Search Cottages in Chesterton

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
18 Apr - 20 Apr
In two weeks
25 Apr - 27 Apr
In one month
9 May - 11 May
In two months
6 Jun - 8 Jun

Compare 106 Cottages in Chesterton with updated reviews, rates, and availability.

Cozy New Buffalo cottage with hot tub & fire pit. Short walk to downtown!
Exterior

Cozy New Buffalo cottage with hot tub & fire pit. Short walk to downtown!

10.0 out of 10, Exceptional, (32)
"Our family enjoyed spending some time off in New Buffalo. Brittany's home gave us this opportunity to enjoy New Buffalo and the surrounding area. It was nice to end our days by enjoying the hot tub or time by the fire. Brittany was an excellent host, responding to a few of our questions in a timely manner. We very much enjoyed our stay!!"
Cozy New Buffalo cottage with hot tub & fire pit. Short walk to downtown!
Charming 3-bedroom Mid-Century cottage in lakeside Miller Beach with WiFi, AC
Oven, stovetop, dishwasher

Charming 3-bedroom Mid-Century cottage in lakeside Miller Beach with WiFi, AC

The price is AED 580
AED 1,563 total
includes taxes & fees
28 Apr - 29 Apr
Charming 3-bedroom Mid-Century cottage in lakeside Miller Beach with WiFi, AC
Vintage Lake Michigan Beach Cottage: 4br+loft,3ba-Sleeps 17
Exterior

Vintage Lake Michigan Beach Cottage: 4br+loft,3ba-Sleeps 17

9.6 out of 10, Exceptional, (91)
"Clean and convenient. "
Vintage Lake Michigan Beach Cottage: 4br+loft,3ba-Sleeps 17
Cozy Michigan City Cottage #1
Fridge, microwave, oven, stovetop

Cozy Michigan City Cottage #1

9.6 out of 10, Exceptional, (17)
"Perfect location for the beach and the cooler on wheels and beach chairs were helpful. The cottage was small but fine for our family and the two kids loved having the loft to themselves. The cottage is definitely older and a bit worn around the edges but great for a long weekend away from the city."
Cozy Michigan City Cottage #1
Treehouse Bungalow- Quaint and Cozy Getaway!
Fridge, microwave, oven, stovetop

Treehouse Bungalow- Quaint and Cozy Getaway!

9.0 out of 10, Wonderful, (46)
"2 of my close friend and I decided to get away for a short stay not too far from home. We had a great relaxing time. This place had everything we needed, short distance from everything. This place was clean and easy to find. The neighborhood felt safe. Even though the place below this apartment looks abandoned."
The price is AED 474
AED 959 total
includes taxes & fees
16 Apr - 17 Apr
Treehouse Bungalow- Quaint and Cozy Getaway!
New Buffalo Beach - Lake Michigan - Harbor Country Winery and Breweries
Terrace/patio

New Buffalo Beach - Lake Michigan - Harbor Country Winery and Breweries

10.0 out of 10, Exceptional, (21)
"Wonderful cottage, perfect for our friends weekend. Great hospitality. "
New Buffalo Beach - Lake Michigan - Harbor Country Winery and Breweries
Fun w/Loft! Beach ~Nature Trails ~Grill~ Firepit ~Indiana Dunes National Park
Terrace/patio

Fun w/Loft! Beach ~Nature Trails ~Grill~ Firepit ~Indiana Dunes National Park

10.0 out of 10, Exceptional, (34)
"The place is incredible, stayed in January when it snowed but the cottage is well insulated and heater works flawlessly. Super clean, colorful and we can only imagine how awesome it would be in the summer. Great communication, great accommodating host. "
Fun w/Loft! Beach ~Nature Trails ~Grill~ Firepit ~Indiana Dunes National Park
Beachglass Cottage - Family Friendly Kids and Pets
Exterior

Beachglass Cottage - Family Friendly Kids and Pets

10.0 out of 10, Exceptional, (3)
"We were thrilled with our experience staying at Beach Glass. It is cozy, clean, and offers top notch amenities that we haven’t found with other properties. Kayse provided a great stay that was geared at making it a great experience for us. The property is clean, in a great location with close access to Grand Beach and New Buffalo, and was kid friendly. Kayse is super friendly and very responsive and we plan to visit again soon! "
The price is AED 433
AED 1,414 total
includes taxes & fees
13 Apr - 14 Apr
Beachglass Cottage - Family Friendly Kids and Pets
Lighthouse Cottage - Family & Pet Friendly
Fridge, microwave, oven, stovetop

Lighthouse Cottage - Family & Pet Friendly

10.0 out of 10, Exceptional, (4)
"Perfect spot for our stay, we really enjoyed our weekend here! "
Lighthouse Cottage - Family & Pet Friendly
Beautiful Private Cottage, Sleeps 6, Walk to Beach
Terrace/patio

Beautiful Private Cottage, Sleeps 6, Walk to Beach

10.0 out of 10, Exceptional, (18)
"Wonderful! The cottage is perfect and provided everything we needed. The beautiful garden and fire area is absolutely magical. The neighborhood is very secluded and family friendly. We felt very safe. The private beach is the icing on top of the cake! Beautiful sunsets and sounds of the waves from the lake took away all of our stress. New Buffalo, an adorable beach town, is a short drive from the property and offers shopping, restaurants and a marina. We would absolutely stay at the...
Beautiful Private Cottage, Sleeps 6, Walk to Beach
Brand New Cottage Walkable to All Downtown Michigan City & Beach!
Fridge, microwave, oven, stovetop

Brand New Cottage Walkable to All Downtown Michigan City & Beach!

The price is AED 477
AED 1,201 total
includes taxes & fees
13 Apr - 14 Apr
Brand New Cottage Walkable to All Downtown Michigan City & Beach!
Adorable Cottage New Buffalo, Mi. Near Grand Beach.1 Bedroom, Sleeps 5
Terrace/patio

Adorable Cottage New Buffalo, Mi. Near Grand Beach.1 Bedroom, Sleeps 5

9.8 out of 10, Exceptional, (179)
"This was a great little get away for our 21st Anniversary. Very clean and neat. Everything we needed!"
Adorable Cottage New Buffalo, Mi. Near Grand Beach.1 Bedroom, Sleeps 5
Walkable cozy cottage, Outlet Mall across street!
Smart TV, fireplace

Walkable cozy cottage, Outlet Mall across street!

9.6 out of 10, Exceptional, (14)
"Enjoyed the time at this beautiful place. Just got to chill out and enjoy the time away. "
Walkable cozy cottage, Outlet Mall across street!
Blocks To Beach Golf Tennis Park & Lake MI Sunsets
Fridge, microwave, oven, stovetop

Blocks To Beach Golf Tennis Park & Lake MI Sunsets

8.8 out of 10, Excellent, (3)
"We had a great time"
The price is AED 1,616
AED 1,829 total
includes taxes & fees
20 Apr - 21 Apr
Blocks To Beach Golf Tennis Park & Lake MI Sunsets
Simple Cottage Set in the Woods by Lake Michigan
Beach

Simple Cottage Set in the Woods by Lake Michigan

9.4 out of 10, Exceptional, (88)
"Wonderful, quiet neighborhood in walking distance to the beach, and easy driving distance to Indiana Dunes State and National parks. Owners have plenty of items on hand if needed, such as beach items, a dog crate if you are traveling with your fur baby, and even a high chair if you are traveling with a small child. There is also a golf cart for your use! Cute shops and great places to eat in downtown New Buffalo. Lots of outdoor seating at the house, including a grill and a firepit."
Simple Cottage Set in the Woods by Lake Michigan
Modern Cottage "M" Luxury home w/hot tub, community pool-walk to town & beach
Fridge, microwave, oven, stovetop

Modern Cottage "M" Luxury home w/hot tub, community pool-walk to town & beach

10.0 out of 10, Exceptional, (35)
"House was nice, clean, comfortable. It was too cold to use the hot tub, but we enjoyed the fireplace very much!"
Modern Cottage "M" Luxury home w/hot tub, community pool-walk to town & beach
Secluded Retreat, Hot Tub, Fire Pit, Wildlife Views, Near New Buffalo Beach!
Terrace/patio

Secluded Retreat, Hot Tub, Fire Pit, Wildlife Views, Near New Buffalo Beach!

The price is AED 1,095
AED 2,072 total
includes taxes & fees
15 Apr - 16 Apr
Secluded Retreat, Hot Tub, Fire Pit, Wildlife Views, Near New Buffalo Beach!
2024 remodeled historic Lake Michigan waterfront Union Pier home with spa.
Outdoor spa tub

2024 remodeled historic Lake Michigan waterfront Union Pier home with spa.

10.0 out of 10, Exceptional, (22)
"Was very nice given the storm that hit a week before. Our need is a bit of a different layout........the kitchen layout with the open stays....we remedied with a chair laid over the entrance, We wish you the best with the repairs and thank you for not cancelling us."
2024 remodeled historic Lake Michigan waterfront Union Pier home with spa.
Dunland Cottage W/hot tub, paddle boards, fire pit
Fridge, coffee/tea maker, cookware/dishes/utensils

Dunland Cottage W/hot tub, paddle boards, fire pit

8.2 out of 10, Very Good, (20)
"Stayed in Naomi’s home for a weekend with some friends visiting from out of town! We had a great time and was pleased with the home + it was very comfortable and easy to drive to the beach. The paddleboards and beach chairs that came included for our use were awesome! There were some small issues - one of the bedrooms had a duvet that unfortunately smelled and we had to remove it, and while we were staying we experienced issues with the hot tub that were not resolved by the time our stay ended,...
Dunland Cottage W/hot tub, paddle boards, fire pit
Pet-friendly Lake Getaway: 1 Block to Beach!
House (3 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Pet-friendly Lake Getaway: 1 Block to Beach!

3.0 star property
Pet-friendly Lake Getaway: 1 Block to 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.
Don't see what you're looking for?
See all available properties in Chesterton
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Chesterton

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

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

10.0 out of 10, Exceptional, (92)
"Watch sunrise & set on Lake Michigan and the Chicago skyline. Incredibly comfortable. Very thoughtful hosts. Definitely an excellent choice! "
Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly
Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes
Fridge, microwave, oven, stovetop

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

9.0 out of 10, Wonderful, (54)
"Checking in was easy. I couldn't get the jets to turn on in the tub. Overall it was money well spent."
The price is AED 290
AED 407 total
includes taxes & fees
14 Apr - 15 Apr
Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes
The Neighborhood Hotel - Grand Beach
Suite 1 - Three Bedroom | Premium bedding, memory foam beds, blackout drapes, free WiFi

The Neighborhood Hotel - Grand Beach

4.0 star property
9.6 out of 10, Exceptional, (44)
"Great place to stay. The property manager Pamela was very kind and helpful and was very sweet to myself and my daughter. We will definitely come back when we can utilize the pool and fire pits. Short walk to small beach great for collecting rocks. "
The Neighborhood Hotel - Grand 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.

Frequently asked questions

Why book your cottage in Chesterton with Expedia?
Booking a cottage in Chesterton is as simple as deciding on your travel dates and picking an ideal place for a vacation in the outdoors. From chic retreats to low-cost properties and cottages that have perks like a hot tub, Expedia has something for all styles and tastes. As for irresistible deals? We have them too!
How can I find cheap cottages in Chesterton?
With Expedia’s convenient filter tool, sourcing cheap cottages in Chesterton has never been easier. To discover properties that are very pocket friendly, narrow your search results by star rating, amenities and budget.