Chesterton Vacation Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    one key icon
    Treat yourself
    Save instantly and earn perks with One Key
    Learn about One Key
    today icon
    Change your mind
    Book hotels with free cancellation

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, (35)
"We LOVED our stay here and plan to be back! Perfect cozy house by the beach. The deck is so nice and gives you so much extra space. Owners were very responsive and helpful during our stay. Steps down to the beach are fairly steep. I brought my arthritic 10 year old dog and she did good, but keep in mind for older dogs or anyone with stair issues. Parking is right next to the house which is so convenient. I honestly can’t think of any other amenities that would have made the trip better!"
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)
"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
Beach nearby
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
10.0 out of 10, Exceptional, (6)
"Great Stay!"
The price is $179
$230 total
includes taxes & fees
Jun 2 - Jun 3
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
The Neighborhood Hotel - Grand Beach
Beach nearby, beach towels
The Neighborhood Hotel - Grand Beach
4.0 star property
9.4 out of 10, Exceptional, (23)
"Un lugar maravilloso para descansar y desconectar. Él apartamento estaba muy bien equipado y super limpio."
The Neighborhood Hotel - Grand Beach
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)
"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 $175
$586 total
includes taxes & fees
Jun 2 - Jun 3
VIP! LUXURY 4BD 5min to Lake Michigan beach Big Pool
Dunes Escape - Minutes from Indiana Dunes National Park
Beach nearby
Dunes Escape - Minutes from Indiana Dunes National Park
9.8 out of 10, Exceptional, (28)
"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 $125
$325 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, (196)
"Enjoyed the troll house. Great location"
Beautiful Family Cottage in Beachwalk-Grill-AC-Free Wifi-Kids Haven.
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)
"Lovely place! Lovely owners! The only negative was highway noise."
Adorable Cottage New Buffalo, Mi. Near Grand Beach.1 Bedroom, Sleeps 5
Treehouse Bungalow- Quaint and Cozy Getaway!
Beach nearby
Treehouse Bungalow- Quaint and Cozy Getaway!
9.4 out of 10, Exceptional, (33)
"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 $229
$388 total
includes taxes & fees
Jun 3 - Jun 4
Treehouse Bungalow- Quaint and Cozy Getaway!
Cozy Michigan City Beach Cottage #2
Exterior
Cozy Michigan City Beach Cottage #2
9.6 out of 10, Exceptional, (66)
"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
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, (78)
"Exactly as stated! So very nice. Exactly what we needed."
The price is $150
$281 total
includes taxes & fees
Jun 4 - Jun 5
BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.
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)
"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.
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)
"Beautiful view, clean … great stay"
BEACHFRONT /HOTTUB/STEAM ROOM/GAME ROOM/JACUZZI/PETS/MASSAGE CHAIR/KAYAKS/BIKES
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)
"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 $122
$368 total
includes taxes & fees
Jun 2 - Jun 3
Newly Renovated City Escape with a private hot tub
Beach, casino, pet-friendly cottage
Beach nearby
Beach, casino, pet-friendly cottage
9.4 out of 10, Exceptional, (43)
"The house was perfect for visiting family for the holidays! Great location. Super clean and comfy! We will definitely be back!"
Beach, casino, pet-friendly cottage
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)
"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.
Hot tub and Golf Cart 6 bedrooms plus coach house. July 26th -Aug 2nd, 2024 open
Dining
Hot tub and Golf Cart 6 bedrooms plus coach house. July 26th -Aug 2nd, 2024 open
10.0 out of 10, Exceptional, (148)
"Will be back again!!"
Hot tub and Golf Cart 6 bedrooms plus coach house. July 26th -Aug 2nd, 2024 open
'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)
"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
Modern Farmhouse Retreat-10 Min Walk to Lake Michigan-Hot Tub-Sauna
Property grounds
Modern Farmhouse Retreat-10 Min Walk to Lake Michigan-Hot Tub-Sauna
10.0 out of 10, Exceptional, (46)
"Our experience with this property was excellent, from start to finish. The property owner was great to interact with and patient with all of my questions. What you see in the pictures posted with this listing is what you experience walking in. They are very true to the property. Great care was given to the finishes, amenities, appliances and décor. It is brand new construction, which felt great, and was very clean. While there were a few minor missing things for the way we utilize a VRBO or...
Modern Farmhouse Retreat-10 Min Walk to Lake Michigan-Hot Tub-Sauna
Spa-quality amenities, dog friendly, close to trails, IN Dunes Nat’l Park
Balcony
Spa-quality amenities, dog friendly, close to trails, IN Dunes Nat’l Park
9.2 out of 10, Wonderful, (45)
"The properties were extremely clean and well-stocked. We appreciated the responsiveness of Miller Beach Vacation Rentals team. We appreciated that the properties accepted dogs. Everyone loved the beaches and dunes, and lots of delicious meals were enjoyed. Check in and check out were super easy."
Spa-quality amenities, dog friendly, close to trails, IN Dunes Nat’l Park
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, (990)
"Overall the stay was great! My only complaints are the beds are too hard, the pillows were flat and the pool towels were child size. The overall building was clean, quiet and welcoming. The onsite breakfast was good and my kiddos really enjoyed the pool."
The price is $120
$134 total
includes taxes & fees
Jun 3 - Jun 4
Best Western Indian Oak
Spring House Inn
Property entrance
Spring House Inn
2.5 star property
8.8 out of 10, Excellent, (891)
"Okay. Needs updated. "
The price is $159
$178 total
includes taxes & fees
Jun 2 - Jun 3
Spring House Inn
Hilton Garden Inn Chesterton
Lobby
Hilton Garden Inn Chesterton
3.0 star property
8.8 out of 10, Excellent, (980)
"We enjoyed the environment and the staff was very nice. "
The price is $129
$145 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, 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 $122 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.

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

Baymont by Wyndham New Buffalo

Baymont by Wyndham New Buffalo

5/5 Excellent
"Great staff"
A verified traveler stayed at Baymont by Wyndham New Buffalo
Posted 13 hours ago
Baymont by Wyndham New Buffalo