Chesterton Vacation Rentals

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Check prices for these dates

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Aug 7 - Aug 8
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Aug 8 - Aug 9
This weekend
Aug 8 - Aug 10
Next weekend
Aug 15 - Aug 17

Vacation Rentals in Chesterton

Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly
Enjoy ocean views from the large window in this room, which features a round table, sofa, and additional seating area.

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
Guests can enjoy a serene beach experience with comfortable seating and shade from umbrellas.

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 ￥23,717
￥30,192 total
includes taxes & fees
Aug 14 - Aug 15
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
Blue Birdhouse - No Cleaning Fee - Pet Friendly - Dunes National Park
Relax by the fire pit in this serene outdoor space, surrounded by a seating area and decorative wooden stump.

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 ￥36,125
￥41,744 total
includes taxes & fees
Aug 17 - Aug 18
Blue Birdhouse - No Cleaning Fee - Pet Friendly - Dunes National Park
2 miles from Dunes National Park. A Unique Boutique Hotel.
Relax in this cozy corner room with a bay window offering a view of the outdoors. Enjoy the comfort of two plush chairs and a small table.

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 ￥192,122
￥262,664 total
includes taxes & fees
Aug 14 - Aug 15
2 miles from Dunes National Park. A Unique Boutique Hotel.
The Neighborhood Hotel - Grand Beach
Relax in this cozy living space with a flat-screen TV, comfortable sofa, and armchair, surrounded by a peaceful wooded view.

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
Enjoy al fresco dining on the patio, surrounded by the marina and its tranquil atmosphere.

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!
Enjoy cooking in this well-equipped kitchen with a convenient island and sink.

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 ￥16,842
￥45,534 total
includes taxes & fees
Sep 3 - Sep 4
Walkable cozy cottage, Outlet Mall across street!
Family Retreat-Beachwalk-Grill-AC-Free WiFi-Pool Table-Bikes-Grill-Golf Cart
Relax by the pool surrounded by lush surroundings and enjoy the scenic views.

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.
Relax in a hot tub with adjustable temperature control.

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 ￥18,403
￥35,451 total
includes taxes & fees
Sep 2 - Sep 3
BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.
Treehouse Bungalow- Quaint and Cozy Getaway!
Standing proudly on a coastal platform, a white lighthouse guides visitors along the pier.

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 ￥39,617
￥64,818 total
includes taxes & fees
Aug 11 - Aug 12
Treehouse Bungalow- Quaint and Cozy Getaway!
Warm late summer dates still open in Sept 2025: 1-4, 7-11, 15-19, 21-26. Enjoy!
Relax on the covered porch with wicker furniture and lush greenery.

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!
Modern kitchen with white cabinetry, black and white herringbone tile backsplash, stainless steel appliances, double sink, and a window above the sink.

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.
Enjoy a serene beach experience with gentle waves and a picturesque pier.

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!
Relax in an outdoor space surrounded by lush greenery and a refreshing pool.

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
Relax in a quiet spot with a comfortable armchair and reading lamp.

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 ￥37,630
￥91,399 total
includes taxes & fees
Aug 25 - Aug 26
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
Enjoy a panoramic ocean view from the comfort of this room, featuring a seating area with sofa and armchairs, flat-screen TV, and ceiling fan.

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
Enjoy ocean views from the balcony through the large sliding glass door.

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
Enjoy the view of the pool and surrounding landscape from this balcony.

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
Relax in this serene room with a high ceiling, wooden floor, and large windows offering a view of the outdoors.

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!
Relax in the covered outdoor seating area with a wooden deck, featuring a small table and comfortable chairs.

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.
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Top Chesterton Hotel Reviews

Four Winds Casino Resort – New Buffalo

Four Winds Casino Resort – New Buffalo

10/10 Excellent
"Fantastic resort "
Gilbert 1-night trip
Posted 1 day ago
Four Winds Casino Resort – New Buffalo

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?

Blue Birdhouse - No Cleaning Fee - Pet Friendly - Dunes National Park: This highly rated vacation home rental in Chesterton offers a patio, a private yard, and a barbecue grill 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 vacation with amenities like a selection of books.

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?

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 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.