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Compare 75 Cottages in Chesterton with updated reviews, rates, and availability.

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
Outdoor pool
Sweet Inn Coach House near beautiful beach on Lake Michigan in Beachwalk
9.6 out of 10, Exceptional, (22)
"Perfect place for a girls weekend! We enjoyed the fire pit."
The price is $195
$440 total
includes taxes & fees
May 17 - May 18
Sweet Inn Coach House near beautiful beach on Lake Michigan in Beachwalk
Terrace/patio
3BR Beach Cottage Steps to the Sandy Shores of Lake Michigan's Sheridan Beach
9.6 out of 10, Exceptional, (34)
"Would recommend! Perfect budget friendly cottage for a stay next to the beach. We loved the beach wagon provided. However no beach chairs or beach towels, so bring your own. Quick drive into new Buffalo to check out Michigan."
3BR Beach Cottage Steps to the Sandy Shores of Lake Michigan's Sheridan Beach
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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
$390 total
includes taxes & fees
May 20 - May 21
Treehouse Bungalow- Quaint and Cozy Getaway!
Property grounds
Private Beach, plenty of sand.
10.0 out of 10, Exceptional, (84)
"This house is a perfect location steps away from the beautiful beach. The house was clean & comfortable & the hosts are very friendly & great communicators. Check in was a breeze. My kids loved the sweet little loft bunk beds. The town is simply charming. We enjoyed a peaceful weekend and would definitely recommend!!"
The price is $550
$1,097 total
includes taxes & fees
May 19 - May 20
Private Beach, plenty of sand.
Exterior
Vintage Lake Michigan Beach Cottage: 4br+loft,3ba-Sleeps 17
9.6 out of 10, Exceptional, (84)
"Great house for our group to spend the weekend catching up and relaxing! Really enjoyed the extra bonus of watching three deer in the back yard every morning during breakfast after we enjoying the quick stroll down to the beach."
Vintage Lake Michigan Beach Cottage: 4br+loft,3ba-Sleeps 17
Fridge, microwave, oven, stovetop
Cozy Michigan City Cottage #1
9.8 out of 10, Exceptional, (10)
"Had a quick stay for the football game. Place was perfect for 2 people."
Cozy Michigan City Cottage #1
Beach
Cottage Retreat close to downtown New Buffalo. Sleeps 12, Pet friendly + Games!
10.0 out of 10, Exceptional, (4)
"This house was the perfect stay for a weekend getaway with friends. The house had an amazing backyard and it was in a great location close to downtown New Buffalo. The only thing was that the oven was dirty, so when we tried to make a frozen pizza the smoke alarm just kept going off. Overall a really great stay for the weekend."
The price is $250
$460 total
includes taxes & fees
May 20 - May 21
Cottage Retreat close to downtown New Buffalo. Sleeps 12, Pet friendly + Games!
Dining
Fun w/Loft! Beach ~Nature Trails ~Grill~ Firepit ~Indiana Dunes National Park
9.8 out of 10, Exceptional, (29)
"We booked this cottage for the quirky colors and the loft space we knew our kids would love sleeping in (which they did, of course). What came as a pleasant surprise was the kitchen, equipped with everything you would ever need and more. We brought in two days worth of meals and were absolutely able to make good use of what we brought. We also loved the hammock, the fire pit, the completely charming front yard, and the on site washer and dryer. A great experience and a great location!"
Fun w/Loft! Beach ~Nature Trails ~Grill~ Firepit ~Indiana Dunes National Park
Interior
Charming cottage with fast WiFi, fire pit, above-ground pool, & huge sunroom
8.4 out of 10, Very Good, (8)
"House was acceptable and as pictured. They weren’t kidding when they said low ceilings on second floor. Just remember to duck! Note 2nd bedroom is also upstairs and low ceilings."
Charming cottage with fast WiFi, fire pit, above-ground pool, & huge sunroom
Fridge, coffee/tea maker, cookware/dishes/utensils
Dunland Cottage W/hot tub, paddle boards, fire pit
9.2 out of 10, Wonderful, (15)
"We booked without any issues, but was surprised 100% was due at booking nearly a year in advance. Loved the location/quiet neighborhood, the beds/bedding and hot hub hangout area. Kitchen sink needed some repairs along with the steps from hot tub to back yard. Upon arrival there was only a roll & half of toilet paper for 6 people for 3 nights😞 I also text the day of our arrival to ask if the golf cart was still available to rent & didn’t get a response. We would still stay again because we...
Dunland Cottage W/hot tub, paddle boards, fire pit
Property grounds
Modern Cottage "M" Luxury home w/hot tub, community pool-walk to town & beach
10.0 out of 10, Exceptional, (20)
"Our group of 6 had a great time at cottage M! The house is beautiful and was very clean! The hot tub was a bonus!"
Modern Cottage "M" Luxury home w/hot tub, community pool-walk to town & beach
Property grounds
Voted Best Family Getaway In SW MI for 2018-2023!
Voted Best Family Getaway In SW MI for 2018-2023!
Interior
Pet-friendly Lake Getaway: 1 Block to Beach!
3.5 star property
Pet-friendly Lake Getaway: 1 Block to Beach!
Beach
Affordable Classic Cottage Charm. Sleeps 8. Internet provided.
9.4 out of 10, Exceptional, (42)
"My husband and I came with two of our grandchildren, ages 3 and 4 to play at the beach. We were hoping to hang out at New Buffalo Beach, but it was very small with limited parking. We went to Warren Dunes State Park instead-a bit further to drive, but more spacious beach. Unfortunately due to weather, we only had part of 2 days at the beach. Our hosts had made suggestions of other activities to do with the kids, which we really appreciated (and needed)! The kids loved the Heston Steam train and...
Affordable Classic Cottage Charm. Sleeps 8. Internet provided.
Fridge, microwave, oven, stovetop
Walkable cozy cottage, Outlet Mall across street!
9.4 out of 10, Exceptional, (3)
"We had a great getaway long weekend! It was perfect for my wife and I. She goes on vacation to do "nothing", and I go on vacation to DO stuff. So while she watched a movie and read a book, I went and ran the trails at Indiana Dunes! There was shopping right across the street! Also, DO NOT leave food laying around...there are little sand ants that will find your food!!!"
The price is $159
$352 total
includes taxes & fees
May 19 - May 20
Walkable cozy cottage, Outlet Mall across street!
Fridge, microwave, oven, stovetop
Peaceful Cottage/Private Parking & Backyard/Strong WiFi/Walk to Sheridan Beach!
10.0 out of 10, Exceptional, (44)
"Our stay was lovely and this house is incredibly well thought out!"
Peaceful Cottage/Private Parking & Backyard/Strong WiFi/Walk to Sheridan Beach!
Interior
Blocks To Beach Golf Tennis Park & Lake MI Sunsets
9.0 out of 10, Wonderful, (2)
"The rental was clean when we arrived. Easy to find with the map/directions given. The rental is a summer beach style home, all of the finishes and furniture are gently used/dated which gave it character. It made it easy to feel comfortable and lived in vs. concerned about everything be so nice that we are afraid to use any of it. The porch area was great to hang out with our family and grab coffee in the morning. Neighborhood was quiet and great to see people coming and going to the beach access...
The price is $430
$492 total
includes taxes & fees
May 28 - May 29
Blocks To Beach Golf Tennis Park & Lake MI Sunsets
Smart TV, fireplace, books, printers
Unique 4br cottage getaway with private, wooded yard
10.0 out of 10, Exceptional, (13)
"Lovely location, close to beach. The house is darling inside & out. We were very comfortable for 4 nights and our pup loved it too. Easy communication with Alannah & Nick."
Unique 4br cottage getaway with private, wooded yard
Beach nearby
Walk to Beach & Stray Dog! Cute Downtown Cottage
9.6 out of 10, Exceptional, (4)
"What a cute, peaceful place to stay! Unfortunately, we were only there for a couple nights and didn't get to take full advantage of everything it had to offer. Loved that it was in walking distance of downtown New Buffalo and the immediate surrounding area! Will stay here again when we get back to the area!"
Walk to Beach & Stray Dog! Cute Downtown Cottage
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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 property types in Chesterton

View from property
Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly
10.0 out of 10, Exceptional, (31)
"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 $179
$230 total
includes taxes & fees
May 20 - May 21
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
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 Cottages information

Number of reviews
521
Accommodation
75 Cottages
Lowest Price
$159
Highest Price
$550

Frequently asked questions

How much do cottages in Chesterton cost?
Expect to pay between $159 and $550 per night for cottages in Chesterton. No matter your budget, a wonderful stay is only a few clicks away on Expedia. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Why book your cottage in Chesterton with Expedia?
Expedia has some wonderful cottages in Chesterton, so get ready for an unforgettable vacay on nature’s doorstep. If you have a budget, choose how much you’re willing to spend and your preferred property star rating. Or, use our filters to search for cottages with free WiFi or a pool. We’ll help you find the perfect fit whatever your getaway looks like.
How can I find cheap cottages in Chesterton?
A wonderful way to compare cheap cottages in Chesterton is with Expedia’s convenient filter tool. Narrow down your search by budget, star rating and amenities to nab awesome prices in just a few keystrokes.
What is there to do in Chesterton near my cottage?
Whatever you love doing, Chesterton has tons to keep you occupied. Indiana Dunes National Park, Indiana Dunes State Park and Lake View Beach are on many visitors’ to-do lists. Don’t leave without exploring Portage Lakefront Beach, Dune Acres Beach and Kemil Beach either. With Expedia’s hotel deals in Chesterton, you’ll be able to see even more neat attractions like these with the cash you save.

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