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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, (71)
"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, (224)
"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, (71)
"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, (2)
"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.

7.4 out of 10, Good, (3)
"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, (45)
"Nice location and very clean"
Perfect Location for your Beach/Lake MI stay! You'll Love This Beautiful Home!

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

10.0 out of 10, Exceptional, (1)
"We came up for a family vacation. Everything was great we had a wonderful time. Plenty of room for everyone and big spaces for hanging out. Awesome back yard for the kids to run around "
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, (189)
"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

(4 bedrooms and 2 full baths; sleeps 11)

9.2 out of 10, Wonderful, (25)
"We had a great stay. Close to attractions and still quiet."
The price is AED 1,157
AED 2,189 total
includes taxes & fees
31 Jul - 1 Aug
(4 bedrooms and 2 full baths; sleeps 11)

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

9.6 out of 10, Exceptional, (40)
"HahahaBut seriously, a great place to stay!"
The price is AED 1,106
AED 2,161 total
includes taxes & fees
3 Aug - 4 Aug
Blue Chill | WalktoBeach | HotTub-all yr | Dogs OK

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

9.8 out of 10, Exceptional, (96)
"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, (19)
"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
9.8 out of 10, Exceptional, (8)
"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

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

10.0 out of 10, Exceptional, (114)
"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!

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

10.0 out of 10, Exceptional, (191)
"Amazing location and such a cute house !"
'Rustic Refined Retreat’ Lakeside Home - Walk to Everything!

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

10.0 out of 10, Exceptional, (166)
"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, (156)
"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

Spacious 4-bedroom Getaway in Portage, Perfect for family get togethers

9.0 out of 10, Wonderful, (2)
"Spacious. Good outdoor area"
Spacious 4-bedroom Getaway in Portage, Perfect for family get togethers

Charming and spacious 3-bedroom townhome with WiFi and amenities in Gary

6.8 out of 10, (6)
"The property itself was ver clean just an older house. Very clean! The neighborhood was a little questionable for families who have never travelex to that area from a rural area. The stay was good and worked for what we needed!"
The price is AED 579
AED 1,323 total
includes taxes & fees
31 Jul - 1 Aug
Charming and spacious 3-bedroom townhome with WiFi and amenities in Gary
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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