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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 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)
"We loved it. The owner added numerous special touches that made us feel special. Very welcoming"
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 775
AED 1,806 total
includes taxes & fees
5 May - 6 May
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
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
Treehouse Bungalow- Quaint and Cozy Getaway!
Beach nearby

Treehouse Bungalow- Quaint and Cozy Getaway!

9.0 out of 10, Wonderful, (46)
"House was clean, cute, in a great location. Would recommend and stay here again. "
The price is AED 547
AED 1,049 total
includes taxes & fees
4 May - 5 May
Treehouse Bungalow- Quaint and Cozy Getaway!
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, (22)
"Clean, roomy, great location, A++"
New Buffalo Beach - Lake Michigan - Harbor Country Winery and Breweries
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, (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, (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
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 AED 408
AED 1,380 total
includes taxes & fees
5 May - 6 May
Lighthouse Cottage - Family & Pet Friendly
Beautiful Private Cottage, Sleeps 6, Walk to Beach
2 bedrooms

Beautiful Private Cottage, Sleeps 6, Walk to Beach

10.0 out of 10, Exceptional, (18)
"The house had everything we needed and is in a great location for the beach, shops, and other activities! The yard is beautiful and our teenagers spent a lot of time out there in the evenings. We would definitely stay again. "
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 1,193 total
includes taxes & fees
4 May - 5 May
Brand New Cottage Walkable to All Downtown Michigan City & Beach!
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
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
20 May - 21 May
Walkable cozy cottage, Outlet Mall across street!
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 AED 1,616
AED 1,825 total
includes taxes & fees
3 May - 4 May
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)
"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
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)
"The property was great - we will definitely consider coming back - and Mike was wonderful. Highly recommend."
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!

10.0 out of 10, Exceptional, (2)
"It was an amazing house, room for everyone. The inside of the home was stunning, the outside was made for entertainment with the hot tub and fire pit. We will definitely stay again."
The price is AED 1,862
AED 2,964 total
includes taxes & fees
2 Jun - 3 Jun
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)
"Gorgeous property with direct beach access in Union Pier."
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)
"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
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.
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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, (54)
"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 AED 290
AED 407 total
includes taxes & fees
4 May - 5 May
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, (96)
"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, (46)
"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.