Chesterton Vacation Rentals

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Vacation Rentals in Chesterton

Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly
10.0 out of 10, Exceptional, 36 reviews
"We immediately fell in love with the property when we walking in and saw the panoramic view from the floor to ceiling windows! The weather wasn’t great for our trip, but thankfully the house was the perfect cozy escape from the rain. Our two dogs loved being close to the beach and the water. Great communication from the owner as well. Would definitely stay again (and hope for better weather) :)"
The price is CA $479
CA $699 total
includes taxes & fees
Jul 7 - Jul 8
Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly
Blue Birdhouse by the Beach
9.6 out of 10, Exceptional, 12 reviews
"My Niece and I stayed at the Blue Birdhouse for her Spring Break and to see if we wanted to visit this area in the summertime, as we had never been there. The Owner of this house was gracious and kind and very responsive to any questions or requests. We also took our dogs with us and they had a blast in the fenced back yard! Every time we went to look somewhere up to visit, it seemed like everywhere was between 5 - 10 minutes away! Location is absolutely awesome and close to virtually...
Blue Birdhouse by the Beach
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
10.0 out of 10, Exceptional, 6 reviews
"Great Stay!"
The price is CA $245
CA $309 total
includes taxes & fees
Jun 12 - Jun 13
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
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The Neighborhood Hotel - Grand Beach
4.0 star property
9.4 out of 10, Exceptional, 24 reviews
"Un lugar maravilloso para descansar y desconectar. Él apartamento estaba muy bien equipado y super limpio."
The Neighborhood Hotel - Grand Beach
BEACHFRONT /HOTTUB/STEAM ROOM/GAME ROOM/JACUZZI/PETS/MASSAGE CHAIR/KAYAKS/BIKES
9.6 out of 10, Exceptional, 292 reviews
"Beautiful view, clean … great stay"
BEACHFRONT /HOTTUB/STEAM ROOM/GAME ROOM/JACUZZI/PETS/MASSAGE CHAIR/KAYAKS/BIKES
VIP! LUXURY 4BD 5min to Lake Michigan beach Big Pool
9.4 out of 10, Exceptional, 10 reviews
"Place was very clean, beds was very comfortable. we slepts like a baby and enjoy the house with the amenities. Great location walk distance from Michigan lake highly recommended! Thank you Hodi"
The price is CA $500
CA $1,140 total
includes taxes & fees
Jun 23 - Jun 24
VIP! LUXURY 4BD 5min to Lake Michigan beach Big Pool
Adorable Cottage New Buffalo, Mi. Near Grand Beach.1 Bedroom, Sleeps 5
9.8 out of 10, Exceptional, 170 reviews
"Lovely place! Lovely owners! The only negative was highway noise."
Adorable Cottage New Buffalo, Mi. Near Grand Beach.1 Bedroom, Sleeps 5
Dunes Escape - Minutes from Indiana Dunes National Park
9.8 out of 10, Exceptional, 29 reviews
"We had a great stay! Everything was just as listed! Every area was very clean, kitchen well stocked, plenty of towels provided for our 2 night stay. If i could change anything it would have been to add a nightlight of some sort in the twin room. Unfamiliar place/noises and it was completely dark for my daughter. No lamp or nightlight in that room. Also a few of the cabinet doors need tightened down."
The price is CA $171
CA $445 total
includes taxes & fees
Jun 27 - Jun 28
Dunes Escape - Minutes from Indiana Dunes National Park
Beautiful Family Cottage in Beachwalk-Grill-AC-Free Wifi-Kids Haven.
9.6 out of 10, Exceptional, 197 reviews
"Super location, super clean, super cute! We enjoyed sitting on the porch talking for hours, the kitchen was well equipped, the beds were all comfortable, plenty of towels in bathrooms, and beach chairs available to use. We also took the bikes on a trail ride! Hosts were wonderful, we plan to come back in the near future 😊"
Beautiful Family Cottage in Beachwalk-Grill-AC-Free Wifi-Kids Haven.
The Victorian Carriage House. Built in 1880, this restored cottage is a charmer.
7.8 out of 10, Good, 12 reviews
"We had a lovely time at this place, it was perfect for a weekend getaway and spending time with friends."
The Victorian Carriage House. Built in 1880, this restored cottage is a charmer.
Treehouse Bungalow- Quaint and Cozy Getaway!
9.4 out of 10, Exceptional, 33 reviews
"We had such an amazing experience with this property and the host. She was very responsive and was so accommodating to some extra requests I had. We would stay again for sure!"
The price is CA $313
CA $530 total
includes taxes & fees
Jun 17 - Jun 18
Treehouse Bungalow- Quaint and Cozy Getaway!
Hot tub open all year! Private heated pool, sleeps 10 near downtown New Buffalo!
9.4 out of 10, Exceptional, 36 reviews
"We loved the location, close to great places to eat. The property itself is secluded yet doesn’t feel isolated. The house layout is welcoming and the backyard is the star of the show. The host was always quick to respond and very accommodating. Some minor improvements (but not enough to reduce the star ratings): We played musical beds as it was hard to find one that’s completely comfortable. Could use an update. The pool area needs a little cleaning. The pool itslef is super clean. It’s the...
Hot tub open all year! Private heated pool, sleeps 10 near downtown New Buffalo!
BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.
9.2 out of 10, Wonderful, 79 reviews
"Cozy, well appointed tiny home."
The price is CA $137
CA $296 total
includes taxes & fees
Jun 7 - Jun 8
BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.
Newly Renovated City Escape with a private hot tub
9.2 out of 10, Wonderful, 22 reviews
"Had a great girls weekend getaway! The home was clean and nicely decorated. We had plenty of space for five ladies. Hot tub was clean and nice and hot! Close to downtown and all the action. We really enjoyed our stay and would definitely come back!"
The price is CA $208
CA $554 total
includes taxes & fees
Jun 10 - Jun 11
Newly Renovated City Escape with a private hot tub
Cozy Michigan City Beach Cottage #2
9.6 out of 10, Exceptional, 66 reviews
"Just right for my two teens and dog and me. Beds were comfy. It had enough kitchenware to cook and serve a couple meals. Neighborhood was cute and quiet. And the beach! The best. Short three block walk to an accessible beach access path."
Cozy Michigan City Beach Cottage #2
Charming 3-bedroom house nestled amidst nightlife, beaches, dunes, and a zoo.
7.0 out of 10, Good, 4 reviews
"My family and I stayed one night here for an event. Getting into the house was simple and the location is great - short distance to the lake and to nearby preserves."
Charming 3-bedroom house nestled amidst nightlife, beaches, dunes, and a zoo.
Juniper Presents: Lakefront Getaway and Outdoor Living Redefined
9.6 out of 10, Exceptional, 91 reviews
"The view is gorgeous, the hot tub is great and the neighborhood is a great location. If I could give 4.5 stars I would; because this place could definitely use a refresh in the interior- in one of the bedrooms, both twin beds are rock hard and very old. In one of the smaller bedrooms, there is peeled paint on the doors, closet doors, walls and ceiling and a LOT of the owners clutter is left behind- both smaller bedroom closets as well as the hall closets were full of the owners' old video games,...
Juniper Presents: Lakefront Getaway and Outdoor Living Redefined
'Summer Breeze' Lakeside Condo - Walk to Town & Marina + POOL
10.0 out of 10, Exceptional, 99 reviews
"We stayed with 2 adults and 4 kids. The place was great for the 6 of us and walkable to downtown NB! Would definitely stay again."
'Summer Breeze' Lakeside Condo - Walk to Town & Marina + POOL
This 3 bedroom, 2 bathroom home is in a scenic area but closes to Indiana Dunes National Park.
8.6 out of 10, Excellent, 7 reviews
"Our family of three adults plus one dog really enjoyed our stay. This property is very clean, attractive, and had extra touches that made us feel comfortable and welcome. Beds were comfortable. Location is very convenient for the Dunes, beaches, and good restaurants. If we’re ever up this way again we’ll definitely want to stay here 😊👍."
This 3 bedroom, 2 bathroom home is in a scenic area but closes to Indiana Dunes National Park.
Rare Private Heated Pool w/in 1.5 Blocks to the Beach!
9.8 out of 10, Exceptional, 72 reviews
"Six female relatives spent two nights here planning a bigger reunion. The house was clean and well supplied as stated in the listing. We had a great week-end."
Rare Private Heated Pool w/in 1.5 Blocks to the Beach!
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See all available properties in Chesterton
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.

Chesterton Vacation Rental Travel Info

Other types of properties in Chesterton you may be interested in

Best Western Indian Oak
2.5 star property
8.4 out of 10, Very good, 997 reviews
"Everything about the hotel was great, except one thing; the hotel sits by this lake which was beautiful, but the outside deck was covered with animal feces and bugs all over the structure. If that deck was cleaned, that would've made my stay excellent."
The price is CA $178
CA $199 total
includes taxes & fees
Jun 12 - Jun 13
Best Western Indian Oak
Spring House Inn
2.5 star property
8.8 out of 10, Excellent, 894 reviews
"Very close to the Indiana Dunes state and national parks. "
The price is CA $136
CA $152 total
includes taxes & fees
Jun 11 - Jun 12
Spring House Inn
Hilton Garden Inn Chesterton
3.0 star property
8.8 out of 10, Excellent, 981 reviews
"Convenient stopover en route OH to WI. Liked it so stayed again on return trip. "
The price is CA $199
CA $223 total
includes taxes & fees
Jun 24 - Jun 25
Hilton Garden Inn Chesterton
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.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Chesterton. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.

How many vacation rentals are there in Chesterton?

Choose from 26 Expedia vacation rentals in Chesterton for a memorable vacation.

What can I see and do in Chesterton?

Indiana Dunes National Park is a spot to get out into nature, whereas other top attractions include Lake Michigan. Other places in town to visit include Indiana Dunes Visitor Center and Indiana Dunes State Park.

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.

Recent reviews of Chesterton properties
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