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Compare 757 Vacation Homes in Chesterton with updated reviews, rates, and availability.

Miller Beach Blue Door By The Shore #2

10.0 out of 10, Exceptional, (4)
"I had a very nice stay the property was very clean. I loved the location probably would’ve been better if I had rented in the summer because it was a little chilly in the home but otherwise everything was great. "
Miller Beach Blue Door By The Shore #2

Sweet Stay By-The-Lake in Michigan City with AC, WiFi

2.0 star property
9.2 out of 10, Wonderful, (5)
"Great location Cozy little house Its was a nice get away "
Sweet Stay By-The-Lake in Michigan City with AC, WiFi

Designer Cottage +Guesthouse on large private estate in Grand Beach with Hot Tub

9.6 out of 10, Exceptional, (36)
"This was a great house, very cozy and homey. It had everything we needed and was nice and clean. Would definitely stay here again. "
Designer Cottage +Guesthouse on large private estate in Grand Beach with Hot Tub

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

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

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

9.0 out of 10, Wonderful, (20)
"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

Designer Luxury Cottage ~ Heated Community Pool ~ Walk to Beach & Town

10.0 out of 10, Exceptional, (78)
"We had a wonderful time in new buffalo. The house was perfect and in an excellent location. Jeff was easy to communicate with a few simple questions. Parking was easy. The house was clean and so spacious. I personally Cannot wait to come back. This stay was 7 adults and we had plenty of room to sleep and relax. "
Designer Luxury Cottage ~ Heated Community Pool ~ Walk to Beach & Town

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

Walk to the beach! Great modern home with spring and early summer availability!

10.0 out of 10, Exceptional, (105)
"This house was the perfect size for our large family. In fact, due to illness, we had more than enough room for our family.The house was clean and provided enough bedrooms and beds for all.It might have been good to add a TV(s) to bedrooms. "
Walk to the beach! Great modern home with spring and early summer availability!

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

10.0 out of 10, Exceptional, (83)
"We stay at a lot of VRBOs. This property was superior to most! The house is modern and aesthetically beautiful with a very well thought out design. There are many little additions, like houseplants that really made it feel homey, extra bedding, plush towels, etc. Our favorite features were the spacious kitchen (well stocked with gadgets and cookware), hot tub, outdoor patio, indoor sauna, large table for meals and games. The property is close to restaurants, casinos and shopping, which we...
Modern Farmhouse Retreat-10 Min Walk to Lake Michigan-Hot Tub-Sauna

Modern Farmhouse steps from downtown! Here comes summer!

10.0 out of 10, Exceptional, (161)
"This house is adorable, very clean, and a short walk away from downtown shops, restaurants, and the lake. We loved everything about it! Owners were very responsive to questions we had before arrival and provided clear information that we needed for our stay. I would highly recommend this property to anyone visiting the area!"
Modern Farmhouse steps from downtown! Here comes summer!

cozy home with hot tub next to downtown Valparaiso

10.0 out of 10, Exceptional, (60)
"This home is very cozy. The kitchen was well stocked and all of the bedrooms had large closets. Beds are comfortable. Living room has ample seating and a relaxed atmosphere. The hosts were easy to communicate with via text. Would stay again!"
cozy home with hot tub next to downtown Valparaiso

Private Wooded Acre, Soaring Windows in Nat’l Park, 2 blocks to the beach

10.0 out of 10, Exceptional, (33)
"Our stay was nothing short of amazing! The host was incredibly responsive and flexible, allowing us to make a last-minute change to our reservation. She went above & beyond to be accommodating, which made it possible for our family to still gather for a special Christmas and New Year celebration. The house itself was full of character, with unique artwork and quirky touches that made it feel like a fun, creative retreat. The serene location, surrounded by nature, provided the perfect backdrop...
Private Wooded Acre, Soaring Windows in Nat’l Park, 2 blocks to the beach

Singing Sands Trl | Hot Tub Retreat | Dogs OK

9.8 out of 10, Exceptional, (12)
"We loved staying at this house for a weekend. It was cozy, had everything we needed and the most exciting it had a hot tub! hot tub looked new and was very clear. The place was also clean and cozy. We had an amazing stay and would stay there again! "
The price is AED 448
AED 993 total
includes taxes & fees
30 Mar - 31 Mar
Singing Sands Trl | Hot Tub Retreat | Dogs OK

7 Bedroom Lake Shore Dr. Beach Home - NEWLY BUILT HOME! Steps to the beach!

9.0 out of 10, Wonderful, (57)
"We had plenty of room for all 17 of us, however, if you have trouble climbing stairs it’s not for you. "
7 Bedroom Lake Shore Dr. Beach Home - NEWLY BUILT HOME! Steps to the beach!

Cozy house with hot tub, firepit, near restaurants + near beach

2.0 star property
10.0 out of 10, Exceptional, (2)
"The home was small, but cozy. It served our family purpose for Thanksgiving. It was nice and cozy. It was clean and everything in place. We enjoyed our time there. "
Cozy house with hot tub, firepit, near restaurants + near beach

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

10.0 out of 10, Exceptional, (3)
"Quiet and comfortable place for your family and friends. "
The price is AED 595
AED 1,466 total
includes taxes & fees
31 Mar - 1 Apr
Michigan City Mansion / Hot Tub / Fire Pit / Pet Friendly

Casa Blanca in Miller Beach!

9.8 out of 10, Exceptional, (69)
"8 of us stayed at the house, plenty of beds, plenty of places to sit and talk / watch TV, kitchen had everything we needed. Highly recommend"
Casa Blanca in Miller Beach!

Beachwalk vacation home . 6 bedrooms plus a den. June 13th - 20th, 2025 open!

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. June 13th - 20th, 2025 open!

Restored Cottage Across The Street From The Beach!

9.8 out of 10, Exceptional, (95)
"Great house for large family. Very cozy, yet spacious. Fenced yard was great as was the close proximity to the beach"
Restored Cottage Across The Street From The 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

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

10.0 out of 10, Exceptional, (87)
"The view is breathtaking. The kitchen has everything you need. The bathrooms are spotless. The beds are comfortable. We really enjoyed our stay. It was cold but not rainy. A great weekend! We recommend!"
The price is AED 790
AED 1,247 total
includes taxes & fees
30 Mar - 31 Mar
Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly

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

9.0 out of 10, Wonderful, (53)
"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 250
AED 362 total
includes taxes & fees
1 Apr - 2 Apr
Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes

The Neighborhood Hotel - Grand Beach

4.0 star property
9.4 out of 10, Exceptional, (41)
"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.