Chesterton Holiday Rentals

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Holiday Rentals in Chesterton

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

9.0 out of 10, Wonderful, (65)
"Great location "
The price is AU$171
includes taxes & fees
27 July - 28 July
Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes

Blue Birdhouse - No Cleaning Fee - Pet Friendly - Dunes National Park

9.2 out of 10, Wonderful, (22)
"Our family had a wonderful time staying and making memories at the bluebird house. The house was very inviting and precious. Would def visit again."
The price is AU$437
includes taxes & fees
11 Aug - 12 Aug
Blue Birdhouse - No Cleaning Fee - Pet Friendly - Dunes National Park

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

8.8 out of 10, Excellent, (10)
"Great pool hostess was very helpful"
The price is AU$315
includes taxes & fees
15 July - 16 July
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes

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

10.0 out of 10, Exceptional, (106)
"Bright, cleam and welcoming. The view of the lake and beach access makes it the perfect getaway."
The price is AU$728
includes taxes & fees
3 Aug - 4 Aug
Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly

2 miles from Dunes National Park. A Unique Boutique Hotel.

8.0 out of 10, Very good, (2)
"Beautiful historic building. "
The price is AU$2,757
includes taxes & fees
14 July - 15 July
2 miles from Dunes National Park. A Unique Boutique Hotel.

The Neighborhood Hotel - Grand Beach

4.0 star property
9.6 out of 10, Exceptional, (53)
"Great hotel. Firepits, common area, s’mores bar and a great patio too. Within walking distance of the beach and you’ll get to see deer too. "
The Neighborhood Hotel - Grand Beach

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

10.0 out of 10, Exceptional, (69)
"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

Treehouse Bungalow- Quaint and Cozy Getaway!

8.8 out of 10, Excellent, (49)
"House was clean, cute, in a great location. Would recommend and stay here again. "
The price is AU$731
includes taxes & fees
4 Aug - 5 Aug
Treehouse Bungalow- Quaint and Cozy Getaway!

Downtown Getaway 1

8.8 out of 10, Excellent, (20)
"The apartment was conveniently located near the Indiana dunes, shopping, and restaurants."
The price is AU$266
includes taxes & fees
13 July - 14 July
Downtown Getaway 1

NEW! Charming 3-Bedroom Hideaway in the Heart of Michigan City!

NEW! Charming 3-Bedroom Hideaway in the Heart of Michigan City!

On Lake Minnehaha, The Funky Turtle @ Lakeshore Camp Resort with all the Campground Amenities!

1.0 star property
8.0 out of 10, Very good, (1)
"We had a great stay at the Funky Turtle. The house was clean and just enough space for my family of 5. The house is close to campground bathrooms if the occasional extra bathroom is needed. We enjoyed the fire pit, use of the grill, and sitting on the porch. Our only complaint is about the noise but it was clear from the map that the campground was located near an interstate. While sitting outside you can hear the noise from the interstate and close by trains. However, inside was much...
The price is AU$516
includes taxes & fees
28 July - 29 July
On Lake Minnehaha, The Funky Turtle @ Lakeshore Camp Resort with all the Campground Amenities!

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!

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

9.4 out of 10, Exceptional, (112)
"It was quiet and clean and very enjoyable for me and my fiance! Will be going again!"
The price is AU$427
includes taxes & fees
21 July - 22 July
BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.

Walkable cozy cottage, Outlet Mall across street!

9.6 out of 10, Exceptional, (17)
"Loved the cottage it had everything we needed very nice!"
The price is AU$463
includes taxes & fees
4 Aug - 5 Aug
Walkable cozy cottage, Outlet Mall across street!

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.

Cozy New Buffalo cottage with hot tub & fire pit. Short walk to downtown!

10.0 out of 10, Exceptional, (38)
"The home was perfect. Right near the downtown area. Had everything you needed. And super cozy!!"
Cozy New Buffalo cottage with hot tub & fire pit. Short walk to downtown!

'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!

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

Stunning Large 6 Room Rental 1000sq ft.

2.0 star property
6.0 out of 10, (2)
"Our stay here was wonderful!! It is a beautiful space. I love antiques charm- this place had it all. Beautiful wood, comfy furniture. Our host even left snacks and drinks for us! It was quiet and comfortable. Communication was great and check-in was super easy. I wish we were able to get there early enough to enjoy the restaurant downstairs. You would never even know it is there- quiet and no smell of food in the apartment. I absolutely plan to book again either for a ND game or a...
The price is AU$442
includes taxes & fees
23 July - 24 July
Stunning Large 6 Room Rental 1000sq ft.

Secluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park

8.2 out of 10, Very good, (35)
"The yard is awesome, of course the hot tub at the top of the hill was the best, and we enjoyed the firepit as well. The house was a tidy little cottage at which we enjoyed our stay. It’s within a short walk to the National Park and downtown Miller Beach. The neighborhood is fine, pretty secluded, and still close to most attractions."
Secluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park
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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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?

Blue Birdhouse - No Cleaning Fee - Pet Friendly - Dunes National Park: This highly rated holiday home rental in Chesterton offers a patio, a private garden and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. You and your friends and family can relax into your holiday with amenities such as a selection of books.

How many holiday rentals are there in Chesterton?

Choose from 29 Expedia holiday rentals in Chesterton for a memorable holiday.

What can I see and do in Chesterton?

Indiana Dunes National Park and Lake Michigan are a couple of scenic spots to enjoy the outdoors, whereas Chesterton Art Center is one of the cultural attractions. Other places in town to visit include Lustron House and Indiana Dunes Visitor Center.

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.