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Check prices for these dates

Next weekend
28 Rab. I - 30 Rab. I
In two weeks
4 Rab. II - 6 Rab. II
In one month
18 Rab. II - 20 Rab. II
In two months
16 Jum. I - 18 Jum. I

Compare 101 Cottages in Chesterton with updated reviews, rates, and availability.

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

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

10.0 out of 10, Exceptional, (20)
"Overall great place to stay. Very clean, centrally located, easy in and out instructions. I would definitely recommend."
New Buffalo Beach - Lake Michigan - Harbor Country Winery and Breweries
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, (30)
"The home was perfect. Right near the downtown area. Had everything you needed. And super cozy!!"
Cozy New Buffalo cottage with hot tub & fire pit. Short walk to downtown!
Lighthouse Cottage - Family & Pet Friendly
Interior

Lighthouse Cottage - Family & Pet Friendly

10.0 out of 10, Exceptional, (4)
"Perfect spot for our stay, we really enjoyed our weekend here! "
The price is SAR 416
SAR 1,379 total
includes taxes & fees
23 Mar - 24 Mar
Lighthouse Cottage - Family & Pet Friendly
Walkable cozy cottage, Outlet Mall across street!
Interior

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!
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 SAR 675
SAR 1,697 total
includes taxes & fees
16 Apr - 17 Apr
Charming 3-bedroom Mid-Century cottage in lakeside Miller Beach with WiFi, AC
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
Treehouse Bungalow- Quaint and Cozy Getaway!
Beach nearby

Treehouse Bungalow- Quaint and Cozy Getaway!

9.2 out of 10, Wonderful, (45)
"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 SAR 484
SAR 970 total
includes taxes & fees
1 Apr - 2 Apr
Treehouse Bungalow- Quaint and Cozy Getaway!
Adorable Cottage New Buffalo, Mi. Near Grand Beach.1 Bedroom, Sleeps 5
Beach

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
Blocks To Beach Golf Tennis Park & Lake MI Sunsets
Interior

Blocks To Beach Golf Tennis Park & Lake MI Sunsets

8.8 out of 10, Excellent, (3)
"We had a great time"
The price is SAR 1,650
SAR 1,864 total
includes taxes & fees
21 Apr - 22 Apr
Blocks To Beach Golf Tennis Park & Lake MI Sunsets
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
Cozy Michigan City Cottage #1
Interior

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
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
Cozy Vintage Michiana Shores Cottage w/Fireplace, Firepit, & Screened-in Porch
Outdoor dining

Cozy Vintage Michiana Shores Cottage w/Fireplace, Firepit, & Screened-in Porch

9.8 out of 10, Exceptional, (18)
"Adorable cabin with great amenities. A bit of a walk to the beach but close to Stop 50 restaurant."
Cozy Vintage Michiana Shores Cottage w/Fireplace, Firepit, & Screened-in Porch
Vintage Beachside Cottage
Fridge, microwave, oven, stovetop

Vintage Beachside Cottage

9.6 out of 10, Exceptional, (65)
"This cottage is perfect for families / friends who want to enjoy the beach! Plenty of space for our group of 6, comfortable bedrooms and living space, 2 bathrooms, an awesome kitchen, and space outside for drying towels and swimsuits to head back to the beach the next day. Just walk over the dune to be on the beach - no roads to cross or parking hassles. Easy! I contacted the owner once to ask a silly question during our stay and the response was immediate. Outstanding communication throughout....
Vintage Beachside Cottage
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!
Cottage Retreat close to downtown New Buffalo. Sleeps 12, Pet friendly + Games!
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 SAR 506
SAR 1,395 total
includes taxes & fees
1 Apr - 2 Apr
Cottage Retreat close to downtown New Buffalo. Sleeps 12, Pet friendly + Games!
Brand New Cottage Walkable to All Downtown Michigan City & Beach!
Private kitchen

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

The price is SAR 488
SAR 1,227 total
includes taxes & fees
23 Mar - 24 Mar
Brand New Cottage Walkable to All Downtown Michigan City & Beach!
Charming downtown cottage near the beach!
Beach nearby

Charming downtown cottage near the beach!

9.6 out of 10, Exceptional, (9)
"It was enjoyable, though we both think the house would benefit from a more comfortable bed. "
Charming downtown cottage near 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.
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Other property types in Chesterton

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

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

10.0 out of 10, Exceptional, (85)
"Great beach location near the park. The cabin had terrific views, an open floor plan, and everything we needed. Will was a wonderful host, and we enjoyed our stay :) Looking forward to coming back."
The price is SAR 806
SAR 1,273 total
includes taxes & fees
30 Mar - 31 Mar
Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly
Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes
Beach nearby

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

9.0 out of 10, Wonderful, (51)
"Nice quiet an around everything "
The price is SAR 255
SAR 370 total
includes taxes & fees
24 Mar - 25 Mar
Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes
The Neighborhood Hotel - Grand Beach
Beach nearby, beach towels

The Neighborhood Hotel - Grand Beach

4.0 star property
9.4 out of 10, Exceptional, (40)
"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
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

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