Search Holiday Rentals in Chesterton

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Top 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, (34)
"My husband and I spent our 25 wedding anniversary here. We took our 2 dogs with us. The house was spectacular and so was the beach. The sunsets were just beautiful. We will be back"
Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly
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
Beach nearby
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
10.0 out of 10, Exceptional, (6)
"Great Stay!"
The price is €217
includes taxes & fees
29 May - 30 May
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
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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 €551
includes taxes & fees
2 Jun - 3 Jun
VIP! LUXURY 4BD 5min to Lake Michigan beach Big Pool
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 €306
includes taxes & fees
4 Jun - 5 Jun
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
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
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 €365
includes taxes & fees
29 May - 30 May
Treehouse Bungalow- Quaint and Cozy Getaway!
Exterior
Cozy Michigan City Beach Cottage #2
9.6 out of 10, Exceptional, (65)
"My husband, my 14 year old daughter and our 1 year old Havanese (first time traveler) had a very relaxing and fun time! We had lazy mornings, walked to the beach (like 10 times), the zoo, watched the sun set and did a 300 piece puzzle! We read books, listened to music, visited Dune Billies (ate delish food and bought T-shirts!). We shared friendly banter with locals and other visitors, too. Awesome memories that we will cherish!! The cottage had everything we needed and was just perfect in...
Cozy Michigan City Beach Cottage #2
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 €264
includes taxes & fees
4 Jun - 5 Jun
BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.
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.
On the beach, sun-loungers
BEACHFRONT /HOTTUB/STEAM ROOM/GAME ROOM/JACUZZI/PETS/MASSAGE CHAIR/KAYAKS/BIKES
9.6 out of 10, Exceptional, (291)
"The place was a perfect location on the beach with several added activities which made the stay enjoyable."
BEACHFRONT /HOTTUB/STEAM ROOM/GAME ROOM/JACUZZI/PETS/MASSAGE CHAIR/KAYAKS/BIKES
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 €369
includes taxes & fees
3 Jun - 4 Jun
Newly Renovated City Escape with a private hot tub
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
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 €313
includes taxes & fees
29 May - 30 May
This 3 bedroom, 2 bathroom home is in a scenic area but closes to Indiana Dunes National Park.
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 nearby, sun-loungers, beach towels
'Summer Breeze' Lakeside Condo - Walk to Town & Marina + POOL
10.0 out of 10, Exceptional, (99)
"Property was as shown on the pics….it was not warm enough to check out the pool but location was great and home was comfortable"
'Summer Breeze' Lakeside Condo - Walk to Town & Marina + POOL
Property grounds
Modern Farmhouse Retreat-10 Min Walk to Lake Michigan-Hot Tub-Sauna
10.0 out of 10, Exceptional, (45)
"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
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.

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, (988)
"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 €124
includes taxes & fees
6 Jun - 7 Jun
Best Western Indian Oak
Property entrance
Spring House Inn
2.5 star property
8.8 out of 10, Excellent, (888)
"Okay. Needs updated. "
The price is €112
includes taxes & fees
29 May - 30 May
Spring House Inn
Lobby
Hilton Garden Inn Chesterton
3.0 star property
8.8 out of 10, Excellent, (978)
"We enjoyed the environment and the staff was very nice. "
The price is €134
includes taxes & fees
16 Jun - 17 Jun
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.

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.

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

Four Winds Casino Resort – New Buffalo

Four Winds Casino Resort – New Buffalo

5/5 Excellent
Awesome place
"The room was comfortable and very clean. Everything there that's needed. The location is beautiful surrounded by trees and foliage. It was a very nice hotel."
A verified traveller stayed at Four Winds Casino Resort – New Buffalo
Posted 1 day ago
Four Winds Casino Resort – New Buffalo