Search Cottages in Chesterton

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Check prices for these dates

Next weekend
6 Jum. II - 8 Jum. II
In two weeks
13 Jum. II - 15 Jum. II
In one month
27 Jum. II - 29 Jum. II
In two months
25 Raj. - 27 Raj.

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

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 SAR 1,823
SAR 2,078 total
includes taxes & fees
1 Jun - 2 Jun
Secluded Retreat, Hot Tub, Fire Pit, Wildlife Views, Near New Buffalo 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!

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 SAR 656
SAR 1,441 total
includes taxes & fees
1 Jun - 2 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)
"The property was just as advertised. The owner was wonderful from booking through check out. Fabulous girls trip. Highly recommend this property. "
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 SAR 559
SAR 1,360 total
includes taxes & fees
30 May - 31 May
Walkable cozy cottage, Outlet Mall across street!
Sweet Inn Coach House near beautiful beach on Lake Michigan in Beachwalk
Outdoor pool

Sweet Inn Coach House near beautiful beach on Lake Michigan in Beachwalk

9.6 out of 10, Exceptional, (38)
"House was immaculately clean, well appointed & extremely comfortable. By far, our best rental at Beachwalk Resort!"
The price is SAR 1,369
SAR 2,474 total
includes taxes & fees
31 May - 1 Jun
Sweet Inn Coach House near beautiful beach on Lake Michigan in Beachwalk
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
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
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 SAR 746
SAR 1,311 total
includes taxes & fees
31 May - 1 Jun
Treehouse Bungalow- Quaint and Cozy Getaway!
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 645
SAR 1,668 total
includes taxes & fees
6 Jun - 7 Jun
Charming 3-bedroom Mid-Century cottage in lakeside Miller Beach with WiFi, AC
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
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!
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
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
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

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, (56)
"Donnie was so kind, and was very prompt with responding. It was a very cute space with plenty of amenities. Would definitely recommend to others. "
The price is SAR 296
SAR 416 total
includes taxes & fees
1 Jun - 2 Jun
Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes
Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly
Outdoor dining

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

10.0 out of 10, Exceptional, (101)
"Bright, cleam and welcoming. The view of the lake and beach access makes it the perfect getaway."
Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly
The Neighborhood Hotel - Grand Beach
Beach nearby, beach towels

The Neighborhood Hotel - Grand Beach

4.0 star property
9.6 out of 10, Exceptional, (48)
"Great hotel. Firepits, common area, s’mores bar and a great patio too. Within walking distance of the beach and you’ll get to see deer too. "
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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How can I find cheap cottages in Chesterton?
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