Holiday Rentals in Chesterton

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Holiday Rentals in Chesterton

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

10.0 out of 10, Exceptional, (69)
"."
The price is €310
includes taxes & fees
2 Dec - 3 Dec
Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly

Blue Birdhouse by the Beach

9.2 out of 10, Wonderful, (21)
"We had a fantastic stay at the Blue Birdhouse. Super close to the beach and a very clean little house. Wagners Ribs were walking distance away and delicious food. We had an issue accessing the house that the owner quickly resolved. Great little place. "
The price is €242
includes taxes & fees
3 Dec - 4 Dec
Blue Birdhouse by the Beach

The "Pool Barn Camper" w/Hot Tub near Indiana Dunes

9.8 out of 10, Exceptional, (8)
"Would reserve this again wonderful host"
The price is €109
includes taxes & fees
1 Dec - 2 Dec
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes

VIP! LUXURY 4BD 5min to Lake Michigan beach Big Pool

9.0 out of 10, Wonderful, (16)
"We had a great time (10 of us) staying in this house! The pool was a hit for the kids and adults and we spent a lot of time sitting outside. Super close to the beach. Beds were comfortable and plenty of space for all. The host was helpful and responded quickly. (The road in front of the house is busy and people drive quite fast so just be mindful if you bring pets or little ones!)"
The price is €493
includes taxes & fees
1 Dec - 2 Dec
VIP! LUXURY 4BD 5min to Lake Michigan beach Big Pool

The Neighborhood Hotel - Grand Beach

4.0 star property
9.6 out of 10, Exceptional, (38)
"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

Newly Renovated City Escape with a private hot tub

9.4 out of 10, Exceptional, (31)
"Great location. Nice Place"
Newly Renovated City Escape with a private hot tub

Hot tub and Golf Cart 6 bedrooms plus coach house.

10.0 out of 10, Exceptional, (165)
"As a repeat visitor the home and hospitality offered by our host continues to amaze as the cleanliness and comfort at their home. Enjoyed thoroughly and will be back!!"
Hot tub and Golf Cart 6 bedrooms plus coach house.

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

10.0 out of 10, Exceptional, (176)
"We loved everything about this place. Neighborhood is adorable, house was clean and comfortable. Check-in was easy and communication was great. We had a blast!"
Family Retreat-Beachwalk-Grill-AC-Free WiFi-Pool Table-Bikes-Grill-Golf Cart

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

9.6 out of 10, Exceptional, (207)
"We spent two wonderful days with friends at Indiana Dunes. We loved the house, the village, proximity to the beach, the area restaurants and a winery that was a delight to spend a quiet afternoon at. "
Beautiful Family Cottage in Beachwalk-Grill-AC-Free Wifi-Kids Haven.

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

9.2 out of 10, Wonderful, (52)
"Property was excellent. Beautiful home in a convenient location."
Hot tub open all year! Private heated pool, sleeps 10 near downtown New Buffalo!

BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.

9.4 out of 10, Exceptional, (98)
"The hosts were very communicative and gave good advice for places to check out in the area (some interesting antique shops). The rental is snug, as expected, but the amenities were pleasant and you can’t go wrong with beach access! Would recommend for others interested in checking out the area ."
The price is €241
includes taxes & fees
1 Dec - 2 Dec
BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.

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

10.0 out of 10, Exceptional, (237)
"A short drive from chicago but a perfect escape from the city. Great property for a quick trip with family and our dog to enjoy walks on the beach and s’mores in the backyard. The pool table and air hockey have the teens plenty to do! Would stay here again!"
Steps from the beach! Pet friendly. Awesome amenities and great location.

BEACHFRONT /HOTTUB/STEAM ROOM/GAME ROOM/JACUZZI/PETS/MASSAGE CHAIR/KAYAKS/BIKES

9.6 out of 10, Exceptional, (306)
"We stayed here for the weekend. We are originally from Michigan City and it was great to have a place to stay nearby that was not a hotel. The arcade games were a nice touch. Didn’t get a chance to use the hot tub, but it was an added bonus. Everything was clean and in good working order. Would definitely stay here again! "
BEACHFRONT /HOTTUB/STEAM ROOM/GAME ROOM/JACUZZI/PETS/MASSAGE CHAIR/KAYAKS/BIKES

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

9.8 out of 10, Exceptional, (130)
"The house is amazing! So much space for people to sleep. Everything was clean. The only suggestion that I would have is to have more bar stools to be in the kitchen for people to sit around. I know the island is small but people still always congregate in the kitchen and it would be nice to have more bar stools! "
Lifetime Memories*Big Beach Front House*Fire Place/Pit*Free WiFi*Paddle Boards

Beachfront Villa + Addition, Skyline views, Hot Tubs, Luxury Smart Home

8.8 out of 10, Excellent, (26)
"House was awesome!! Communication was great from beginning to end of our stay!! Loved that we could walk to the beach from the home! The only negative was that the patio over looked a public access parking lot but we loved the house & would rent it again !!"
Beachfront Villa + Addition, Skyline views, Hot Tubs, Luxury Smart Home

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

10.0 out of 10, Exceptional, (74)
"We live in the neighboring town and were looking for a little getaway. This house was perfect for us. We really enjoyed the hot tub and sauna. The outlet mall and lots of nice restaurants close by. The home is beautiful and spacious. Thank you for letting us stay. spacious "
Modern Farmhouse Retreat-10 Min Walk to Lake Michigan-Hot Tub-Sauna

Adorable Cottage New Buffalo, Mi. Near Grand Beach.1 Bedroom, Sleeps 5

9.8 out of 10, Exceptional, (179)
"This was a great little get away for our 21st Anniversary. Very clean and neat. Everything we needed!"
Adorable Cottage New Buffalo, Mi. Near Grand Beach.1 Bedroom, Sleeps 5

Treehouse Bungalow- Quaint and Cozy Getaway!

9.2 out of 10, Wonderful, (44)
"2 of my close friend and I decided to get away for a short stay not too far from home. We had a great relaxing time. This place had everything we needed, short distance from everything. This place was clean and easy to find. The neighborhood felt safe. Even though the place below this apartment looks abandoned."
The price is €264
includes taxes & fees
2 Dec - 3 Dec
Treehouse Bungalow- Quaint and Cozy Getaway!

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

9.8 out of 10, Exceptional, (90)
"We had a perfect stay. Big enough for lots of us, super well taken care of and not too terribly far from campus!"
Big Family House 5 Minutes from Lake Michigan/Blue Chip Casino/Brewery/Wineries!

WEEKEND RESTORATION: Hot Tub - Fire Pit - Walk to Lake Michigan - Grand Beach

9.8 out of 10, Exceptional, (86)
"Place was really lovely, we loved staying here and would absolutely come back. Thanks!"
WEEKEND RESTORATION: Hot Tub - Fire Pit - Walk to Lake Michigan - 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.
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Other types of properties in Chesterton you may be interested in

Spring House Inn

2.5 star property
8.8 out of 10, Excellent, (1091)
"Five Star if you consider price. Very clean. Shows its age in some areas but everything worked well. Breakfast consistent with chains would be nice for groups with nice gathering space Staff friendly and attentive Would recommend and stay again"
The price is €94
includes taxes & fees
1 Dec - 2 Dec
Spring House Inn

Best Western Indian Oak

2.5 star property
8.4 out of 10, Very good, (1095)
"I killed a cockroach in my room. Reported to front desk. "
The price is €95
includes taxes & fees
9 Dec - 10 Dec
Best Western Indian Oak

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

10.0 out of 10, Exceptional, (69)
"."
The price is €310
includes taxes & fees
2 Dec - 3 Dec
Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly
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.

Frequently asked questions

Are there holiday rentals in Chesterton?

Yes, there are holiday rentals close to the most popular sights in Chesterton, or you can select a more secluded option if you're looking for a relaxing stay. Discover why Chesterton is known for its shops and beaches. While you're here, grab a bite or have a drink at the restaurants.

What are some of the best holiday rentals that Chesterton has to offer?

Newly Renovated City Escape with a private hot tub: This holiday home rental outside of Chesterton offers a balcony, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 1 hot tub.

How many holiday rentals are there in Chesterton?

Choose from 28 Expedia holiday rentals in Chesterton for a memorable holiday.

What can I see and do in Chesterton?

Lake Michigan and Indiana Dunes Visitor Center are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Coffee Creek Watershed Conservancy Preserve and Indiana Dunes National Park.

What are holiday rentals like in Chesterton?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chesterton. Holiday rentals offer amenities such as patios, hot tubs and fire pits so you'll be comfy for your stay. If you're concerned about a clean environment, a holiday rental can provide a sense of security away from shared hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for family gatherings.