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Compare 754 Vacation Homes in Chesterton with updated reviews, rates, and availability.

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

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

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

10.0 out of 10, Exceptional, (83)
"We stay at a lot of VRBOs. This property was superior to most! The house is modern and aesthetically beautiful with a very well thought out design. There are many little additions, like houseplants that really made it feel homey, extra bedding, plush towels, etc. Our favorite features were the spacious kitchen (well stocked with gadgets and cookware), hot tub, outdoor patio, indoor sauna, large table for meals and games. The property is close to restaurants, casinos and shopping, which we...
Modern Farmhouse Retreat-10 Min Walk to Lake Michigan-Hot Tub-Sauna

Modern Farmhouse steps from downtown! Here comes summer!

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! Here comes summer!

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

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

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

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!

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!

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!

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

10.0 out of 10, Exceptional, (71)
"We thoroughly enjoyed our stay at the Nook. It had everything and more that we needed. Game room was super fun. Close to Porter Beach, and would love to return during summer to use bikes to head to beach. Thank you for your hospitality! "
"The Nook"- ROOMY Home 2mi- Dunes & Chesterton, Yard, Fire Pit, Grill, Game Room

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!

Sister Shores Sheridan Beach House

8.4 out of 10, Very Good, (16)
"The property was just as displayed, the manager was great at providing check-in instructions and followed up upon check-in. The location is perfect with a quick five-minute walk to the beach, next to Dune Billie's delicious breakfast/lunch restaurant and walking distance to parks and other restaurants. The only minor complaint is that the neighbors were loud with a party outside past midnight, but maybe that doesn't happen often. We hope to return soon! "
The price is SAR 1,688
SAR 2,882 total
includes taxes & fees
22 Mar - 23 Mar
Sister Shores Sheridan Beach House

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 1,455 total
includes taxes & fees
23 Mar - 24 Mar
Fall Getaway: Downtown New Buffalo Suite w King Beds!

Valpo's Journey Home on Center

10.0 out of 10, Exceptional, (1)
"We stayed at this property as a family while we were visiting for a celebration of life. It is a great home in a good location. We will definitely book this property again!"
Valpo's Journey Home on Center

New Private Pool Opening May 2023, Hot Tub, Renovated Home, Ping Pong Table!

9.8 out of 10, Exceptional, (124)
"They make good use of the entire property. Very well located in New Buffalo. "
New Private Pool Opening May 2023, Hot Tub, Renovated Home, Ping Pong Table!

5 BR, 5.5 BATH lux home w private hot tub and assoc pool. Short stroll to beach

10.0 out of 10, Exceptional, (124)
"Had a wonderful time at an absolutely beautiful house with 14 of our closest friends. The decor was wonderfully designed and implemented. We loved sitting by the fire in the outdoor living space and catching up. Easy trip to South Bend for the ND game. Will be back again."
5 BR, 5.5 BATH lux home w private hot tub and assoc pool. Short stroll to beach

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

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

9.6 out of 10, Exceptional, (39)
"Cottage was adorable and very clean. We enjoyed the fireplace and the view of the backyard. Cottage was comfortable and charming. "
Adorable Downtown Cottage with Firepit, Fireplace, & Yard - Walk Everywhere

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
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

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

10.0 out of 10, Exceptional, (85)
"Great beach location near the park. The cabin had terrific views, an open floor plan, and everything we needed. Will was a wonderful host, and we enjoyed our stay :) Looking forward to coming back."
The price is SAR 806
SAR 1,273 total
includes taxes & fees
30 Mar - 31 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

9.0 out of 10, Wonderful, (51)
"Nice quiet an around everything "
The price is SAR 255
SAR 370 total
includes taxes & fees
26 Mar - 27 Mar
Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes

The Neighborhood Hotel - Grand Beach

4.0 star property
9.4 out of 10, Exceptional, (40)
"Overall the place is wonderful and we enjoyed the amenities. My teenaged boys enjoyed the game room, pool at night, beach, fire pit. I loved the bed, having a kitchenette, and the coffeemaker. Much better than a typical hotel version. I’d caution using suite 10 for more than two people. The sleeper was what you’d expect a sleeper to be - not comfortable! The bed is amazing though. The bathroom could use more hooks for drying beachwear. I think instructions or information in general could be...
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.