Search Holiday Rentals in Chesterton

    price find illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Save instantly and earn perks with One Key
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Top Holiday Rentals in Chesterton

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

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 £158
includes taxes & fees
11 Aug - 12 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, (25)
"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 £218
includes taxes & fees
17 Aug - 18 Aug
Blue Birdhouse - No Cleaning Fee - Pet Friendly - Dunes National Park

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 £1,382
includes taxes & fees
7 Aug - 8 Aug
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, (55)
"Had a wonderful stay at cottage 13, all necessary amenities were available and nice quaint location. Very nice stay overall. "
The Neighborhood Hotel - Grand Beach

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

10.0 out of 10, Exceptional, (72)
"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

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 £237
includes taxes & fees
3 Sept - 4 Sept
Walkable cozy cottage, Outlet Mall across street!

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

10.0 out of 10, Exceptional, (193)
"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, (116)
"It was quiet and clean and very enjoyable for me and my fiance! Will be going again!"
The price is £184
includes taxes & fees
2 Sept - 3 Sept
BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.

Treehouse Bungalow- Quaint and Cozy Getaway!

8.8 out of 10, Excellent, (49)
"Unsafe parking, uncomfortable couch and beds. We didn’t stay the night due to the poor conditions."
The price is £337
includes taxes & fees
10 Aug - 11 Aug
Treehouse Bungalow- Quaint and Cozy Getaway!

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

10.0 out of 10, Exceptional, (168)
"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!

Kid-friendly Michiana cottage! Summer dates open - including 4th of July!

10.0 out of 10, Exceptional, (56)
"Loved this place and so clean and perfect for our girls weekend!"
Kid-friendly Michiana cottage! Summer dates open - including 4th of July!

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

7.6 out of 10, Good, (22)
"Had a great time and enjoyed our stay "
Spacious home near nightlife, beaches, dunes, zoo, and Lake Michigan charters.

Hot tub open all year! Private heated pool, sleeps 10 near downtown New Buffalo!

9.2 out of 10, Wonderful, (65)
"Had the best weekend at this house. The house was clean, updated, and had everything we could need. Will be staying again. "
Hot tub open all year! Private heated pool, sleeps 10 near downtown New Buffalo!

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

8.6 out of 10, Excellent, (82)
"Great house, beautiful view, very clean"
The price is £476
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

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

Lifetime Memories*Big Beach Front House*Fire Place/Pit*Free WiFi*Paddle Boards

9.8 out of 10, Exceptional, (140)
"Just perfect!! 4 levels. Plenty of back yard room and the beach was fantastic!!Everything was as stated in information!!Recommend to anybody. !!!"
Lifetime Memories*Big Beach Front House*Fire Place/Pit*Free WiFi*Paddle Boards

3BR Condo Close To The Beach! In/OutDoor Pools

10.0 out of 10, Exceptional, (96)
"Lovely condo in great location"
3BR Condo Close To The Beach! In/OutDoor Pools

Amazing Lake Views, Beach Access, Hot Tub, Fire Pit, Screened Porch & Game Room

10.0 out of 10, Exceptional, (209)
"We had a great stay; the layout was great for our family vacation."
Amazing Lake Views, Beach Access, Hot Tub, Fire Pit, Screened Porch & Game Room

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

9.0 out of 10, Wonderful, (61)
"We had a fantastic time together."
7 Bedroom Lake Shore Dr. Beach Home - NEWLY BUILT HOME! Steps to the beach!
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.
Save an average of 15% on thousands of hotels when you're signed in

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.