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Check prices for these dates

Next weekend
6 Jun - 8 Jun
In two weeks
13 Jun - 15 Jun
In one month
27 Jun - 29 Jun
In two months
25 Jul - 27 Jul

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

Brand New Cottage Walkable to All Downtown Michigan City & Beach!
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (1)
"We really enjoyed our stay. The home was very comfortable and close to downtown. We were minutes away from the mall, casino and breweries. The owner was very responsive to all our needs. We would definitely stay here again. "
The price is AED 643
AED 1,411 total
includes taxes & fees
2 Jun - 3 Jun
Brand New Cottage Walkable to All Downtown Michigan City & Beach!
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)
"Really nice neighborhood and beach. Humble home suited my families needs. Enjoyed grilling and dining on the deck"
Simple Cottage Set in the Woods by Lake Michigan
New Buffalo Beach - SW Lake Michigan - Beaches, Wineries & Breweries
Outdoor dining

New Buffalo Beach - SW Lake Michigan - Beaches, Wineries & Breweries

10.0 out of 10, Exceptional, (23)
"Clean and comfortable property with large open kitchen, dining, living area."
New Buffalo Beach - SW Lake Michigan - Beaches, Wineries & Breweries
The Hideaway House - Private, Peaceful, Cozy
Beach

The Hideaway House - Private, Peaceful, Cozy

10.0 out of 10, Exceptional, (3)
"Communication with management made our minds at ease when booking our stay. House was very clean, peaceful settings. The Beach was absolutely beautiful. Our family with definitely stay again. "
The Hideaway House - Private, Peaceful, Cozy
Cozy Michigan City Cottage #1
Interior

Cozy Michigan City Cottage #1

9.6 out of 10, Exceptional, (17)
"The house was the perfect location to the beach, zoo, and parks. It was great for our family trip."
Cozy Michigan City Cottage #1
Walkable cozy cottage, Outlet Mall across street!
Interior

Walkable cozy cottage, Outlet Mall across street!

9.6 out of 10, Exceptional, (14)
"Loved the cottage it had everything we needed very nice!"
The price is AED 547
AED 1,332 total
includes taxes & fees
2 Jun - 3 Jun
Walkable cozy cottage, Outlet Mall across street!
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!

10.0 out of 10, Exceptional, (4)
"This is such a nice place! We really enjoyed the fire pit area! Hot tub was wonderful! The house had everything we needed. Totally recommend! "
The price is AED 1,421
AED 1,623 total
includes taxes & fees
2 Jun - 3 Jun
Secluded Retreat, Hot Tub, Fire Pit, Wildlife Views, Near New Buffalo Beach!
Beachglass Cottage - Family Friendly Kids and Pets
Exterior

Beachglass Cottage - Family Friendly Kids and Pets

10.0 out of 10, Exceptional, (4)
"We loved our stay at the Beachglass Cottage! The host was very accommodating and made sure we had everything we needed. The golf cart is a wonderful addition to the rental and was perfect for exploring the Grand Beach neighborhood/beaches. Would highly recommend the Beachglass Cottage to Chicago residents looking for a quick beach getaway!"
Beachglass Cottage - Family Friendly Kids and Pets
Tranquil Wooded Retreat – Walk to Beach & Downtown | Tallgrass Cottage
Interior

Tranquil Wooded Retreat – Walk to Beach & Downtown | Tallgrass Cottage

9.8 out of 10, Exceptional, (50)
"Great property, location, and overall experience"
Tranquil Wooded Retreat – Walk to Beach & Downtown | Tallgrass Cottage
Fun w/Loft! Beach ~Nature Trails ~Grill~ Firepit ~Indiana Dunes National Park
Outdoor dining

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

10.0 out of 10, Exceptional, (36)
"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
Walk to Private Beach, Great screened porch, Chefs kitchen, Open beam design
Exterior

Walk to Private Beach, Great screened porch, Chefs kitchen, Open beam design

10.0 out of 10, Exceptional, (57)
"Perfect beach house in Union Pier! Cute, comfortable and a short walk to a beautiful private beach. House fully stocked with everything you need. Host was very responsive. "
Walk to Private Beach, Great screened porch, Chefs kitchen, Open beam design
Treehouse Bungalow- Quaint and Cozy Getaway!
Beach nearby

Treehouse Bungalow- Quaint and Cozy Getaway!

9.0 out of 10, Wonderful, (47)
"House was clean, cute, in a great location. Would recommend and stay here again. "
The price is AED 1,098
AED 1,761 total
includes taxes & fees
2 Jun - 3 Jun
Treehouse Bungalow- Quaint and Cozy Getaway!
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, (36)
"This was a great place for a girls weekend getaway! We walked to all the restaurants. Plenty of space for the 7 of us. Loved how comfy and cozy it all was. Will definitely be coming again!"
Modern Cottage "M" Luxury home w/hot tub, community pool-walk to town & beach
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
Peaceful Cottage/Private Parking & Backyard/Strong WiFi/Walk to Sheridan Beach!
Fridge, microwave, oven, stovetop

Peaceful Cottage/Private Parking & Backyard/Strong WiFi/Walk to Sheridan Beach!

10.0 out of 10, Exceptional, (55)
"Our stay was lovely and this house is incredibly well thought out!"
Peaceful Cottage/Private Parking & Backyard/Strong WiFi/Walk to Sheridan Beach!
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)
"Great house near the beach (host will give you ideas on how to park closer) perfect for hosting a group of friends or family! Host was also super responsive and helpful in accommodating us all for a wonderful birthday weekend!"
Dunland Cottage W/hot tub, paddle boards, fire pit
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)
"Gorgeous property with direct beach access in Union Pier."
2024 remodeled historic Lake Michigan waterfront Union Pier home with spa.
Vintage Beachside Cottage
Fridge, microwave, oven, stovetop

Vintage Beachside Cottage

9.6 out of 10, Exceptional, (65)
"The cottage was so cute. We enjoyed our stay!"
Vintage Beachside Cottage
Walk to Lake Michigan Beach from Cottage in the Woods - *Seaside Fired Smores*
Property grounds

Walk to Lake Michigan Beach from Cottage in the Woods - *Seaside Fired Smores*

9.4 out of 10, Exceptional, (19)
"It was perfect for 3 brothers and sisters. Close to the beach, quiet area."
Walk to Lake Michigan Beach from Cottage in the Woods - *Seaside Fired Smores*
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, (181)
"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
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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Frequently asked questions

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