Chesterton Vacation Rentals

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Vacation Rentals in Chesterton

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

Porter Beach
10.0 out of 10, Exceptional, (130)
"Awesome location and view. lots of beach amenities and everything you need to have fun. The only thing I would like are better bigger beds. "
United States
Chris W.
Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly

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

Chesterton
8.8 out of 10, Excellent, (90)
"I stayed one night in this apartment and had a great experience. The town is cute, the location is perfect, just a short drive from the Indiana Dunes, and the place was clean and convenient for a quick trip. The host communicated clearly and promptly, which made everything easy. Highly recommend!"
United States
Megan M.
$100 nightly
The price is $112
Nov 17 - Nov 18
Total with taxes and fees
Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes

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

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.
$1,394 nightly
The price is $1,561
Nov 17 - Nov 18
Total with taxes and fees
2 miles from Dunes National Park. A Unique Boutique Hotel.

Cozy Retreat w/Hot tub Indiana dunes Beaches Trails

Chesterton
10.0 out of 10, Exceptional, (11)
"This was one of the nicest, cleanest VRBO we have stated in. Don’t let the neighborhood detour you from staying. We felt safe and slept amazing in the VERY comfy king bed !! The master shower drain wasn’t working during our stay but the owner was very responsive and apologized for the inconvenience. "
United States
Dot Dot Smile Nichole W.
$247 nightly
The price is $277
Dec 9 - Dec 10
Total with taxes and fees
Cozy Retreat w/Hot tub Indiana dunes Beaches Trails

The Neighborhood Hotel - Grand Beach

4.0 star property
New Buffalo
9.6 out of 10, Exceptional, (64)
"Great stay for a large family, stayed in the 3 bedroom suite. "
United States
Mario-Julie
The Neighborhood Hotel - Grand Beach

Big Family House 5 Minutes from Lake Michigan/Blue Chip Casino/Brewery/Wineries!

Michigan City
9.6 out of 10, Exceptional, (121)
"the house was very spacious and clean. "
United States
Haley G.
Big Family House 5 Minutes from Lake Michigan/Blue Chip Casino/Brewery/Wineries!

Beautiful Family Cottage in Beachwalk-Grill-AC-Free Wifi-Kids Haven.

Michigan City
9.6 out of 10, Exceptional, (243)
"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.

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

Michigan City
9.4 out of 10, Exceptional, (125)
"The location was PERFECT. Just a 5 minute walk down a sandy path to a beautiful beach and Lake Michigan! The tiny cottage was perfect for two people. The bed however is very very hard. If you’re young you’d be okay, but us older folks don’t do well on firm beds lolOther than that our weekend stay was perfect!"
United States
Natasha W.
$180 nightly
The price is $202
Nov 17 - Nov 18
Total with taxes and fees
BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.

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

New Buffalo
10.0 out of 10, Exceptional, (79)
"Our stay at Red Oak was wonderful! The house was beautiful! Mary was an excellent host!"
United States
Kelly D.
Red Oak-5 bedroom with in ground pool, fireplace-walk to restaurants

15 mins to beach/Renew+Relax/Clean/ Nat’l Park!/Theater/Game Room/Pet Friendly

Gary
8.4 out of 10, Very Good, (16)
"Great place, nice location and the Hosts are extremely good to work with. Highly recommend this just out of the city stay!"
United States
Alyssa M.
$399 nightly
The price is $447
Nov 17 - Nov 18
Total with taxes and fees
15 mins to beach/Renew+Relax/Clean/ Nat’l Park!/Theater/Game Room/Pet Friendly

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

Michigan City
9.8 out of 10, Exceptional, (149)
"My family has rented this property for a number of years now and always enjoy our time. Plenty of space and amenities for all. We were blessed with great weather, which always adds to vacation time. We will do it again!"
United States
Mari S.
Lifetime Memories*Big Beach Front House*Fire Place/Pit*Free WiFi*Paddle Boards

Sand & Sun Getaway | 4BR w/ Game Room + 2 Living Areas |Game Room | Minutes to Beach

Michigan City
9.4 out of 10, Exceptional, (31)
"Nice"
United States
Maryellen W.
$309 nightly
The price is $346
Nov 17 - Nov 18
Total with taxes and fees
Sand & Sun Getaway | 4BR w/ Game Room + 2 Living Areas |Game Room | Minutes to Beach

Beachwalk - 7 bedrooms near the beach. Hot tub & golf cart. Great family house

Michigan City
10.0 out of 10, Exceptional, (244)
"Great house for a Blue Chip weekend with friends"
United States
Kyle W.
Beachwalk - 7 bedrooms near the beach. Hot tub & golf cart. Great family house

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

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!

BEACHFRONT /HOTTUB/STEAM ROOM/GAME ROOM/JACUZZI/PETS/MASSAGE CHAIR/KAYAKS/BIKES

Michigan City
9.6 out of 10, Exceptional, (328)
"We had a great stay. The listing and all the amenities were exactly as listed. Great place, great area, great host."
United States
Murphy R.
BEACHFRONT /HOTTUB/STEAM ROOM/GAME ROOM/JACUZZI/PETS/MASSAGE CHAIR/KAYAKS/BIKES

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

Downtown New Buffalo
10.0 out of 10, Exceptional, (182)
"Great house for our family! It was clean and spacious and very convenient to everything fun in New Buffalo!"
United States
Amelia F.
Warm late summer dates still open in Sept 2025: 1-4, 7-11, 15-19, 21-26. Enjoy!

VIP! LUXURY 4BD 5min to Lake Michigan beach Big Pool with heater!!

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 17 - Nov 18
Total with taxes and fees
VIP! LUXURY 4BD 5min to Lake Michigan beach Big Pool with heater!!

Modern Farmhouse Retreat-10 Min Walk to Lake Michigan-Hot Tub-Sauna

Michigan City
10.0 out of 10, Exceptional, (118)
"The house was great! The only issue was getting there with Apple Maps. It took me to the wrong place, but once I was there it was a fantastic place to stay!"
United States
Allyson L.
Modern Farmhouse Retreat-10 Min Walk to Lake Michigan-Hot Tub-Sauna

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

Michigan City
10.0 out of 10, Exceptional, (204)
"Super host, great amenities and really nice home for 6 adults and 4 children. "
United States
Judith M.
Family Retreat-Beachwalk-Grill-AC-Free WiFi-Pool Table-Bikes-Grill-Golf Cart

Uptown Penthouse on Pine: By Lake Michigan, Shopping & Casino!

Michigan City
9.8 out of 10, Exceptional, (34)
"We had a wonderful stay at the Penthouse. It was the perfect location for everything we wanted to. Many things in walking distance which was super convenient. We definitely hope to return for another long weekend!"
United States
Katie E.
$306 nightly
The price is $343
Dec 1 - Dec 2
Total with taxes and fees
Uptown Penthouse on Pine: By Lake Michigan, Shopping & Casino!
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 $112 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.