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Check prices for these dates

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28 Saf. - 2 Rab. I
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Compare 627 Vacation Homes in Chesterton with updated reviews, rates, and availability.

Beautiful Family Cottage in Beachwalk-Grill-AC-Free Wifi-Kids Haven.
The Troll's Den

Beautiful Family Cottage in Beachwalk-Grill-AC-Free Wifi-Kids Haven.

9.6 out of 10, Exceptional, (210)
"Just a quick weekend with my family. We had a wonderful time, my kids had fun playing board games and watching movies with their cousins. We walked to the beach, although, it was cold but it was lovely. It was definitely a wonderful trip. Would do it again. "
Beautiful Family Cottage in Beachwalk-Grill-AC-Free Wifi-Kids Haven.
Farmesque with a splash of modern
Exterior

Farmesque with a splash of modern

10.0 out of 10, Exceptional, (29)
"Quiet, clean and spacious house to gather with family and/or friends. "
The price is SAR 746
SAR 1,688 total
includes taxes & fees
23 Feb - 24 Feb
Farmesque with a splash of modern
Roomy Retreat-Family & Friends|2 King B|Game Room| | Valpo University | Dunes
Huge Living Room with a | Smart TV || Google Hub for music || Open Layout |

Roomy Retreat-Family & Friends|2 King B|Game Room| | Valpo University | Dunes

10.0 out of 10, Exceptional, (8)
"Lovely house in a good location with plenty of rooms, beds, and parking for everyone. Awesome communication with host. Highly recommend. "
The price is SAR 529
SAR 1,844 total
includes taxes & fees
24 Feb - 25 Feb
Roomy Retreat-Family & Friends|2 King B|Game Room| | Valpo University | Dunes
BEACHFRONT LAKE MICHIGAN w/Lookout Tower & Lake Views - Sleeps 13
Main Level | Living Room

BEACHFRONT LAKE MICHIGAN w/Lookout Tower & Lake Views - Sleeps 13

9.4 out of 10, Exceptional, (51)
"Christmas whit the family, nice view "
BEACHFRONT LAKE MICHIGAN w/Lookout Tower & Lake Views - Sleeps 13
Modern Farmhouse Retreat-10 Min Walk to Lake Michigan-Hot Tub-Sauna
Exterior

Modern Farmhouse Retreat-10 Min Walk to Lake Michigan-Hot Tub-Sauna

10.0 out of 10, Exceptional, (81)
"This is our third time staying at this property and we LOVE it. This fits our needs and preferences so perfectly. The location is great for those wanting to head into New Buffalo as it is just a short drive away. Love the ability to have access to a pantry area to tuck in all of the items we tend to bring with which helps to keep things neat and tidy, tucked away. There is also the extra bonus of having a garage to pull in. So love that during any messy weather!"
Modern Farmhouse Retreat-10 Min Walk to Lake Michigan-Hot Tub-Sauna
Roomy and Cozy 3bd 2ba just mins from Indiana Dunes
Outdoor dining

Roomy and Cozy 3bd 2ba just mins from Indiana Dunes

9.6 out of 10, Exceptional, (17)
"Had a great time at this cottage. Convenient location in between Michigan City and Chesterton. Plenty of space and large fenced in back yard. Right on W. Dunes Highway, so super easy to get anywhere. Kitchen was fully stocked to cook our own meals and 3 different areas for people to watch tv. Never felt like we were on top of each other, Had a great holiday weekend stay!"
Roomy and Cozy 3bd 2ba just mins from Indiana Dunes
Perfect Family Retreat-Beachwalk-AC-Free WiFi-GolfCart-Grill--Music Lovers-Bikes
East of the Sun - front view

Perfect Family Retreat-Beachwalk-AC-Free WiFi-GolfCart-Grill--Music Lovers-Bikes

10.0 out of 10, Exceptional, (96)
"Property was clean and comfortable, plenty of room, everyone enjoyed the karaoke "
Perfect Family Retreat-Beachwalk-AC-Free WiFi-GolfCart-Grill--Music Lovers-Bikes
View of the lake from 2 decks in this 6BR Lake Shore Dr home, steps to the beach
View of the lake from the huge front deck

View of the lake from 2 decks in this 6BR Lake Shore Dr home, steps to the beach

9.0 out of 10, Wonderful, (74)
"The house was clean and quite adequate for our 3 day stay. We met Mr. Marshall when we arrived (he was there with a crew working on furniture and some repairs). He was very pleasant, as was the crew. We like to cook for ourselves. The stove was not completely functional -- shelves do not fit, and the interior needs a good cleaning. The towel rack above the second floor bathroom toilet is pulling of the wall and could use some attention. Rick Ginther (for the Ginther Siblings)"
The price is SAR 1,496
SAR 3,016 total
includes taxes & fees
23 Feb - 24 Feb
View of the lake from 2 decks in this 6BR Lake Shore Dr home, steps to the beach
Family Retreat-Beachwalk-Grill-AC-Free WiFi-Pool Table-Bikes-Grill-Golf Cart
Exterior

Family Retreat-Beachwalk-Grill-AC-Free WiFi-Pool Table-Bikes-Grill-Golf Cart

10.0 out of 10, Exceptional, (180)
"We recently stayed at the Valhalla! The home was exactly has described and was even decorated for Christmas! Any questions we had were promptly answered by Anders. Cozy fireplace and plenty of games for us to use along with a pool table in the basement. We are hoping to visit another time! "
Family Retreat-Beachwalk-Grill-AC-Free WiFi-Pool Table-Bikes-Grill-Golf Cart
Big Family House 5 Minutes from Lake Michigan/Blue Chip Casino/Brewery/Wineries!
Dining Table

Big Family House 5 Minutes from Lake Michigan/Blue Chip Casino/Brewery/Wineries!

9.8 out of 10, Exceptional, (95)
"This was the second time we stayed at this house. It is well appointed and in a good location. We will definitely stay there again."
Big Family House 5 Minutes from Lake Michigan/Blue Chip Casino/Brewery/Wineries!
Beautiful 4 Bed House in New Buffalo with Pool & Hot Tub Close to Lake & Main St
Pool

Beautiful 4 Bed House in New Buffalo with Pool & Hot Tub Close to Lake & Main St

9.2 out of 10, Wonderful, (19)
"Great location, quiet neighborhood. One hiccup but Rishi was quick to resolve. The kitchen/dining was smaller than what the pictures led us to believe otherwise, all was good. "
Beautiful 4 Bed House in New Buffalo with Pool & Hot Tub Close to Lake & Main St
Beachwalk vacation home . 6 bedrooms plus a den.
Royal Retreat with the golf cart ! Golf cart for use spring through December 1st

Beachwalk vacation home . 6 bedrooms plus a den.

10.0 out of 10, Exceptional, (229)
"We had an amazing time at the royal retreat. We were three families and comfortably had space for kid play and adult leisure. The location of the park and woods made for great winter fun. Would love to return someday!"
Beachwalk vacation home . 6 bedrooms plus a den.
2025 Open! Three Night Min! New Buffalo Home Walking Distance To Downtown and Be
Lots Of Light!

2025 Open! Three Night Min! New Buffalo Home Walking Distance To Downtown and Be

9.4 out of 10, Exceptional, (19)
"Great location and perfect size for a large group "
2025 Open! Three Night Min! New Buffalo Home Walking Distance To Downtown and Be
Kid-friendly Michiana cottage! Summer dates open - including 4th of July!
Front Porch

Kid-friendly Michiana cottage! Summer dates open - including 4th of July!

10.0 out of 10, Exceptional, (51)
"Loved this place and so clean and perfect for our girls weekend!"
Kid-friendly Michiana cottage! Summer dates open - including 4th of July!
5BR on 5 Acres Hot Tub Pickleball Huge Game Rm

5BR on 5 Acres Hot Tub Pickleball Huge Game Rm

9.4 out of 10, Exceptional, (8)
"We had a great holiday stay. We enjoyed almost all of available outdoor and indoor activities. "
5BR on 5 Acres Hot Tub Pickleball Huge Game Rm
Boho Beach House 3-bedroom in Michigan City
Living area

Boho Beach House 3-bedroom in Michigan City

10.0 out of 10, Exceptional, (1)
"Super simple and has all we need for our annual birthday getaway weekend. We rent this house every year"
The price is SAR 431
SAR 1,016 total
includes taxes & fees
23 Feb - 24 Feb
Boho Beach House 3-bedroom in Michigan City
Nestled just behind Marquette Park. 5 minute walk to beach.
Interior

Nestled just behind Marquette Park. 5 minute walk to beach.

10.0 out of 10, Exceptional, (9)
"Could not be more thankful for her prompt replies and accommodations."
Nestled just behind Marquette Park. 5 minute walk to beach.
Sand & Sun Retreat|2 Living Rooms | Game Room |Game Room | Minutes to Beach
Huge Living Room with a | Smart TV || Google Hub for music || Open Layout |

Sand & Sun Retreat|2 Living Rooms | Game Room |Game Room | Minutes to Beach

10.0 out of 10, Exceptional, (17)
"Booked this weekend away for my kids and significants for Christmas. Great location between Grand Rapids and Chicago. House was well maintained and many extras! Would definitely recommend!!"
The price is SAR 330
SAR 1,292 total
includes taxes & fees
24 Feb - 25 Feb
Sand & Sun Retreat|2 Living Rooms | Game Room |Game Room | Minutes to Beach
Michigan City Mansion / Hot Tub / Fire Pit / Pet Friendly
Unwind in Your Private Backyard Oasis

Michigan City Mansion / Hot Tub / Fire Pit / Pet Friendly

10.0 out of 10, Exceptional, (3)
"This home accommodated our crew with adequate space. The host was very responsive, and we look forward to staying in the future."
The price is SAR 533
SAR 1,552 total
includes taxes & fees
23 Feb - 24 Feb
Michigan City Mansion / Hot Tub / Fire Pit / Pet Friendly
Hot tub open all year! Private heated pool, sleeps 10 near downtown New Buffalo!
Heated pool open late April to mid October!

Hot tub open all year! Private heated pool, sleeps 10 near downtown New Buffalo!

9.2 out of 10, Wonderful, (57)
"We rented the unit for a family gathering, multiple family units gathering in a central location. House worked great for our needs. Listing accurate to description. Open floor plan was very accommodating for family socializing together."
Hot tub open all year! Private heated pool, sleeps 10 near downtown New Buffalo!
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, (82)
"Immaculately clean, nice furnishings, and very accommodating host. Great views of the lake from the living room. Definitely would come back!"
The price is SAR 619
SAR 1,029 total
includes taxes & fees
23 Feb - 24 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, (50)
"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 244
SAR 357 total
includes taxes & fees
24 Feb - 25 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, (40)
"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.