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Chesterton Vacation Rentals

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Vacation Rentals in Chesterton

Apartment in Chesterton

8.8 out of 10, Excellent, (90)
"Great location for visiting the Dunes. Having a gas grill available was a nice perk. Was what we needed at a great value. "
United States
Brian L.
$100 nightly
The price is $112
Nov 30 - Dec 1
Total with taxes and fees
Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes

Cabin in Porter Beach

10.0 out of 10, Exceptional, (131)
"The view is stunning, cottage is very well maintained, and the owners are courteous and helpful!"
United States
Julie R.
Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly

Aparthotel in Chesterton

9.0 out of 10, Wonderful, (4)
"Great Vrbo! Very nice, very clean, enough room for everyone! We loved it!"
United States
Val S.
$1,399 nightly
The price is $1,567
Nov 24 - Nov 25
Total with taxes and fees
2 miles from Dunes National Park. A Unique Boutique Hotel.

Vacation Home in Chesterton

8.6 out of 10, Excellent, (7)
"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
Nick R.
$266 nightly
The price is $297
Nov 24 - Nov 25
Total with taxes and fees
Balcony/Patio/ Separate Fenced Yard + Beach, Park & Downtown+close to Chicago

Mobile Home in Porter

9.0 out of 10, Wonderful, (12)
"Great pool hostess was very helpful"
United States
regina
$79 nightly
The price is $88
Nov 26 - Nov 27
Total with taxes and fees
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes

Apartment in New Buffalo

4.0 star property
9.6 out of 10, Exceptional, (64)
"Absolutely perfect, we loved every bit of our stay!"
United States
Rebecca
The Neighborhood Hotel - Grand Beach

Vacation Home in Michigan City

9.6 out of 10, Exceptional, (244)
"House had everything we needed, great resort neighborhood for kids "
United States
Kathryne I.
Beautiful Family Cottage in Beachwalk-Grill-AC-Free Wifi-Kids Haven.

Vacation Home in New Buffalo

10.0 out of 10, Exceptional, (79)
"The house was perfect for our family vacation with the pool and location!! Better than advertised. "
United States
Michael D.
Red Oak-5 bedroom with in ground pool, fireplace-walk to restaurants

Apartment in Michigan City

9.4 out of 10, Exceptional, (125)
"Was as described great stay"
United States
Amber C.
$169 nightly
The price is $189
Nov 25 - Nov 26
Total with taxes and fees
BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.

Vacation Home in Michigan City

9.6 out of 10, Exceptional, (121)
"We enjoyed everything about the house it could have used a little weed eating but other than that it was perfect my family enjoyed their stay Thank you again"
United States
Barb W.
Big Family House 5 Minutes from Lake Michigan/Blue Chip Casino/Brewery/Wineries!

Vacation Home in Michigan City

9.8 out of 10, Exceptional, (149)
"The house was a great location. Close to the beach. We had a wonderful time!"
United States
Jim W.
Lifetime Memories*Big Beach Front House*Fire Place/Pit*Free WiFi*Paddle Boards

Vacation Home in Downtown New Buffalo

10.0 out of 10, Exceptional, (32)
"Heather's home is amazing - beautifully appointed, amazing location, and perfect for a large group. Her hospitality is the best in a vacation home we've ever experienced, and we will return! "
United States
Monica B.
New luxury home steps to downtown w/yr round heated pool

Vacation Home in Michigan City

9.4 out of 10, Exceptional, (31)
"Nice"
United States
Maryellen W.
$316 nightly
The price is $354
Nov 24 - Nov 25
Total with taxes and fees
Sand & Sun Getaway | 4BR w/ Game Room + 2 Living Areas |Game Room | Minutes to Beach

Vacation Home in Michigan City

10.0 out of 10, Exceptional, (244)
"Great place to stay with a big family "
United States
Larry Y.
Beachwalk - 7 bedrooms near the beach. Hot tub & golf cart. Great family house

Cabin in Griffith

9.8 out of 10, Exceptional, (16)
"We had a very nice stay. The cabin was quite cozy and comfortable."
United States
Jeremy & Rebecca F.
$92 nightly
The price is $103
Nov 30 - Dec 1
Total with taxes and fees
Beautiful Rustic Cabin for Two!

Villa in Michigan City

8.8 out of 10, Excellent, (23)
"Good location great pool host was nice to deal with. Had a good time"
United States
T H.
$464 nightly
The price is $520
Nov 24 - Nov 25
Total with taxes and fees
VIP! LUXURY 4BD 5min to Lake Michigan beach Big Pool with heater!!

Vacation Home in Miller Beach

9.2 out of 10, Wonderful, (62)
"The property was wonderful. So many amenities that our team loved! The sauna, proximity to the beach and the two kitchens were highlights. It was clean and well-maintained."
United States
Audrey H.
Spa-quality amenities, dog friendly, close to trails, IN Dunes Nat’l Park

Villa in Miller Beach

9.0 out of 10, Wonderful, (37)
"Had a great time with our family for the weekend. "
United States
Caroline R.
Beachfront Villa + Addition, Skyline views, Hot Tubs, Luxury Smart Home

Vacation Home in Michigan City

10.0 out of 10, Exceptional, (118)
"The place was even better than the photos. It was a great place to stay."
United States
Alex B.
Modern Farmhouse Retreat-10 Min Walk to Lake Michigan-Hot Tub-Sauna

Vacation Home in New Buffalo

9.2 out of 10, Wonderful, (70)
"Great backyard space to hang out. Awesome location to walk and explore the area and an easy drive to other spots along the lake. The few minor issues we had were quickly communicated and addressed with the owner, so the trip went on without a hitch."
United States
Laura P.
Hot tub open all year! Private heated pool, sleeps 10 near downtown New Buffalo!
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

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 $88 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.

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?

Big Family House 5 Minutes from Lake Michigan/Blue Chip Casino/Brewery/Wineries!: You might want to consider this vacation home rental near Chesterton, which is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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?

Lake Michigan and Indiana Dunes Visitor Center 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 Chellberg Farm.

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.