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Vacation Homes in Chesterton

Adorable cottage in the Michiana Shores area! Close to Lake Michigan and Dunes

10.0 out of 10, Exceptional, (74)
"Lovely home for a long weekend with family! Super comfortable, cute and convenient to everything. We will definitely be back!"
Adorable cottage in the Michiana Shores area! Close to Lake Michigan and Dunes

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

9.6 out of 10, Exceptional, (226)
"We enjoyed our stay. Everything was picturesque and would definitely recommend staying here."
Beautiful Family Cottage in Beachwalk-Grill-AC-Free Wifi-Kids Haven.

House of TarTar with year long hot tub next to adorable downtown Valparaiso

10.0 out of 10, Exceptional, (73)
"Great place to stay, easy check in and check out. Very nice place we will be back to visit."
House of TarTar with year long hot tub next to adorable downtown Valparaiso

Driftwood Cottage, a charming 3-bed/2-bath home in peaceful Union Pier!

9.0 out of 10, Wonderful, (4)
"Great spot for a weekend getaway. Close to a great beach, shops, restaurants and a weekend farmers market. Check in was easy and the kitchen had all the supplies we needed. "
Driftwood Cottage, a charming 3-bed/2-bath home in peaceful Union Pier!

A cozy little house along Trail Creek awaits you. Relax. Unwind. Enjoy.

6.0 out of 10, (5)
"Had a great time in Michigan city but I do wish the property was cleaner and the hot water did not work"
A cozy little house along Trail Creek awaits you. Relax. Unwind. Enjoy.

Perfect Location for your Beach/Lake MI stay! You'll Love This Beautiful Home!

10.0 out of 10, Exceptional, (47)
"The house was very clean and in a grrat location "
Perfect Location for your Beach/Lake MI stay! You'll Love This Beautiful Home!

Central location ND games, lakes, casino, shopping, highways and interstates.

8.0 out of 10, Very Good, (5)
Central location ND games, lakes, casino, shopping, highways and interstates.

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

10.0 out of 10, Exceptional, (193)
"We loved our stay here. I can’t wait to come back in the summer months"
Family Retreat-Beachwalk-Grill-AC-Free WiFi-Pool Table-Bikes-Grill-Golf Cart

'Rustic Refined Retreat’ Lakeside Home - Walk to Everything!

10.0 out of 10, Exceptional, (192)
"Awesome property for a single family..great layout..perfect location "
'Rustic Refined Retreat’ Lakeside Home - Walk to Everything!

Blue Chill | WalktoBeach | HotTub-all yr | Dogs OK

9.6 out of 10, Exceptional, (42)
"Perfect house for our girls trip weekend. Lots of room, house was clean, we had a great time! "
$491 nightly
The price is $529
Sep 2 - Sep 3
Total includes taxes and fees
Blue Chill | WalktoBeach | HotTub-all yr | Dogs OK

(4 bedrooms and 2 full baths; sleeps 11)

9.0 out of 10, Wonderful, (28)
"We had a great stay. Close to attractions and still quiet."
$509 nightly
The price is $570
Aug 19 - Aug 20
Total includes taxes and fees
(4 bedrooms and 2 full baths; sleeps 11)

Just Steps Away from The Beach on Lake Michigan - Sheridan Beach

9.8 out of 10, Exceptional, (98)
"Wonderful stay with our family. The house met all our needs."
Just Steps Away from The Beach on Lake Michigan - Sheridan Beach

A cozy home between the Indiana Dunes and town of Chesterton.

10.0 out of 10, Exceptional, (20)
"The property was amazing and its nice a cozy and overall amazing. Would recommend! "
A cozy home between the Indiana Dunes and town of Chesterton.

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

2.0 star property
9.6 out of 10, Exceptional, (9)
"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

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

9.8 out of 10, Exceptional, (117)
"Great location. Close to the beach, fun restaurants, and stores. Perfect for families. Spacious common areas and lots of bathrooms. "
Walk to the beach! Great modern home with spring and early summer availability!

Warm late summer dates still open in Sept 2025: 1-4, 7-11, 15-19, 21-26. Enjoy!

10.0 out of 10, Exceptional, (168)
"This property is beautiful with a lot of space, bedrooms, and bathrooms. The location was perfect for walking to the beach, restaurants, and shopping. Can't wait to visit again!"
Warm late summer dates still open in Sept 2025: 1-4, 7-11, 15-19, 21-26. Enjoy!

Huge yard, Family-friendly, Hot Tub, walk to Beach, Dunes, Hiking Trails

8.8 out of 10, Excellent, (37)
"We had a great stay! The property was perfect- hot tub, plenty of beds, comfortable beds, walking distance to Lake Michigan! Home was comfortable and clean and the managers were easy to reach with questions-just a text away. Would definitely stay here again"
Huge yard, Family-friendly, Hot Tub, walk to Beach, Dunes, Hiking Trails

Charming & cozy in-town retreat in the heart of New Buffalo

10.0 out of 10, Exceptional, (159)
"Fantastic stay! We celebrated two milestones - our 18th wedding anniversary, as well as our first vacation as a family of three (8 month old daughter). We can’t say enough wonderful things about the house, location, and excellent communication with the property owners! They thought of everything with all the labeled items and beautiful decor to make your stay comfortable. Walkable and close to restaurants, shopping, and more. Thank you for the special memories! "
Charming & cozy in-town retreat in the heart of New Buffalo

Quiet neighborhood home Hot tub Fire pit Large deck Bar blocks to brewery

9.8 out of 10, Exceptional, (100)
"Loved the property and space inside the house. Will definitely return."
Quiet neighborhood home Hot tub Fire pit Large deck Bar blocks to brewery

5BR Hot Tub, Pickleball, Arcade

5BR Hot Tub, Pickleball, Arcade
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