Chesterton Vacation Rentals

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Vacation Rentals in Chesterton

Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly
View from property
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) :)"
Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly
Blue Birdhouse by the Beach
Property grounds
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...
The price is CA $204
CA $433 total
includes taxes & fees
Jun 6 - Jun 7
Blue Birdhouse by the Beach
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
Beach nearby
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
10.0 out of 10, Exceptional, 6 reviews
"Great Stay!"
The price is CA $244
CA $313 total
includes taxes & fees
Jun 9 - Jun 10
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
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The Neighborhood Hotel - Grand Beach
Beach nearby, beach towels
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
On the beach, sun loungers
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
Outdoor pool, a heated pool
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 $375
CA $971 total
includes taxes & fees
Jun 12 - Jun 13
VIP! LUXURY 4BD 5min to Lake Michigan beach Big Pool
Adorable Cottage New Buffalo, Mi. Near Grand Beach.1 Bedroom, Sleeps 5
Beach
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
Beach nearby
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 $170
CA $443 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.
Pool
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.
Outdoor dining
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!
Beach nearby
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 $312
CA $528 total
includes taxes & fees
Jun 6 - Jun 7
Treehouse Bungalow- Quaint and Cozy Getaway!
Hot tub open all year! Private heated pool, sleeps 10 near downtown New Buffalo!
Outdoor pool, a heated pool
Hot tub open all year! Private heated pool, sleeps 10 near downtown New Buffalo!
9.4 out of 10, Exceptional, 35 reviews
"The house was everything that was promised. We had a great time and the house is well prepared for a group to relax, cook, swim and enjoy your time together! Great location!"
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.
Property grounds
BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.
9.2 out of 10, Wonderful, 79 reviews
"Exactly as stated! So very nice. Exactly what we needed."
The price is CA $136
CA $296 total
includes taxes & fees
Jun 6 - Jun 7
BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.
Newly Renovated City Escape with a private hot tub
Property grounds
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 $213
CA $557 total
includes taxes & fees
Jun 10 - Jun 11
Newly Renovated City Escape with a private hot tub
Cozy Michigan City Beach Cottage #2
Exterior
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.
On the beach
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
Smart TV, fireplace, DVD player, printers
Juniper Presents: Lakefront Getaway and Outdoor Living Redefined
9.6 out of 10, Exceptional, 90 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
Beach nearby, sun loungers, beach towels
'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.
Terrace/patio
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!
Exterior
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!
Don't see what you're looking for?
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

Number of vacation rentals
5
Popular accommodation
Chesterton private vacation homes
Known landmarks
Indiana Dunes National Park, Indiana Dunes State Park and Lake View Beach
International airports
Chicago, IL (ORD-O'Hare Intl.), Chicago, IL (MDW-Midway Intl.) and Belo Horizonte (PLU)

Other types of properties in Chesterton you may be interested in

Best Western Indian Oak
Lobby
Best Western Indian Oak
2.5 star property
8.4 out of 10, Very good, 995 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 $164
CA $183 total
includes taxes & fees
Jun 6 - Jun 7
Best Western Indian Oak
Spring House Inn
Property entrance
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 $162
CA $182 total
includes taxes & fees
Jun 5 - Jun 6
Spring House Inn
Hilton Garden Inn Chesterton
Lobby
Hilton Garden Inn Chesterton
3.0 star property
8.8 out of 10, Excellent, 981 reviews
"Friendly staff, clean hotel. Pool was closed due to a chemical issue, so my kids were bummed. Breakfast isn't free, so we went across the street to Biggby. Overall, a good stay."
The price is CA $175
CA $196 total
includes taxes & fees
Jun 16 - Jun 17
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.

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, cottages, cabins, villas... 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chesterton vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chesterton vacation rentals we have selected for you start as low as CA $136 per night. Entering your travel dates in the search wizard 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.

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
Expedia verified reviews

Blue Chip Casino Hotel and Spa

Blue Chip Casino Hotel and Spa

5/5 Excellent
"What I liked best is that I won some money in the casino. Room was comfortable and convenient."
A verified traveller stayed at Blue Chip Casino Hotel and Spa
Posted 22 hours ago
Blue Chip Casino Hotel and Spa