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Holiday homes in Chesterton You’ll Love

Top-Rated Chesterton Holiday homes for Every Budget and Style!

Looking for a holiday home in Chesterton (Indiana)? Browse a wide range of vacation rentals – from cozy retreats to spacious family homes – starting at just $50.00 per night. Whether you are planning a weekend getaway or a longer stay, you will find the perfect home away from home in the heart of Chesterton.

We found 11 Holiday-homes in Chesterton and the surrounding area (within 40 miles)

Indiana Vacation Rental Near Lake Michigan in Valparaiso, USA

Indiana Vacation Rental Near Lake Michig...

Holiday home in Valparaiso near Chesterton, Indiana
Indiana Vacation Rental Near Lake Michigan offers accommodations in Valparaiso, 13 miles from Deep River Waterpark.
  • Parking
  • Pets allowed

Good 4 Reviews 7.2

from $217.65 Show details »

Roomy Retreat-Family & Friends 2 King Bed Game Room in Chesterton, USA

Roomy Retreat-Family & Friends 2 King Be...

Holiday home in Chesterton, Indiana , 130 Washington Avenue
Roomy Retreat-Family & Friends 2 King Bed Game Room offers accommodations in Chesterton, 11 miles from Valparaiso University: Brauer Museum of Art and...
  • Parking
  • Pets allowed
  • Bar
  • Family rooms

Fabulous 6 Reviews 8.8

from $266.46 Show details »

Cozy Abode about 3 Mi to Indiana Dunes Natl Park in Chesterton, USA

Cozy Abode about 3 Mi to Indiana Dunes N...

Holiday home in Chesterton, Indiana
Cozy Abode about 3 Mi to Indiana Dunes Natl Park offers accommodations in Chesterton, 22 miles from Deep River Waterpark.
  • Parking

Exceptional 4 Reviews 9.8

from $356.96 Show details »

Charming Chesterton Home with Idyllic Location! in Chesterton, USA

Charming Chesterton Home with Idyllic Lo...

Holiday home in Chesterton, Indiana
Charming Chesterton Home with Idyllic Location! offers accommodations in Chesterton, 20 miles from Deep River Waterpark.
  • Parking

Exceptional 1 Reviews 10.0

from $261.12 Show details »

Modern 2BR Near Indiana Dunes, Beaches, Wineries, & downtown Chesterton in Porter, USA

Modern 2BR Near Indiana Dunes, Beaches,...

Holiday home in Porter near Chesterton, Indiana , 1913 Broadway Avenue
Modern 2BR Near Indiana Dunes, Beaches, Wineries, & downtown Chesterton offers accommodations in Porter, 13 miles from Valparaiso University: Brauer M...
  • Parking
  • Family rooms

Exceptional 2 Reviews 9.5

from $70.00 Show details »

Dunes Home 3 Bedroom I 2 Baths I 2 Living rooms in Chesterton, USA

Dunes Home 3 Bedroom I 2 Baths I 2 Livin...

Holiday home in Chesterton, Indiana , 105 West Michigan Avenue
Featuring a garden, Dunes Home 3 Bedroom I 2 Baths I 2 Living rooms offers accommodations in Chesterton.
  • Parking
  • Pets allowed

Very good 28 Reviews 8.2

from $151.98 Show details »

Blue Birdhouse by the Beach in Chesterton, USA

Blue Birdhouse by the Beach

Holiday home in Chesterton, Indiana , 5 West Beam Street
With free private parking, the property is 14 miles from Valparaiso University: Brauer Museum of Art and 18 miles from Deep River Waterpark.
  • Parking
  • Pets allowed

Exceptional 32 Reviews 9.5

from $114.61 Show details »

Serenity on the Shores in Portage, USA

Serenity on the Shores

Holiday home in Portage near Chesterton, Indiana , 6069 South Dune Harbor Drive
1.8 miles from Ogden Dunes Beach in Portage, Serenity on the Shores features accommodations with access to a fitness center.
  • Parking
  • Pets allowed
  • Bar
  • Fitness centre
  • Family rooms

Exceptional 19 Reviews 9.7

from $239.99 Show details »

Unique! Retro 1950s wooded retreat near Indiana Dunes National Park in Chesterton, USA

Unique! Retro 1950s wooded retreat near...

Holiday home in Chesterton, Indiana , 1835 Riverline Drive
Offering a bar, Unique!
  • Parking
  • Bar
  • Family rooms

Exceptional 2 Reviews 10.0

from $662.57 Show details »

Heart of Indiana Dunes National Park, Hot Tub in Chesterton, USA

Heart of Indiana Dunes National Park, Ho...

Holiday home in Chesterton, Indiana , 1835 Riverline Drive
Featuring a garden, Heart of Indiana Dunes National Park, Hot Tub features accommodations in Chesterton.

no reviews

from $247.43 Show details »

Econo Lodge Portage in Portage, USA

Econo Lodge Portage

Lodge in Portage near Chesterton, Indiana , 6101 Melton Road, Bldg A
Located in Portage in the Indiana region, Econo Lodge Portage provides accommodations with free WiFi and free private parking.
  • Parking
  • Pets allowed

Disappointing 122 Reviews 4.9

from $56.17 Show details »

Number of Holiday homes in Chesterton 11
Number of guest ratings 1,173
Average price per night $505.00
Lowest price per night $50,00
Highest price per night $3.939,67

Top 10 Cheapest Holiday-homes in Chesterton

Discover the Cheapest Holiday-homes in Chesterton – Ranked by Lowest Nightly Rates.

Top 10 Most Booked Holiday-homes in Chesterton

Check out the Most Booked Holiday-homes in Chesterton – Based on Guest Popularity.

Holiday homes in Chesterton (Indiana), comfortable and familiar

Staying in a holiday or vacation home in Chesterton can be a great alternative to a hotel or resort. They can range from small cottages to luxurious villas, and are often located in popular tourist destinations such as beaches or mountains. One of the main benefits is the privacy and flexibility that comes with having your own space. Unlike a hotel room, a holiday home provides you with a living area, kitchen, and sometimes even outdoor space, allowing you to cook your own meals, relax in comfort, and enjoy the company of your friends or family without the interruptions of other guests.

Holiday homes often offer more space than a hotel room. This can be particularly useful for families or groups of friends traveling together, who may need more than one room or want to avoid the cramped feeling of a single hotel room. They can also provide a more authentic travel experience, allowing guests to immerse themselves in the local culture and lifestyle. This can be particularly appealing for those who prefer to stay in quieter, residential areas away from the hustle and bustle of tourist hotspots.

Find the best Holiday home in Chesterton for your needs

Holiday homes should offer a comfortable and enjoyable stay, providing all the necessary amenities and conveniences to make your vacation experience memorable. At a minimum, your holiday home in Chesterton should offer a clean and well-maintained living space with comfortable furnishings, adequate lighting, and climate control.

In addition to basic amenities such as a fully equipped kitchen, comfortable bedding, and clean linens and towels, holiday homes should also offer modern conveniences such as Wi-Fi, cable or streaming TV, and laundry facilities. A private outdoor space, such as a balcony or terrace, can also add to the overall enjoyment. They can also offer additional features such as a swimming pool, hot tub, or outdoor grill. Location is also important, for example, close to popular tourist attractions, restaurants and shopping areas.

Accommodation data and pictures provided by Booking.com