Holiday Rentals in Chesterton

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Holiday Rentals in Chesterton

Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly
10.0 out of 10, Exceptional, 40 reviews
"House clean great view"
Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
9.8 out of 10, Exceptional, 7 reviews
"This rental is right by Indiana Dunes and in a nice neighborhood. Main bed was comfortable and we slept well. The shower needs repaired. There was not a cloth to wash dishes with. The skillet in the cabinet still had food in it. We did walk around the block to get Uno Pizza which is in a speakeasy setting. Nice place. It was early for swimming but we did take a dip. Don let us stay late to enjoy the sun. The pool is well cared for. Overall a good rental."
The price is €219
includes taxes & fees
24 Jun - 25 Jun
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
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 €426
includes taxes & fees
22 Jul - 23 Jul
Blue Birdhouse by the Beach
The Neighborhood Hotel - Grand Beach
4.0 star property
9.4 out of 10, Exceptional, 26 reviews
"It was very relaxing and enjoyable "
The Neighborhood Hotel - Grand Beach
BEACHFRONT /HOTTUB/STEAM ROOM/GAME ROOM/JACUZZI/PETS/MASSAGE CHAIR/KAYAKS/BIKES
9.6 out of 10, Exceptional, 295 reviews
"Check in was easy with all instructions given for easy access. The view from the patio is perfect. Would’ve like to have a few housing updates like the blinds so they don’t click against the windows when the fans are going. Everything else was great."
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 €673
includes taxes & fees
9 Jul - 10 Jul
VIP! LUXURY 4BD 5min to Lake Michigan beach Big Pool
Dunes Escape - Minutes from Indiana Dunes National Park
9.8 out of 10, Exceptional, 31 reviews
"This property was a very very nice place. Very comfortable and cozy. The backyard is great for kids since it’s all fenced in. Simple and quick drive to the dunes. Nice place to come back to after a long hot day at the beach! ❤️"
The price is €312
includes taxes & fees
27 Jun - 28 Jun
Dunes Escape - Minutes from Indiana Dunes National Park
Treehouse Bungalow- Quaint and Cozy Getaway!
9.2 out of 10, Wonderful, 34 reviews
"We just needed one night to recover from our day at Indiana Dunes before we headed out of town. It was a great spot. The decor is so cute. Beds were comfortable. Everything worked just fine. We had a little trouble with the key code on the door when we checked in, but the host was VERY responsive and quick. Hardly a moment of delay accessing the property."
The price is €372
includes taxes & fees
25 Jun - 26 Jun
Treehouse Bungalow- Quaint and Cozy Getaway!
Adorable Cottage New Buffalo, Mi. Near Grand Beach.1 Bedroom, Sleeps 5
9.8 out of 10, Exceptional, 171 reviews
"This is a very cute little cottage! Nice and cozy and has everything you need! It is right off of the highway so really convenient to get to. There is a train that goes by out front but, the house is surrounded with beautiful landscaping and plants and it’s like you’re in your own little world inside the home and out in the back of the house. The back has a small little pond with a water fountain, a nice deck and screened in porch that overlooks the pretty garden/patio area with a fire pit,...
The price is €329
includes taxes & fees
14 Jul - 15 Jul
Adorable Cottage New Buffalo, Mi. Near Grand Beach.1 Bedroom, Sleeps 5
Beautiful Family Cottage in Beachwalk-Grill-AC-Free Wifi-Kids Haven.
9.6 out of 10, Exceptional, 198 reviews
"We usually come to stay at the Troll’s Den at least once a year, sometimes twice! It is the perfect place for our little family! Everything is always perfect on our arrival, and Anders is very communicative during our stay if anything comes up."
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.
BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.
9.2 out of 10, Wonderful, 80 reviews
"Cozy, well appointed tiny home."
The price is €270
includes taxes & fees
23 Jun - 24 Jun
BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.
Beach, casino, pet-friendly cottage
9.4 out of 10, Exceptional, 46 reviews
"The house was perfect for a quick beach get away. Close proximity to the beahc, parks, and zoo. Host was great with communication."
Beach, casino, pet-friendly cottage
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 €417
includes taxes & fees
24 Jun - 25 Jun
Newly Renovated City Escape with a private hot tub
Family Retreat-Beachwalk-Grill-AC-Free WiFi-Pool Table-Bikes-Grill-Golf Cart
10.0 out of 10, Exceptional, 163 reviews
"My mom, who is 91, along with my two neices and their mother, take an annual girl's trip. We rypically get a hotel, but this year we changed it up for a beachy vibe. The house is gorgeous and very comfortable. The neighborhood of mostly vacation rentals was quiet and low key. The property manager was super responsive to our needs and friendly. The golf cart was a big hit! It was such fun driving around the little neighborhood and to the beach. We really enjoyed our time at the Vahalla."
Family Retreat-Beachwalk-Grill-AC-Free WiFi-Pool Table-Bikes-Grill-Golf Cart
Modern Beach Bungalow, Hot tub, Firepit, Foosball, IN Dunes Nat'l Park
8.6 out of 10, Excellent, 17 reviews
"This rental by far is one of the best rentals I’ve rented and I rent 5+ a year. Very clean and updated home with plenty of space. Comfy beds, plenty of blankets and pillows. Fully stocked kitchen with all the Necessities! Also was very impressed with the stocked coffee, toilet paper, trash bags, spices that came with it. This is not typical for a rental. They typically leave you enough for a day. We were there for 5 days and still didn’t run out! There was enough parking and the double garage...
Modern Beach Bungalow, Hot tub, Firepit, Foosball, IN Dunes Nat'l Park
Secluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park
8.2 out of 10, Very good, 34 reviews
"The yard is awesome, of course the hot tub at the top of the hill was the best, and we enjoyed the firepit as well. The house was a tidy little cottage at which we enjoyed our stay. It’s within a short walk to the National Park and downtown Miller Beach. The neighborhood is fine, pretty secluded, and still close to most attractions."
Secluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park
Big old fashioned house nestled amidst nightlife, beaches, dunes, and a zoo.
6.4 out of 10, 7 reviews
"We traveled about 3 hours from Wisconsin to see my niece graduate high school. We stayed in the house - myself, my sister and my mom who is 80. I should have read the description better, I thought one of the bedrooms was on the main level of the house. The main bathroom with shower was upstairs. The stairs were solid with a good railing, so mom did okay. I think this might be more my mistake than the description, but a small challenge. The house has a bunch of improvements/renovation work but it...
Big old fashioned 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
"Very clean and easy process"
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
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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.

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, 1,003 reviews
"Nice clean place "
The price is €135
includes taxes & fees
23 Jun - 24 Jun
Best Western Indian Oak
Spring House Inn
2.5 star property
8.8 out of 10, Excellent, 911 reviews
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The price is €103
includes taxes & fees
23 Jun - 24 Jun
Spring House Inn
Hilton Garden Inn Chesterton
3.0 star property
8.8 out of 10, Excellent, 992 reviews
"The property is located close to an Interstare Tollroad. Convenient for access to the tollroad but located in a non-residential area. The room is nice and clean. Had a traditional tub/shower and not a roomy walk-in shower like some other hotel properties."
The price is €148
includes taxes & fees
3 Jul - 4 Jul
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 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, apart-hotels, 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 favorite 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 depends 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 €219 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 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.

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