Chesterton Holiday Rentals

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Holiday Rentals in Chesterton

View from property
Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly
10.0 out of 10, Exceptional, (32)
"Wonderful home and location."
Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly
Beach nearby
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
10.0 out of 10, Exceptional, (6)
"Great Stay!"
The price is AU$351
per night
28 May - 29 May
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
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
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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
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 AU$1,274
per night
23 June - 24 June
VIP! LUXURY 4BD 5min to Lake Michigan beach Big Pool
Property grounds
BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.
9.2 out of 10, Wonderful, (77)
"Very relaxing"
The price is AU$431
per night
4 June - 5 June
BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.
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 AU$503
per night
4 June - 5 June
Dunes Escape - Minutes from Indiana Dunes National Park
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.
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 AU$595
per night
29 May - 30 May
Treehouse Bungalow- Quaint and Cozy Getaway!
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
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
Exterior
Cozy Michigan City Beach Cottage #2
9.6 out of 10, Exceptional, (65)
"Overall everything was great. Had a little hiccup at check in with the code provided not working, but we were able to contact the host and fixed asap. Cozy little spot to respite for a few days."
Cozy Michigan City Beach Cottage #2
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.
Outdoor spa tub
Walk Downtown, Huge Hot tub, Coffee on the Porch!
9.8 out of 10, Exceptional, (11)
"Great place close to everything. Hosts were awesome"
Walk Downtown, Huge Hot tub, Coffee on the Porch!
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 AU$640
per night
30 May - 31 May
Newly Renovated City Escape with a private hot tub
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 😊👍."
The price is AU$507
per night
28 May - 29 May
This 3 bedroom, 2 bathroom home is in a scenic area but closes to Indiana Dunes National Park.
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, (34)
"Very good minus the pool boy showing up unexpectedly and being rude to us. Tossing chemicals in hot tub with not warning us and they blew in all of our faces and food as we ate at the outside table."
Hot tub open all year! Private heated pool, sleeps 10 near downtown New Buffalo!
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
TV, video games, offices
Walking distance to beach, 2 Bedroom, Pet Friendly
9.8 out of 10, Exceptional, (8)
"We wanted to do some outlet shopping. This lovely old house is right across the street from the mall. It was very clean and well furnished. The beds were comfy and the neighborhood was quiet. We had a lovely weekend."
Walking distance to beach, 2 Bedroom, Pet Friendly
Terrace/patio
7 Bedroom Lake Shore Dr. Beach Home - NEWLY BUILT HOME! Steps to the beach!
9.6 out of 10, Exceptional, (44)
"The shore line was just steps away and being out there looking at that huge body of water was breathtaking! It was cool but refreshing at the same time! The house had plenty of room the beds were comfortable and we all slept great! I had some questions about the area before we arrived and Collin our host replied within the hour with all kinds of resources and we appreciated that so much! We hope to be back again next year!"
7 Bedroom Lake Shore Dr. Beach Home - NEWLY BUILT HOME! Steps 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 Holiday Home Travel Info

Number of holiday homes
5
Popular accommodation
Chesterton private holiday 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

Lobby
Best Western Indian Oak
2.5 star property
8.4 out of 10, Very good, (982)
"The pool and sauna was very nice."
The price is AU$187
per night
9 June - 10 June
Best Western Indian Oak
Property entrance
Spring House Inn
2.5 star property
8.8 out of 10, Excellent, (887)
"The Spring House Inn is located in a very quiet, woodsy residential area with plenty of parking spaces and close to nearby restaurants."
The price is AU$184
per night
29 May - 30 May
Spring House Inn
Room, Lake View
Waterbird Lakeside Inn
2.0 star property
8.0 out of 10, Very good, (700)
"We’ve stayed here many times. The only concern is the sometimes spotty wi-fi. Always comfortable and the wildlife is entertaining, especially the turtles and swallows. Will return."
The price is AU$152
per night
29 May - 30 May
Waterbird Lakeside Inn
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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chesterton holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Chesterton holiday 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chesterton holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chesterton holiday rentals we have selected for you start as low as AU$351 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Chesterton rentals

At Expedia, we put the best Chesterton holiday 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 holiday.

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 holiday rentals in Chesterton?

Yes, there are holiday rentals close to the most popular sights in Chesterton, or you can select a more secluded option if you're looking for a relaxing stay. 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 are some of the best holiday rentals that Chesterton has to offer?

Cozy House with YEAR ROUND Hot Tub!: This holiday home rental outside of Chesterton offers a patio, a selection of games and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. You and your friends and family can relax into your holiday with amenities such as 1 hot tub.

How many holiday rentals are there in Chesterton?

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

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 holiday rentals like in Chesterton?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chesterton. Holiday rentals offer amenities such as patios, hot tubs and fire pits so you'll be comfy for your stay. If you're concerned about a clean environment, a holiday rental can provide a sense of security away from shared hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for family gatherings.

Recent reviews of Chesterton properties
Expedia verified reviews

Spring House Inn

Spring House Inn

5/5 Excellent
"The Spring House Inn is located in a very quiet, woodsy residential area with plenty of parking spaces and close to nearby restaurants."
A verified traveller from Westfield stayed at Spring House Inn
Posted 3 days ago
Spring House Inn