Search Chesterton Cottage Rentals from CA $157

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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Chesterton Cottages

The Hideaway House - Private, Peaceful, Cozy
Stairs lead down to a sandy beach with ocean views.

The Hideaway House - Private, Peaceful, Cozy

10.0 out of 10, Exceptional, (9)
"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
Brand New Cottage Walkable to All Downtown Michigan City & Beach!
Enjoy cooking in this well-equipped kitchen with a stainless steel refrigerator, double oven, and microwave.

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

10.0 out of 10, Exceptional, (5)
"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 CA $216
CA $498 total
includes taxes & fees
Aug 18 - Aug 19
Brand New Cottage Walkable to All Downtown Michigan City & Beach!
Blue Haven Cottage - New Buffalo Beach, near Wineries & Breweries
Enjoy dining al fresco on the deck, surrounded by lush greenery and a charming fence.

Blue Haven Cottage - New Buffalo Beach, near Wineries & Breweries

10.0 out of 10, Exceptional, (27)
"Wonderful cottage, perfect for our friends weekend. Great hospitality. "
Blue Haven Cottage - New Buffalo Beach, near Wineries & Breweries
Grand Beach Getaway – Hot Tub, Fire Pit & walk to the Lake | Weekend Restoration
Cozy living area with a stone fireplace, flat-screen TV, and comfortable seating.

Grand Beach Getaway – Hot Tub, Fire Pit & walk to the Lake | Weekend Restoration

9.6 out of 10, Exceptional, (93)
"The house is bright and sunny, warm and inviting. Even after it snowed and was cold outside. We enjoyed all the sunlight. The thoughtful details and amenities for everything we needed. We’re looking forward to coming again in the summer. "
Grand Beach Getaway – Hot Tub, Fire Pit & walk to the Lake | Weekend Restoration
Walkable cozy cottage, Outlet Mall across street!
Enjoy cooking in this well-equipped kitchen with a convenient island and sink.

Walkable cozy cottage, Outlet Mall across street!

9.6 out of 10, Exceptional, (17)
"Loved the cottage it had everything we needed very nice!"
The price is CA $157
CA $425 total
includes taxes & fees
Sep 3 - Sep 4
Walkable cozy cottage, Outlet Mall across street!
Treehouse Bungalow- Quaint and Cozy Getaway!
Standing proudly on a coastal platform, a white lighthouse guides visitors along the pier.

Treehouse Bungalow- Quaint and Cozy Getaway!

8.8 out of 10, Excellent, (49)
"Unsafe parking, uncomfortable couch and beds. We didn’t stay the night due to the poor conditions."
The price is CA $370
CA $602 total
includes taxes & fees
Aug 10 - Aug 11
Treehouse Bungalow- Quaint and Cozy Getaway!
Sweet Inn Coach House near beautiful beach on Lake Michigan in Beachwalk
Relax by the pool surrounded by a wooden deck and lounge chairs.

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

9.6 out of 10, Exceptional, (42)
"House was immaculately clean, well appointed & extremely comfortable. By far, our best rental at Beachwalk Resort!"
The price is CA $412
CA $780 total
includes taxes & fees
Sep 3 - Sep 4
Sweet Inn Coach House near beautiful beach on Lake Michigan in Beachwalk
Adorable Cottage New Buffalo, Mi. Near Grand Beach.1 Bedroom, Sleeps 5
Sit and unwind in this serene garden setting, surrounded by lush greenery and a tranquil water feature.

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

9.8 out of 10, Exceptional, (190)
"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
Private Beach Steps to the Beach.
Enjoy the serene views from this deck, which offers a bench with comfortable seating.

Private Beach Steps to the Beach.

10.0 out of 10, Exceptional, (91)
"Such a cute house and John was a great host!"
The price is CA $755
CA $1,501 total
includes taxes & fees
Aug 31 - Sep 1
Private Beach Steps to the Beach.
Cozy Michigan City Cottage #1
Cozy living area with a sofa and coffee table, adjacent to a compact kitchen with a window and a lofted ceiling.

Cozy Michigan City Cottage #1

9.6 out of 10, Exceptional, (21)
"We really enjoyed our stay. The cottage is very nice, very clean, recently upgraded. Susan and Tom were very responsive and provided helpful information We are planning to come back"
Cozy Michigan City Cottage #1
Spacious 3BR House With Firepit & Grill, Near Beach
Front of property

Spacious 3BR House With Firepit & Grill, Near Beach

2.0 star property
5.0 out of 10, (2)
"It is a beautiful residence. This is a relatively new residence, evidenced by all the brand new with tags furniture, lamps, appliances etc. No internet or cable, which was sort of a downer. Did not get the code until 15 minutes after check in time. No coffee or silverware. We only found one spoon. "
The price is CA $168
CA $394 total
includes taxes & fees
Aug 13 - Aug 14
Spacious 3BR House With Firepit & Grill, Near Beach
Charming cottage with fast WiFi, fire pit, above-ground pool, & huge sunroom
Cozy living room with a fireplace, bookshelf, and comfortable seating area.

Charming cottage with fast WiFi, fire pit, above-ground pool, & huge sunroom

8.6 out of 10, Excellent, (17)
"The house is clean, comfortable and relaxing. The pool was clean and so very lovely in the last days of summer."
Charming cottage with fast WiFi, fire pit, above-ground pool, & huge sunroom
Beautiful Private Cottage, Sleeps 6, Walk to Beach
Enjoy a serene outdoor space surrounded by lush plants and trees, with a bench for relaxation.

Beautiful Private Cottage, Sleeps 6, Walk to Beach

10.0 out of 10, Exceptional, (22)
"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
Modern Cottage "M" Luxury home w/hot tub, community pool-walk to town & beach
Enjoy cooking in this well-equipped kitchen with a large island, refrigerator, oven, and microwave.

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

10.0 out of 10, Exceptional, (41)
"Adorable cottage and perfect for a girls weekend. Comfortable furnishings and really well kept! Would love to book again!"
Modern Cottage "M" Luxury home w/hot tub, community pool-walk to town & beach
Fun w/Loft! Beach ~Nature Trails ~Grill~ Firepit ~Indiana Dunes National Park
Enjoy a serene outdoor space with a deck leading to a patio area, complete with a table and chairs.

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

10.0 out of 10, Exceptional, (42)
"Perfect little spot for a quick family getaway. We loved the fire pit and the screened in porch!"
Fun w/Loft! Beach ~Nature Trails ~Grill~ Firepit ~Indiana Dunes National Park
Cozy New Buffalo cottage with hot tub & fire pit. Short walk to downtown!
Stroll up to the welcoming front door, flanked by lantern-style lights, and enter a serene home with a beautifully manicured lawn and garden.

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

10.0 out of 10, Exceptional, (41)
"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!
Simple Cottage Set in the Woods by Lake Michigan
Guests can walk along the beach, bordered by trees and a distant structure, with the ocean at their feet.

Simple Cottage Set in the Woods by Lake Michigan

9.4 out of 10, Exceptional, (97)
"Great location, golf cart was fantastic, host was very responsive -- looking forward to returning!"
Simple Cottage Set in the Woods by Lake Michigan
The Yellow House Near the Shore Walking distance to Sheridan Beach,
Enjoy cooking in this fully equipped kitchen with appliances, a sink, and a coffee station.

The Yellow House Near the Shore Walking distance to Sheridan Beach,

10.0 out of 10, Exceptional, (2)
"Cute little home! Perfect for our family. So close to everything. The walk to the beach was perfect!! "
The Yellow House Near the Shore Walking distance to Sheridan Beach,
Bright Scandinavian-style cottage with large, private wooded yard
Stroll up to this charming single-story home, surrounded by a lush garden and a serene wooded area.

Bright Scandinavian-style cottage with large, private wooded yard

10.0 out of 10, Exceptional, (21)
"We had a great stay for a long holiday weekend. Would recommend a visit. "
Bright Scandinavian-style cottage with large, private wooded yard
Peaceful Cottage/Private Parking & Backyard/Strong WiFi/Walk to Sheridan Beach!
Prepare meals in the fully equipped kitchen with a gas stove, microwave, and ample counter space.

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

10.0 out of 10, Exceptional, (60)
"Our stay was lovely and this house is incredibly well thought out!"
Peaceful Cottage/Private Parking & Backyard/Strong WiFi/Walk to Sheridan 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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Top Chesterton Hotel Reviews

Best Western Indian Oak

Best Western Indian Oak

10/10 Excellent
"Loved the lake"
Donelle 1-night trip
Posted 1 day ago
Best Western Indian Oak