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Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

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

Miller Beach Blue Door By The Shore #2
Beach

Miller Beach Blue Door By The Shore #2

10.0 out of 10, Exceptional, (4)
"Perfect!"
Miller Beach Blue Door By The Shore #2
Sweet Stay By-The-Lake in Michigan City with AC, WiFi
Fridge, microwave, oven, stovetop

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

2.0 star property
9.6 out of 10, Exceptional, (8)
"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
TV, fireplace

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

9.6 out of 10, Exceptional, (38)
"This was a great house, very cozy and homey. It had everything we needed and was nice and clean. Would definitely stay here again. "
The price is AED 3,673
AED 5,664 total
includes taxes & fees
18 May - 19 May
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
A heated pool

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

10.0 out of 10, Exceptional, (183)
"Perfect house for our 4 families to come together and celebrate the holidays. Quiet, friendly neighborhood. House was clean and very family friendly. "
Family Retreat-Beachwalk-Grill-AC-Free WiFi-Pool Table-Bikes-Grill-Golf Cart
BEACHFRONT LAKE MICHIGAN w/Lookout Tower & Lake Views - Sleeps 13
Fridge, microwave, oven, stovetop

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
Fridge, microwave, oven, stovetop

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. Great house. Great host. "
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
Pool

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

10.0 out of 10, Exceptional, (80)
"Had a dad's weekend and really enjoyed this place. It was clean and perfect for what we were doing. The host was responsive and nice. Would definitely stay here again!"
Designer Luxury Cottage ~ Heated Community Pool ~ Walk to Beach & Town
Roomy and Cozy 3bd 2ba just mins from Indiana Dunes
Fridge, microwave, oven, stovetop

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!
Exterior

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

10.0 out of 10, Exceptional, (106)
"This was our fifth stay at this wonderful house and it was amazing as always!"
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
Property grounds

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

10.0 out of 10, Exceptional, (84)
"Family enjoyed the stay. Great location "
Modern Farmhouse Retreat-10 Min Walk to Lake Michigan-Hot Tub-Sauna
Modern Farmhouse steps from downtown! Here comes summer!
Beach nearby, sun loungers, beach towels

Modern Farmhouse steps from downtown! Here comes summer!

10.0 out of 10, Exceptional, (165)
"Wonderful property and hosts, close to everything that SW Michigan has to offer. House is fully stocked and was a perfect option for our family Thanksgiving celebration! "
The price is AED 1,653
AED 2,872 total
includes taxes & fees
5 Jun - 6 Jun
Modern Farmhouse steps from downtown! Here comes summer!
cozy home with hot tub next to downtown Valparaiso
Terrace/patio

cozy home with hot tub next to downtown Valparaiso

10.0 out of 10, Exceptional, (61)
"We had a great visit. This space was comfortable and met all our needs. "
cozy home with hot tub next to downtown Valparaiso
Private Wooded Acre, Soaring Windows in Nat’l Park, 2 blocks to the beach
Beach nearby, sun loungers

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

10.0 out of 10, Exceptional, (33)
"Clean, quiet and comfortable! The host was pleasant!"
Private Wooded Acre, Soaring Windows in Nat’l Park, 2 blocks to the beach
Singing Sands Trl | Hot Tub Retreat | Dogs OK
Point of interest

Singing Sands Trl | Hot Tub Retreat | Dogs OK

9.8 out of 10, Exceptional, (16)
"Such an amazing place to stay. The location was great, very close to the beach. The house was very clean and had great amenities. We thoroughly enjoyed ourselves and would be glad to come back!"
The price is AED 503
AED 1,042 total
includes taxes & fees
6 May - 7 May
Singing Sands Trl | Hot Tub Retreat | Dogs OK
7 Bedroom Lake Shore Dr. Beach Home - NEWLY BUILT HOME! Steps to the beach!
Property grounds

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
Fridge, microwave, oven, stovetop

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

2.0 star property
9.6 out of 10, Exceptional, (4)
"Host was very nice and extremely quick to respond to texts or calls. House was clean and in great condition. 10/10"
Cozy house with hot tub, firepit, near restaurants + near beach
Michigan City Mansion / Hot Tub / Fire Pit / Pet Friendly
Exterior detail

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

9.4 out of 10, Exceptional, (6)
"This home accommodated our crew with adequate space. The host was very responsive, and we look forward to staying in the future."
Michigan City Mansion / Hot Tub / Fire Pit / Pet Friendly
Casa Blanca in Miller Beach!
Exterior

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!
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (231)
"This is also our winter home away from home. Our place to come together and have a fabulous time."
Beachwalk vacation home . 6 bedrooms plus a den. June 13th - 20th, 2025 open!
Restored Cottage Across The Street From The Beach!
On the beach, sun loungers, beach towels

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

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
11 May - 12 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, (47)
"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.