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Check prices for these dates

Next weekend
7 Saf. - 9 Saf.
In two weeks
14 Saf. - 16 Saf.
In one month
28 Saf. - 2 Rab. I
In two months
28 Rab. I - 30 Rab. I

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

Peaceful Cottage/Private Parking & Backyard/Strong WiFi/Walk to Sheridan Beach!
Welcome to our front porch where you can sit in mornings with your coffee/tea!

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

10.0 out of 10, Exceptional, (54)
"Great stay in Michigan city property was very clean and had everything we needed with close walk to the beach. Also equipped with everything we needed for our baby including baby monitor and high chair. Loved the back yard for fires every night. "
Peaceful Cottage/Private Parking & Backyard/Strong WiFi/Walk to Sheridan Beach!
Vintage Lake Michigan Beach Cottage: 4br+loft,3ba-Sleeps 17
View from the street

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
Simple Cottage Set in the Woods by Lake Michigan
Ample parking on the side of the house.

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

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

10.0 out of 10, Exceptional, (33)
"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
Blocks To Beach Golf Tennis Park & Lake MI Sunsets
Exterior

Blocks To Beach Golf Tennis Park & Lake MI Sunsets

8.8 out of 10, Excellent, (3)
"We had a great time"
Blocks To Beach Golf Tennis Park & Lake MI Sunsets
Dunland Cottage W/hot tub, paddle boards, fire pit

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
Pet-friendly Lake Getaway: 1 Block to Beach!
Living area

Pet-friendly Lake Getaway: 1 Block to Beach!

3.0 star property
Pet-friendly Lake Getaway: 1 Block to Beach!
Treehouse Bungalow- Quaint and Cozy Getaway!
Living area

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 521
SAR 1,029 total
includes taxes & fees
3 Feb - 4 Feb
Treehouse Bungalow- Quaint and Cozy Getaway!
Cottage Retreat close to downtown New Buffalo. Sleeps 12, Pet friendly + Games!
Cozy Living Room with space to kick back, relax, and share a meal.

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 375
SAR 1,253 total
includes taxes & fees
3 Feb - 4 Feb
Cottage Retreat close to downtown New Buffalo. Sleeps 12, Pet friendly + Games!
Charming cottage with fast WiFi, fire pit, above-ground pool, & huge sunroom

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

8.4 out of 10, Very Good, (15)
"House is nicely updated. Beds are comfortable. Screened in back porch is a wonderful space. Loved the fire pit as well. Location is quiet but still close enough to everything else. I would stay here again. "
Charming cottage with fast WiFi, fire pit, above-ground pool, & huge sunroom
Cozy New Buffalo cottage with hot tub & fire pit. Short walk to downtown!
Front porch

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

10.0 out of 10, Exceptional, (27)
"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!
WEEKEND RESTORATION: Hot Tub - Fire Pit - Walk to Lake Michigan - Grand Beach

WEEKEND RESTORATION: Hot Tub - Fire Pit - Walk to Lake Michigan - Grand Beach

9.8 out of 10, Exceptional, (87)
"We thoroughly enjoyed the property. The kitchen was fully stocked and the house layout was wonderful for a group of 4 of us women. The Hot tub and fireplace were also wonderful. The short walk to the beach was great. Additionally, Ron was a delight to work with and incredibly responsive! One quick note is you might think about getting some new bar stools for the kitchen as the ones there are getting 'soft'. Thanks for a great stay! "
WEEKEND RESTORATION: Hot Tub - Fire Pit - Walk to Lake Michigan - Grand Beach
Adorable Cottage New Buffalo, Mi. Near Grand Beach.1 Bedroom, Sleeps 5
Front yard view Iris in full bloom May

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
Private Beach, Sleeps 8, dog friendly. Steps to the Beach.
Exterior

Private Beach, Sleeps 8, dog friendly. Steps to the Beach.

10.0 out of 10, Exceptional, (90)
"I had a wonderful time staying at this property for a weekend get away. The property is steps away from a private beach! John the owner was extremely kind and helpful with the check in process. The home was very clean and cozy. Would definitely recommend! "
The price is SAR 2,063
SAR 4,115 total
includes taxes & fees
3 Feb - 4 Feb
Private Beach, Sleeps 8, dog friendly. Steps to the Beach.
Cozy downtown cottage perfect for a fall escape
Welcome to the pinewood cottage

Cozy downtown cottage perfect for a fall escape

9.6 out of 10, Exceptional, (9)
"What a great winter retreat! Loved the decor, the property management, and most especially the fireplace. The kitchen had everything I needed to make some great meals. Great oversized hot tub too. Unfortunately, the jets didn’t work, but still a great way to relax and unwind after a long day climbing the dunes. Great location too! 100% would come back again!"
Cozy downtown cottage perfect for a fall escape
Walkable cozy cottage, Outlet Mall across street!
Queen pull-out sofa

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

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

10.0 out of 10, Exceptional, (17)
"This was the perfect place for a girls trip. Plenty of indoor and outdoor space to gather and having two bathrooms is a definite plus. The location is wonderful! It's under a 5 minute drive to everything in New Buffalo, but you feel like you're a million miles away at your own private oasis at the house. We would absolutely stay here again!"
New Buffalo Beach - Lake Michigan - Harbor Country Winery and Breweries
2024 remodeled historic Lake Michigan waterfront Union Pier home with spa.
Terrace/patio

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.
Lighthouse Cottage - Family & Pet Friendly
Bedroom 1 - Queen Bed

Lighthouse Cottage - Family & Pet Friendly

10.0 out of 10, Exceptional, (4)
"Perfect spot for our stay, we really enjoyed our weekend here! "
Lighthouse Cottage - Family & Pet Friendly
The Victorian Carriage House. Built in 1880, this restored cottage is a charmer.
Exterior detail

The Victorian Carriage House. Built in 1880, this restored cottage is a charmer.

8.2 out of 10, Very Good, (23)
"Nice little place. Close to everything "
The Victorian Carriage House. Built in 1880, this restored cottage is a charmer.
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
Property grounds

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

10.0 out of 10, Exceptional, (80)
"This cabin has an amazing views of Lake Michigan!! We loved our stay here...so peaceful and relaxing. The cabin was clean and the hosts provided lots of little extras (shampoo, bar soap, coffee pods). It is not a "luxury" feel....but everything is well maintained and very clean. We will definitely stay here again!!! "
The price is SAR 675
SAR 1,101 total
includes taxes & fees
3 Feb - 4 Feb
Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly
Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes
The Downtown Apartment in Chesterton. Convenient, cozy, and completely private!

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

9.0 out of 10, Wonderful, (48)
"I booked this stay as a birthday gift for my son. He and his fiancé stayed for 2 nights/3 days. They absolutely enjoyed there stay. The place was clean and just like the pictures displayed. They had an issue with the code not working to enter the property, Don the host got in touch with us immediately and even refunded some money for the inconvenience! I will definitely be booking again for my daughters birthday!!"
The price is SAR 296
SAR 416 total
includes taxes & fees
3 Feb - 4 Feb
Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes
The Neighborhood Hotel - Grand Beach
Property grounds

The Neighborhood Hotel - Grand Beach

4.0 star property
9.4 out of 10, Exceptional, (39)
"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.

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