Search Vacation Homes in Chesterton

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
21 Rab. I - 23 Rab. I
In two weeks
28 Rab. I - 30 Rab. I
In one month
11 Rab. II - 13 Rab. II
In two months
9 Jum. I - 11 Jum. I

Compare 635 Vacation Homes in Chesterton with updated reviews, rates, and availability.

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, (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
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, (82)
"Beautiful dream home!!! Perfect place to spend the weekend with the girls! Fun hot tub, cute sauna, fun games, & everything was very clean! (there’s an amazing winery 5 min away, huge bonus!!) We’ll be coming back for sure in the summer!! :) "
Modern Farmhouse Retreat-10 Min Walk to Lake Michigan-Hot Tub-Sauna
Journey To Valpo | Home Near Downtown!
Interior

Journey To Valpo | Home Near Downtown!

9.8 out of 10, Exceptional, (22)
"The home provided enough sleeping quarters and the layout was perfect for entertaining for Christmas. I conquered at the ping pong table. Yea Dad. "
Journey To Valpo | Home Near Downtown!
Miller Beach Blue Door By The Shore #2
Beach

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
"The Nook"- ROOMY Home 2mi- Dunes & Chesterton, Yard, Fire Pit, Grill, Game Room
Exterior

"The Nook"- ROOMY Home 2mi- Dunes & Chesterton, Yard, Fire Pit, Grill, Game Room

10.0 out of 10, Exceptional, (70)
"The Nook was the perfect place to rest and hangout for a wedding weekend. It is beautiful, spacious, well equipped with everything we needed. We loved the large kitchen where everyone gathered and the private game room was so fun! We would definitely stay here again and highly recommend."
"The Nook"- ROOMY Home 2mi- Dunes & Chesterton, Yard, Fire Pit, Grill, Game Room
Serene Wooded Home w/ Private Hot Tub, Firepit & Porch, Dog-Friendly
Outdoor spa tub

Serene Wooded Home w/ Private Hot Tub, Firepit & Porch, Dog-Friendly

2.0 star property
9.8 out of 10, Exceptional, (10)
"Our second stay this year and it’s a wonderful place to get away. So many amenities, the only downfall we had tbi"
Serene Wooded Home w/ Private Hot Tub, Firepit & Porch, Dog-Friendly
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, (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
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, (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
Modern Farmhouse - steps from downtown!! Stay 2-nights, get 1 free thru March!!
Beach nearby, sun loungers, beach towels

Modern Farmhouse - steps from downtown!! Stay 2-nights, get 1 free thru March!!

10.0 out of 10, Exceptional, (161)
"The house was brilliant, extremely clean and close to everything. Geoff was a great host and was always helpful and quick at responding to any questions. Would 100% recommend! House was decorated beautifully for the holidays-thank you for making Christmas memories for me and my family. "
Modern Farmhouse - steps from downtown!! Stay 2-nights, get 1 free thru March!!
INCREDIBLE Lake and City views, Open 4 bed 5 bath 5 min to sand, sleeps 14 to 17
Smart TV, fireplace, printers

INCREDIBLE Lake and City views, Open 4 bed 5 bath 5 min to sand, sleeps 14 to 17

10.0 out of 10, Exceptional, (2)
"We had a wonderful stay - house was beautiful and extremely clean. The views were really amazing - day and night. The layout of the house was great with the bedrooms upstairs (all with attached bathrooms) and the living space downstairs. Sunsets from the patio were awesome. Way more to do in the area than we had imagined. Great experience for all of us."
INCREDIBLE Lake and City views, Open 4 bed 5 bath 5 min to sand, sleeps 14 to 17
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, (59)
"Such a cute house and great hot tub - we really enjoyed our stay!"
cozy home with hot tub next to downtown Valparaiso
Fall Getaway: Downtown New Buffalo Suite w King Beds!
TV

Fall Getaway: Downtown New Buffalo Suite w King Beds!

10.0 out of 10, Exceptional, (5)
"Great spot and really clean "
The price is SAR 844
SAR 1,463 total
includes taxes & fees
13 Mar - 14 Mar
Fall Getaway: Downtown New Buffalo Suite w King Beds!
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, (210)
"Just a quick weekend with my family. We had a wonderful time, my kids had fun playing board games and watching movies with their cousins. We walked to the beach, although, it was cold but it was lovely. It was definitely a wonderful trip. Would do it again. "
Beautiful Family Cottage in Beachwalk-Grill-AC-Free Wifi-Kids Haven.
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!
Perfect Location Great Price All Year Long! You'll Love This Beautiful Home!
Fridge, microwave, oven, stovetop

Perfect Location Great Price All Year Long! You'll Love This Beautiful Home!

10.0 out of 10, Exceptional, (41)
"This property was exactly what we were looking for! The open floor plan and beautiful fire pit made for the perfect fall weekend - just a 10-15min walk to the beach/city center. We plan to stay again!"
Perfect Location Great Price All Year Long! You'll Love This Beautiful Home!
The Whit: Spring Into Comfort with Poolside Views and Nearby Beaches
Fridge, microwave, oven, stovetop

The Whit: Spring Into Comfort with Poolside Views and Nearby Beaches

9.4 out of 10, Exceptional, (8)
"wonderful fall weekend in a place I love to visit. "
The Whit: Spring Into Comfort with Poolside Views and Nearby Beaches
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, (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!
'Rustic Refined Retreat’ Lakeside Home - Walk to Everything!
Beach nearby, sun loungers, beach towels

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

10.0 out of 10, Exceptional, (185)
"Wonderful home in a great location. The house has everything you need, well appointed and walking distance to the beach and town. Communication was very good, What few questions we had were quickly answered. We would definitely stay here again on future visits to New Buffalo."
'Rustic Refined Retreat’ Lakeside Home - Walk to Everything!
Pet-Friendly Lake Getaway: 1 Block to Beach!
Fridge, microwave, stovetop, dishwasher

Pet-Friendly Lake Getaway: 1 Block to Beach!

10.0 out of 10, Exceptional, (34)
"Property was very clean and photos accurate. Check in process was easy and we enjoyed a quick fall weekend get away to hike the Dunes. Good communication from owner. Thanks!"
Pet-Friendly Lake Getaway: 1 Block to Beach!
View of the lake from 2 decks in this 6BR Lake Shore Dr home, steps to the beach
TV, fireplace, books, stereo

View of the lake from 2 decks in this 6BR Lake Shore Dr home, steps to the beach

9.0 out of 10, Wonderful, (74)
"The house was clean and quite adequate for our 3 day stay. We met Mr. Marshall when we arrived (he was there with a crew working on furniture and some repairs). He was very pleasant, as was the crew. We like to cook for ourselves. The stove was not completely functional -- shelves do not fit, and the interior needs a good cleaning. The towel rack above the second floor bathroom toilet is pulling of the wall and could use some attention. Rick Ginther (for the Ginther Siblings)"
The price is SAR 1,497
SAR 3,017 total
includes taxes & fees
20 Mar - 21 Mar
View of the lake from 2 decks in this 6BR Lake Shore Dr home, steps to 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.
Don't see what you're looking for?
See all available properties in Chesterton
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Chesterton

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

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

10.0 out of 10, Exceptional, (83)
"Our stay at this Vrbo was absolutely incredible! The home was cozy, very clean, and had everything we needed for a relaxing getaway. The large windows offered breathtaking views of Lake Michigan, and even though the lake was partially frozen, it was still beautiful to see. The peaceful winter scenery made our stay even more special.The location was perfect—just a short drive to plenty of hiking trails, which were not only stunning but also very dog-friendly! Our pup loved exploring alongside us,...
The price is SAR 750
SAR 1,197 total
includes taxes & fees
12 Mar - 13 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
Beach nearby

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

9.0 out of 10, Wonderful, (51)
"Nice quiet an around everything "
The price is SAR 296
SAR 416 total
includes taxes & fees
13 Mar - 14 Mar
Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes
Dunes Home 3 Bedroom I 2 BHR I 2 Living rooms Home | Valpo University | Dunes
Fridge, microwave, oven, stovetop

Dunes Home 3 Bedroom I 2 BHR I 2 Living rooms Home | Valpo University | Dunes

9.8 out of 10, Exceptional, (51)
"This quaint house was perfectly located for attending the Trojan Classic showchoir competition. Plenty of room and nicely equipped. Though it was too cold to use the backyard it looked very nice."
The price is SAR 319
SAR 1,165 total
includes taxes & fees
16 Mar - 17 Mar
Dunes Home 3 Bedroom I 2 BHR I 2 Living rooms Home | Valpo University | Dunes
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.