Chesterton Holiday Rentals

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Holiday Rentals in Chesterton

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

9.0 out of 10, Wonderful, (66)
"Great location "
The price is AU$171
includes taxes & fees
13 Aug - 14 Aug
Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes

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

8.8 out of 10, Excellent, (10)
"Great pool hostess was very helpful"
The price is AU$311
includes taxes & fees
3 Aug - 4 Aug
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes

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

9.2 out of 10, Wonderful, (24)
"Our family had a wonderful time staying and making memories at the bluebird house. The house was very inviting and precious. Would def visit again."
The price is AU$416
includes taxes & fees
6 Aug - 7 Aug
Blue Birdhouse - No Cleaning Fee - Pet Friendly - Dunes National Park

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

10.0 out of 10, Exceptional, (108)
"Great location near the beach. Comfortable house and clean with nice amenities. Check in was super easy. "
Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly

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

9.0 out of 10, Wonderful, (4)
"Great Vrbo! Very nice, very clean, enough room for everyone! We loved it!"
The price is AU$2,757
includes taxes & fees
30 July - 31 July
2 miles from Dunes National Park. A Unique Boutique Hotel.

The Neighborhood Hotel - Grand Beach

4.0 star property
9.6 out of 10, Exceptional, (54)
"Manager stuff was very nice and pleasant, but bed and sofa were very old and not comfortable, otherwise we liked our stay "
The Neighborhood Hotel - Grand Beach

Red Oak-5 bedroom with in ground pool, fireplace-walk to restaurants

10.0 out of 10, Exceptional, (71)
"This house is a great setup and well taken care of. The owners are very responsive and location is close to everything."
Red Oak-5 bedroom with in ground pool, fireplace-walk to restaurants

NEW! Charming 3-Bedroom Hideaway in the Heart of Michigan City!

NEW! Charming 3-Bedroom Hideaway in the Heart of Michigan City!

Treehouse Bungalow- Quaint and Cozy Getaway!

8.8 out of 10, Excellent, (49)
"House was clean, cute, in a great location. Would recommend and stay here again. "
The price is AU$672
includes taxes & fees
4 Aug - 5 Aug
Treehouse Bungalow- Quaint and Cozy Getaway!

On Lake Minnehaha, The Funky Turtle @ Lakeshore Camp Resort with all the Campground Amenities!

1.0 star property
7.0 out of 10, Good, (2)
"We had a great stay at the Funky Turtle. The house was clean and just enough space for my family of 5. The house is close to campground bathrooms if the occasional extra bathroom is needed. We enjoyed the fire pit, use of the grill, and sitting on the porch. Our only complaint is about the noise but it was clear from the map that the campground was located near an interstate. While sitting outside you can hear the noise from the interstate and close by trains. However, inside was much...
The price is AU$522
includes taxes & fees
28 July - 29 July
On Lake Minnehaha, The Funky Turtle @ Lakeshore Camp Resort with all the Campground Amenities!

Warm late summer dates still open in Sept 2025: 1-4, 7-11, 15-19, 21-26. Enjoy!

10.0 out of 10, Exceptional, (167)
"This property is beautiful with a lot of space, bedrooms, and bathrooms. The location was perfect for walking to the beach, restaurants, and shopping. Can't wait to visit again!"
Warm late summer dates still open in Sept 2025: 1-4, 7-11, 15-19, 21-26. Enjoy!

Juniper Presents: Lakefront Getaway and Outdoor Living Redefined

9.4 out of 10, Exceptional, (100)
"Our family spent the holiday at this incredible house and everything was perfect. We would definitely stay here again and highly recommend it. "
Juniper Presents: Lakefront Getaway and Outdoor Living Redefined

Family Retreat-Beachwalk-Grill-AC-Free WiFi-Pool Table-Bikes-Grill-Golf Cart

10.0 out of 10, Exceptional, (190)
"We loved our stay here. I can’t wait to come back in the summer months"
Family Retreat-Beachwalk-Grill-AC-Free WiFi-Pool Table-Bikes-Grill-Golf Cart

BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.

9.4 out of 10, Exceptional, (113)
"It was quiet and clean and very enjoyable for me and my fiance! Will be going again!"
The price is AU$383
includes taxes & fees
28 July - 29 July
BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.

'Rustic Refined Retreat’ Lakeside Home - Walk to Everything!

10.0 out of 10, Exceptional, (191)
"Amazing location and such a cute house !"
'Rustic Refined Retreat’ Lakeside Home - Walk to Everything!

Walkable cozy cottage, Outlet Mall across street!

9.6 out of 10, Exceptional, (17)
"Loved the cottage it had everything we needed very nice!"
The price is AU$463
includes taxes & fees
4 Aug - 5 Aug
Walkable cozy cottage, Outlet Mall across street!

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

8.8 out of 10, Excellent, (80)
"Great house, beautiful view, very clean"
The price is AU$950
includes taxes & fees
25 Aug - 26 Aug
View of the lake from 2 decks in this 6BR Lake Shore Dr home, steps to the beach

Spacious home near nightlife, beaches, dunes, zoo, and Lake Michigan charters.

7.6 out of 10, Good, (21)
"Had a great time and enjoyed our stay "
Spacious home near nightlife, beaches, dunes, zoo, and Lake Michigan charters.

7 Bedroom Lake Shore Dr. Beach Home - NEWLY BUILT HOME! Steps to the beach!

9.0 out of 10, Wonderful, (60)
"We had a fantastic time together."
7 Bedroom Lake Shore Dr. Beach Home - NEWLY BUILT HOME! Steps to the beach!

Fun w/Loft! Beach ~Nature Trails ~Grill~ Firepit ~Indiana Dunes National Park

10.0 out of 10, Exceptional, (40)
"Perfect little spot for a quick family getaway. We loved the fire pit and the screened in porch!"
Fun w/Loft! Beach ~Nature Trails ~Grill~ Firepit ~Indiana Dunes National Park
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

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?

Blue Birdhouse - No Cleaning Fee - Pet Friendly - Dunes National Park: This highly rated holiday home rental in Chesterton offers a patio, a private garden and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. You and your friends and family can relax into your holiday with amenities such as a selection of books.

How many holiday rentals are there in Chesterton?

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

What can I see and do in Chesterton?

Indiana Dunes National Park and Lake Michigan 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 Indiana Dunes Visitor Center.

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.