/patio](https://images.trvl-media.com/lodging/35000000/34520000/34512900/34512802/eb541ffe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/35000000/34520000/34512900/34512802/90-6159383e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34520000/34512900/34512802/3019420f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private beach, sun loungers, beach towels](https://images.trvl-media.com/lodging/35000000/34520000/34512900/34512802/9b766e8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Private Beach Steps to the Beach.

[](https://www.expedia.com/Union-Pier-Hotels-Private-Beach.h34512802.Hotel-Information)

Union Pier

10/10

Exceptional

(93 reviews)

"Great stay for a week by the beach with family! Perfect location to walk right down to the beach each day. Excited to come back one day!"

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

Jalen W.

$1,090 nightly

$1,090 total

Mar 1 - Mar 2

Total with taxes and fees

[](https://www.expedia.com/Union-Pier-Hotels-Private-Beach.h34512802.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)

![TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/35000000/34340000/34331200/34331150/871aa371.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)

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

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

Michigan City

8.4/10

Very Good

(89 reviews)

"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.

$414 nightly

$464 total

Mar 2 - Mar 3

Total with taxes and fees

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

![Interior](https://images.trvl-media.com/lodging/113000000/112100000/112097500/112097460/13170c89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/113000000/112100000/112097500/112097460/0eea790b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/113000000/112100000/112097500/112097460/3f786570.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/113000000/112100000/112097500/112097460/53a5499f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy loft inside a vintage store on an animal rescue farm in Westville, IN

[](https://www.expedia.com/Westville-Hotels-Cozy-Loft-Inside-A-Vintage-Store-On-An-Animal-Rescue-Farm-In-Westville.h112097460.Hotel-Information)

Westville

10/10

Exceptional

(9 reviews)

"We stayed one night last weekend and had an amazing experience! We highly recommend this location. The setting is so serene and tranquil. The host is fabulous. The loft is beautiful and comfortable. "

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

Mary A.

$279 nightly

$312 total

Feb 27 - Feb 28

Total with taxes and fees

[](https://www.expedia.com/Westville-Hotels-Cozy-Loft-Inside-A-Vintage-Store-On-An-Animal-Rescue-Farm-In-Westville.h112097460.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/113000000/112740000/112733400/112733347/9d8c9b82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/113000000/112740000/112733400/112733347/0de38273.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/113000000/112740000/112733400/112733347/2bb9dc41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, in-room safe, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/113000000/112740000/112733400/112733347/c7069d9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.com/Michigan-City-Hotels-Brand-New-Cottage-Walkable-To-All-Downtown-Michigan-City-Beach.h112733347.Hotel-Information)

Michigan City

9.8/10

Exceptional

(16 reviews)

"Cute place, extremely clean, comfortable and well-outfitted. It's very convenient, with easy parking and great proximity to downtown Michigan City. "

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

Heather O.

$273 nightly

$306 total

Mar 1 - Mar 2

Total with taxes and fees

[](https://www.expedia.com/Michigan-City-Hotels-Brand-New-Cottage-Walkable-To-All-Downtown-Michigan-City-Beach.h112733347.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.com/Hotel-Search?startDate=2026-03-12&endDate=2026-03-13&regionId=7214&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## Find vacation rentals that suit your style

Cabins

[](https://www.expedia.com/Hotel-Search?destination=Chesterton%2C+Indiana%2C+United+States+of+America&regionId=7214&latLong=41.610592%2C-87.064201&adults=2&startDate=2026-05-26&d1=2026-05-26&endDate=2026-05-29&d2=2026-05-29&lodging=CABIN)

Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=Chesterton%2C+Indiana%2C+United+States+of+America&regionId=7214&latLong=41.610592%2C-87.064201&adults=2&startDate=2026-05-26&d1=2026-05-26&endDate=2026-05-29&d2=2026-05-29&lodging=VACATION_HOME)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Chesterton%2C+Indiana%2C+United+States+of+America&regionId=7214&latLong=41.610592%2C-87.064201&adults=2&startDate=2026-05-26&d1=2026-05-26&endDate=2026-05-29&d2=2026-05-29&lodging=COTTAGE)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Chesterton%2C+Indiana%2C+United+States+of+America&regionId=7214&latLong=41.610592%2C-87.064201&adults=2&startDate=2026-05-26&d1=2026-05-26&endDate=2026-05-29&d2=2026-05-29&lodging=APARTMENT)

Condos

[](https://www.expedia.com/Hotel-Search?destination=Chesterton%2C+Indiana%2C+United+States+of+America&regionId=7214&latLong=41.610592%2C-87.064201&adults=2&startDate=2026-05-26&d1=2026-05-26&endDate=2026-05-29&d2=2026-05-29&lodging=CONDO)

Villas

[](https://www.expedia.com/Hotel-Search?destination=Chesterton%2C+Indiana%2C+United+States+of+America&regionId=7214&latLong=41.610592%2C-87.064201&adults=2&startDate=2026-05-26&d1=2026-05-26&endDate=2026-05-29&d2=2026-05-29&lodging=VILLA)

Aparthotels

[](https://www.expedia.com/Hotel-Search?destination=Chesterton%2C+Indiana%2C+United+States+of+America&regionId=7214&latLong=41.610592%2C-87.064201&adults=2&startDate=2026-05-26&d1=2026-05-26&endDate=2026-05-29&d2=2026-05-29&lodging=APART_HOTEL)

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## Top Chesterton Hotel Reviews

![Best Western Indian Oak](https://images.trvl-media.com/lodging/1000000/50000/49800/49736/d30c38a4_y.jpg)

### Best Western Indian Oak

10/10 Excellent

"Clean rooms but hotel getting ready for renovation. Loud noises at 8 am."

[](https://expedia.com/Chesterton-Hotels-Best-Western-Indian-Oak.h49736.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 man at the front desk was so pleasant and helpful, the bed was comfortable, and the breakfast was complete and delicious."

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

![Holiday Inn Express & Suites New Buffalo by IHG](https://images.trvl-media.com/lodging/1000000/550000/544000/543985/7a2e1c74_y.jpg)

### Holiday Inn Express & Suites New Buffalo by IHG

10/10 Excellent

"Room very clean,hotel staff very pleasant and knowledgeable. Breakfast was hot."

[](https://expedia.com/Benton-Harbor-Hotels-Holiday-Inn-Express-Suites-New-Buffalo.h543985.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

"The rooms are always clean."

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

![Ameristar Casino Hotel East Chicago](https://images.trvl-media.com/lodging/3000000/2520000/2518200/2518162/429a2c05_y.jpg)

### Ameristar Casino Hotel East Chicago

10/10 Excellent

"Great space, comfortable and quiet"

[](https://expedia.com/East-Chicago-Hotels-Ameristar-Casino-Hotel-East-Chicago.h2518162.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

"Clean room Friendly check in"

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

![Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly](https://images.trvl-media.com/lodging/97000000/96750000/96743200/96743172/48dc1df9_y.jpg)

### Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly

10/10 Excellent

"Wonderful home, gorgeous views, everything we needed for weekend. Exactly as described. "

[](https://expedia.com/Chesterton-Hotels-Cabin-53-Steps-From-Porter-Beach-On-Lake-Michigan-Family-Pet-Friendly.h96743172.Hotel-Information)

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

### Spring House Inn

10/10 Excellent

"This is a super cute Inn nestled in some woods. We were greeted by a family of deer right outside our room. Room was clean, quiet and affordable! Felt more like a State Park Inn. "

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

![Baymont by Wyndham New Buffalo](https://images.trvl-media.com/lodging/1000000/870000/867300/867230/6dac1343_y.jpg)

### Baymont by Wyndham New Buffalo

10/10 Excellent

"Great "

[](https://expedia.com/Benton-Harbor-Hotels-Baymont-By-Wyndham-New-Buffalo.h867230.Hotel-Information)

## Find out more about Chesterton

**Everything you need to know about Chesterton vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chesterton vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

**Chesterton vacation 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 low season months. For more hustle and bustle, you may prefer to visit Chesterton in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $98 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

**How to find incredible deals on Chesterton rentals**

At Expedia, we put the best Chesterton vacation 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 vacation.

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.

## Explore a world of travel with Expedia

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- [Michigan Vacation Rentals ](https://www.expedia.com/Destinations-In-Michigan.d224.Vacation-Rental-Destinations)

- [Vacation Homes in Chesterton ](https://expedia.com/Chesterton-Private-Vacation-Homes.d7214-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Apartments in Chesterton ](https://expedia.com/Chesterton-Apartments.d7214-aaApartments.Travel-Guide-Accommodation)
- [Cottages in Chesterton ](https://expedia.com/Chesterton-Cottages.d7214-aaCottages.Travel-Guide-Accommodation)
- [Condo Rentals in Chesterton ](https://expedia.com/Chesterton-Condos.d7214-aaCondos.Travel-Guide-Accommodation)
- [Guest Houses in Chesterton ](https://expedia.com/Chesterton-Guest-Houses.d7214-aaGuestHouses.Travel-Guide-Accommodation)
- [Motels in Chesterton ](https://expedia.com/Chesterton-Motels.d7214-aaMotels.Travel-Guide-Accommodation)
- [Cabin Rentals in Chesterton ](https://expedia.com/Chesterton-Cabins.d7214-aaCabins.Travel-Guide-Accommodation)
- [Farmstay in Chesterton ](https://expedia.com/Chesterton-Agritourism.d7214-aaAgritourism.Travel-Guide-Accommodation)
- [RV Parks in Chesterton ](https://expedia.com/Chesterton-RV-Parks.d7214-aaRVParks.Travel-Guide-Accommodation)
- [Villas in Chesterton ](https://expedia.com/Chesterton-Villas.d7214-aaVillas.Travel-Guide-Accommodation)
- [Aparthotels in Chesterton ](https://expedia.com/Chesterton-Apart-Hotels.d7214-aaApartHotels.Travel-Guide-Accommodation)
- [Inns in Chesterton ](https://expedia.com/Chesterton-Inns.d7214-aaInns.Travel-Guide-Accommodation)
- [B&B in Chesterton ](https://expedia.com/Chesterton-Bed-And-Breakfast.d7214-aaBedAndBreakfast.Travel-Guide-Accommodation)

## Frequently asked questions

### Are there vacation rentals in Chesterton?

### What's the top vacation rental that Chesterton has to offer?

### How many vacation rentals are there in Chesterton?

### What can I see and do in Chesterton?

### What are vacation rentals like in Chesterton?

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- [Hotel Rooms in Valparaiso](https://expedia.com/Valparaiso-Hotels.d10288.Travel-Guide-Hotels)
- [Hotel Rooms in Kokomo](https://expedia.com/Kokomo-Hotels.d6059761.Travel-Guide-Hotels)
- [Hotel Rooms in Michigan City](https://expedia.com/Michigan-City-Hotels.d8727.Travel-Guide-Hotels)
- [Hotel Rooms in Shipshewana](https://expedia.com/Shipshewana-Hotels.d157707.Travel-Guide-Hotels)
- [Hotel Rooms in La Porte](https://expedia.com/La-Porte-Hotels.d8562.Travel-Guide-Hotels)
- [Hotel Rooms in Nashville](https://expedia.com/Nashville-Hotels.d136862.Travel-Guide-Hotels)
- [Hotel Rooms in West Lafayette](https://expedia.com/West-Lafayette-Hotels.d6218.Travel-Guide-Hotels)
- [Hotel Rooms in Crown Point](https://expedia.com/Crown-Point-Hotels.d94141.Travel-Guide-Hotels)
- [Hotel Rooms in Richmond](https://expedia.com/Richmond-Hotels.d6059768.Travel-Guide-Hotels)
- [Hotel Rooms in Madison](https://expedia.com/Madison-Hotels.d6059636.Travel-Guide-Hotels)
- [Hotel Rooms in Muncie](https://expedia.com/Muncie-Hotels.d6059766.Travel-Guide-Hotels)
- [Hotel Rooms in Columbus](https://expedia.com/Columbus-Hotels.d6059773.Travel-Guide-Hotels)
- [Hotel Rooms in Elkhart](https://expedia.com/Elkhart-Hotels.d7073.Travel-Guide-Hotels)
- [Hotel Rooms in Merrillville](https://expedia.com/Merrillville-Hotels.d8898.Travel-Guide-Hotels)
- [Hotel Rooms in French Lick](https://expedia.com/French-Lick-Hotels.d6059639.Travel-Guide-Hotels)
- [Hotel Rooms in Crawfordsville](https://expedia.com/Crawfordsville-Hotels.d7699.Travel-Guide-Hotels)
- [Hotel Rooms in Santa Claus](https://expedia.com/Santa-Claus-Hotels.d183202.Travel-Guide-Hotels)
- [Hotel Rooms in Terre Haute](https://expedia.com/Terre-Haute-Hotels.d6059777.Travel-Guide-Hotels)
- [Hotel Rooms in Anderson](https://expedia.com/Anderson-Hotels.d325.Travel-Guide-Hotels)
- [Hotel Rooms in South Bend](https://expedia.com/South-Bend-Hotels.d6023340.Travel-Guide-Hotels)
- [Hotel Rooms in Evansville](https://expedia.com/Evansville-Hotels.d1179.Travel-Guide-Hotels)

Flights

- [Flights to EVV](https://expedia.com/Cheap-Flights-To-Evansville.d1179.Travel-Guide-Flights)
- [Flights to SBN](https://expedia.com/Cheap-Flights-To-South-Bend.d6023340.Travel-Guide-Flights)

Cars

- [Car rentals in Evansville](https://expedia.com/Car-Rentals-In-Evansville.d1179.Car-Rental-Guide)
- [Car rentals in South Bend](https://expedia.com/Car-Rentals-In-South-Bend.d6023340.Car-Rental-Guide)
- [Car rentals in Gary](https://expedia.com/Car-Rentals-In-Gary.d7549.Car-Rental-Guide)

General

- [Visit Michigan City](https://expedia.com/Michigan-City.dx8727)

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