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Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct

Browse Select Chesterton Holiday Homes

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

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

9.6 out of 10, Exceptional, (227)
"We enjoyed our stay. Everything was picturesque and would definitely recommend staying here."
Beautiful Family Cottage in Beachwalk-Grill-AC-Free Wifi-Kids Haven.
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, (197)
"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
Huge Family Home w/ Pool - 13 Mi to Lake Michigan!
A heated pool

Huge Family Home w/ Pool - 13 Mi to Lake Michigan!

9.4 out of 10, Exceptional, (44)
"Great and relaxing home"
Huge Family Home w/ Pool - 13 Mi to Lake Michigan!
Lifetime Memories*Big Beach Front House*Fire Place/Pit*Free WiFi*Paddle Boards
Interior

Lifetime Memories*Big Beach Front House*Fire Place/Pit*Free WiFi*Paddle Boards

9.8 out of 10, Exceptional, (141)
"Just perfect!! 4 levels. Plenty of back yard room and the beach was fantastic!!Everything was as stated in information!!Recommend to anybody. !!!"
Lifetime Memories*Big Beach Front House*Fire Place/Pit*Free WiFi*Paddle Boards
Hot tub open all year! Private heated pool, sleeps 10 near downtown New Buffalo!
Outdoor pool, a heated pool

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

9.2 out of 10, Wonderful, (67)
"Had the best weekend at this house. The house was clean, updated, and had everything we could need. Will be staying again. "
Hot tub open all year! Private heated pool, sleeps 10 near downtown New Buffalo!
Adorable cottage in the Michiana Shores area! Close to Lake Michigan and Dunes
Property grounds

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

10.0 out of 10, Exceptional, (77)
"Beautiful home...It was close to all the places we wanted to see."
Adorable cottage in the Michiana Shores area! Close to Lake Michigan and Dunes
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, (103)
"Family enjoyed the stay. Great location "
Modern Farmhouse Retreat-10 Min Walk to Lake Michigan-Hot Tub-Sauna
Kid-friendly Michiana cottage! Summer dates open - including 4th of July!
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (58)
"Loved this place and so clean and perfect for our girls weekend!"
Kid-friendly Michiana cottage! Summer dates open - including 4th of July!
Adorable Downtown Cottage with Firepit, Fireplace, & Yard - Walk Everywhere
Fridge, microwave, oven, stovetop

Adorable Downtown Cottage with Firepit, Fireplace, & Yard - Walk Everywhere

9.6 out of 10, Exceptional, (45)
"This is our second time at Happy Thoughts Cottage. We love the cozy den, front yard for kids to play, and walkability to the main street. "
Adorable Downtown Cottage with Firepit, Fireplace, & Yard - Walk Everywhere
House of TarTar with year long hot tub next to adorable downtown Valparaiso
Terrace/patio

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

10.0 out of 10, Exceptional, (75)
"Love the hot tub! "
House of TarTar with year long hot tub next to adorable downtown Valparaiso
Afterdune Delight NO CLEANING FEES 3 bed 1 bath just steps away from the beach
Private kitchen

Afterdune Delight NO CLEANING FEES 3 bed 1 bath just steps away from the beach

6.0 out of 10, (2)
"We needed a one night stay for a family wedding. It is a mostly quiet neighborhood close to business district. Did hear trains during the night, though. Overall it suited our needs for the night."
The price is £144
includes taxes & fees
4 Sept - 5 Sept
Afterdune Delight NO CLEANING FEES 3 bed 1 bath just steps away from the beach
Downtown 2 BR Cottage w/ King Bed
Fridge, microwave, oven, stovetop

Downtown 2 BR Cottage w/ King Bed

9.6 out of 10, Exceptional, (5)
"Nicely renovated house, comfortable for adults.Perfect for staying in Valpo during graduation weekend. Many thoughtful touches! Highly recommend for low maintenance travelers!"
The price is £248
includes taxes & fees
24 Aug - 25 Aug
Downtown 2 BR Cottage w/ King Bed
Moody Modern Dunes • Hot tub + Beaches & Trails
3 bedrooms, desk, iron/ironing board, travel cot

Moody Modern Dunes • Hot tub + Beaches & Trails

10.0 out of 10, Exceptional, (2)
"Jessica has done a truly outstanding job in providing all the little things for making a great stay. The finishes, kitchen & equipment, towels & bedding and snacks/coffee/spices are all best I have seen through many short-term stays. The unit is in a very central location with access to Chesterton, Valpo, the dunes and all transportation. Thanks Jessica!"
The price is £284
includes taxes & fees
3 Sept - 4 Sept
Moody Modern Dunes • Hot tub + Beaches & Trails
Red Oak-5 bedroom with in ground pool, fireplace-walk to restaurants
Outdoor dining

Red Oak-5 bedroom with in ground pool, fireplace-walk to restaurants

10.0 out of 10, Exceptional, (74)
"This house is a great setup and well taken care of. The owners are very responsive and location is close to everything."
Red Oak-5 bedroom with in ground pool, fireplace-walk to restaurants
Big Family House 5 Minutes from Lake Michigan/Blue Chip Casino/Brewery/Wineries!
Exterior

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

9.8 out of 10, Exceptional, (112)
"The house was super clean and had everything we could have needed! Super nice house for the area and more than enough parking for a large group!"
Big Family House 5 Minutes from Lake Michigan/Blue Chip Casino/Brewery/Wineries!
Steps from the beach! Pet friendly. Awesome amenities and great location.
Miscellaneous

Steps from the beach! Pet friendly. Awesome amenities and great location.

10.0 out of 10, Exceptional, (249)
"We greatly enjoyed our stay! It was perfect for a Spring Break get away. Quiet area, close to the beach/lake, the National and State Parks, and in between the campuses we were touring. The property was in great condition with recent updates and just as listed, Great communication as well!"
Steps from the beach! Pet friendly. Awesome amenities and great location.
Eagles Beach Nest 2:Pet-Friendly*Fenced*Walk2Beach
Fridge, microwave, oven, stovetop

Eagles Beach Nest 2:Pet-Friendly*Fenced*Walk2Beach

10.0 out of 10, Exceptional, (19)
"Quiet area and warmly decorated. "
The price is £372
includes taxes & fees
16 Sept - 17 Sept
Eagles Beach Nest 2:Pet-Friendly*Fenced*Walk2Beach
Brand New House with Hot Tub! Gameroom! Workspace!
Outdoor dining

Brand New House with Hot Tub! Gameroom! Workspace!

2.0 star property
9.4 out of 10, Exceptional, (6)
"Stephanie was a wonderful host! Home was beautiful and something for everyone. Very spacious! Still smells new when we walked in. Would definitely recommend. Would definitely want to come back again "
The price is £398
includes taxes & fees
16 Sept - 17 Sept
Brand New House with Hot Tub! Gameroom! Workspace!
Perfect Family Retreat-Beachwalk-AC-Free WiFi-GolfCart-Grill--Music Lovers-Bikes
Property grounds

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

10.0 out of 10, Exceptional, (103)
"A group of us rented this property to celebrate a co-worker’s retirement. It was the perfect gathering spot! We walked to the beach, hung out around the fire pit, played games, and did lots of karaoke. Such an amazing weekend at a beautiful place!"
Perfect Family Retreat-Beachwalk-AC-Free WiFi-GolfCart-Grill--Music Lovers-Bikes
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, (44)
"The home, property, and location were amazing! It was so peaceful! Everything was very nice and the home was well furnished. I loved my stay and hope to come back!"
Designer Cottage +Guesthouse on large private estate in Grand Beach with Hot Tub
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

Comfort Inn & Suites Porter near Indiana Dunes

Comfort Inn & Suites Porter near Indiana Dunes

10/10 Excellent
"Our bathroom shower and area around it was in bad shape , the shower curtain rod was not attached properly so it was allowing water to leak outside of area and it has been that way for a long time because the damp odor was very prominent!!"
Mark 1-night trip
Posted 1 day ago
Comfort Inn & Suites Porter near Indiana Dunes