Chesterton Holiday Rentals

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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, (81)
"The pictures do no justice. This location was beyond our expectations and exactly what was needed as a getaway. Will and Liz have an exceptional home with such an amazing view. Hope to be back someday soon. Thank you so very much. "
The price is AU$437
includes taxes & fees
18 Feb - 19 Feb
Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly

Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes

9.0 out of 10, Wonderful, (49)
"I booked this stay as a birthday gift for my son. He and his fiancé stayed for 2 nights/3 days. They absolutely enjoyed there stay. The place was clean and just like the pictures displayed. They had an issue with the code not working to enter the property, Don the host got in touch with us immediately and even refunded some money for the inconvenience! I will definitely be booking again for my daughters birthday!!"
The price is AU$178
includes taxes & fees
17 Feb - 18 Feb
Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes

The Neighborhood Hotel - Grand Beach

4.0 star property
9.4 out of 10, Exceptional, (39)
"Overall the place is wonderful and we enjoyed the amenities. My teenaged boys enjoyed the game room, pool at night, beach, fire pit. I loved the bed, having a kitchenette, and the coffeemaker. Much better than a typical hotel version. I’d caution using suite 10 for more than two people. The sleeper was what you’d expect a sleeper to be - not comfortable! The bed is amazing though. The bathroom could use more hooks for drying beachwear. I think instructions or information in general could be...
The Neighborhood Hotel - Grand Beach

Beautiful Family Cottage in Beachwalk-Grill-AC-Free Wifi-Kids Haven.

9.6 out of 10, Exceptional, (209)
"Took my small work team up for our planning sesh and we hunkered down at the cozy Trolls Den and got ‘er done. It was priced great and gave us all we needed. The host staff even shoveled the snow off our porch and under our car!! The greater Beachwalk community is beautiful and idyllic with the fresh snow and bright colored homes - we even bundled up and took a walk down to Lake Michigan and through neighborhood. #greatteammemories!!! "
Beautiful Family Cottage in Beachwalk-Grill-AC-Free Wifi-Kids Haven.

Farmesque with a splash of modern

10.0 out of 10, Exceptional, (29)
"Quiet, clean and spacious house to gather with family and/or friends. "
The price is AU$718
includes taxes & fees
17 Feb - 18 Feb
Farmesque with a splash of modern

Modern Farmhouse Retreat-10 Min Walk to Lake Michigan-Hot Tub-Sauna

10.0 out of 10, Exceptional, (80)
"This is our third time staying at this property and we LOVE it. This fits our needs and preferences so perfectly. The location is great for those wanting to head into New Buffalo as it is just a short drive away. Love the ability to have access to a pantry area to tuck in all of the items we tend to bring with which helps to keep things neat and tidy, tucked away. There is also the extra bonus of having a garage to pull in. So love that during any messy weather!"
Modern Farmhouse Retreat-10 Min Walk to Lake Michigan-Hot Tub-Sauna

'Summer Breeze' Lakeside Condo - Walk to Town & Marina + POOL

10.0 out of 10, Exceptional, (113)
"Property just as advertised. Clean and easy to access. Great location. I would stay again"
'Summer Breeze' Lakeside Condo - Walk to Town & Marina + POOL

Big Family House 5 Minutes from Lake Michigan/Blue Chip Casino/Brewery/Wineries!

9.8 out of 10, Exceptional, (95)
"This was the second time we stayed at this house. It is well appointed and in a good location. We will definitely stay there again."
Big Family House 5 Minutes from Lake Michigan/Blue Chip Casino/Brewery/Wineries!

View of the lake from 2 decks in this 6BR Lake Shore Dr home, steps to the beach

9.0 out of 10, Wonderful, (74)
"The house was clean and quite adequate for our 3 day stay. We met Mr. Marshall when we arrived (he was there with a crew working on furniture and some repairs). He was very pleasant, as was the crew. We like to cook for ourselves. The stove was not completely functional -- shelves do not fit, and the interior needs a good cleaning. The towel rack above the second floor bathroom toilet is pulling of the wall and could use some attention. Rick Ginther (for the Ginther Siblings)"
The price is AU$1,280
includes taxes & fees
17 Feb - 18 Feb
View of the lake from 2 decks in this 6BR Lake Shore Dr home, steps to the beach

Spa-quality amenities, dog friendly, close to trails, IN Dunes Nat’l Park

9.2 out of 10, Wonderful, (57)
"We recently rented this home for our church's women's fall spiritual retreat. This stay for our group of 21 ladies was more than we expected. We chose this home for its size, proximity to the shore, and great accommodations. Upon our arrival we were pleasantly surprised to find the house had been recently updated. It was absolutely beautiful...bright, serene, and peaceful! The cleanliness of the home was great! The attention to detail was appreciated. I love a well stocked kitchen and this...
Spa-quality amenities, dog friendly, close to trails, IN Dunes Nat’l Park

Sand & Sun Retreat|2 Living Rooms | Game Room |Game Room | Minutes to Beach

10.0 out of 10, Exceptional, (17)
"Booked this weekend away for my kids and significants for Christmas. Great location between Grand Rapids and Chicago. House was well maintained and many extras! Would definitely recommend!!"
The price is AU$601
includes taxes & fees
24 Feb - 25 Feb
Sand & Sun Retreat|2 Living Rooms | Game Room |Game Room | Minutes to Beach

Juniper Presents: Lakefront Getaway and Outdoor Living Redefined

9.4 out of 10, Exceptional, (99)
"Our family spent the holiday at this incredible house and everything was perfect. We would definitely stay here again and highly recommend it. "
Juniper Presents: Lakefront Getaway and Outdoor Living Redefined

Hot tub open all year! Private heated pool, sleeps 10 near downtown New Buffalo!

9.2 out of 10, Wonderful, (57)
"We rented the unit for a family gathering, multiple family units gathering in a central location. House worked great for our needs. Listing accurate to description. Open floor plan was very accommodating for family socializing together."
Hot tub open all year! Private heated pool, sleeps 10 near downtown New Buffalo!

Beachfront Villa + Addition, Skyline views, Hot Tubs, Luxury Smart Home

8.8 out of 10, Excellent, (27)
"Lovely space to red a big group to gather,plus smaller living spaces fur sac mallet subgroups. "
Beachfront Villa + Addition, Skyline views, Hot Tubs, Luxury Smart Home

VIP! LUXURY 4BD 5min to Lake Michigan beach Big Pool

9.0 out of 10, Wonderful, (18)
"Me and my family stayed here on Thanksgiving it was so comfortable and cozy any very clean l will definitely will book again checking in process was very easy!"
VIP! LUXURY 4BD 5min to Lake Michigan beach Big Pool

Beautiful 4 Bed House in New Buffalo with Pool & Hot Tub Close to Lake & Main St

9.2 out of 10, Wonderful, (19)
"Great location, quiet neighborhood. One hiccup but Rishi was quick to resolve. The kitchen/dining was smaller than what the pictures led us to believe otherwise, all was good. "
Beautiful 4 Bed House in New Buffalo with Pool & Hot Tub Close to Lake & Main St

Family Retreat-Beachwalk-Grill-AC-Free WiFi-Pool Table-Bikes-Grill-Golf Cart

10.0 out of 10, Exceptional, (180)
"We recently stayed at the Valhalla! The home was exactly has described and was even decorated for Christmas! Any questions we had were promptly answered by Anders. Cozy fireplace and plenty of games for us to use along with a pool table in the basement. We are hoping to visit another time! "
Family Retreat-Beachwalk-Grill-AC-Free WiFi-Pool Table-Bikes-Grill-Golf Cart

Luxury Estate with 3 Homes, Pool, Hot Tubs, Basketball/Tennis Court near Lake

10.0 out of 10, Exceptional, (66)
"Everything was amazing during our stay at this property. The amenities were great… house was clean and there were so many things to do around the house with the adults and the kids. We will definitely be coming back in the future. Thanks Jorge for all your help!"
Luxury Estate with 3 Homes, Pool, Hot Tubs, Basketball/Tennis Court near Lake

Spacious, dog-friendly home with a gas fireplace, pool, hot tub, & golf carts

3.4 out of 10, (3)
"Not able to get into the house until 30 mins after check-in time due to the cleaning staff. When we did walk in, the house had a bad odor, like wet dog, or a dirty wet mop. Our children were so excited to use the swimming pool/hot tub, but when we arrived, both were unusable and the outside sitting area was a complete mess. The pool was filled with debris and a greenish color. There was mold/scum all over the steps/entrance into the pool that we had to scrub ourselves. The hot tub smelled like...
Spacious, dog-friendly home with a gas fireplace, pool, hot tub, & golf carts

BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.

9.4 out of 10, Exceptional, (100)
"Good for relaxing "
The price is AU$338
includes taxes & fees
17 Feb - 18 Feb
BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.
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.
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Other types of properties in Chesterton you may be interested in

Spring House Inn

2.5 star property
9.0 out of 10, Wonderful, (1001)
"Great front desk experience"
The price is AU$139
includes taxes & fees
17 Feb - 18 Feb
Spring House Inn

Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly

10.0 out of 10, Exceptional, (81)
"The pictures do no justice. This location was beyond our expectations and exactly what was needed as a getaway. Will and Liz have an exceptional home with such an amazing view. Hope to be back someday soon. Thank you so very much. "
The price is AU$437
includes taxes & fees
18 Feb - 19 Feb
Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly

Best Western Indian Oak

2.5 star property
8.6 out of 10, Excellent, (1001)
"We enjoyed our stay. Staff was friendly and helpful "
The price is AU$150
includes taxes & fees
22 Feb - 23 Feb
Best Western Indian Oak
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.

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?

BEACHFRONT LAKE MICHIGAN w/Lookout Tower & Lake Views - Sleeps 13: This holiday home rental outside of Chesterton is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and an arcade/games room.

How many holiday rentals are there in Chesterton?

Choose from 30 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 Chellberg Farm and Indiana Dunes Visitor Center.

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.