Chesterton holiday homes

We found 1,336 holiday rentals — enter your dates for availability
Discover a selection of 32 homes and other holiday rentals in Chesterton that are perfect for your trip. Whether you’re staying in a holiday home with a group or just with your pet, you'll find the amenities that you need and want, which might include a fireplace and a washer and dryer. No matter what you're looking for, you're sure to find a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Chesterton

Showing deals for:25 Dec - 1 Jan

All seasons, quaint & cozy and very spacious living and yard area.
cozy living room area seasonal fireplace
Firepit area. Great to relax, fun s'mores & converstions by the fire
master bedroom king large walk in closet
Exceptional
(20 reviews)

FALL for a farm- Campfires, Wildlife, close to Lake, Book Llama programs or Chef

Chesterton

8% off
NZ$5,212
for 7 nights, 1 room
NZ$745 per night
includes taxes & fees
FALL for a farm- Campfires, Wildlife, close to Lake, Book Llama programs or Chef
Stairs going down to the cottage from the road, parking and unloading area.
View of cottage from the beach.
Living area
Dining
Exceptional
(44 reviews)

Charming Beach Front Cottages at Duneland Rentals.

Chesterton

7% off
NZ$4,614
for 7 nights, 1 cottage
NZ$659 per night
includes taxes & fees
Charming Beach Front Cottages at Duneland Rentals.
Private kitchen
Exterior detail
Cottage community pool
Terrace/patio
Exceptional
(87 reviews)

~~~~~Cottage Moe~~~~~

New Buffalo

8% off
NZ$5,649
for 7 nights, 1 cottage
NZ$807 per night
includes taxes & fees
~~~~~Cottage Moe~~~~~
Living room- seating area, TV, gas fire place
Office area- door to the rooftop
Dining room area
Kitchen- stove and island area
Exceptional
(22 reviews)

Rivera House-fun and comfort steps from the beach

Gary

8% off
NZ$6,874
for 7 nights, 1 home
NZ$982 per night
includes taxes & fees
Rivera House-fun and comfort steps from the beach
Living Room
Visit the Blue Chip Casino in Michigan City, just a 6 minute drive away.
El Cantarito off Franklin is some of the best Mexican food in town!
Kitchen
Exceptional
(141 reviews)

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

Michigan City

8% off
NZ$8,128
for 7 nights, 1 home
NZ$1,161 per night
includes taxes & fees
Big Family House 5 Minutes from Lake Michigan/Blue Chip Casino/Brewery/Wineries!
Living area
Terrace/patio
Dining
Pool
Exceptional
(136 reviews)

Salt water Pool.Remodeled 5 bed.4 bath home! Private! Saltwater heated pool open

New Buffalo

8% off
NZ$12,699
for 7 nights, 1 home
NZ$1,814 per night
includes taxes & fees
Salt water Pool.Remodeled 5 bed.4 bath home! Private! Saltwater heated pool open
Living room and dining room are both spacious and comfortable.
The kitchen has a peninsula with counter seating. Great for visiting the chef!
Dining
Great living room space with plenty of space to relax.
Exceptional
(38 reviews)

The 8th Street ART House. Relax and be inspired!

Michigan City

8% off
NZ$3,934
for 7 nights, 1 home
NZ$562 per night
includes taxes & fees
The 8th Street ART House. Relax and be inspired!
Living room in main house
Screened in porch on back deck
Living room in main house
Kitchen and dining room table
Exceptional
(128 reviews)

LUXURY Lakefront Property on Private Beach with Stunning Lake Views and Sunsets

Union Pier

8% off
NZ$29,876
for 7 nights, 1 home
NZ$4,268 per night
includes taxes & fees
LUXURY Lakefront Property on Private Beach with Stunning Lake Views and Sunsets
Room
Outdoor dining
Interior
Living area
Exceptional
(41 reviews)

Cool Beach House - new & improved - 3bd-2 ba

Gary

8% off
NZ$4,018
for 7 nights, 1 home
NZ$574 per night
includes taxes & fees
Cool Beach House - new & improved - 3bd-2 ba
The kitchen has sink, stovetop, microwave, toaster, and Keurig coffee maker
The Pool Barn Camper sits in the drive of our Pool Barn
Share time with family and friends around the fire
Enjoy endless bike trails starting at the Camper driveway
Excellent
(23 reviews)

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

Chesterton

8% off
NZ$1,890
for 7 nights, 1 home
NZ$270 per night
includes taxes & fees
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
Exterior
Property grounds
Private kitchen
Terrace/patio
Exceptional
(88 reviews)

Brand New House, Sleeps 8, Private Beach Rights, Hot Tub!

Lakeside

8% off
NZ$3,299
for 7 nights, 1 home
NZ$471 per night
includes taxes & fees
Brand New House, Sleeps 8, Private Beach Rights, Hot Tub!
Interior
Private kitchen
Property grounds
Living area
Excellent
(60 reviews)

Treehouse Bungalow- Quaint and Cozy Getaway!

Michigan City

8% off
NZ$2,625
for 7 nights, 1 cottage
NZ$375 per night
includes taxes & fees
Treehouse Bungalow- Quaint and Cozy Getaway!
The home has tons of real stone on the outside and inside.
Wood burning fireplace, vaulted ceilings and an open concept floorplan.
Vaulted ceilings, open floorplan, and loft with additional queen bed.
Huge wraparound porch
Exceptional
(35 reviews)

Private Home w/ Fireplace & Golf Cart on Wooded Lot Near Lake Michigan Beaches

Michigan City

15% off
NZ$3,338
for 7 nights, 1 home
NZ$477 per night
includes taxes & fees
Private Home w/ Fireplace & Golf Cart on Wooded Lot Near Lake Michigan Beaches
Dining Room / Living Room area
Cottages along Lake Kai
Resort Clubhouse
Kitchen
Exceptional
(120 reviews)

Perfect Family Retreat-Beachwalk-AC-Free WiFi-GolfCart-Grill--Music Lovers-Bikes

Michigan City

8% off
NZ$7,710
for 7 nights, 1 home
NZ$1,101 per night
includes taxes & fees
Perfect Family Retreat-Beachwalk-AC-Free WiFi-GolfCart-Grill--Music Lovers-Bikes
Comfy sectional and fireplace
Exterior
Open kitchen concept with sectional, great for family gatherings
Merchant Cottage "M"
Exceptional
(65 reviews)

Modern Cottage "M" Luxury home w/hot tub, community pool-walk to town & beach

New Buffalo

9% off
NZ$6,828
for 7 nights, 1 cottage
NZ$975 per night
includes taxes & fees
Modern Cottage "M" Luxury home w/hot tub, community pool-walk to town & beach
Outdoor dining
Private kitchen
Room
Interior
Exceptional
(8 reviews)

Sycamore Suites-Entire Home Steps from Journeyman

Three Oaks

8% off
NZ$4,002
for 7 nights, 1 home
NZ$572 per night
includes taxes & fees
Sycamore Suites-Entire Home Steps from Journeyman
Outdoor dining
Dining
Exterior
Living area
Exceptional
(13 reviews)

Endless Summer Escape, Charming Cottage: 1 blk from beach!

New Buffalo

7% off
NZ$7,393
for 7 nights, 1 home
NZ$1,056 per night
includes taxes & fees
Endless Summer Escape, Charming Cottage: 1 blk from beach!
Living area
Great room, gas fireplace.
Interior
Dining
Wonderful
(93 reviews)

Located in beautiful Union Pier Michigan. Private beach less than 2 blocks away

Union Pier

8% off
NZ$6,852
for 7 nights, 1 home
NZ$979 per night
includes taxes & fees
Located in beautiful Union Pier Michigan. Private beach less than 2 blocks away
This kitchen is what chefs dream about! It has everything you could possibly need for cooking throughout each day of your trip. There is also a grill and solo stove pizza oven available for guest use.
5 bedroom home situated on the Galien River with private beach access, a quick 5 minute walk to the New Buffalo public beach, and walking distance to all downtown restaurants.
Have a wonderful night of rest in this cozy king bed.
Lux Leather Sofa in the Living Room
Exceptional
(8 reviews)

Riverfront Retreat, Hot Tub, Walk to Beach + Downtown, Kayaks & Bikes!

New Buffalo

17% off
NZ$20,035
for 7 nights, 1 home
NZ$2,862 per night
includes taxes & fees
Riverfront Retreat, Hot Tub, Walk to Beach + Downtown, Kayaks & Bikes!
Interior
Private kitchen
Dining
Private kitchen
Exceptional
(25 reviews)

A Beautiful, 5 bedroom home, 5 Minutes from Lake Michigan and pool! Sleeps 20.

Michigan City

8% off
NZ$10,412
for 7 nights, 1 home
NZ$1,487 per night
includes taxes & fees
A Beautiful, 5 bedroom home, 5 Minutes from Lake Michigan and pool! Sleeps 20.
Private kitchen
Terrace/patio
Living area
Dining
Exceptional
(31 reviews)

Charming Victorian, Private Hot Tub

New Buffalo

8% off
NZ$10,885
for 7 nights, 1 home
NZ$1,555 per night
includes taxes & fees
Charming Victorian, Private Hot Tub
Interior
Exterior
Room
Living area
Exceptional
(8 reviews)

The Porter Nook! 5 minutes to Indiana Dunes, Pet Friendly

Chesterton

8% off
NZ$2,706
for 7 nights, 1 home
NZ$387 per night
includes taxes & fees
The Porter Nook! 5 minutes to Indiana Dunes, Pet Friendly
Terrace/patio
Living area
Pool
Dining
Wonderful
(82 reviews)

Hot tub, heated pool, great getaway in New Buffalo

New Buffalo

9% off
NZ$7,896
for 7 nights, 1 home
NZ$1,128 per night
includes taxes & fees
Hot tub, heated pool, great getaway in New Buffalo
Interior
Interior
Property grounds
Room
Exceptional
(11 reviews)

Cozy 3-bedroom 3 bathroom condo with AC, WiFi in charming Miller Beach

Gary

8% off
NZ$5,817
for 7 nights, 1 apartment
NZ$831 per night
includes taxes & fees
Cozy 3-bedroom 3 bathroom condo with AC, WiFi in charming Miller Beach

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    Enjoy full kitchens, laundry, pools, gardens and more

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    More space, more privacy, more amenities — more value

Relaxing Chesterton will entice you

The riverfront, beaches and lake are the perfect backdrop to your holiday home in Chesterton. Travellers to this relaxing city praise the coffee shops, bird watching and shopping. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Sightseeing in and around Chesterton

Are you hoping to discover attractions to see in the city? Venture out of your holiday home and experience everything that makes Chesterton a fun place to get away to. These are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Washington Park Zoo (11.6 mi / 18.6 km)
  • The Course at Aberdeen (11.9 mi / 19.1 km)
  • Deep River Water Park (12.9 mi / 20.8 km)
  • Team Combat LIVE (14.4 mi / 23.1 km)
  • Shady Creek Winery (14.5 mi / 23.3 km)
  • Whittaker Woods Golf Course (19.2 mi / 30.9 km)

Exploring the natural landscape of Chesterton

Travellers enjoy Chesterton for its beaches and lakeside setting. Whether you're looking for adventure or just want to take in the scenery, you'll be sure to find the perfect setting for your holiday in Chesterton. Here are a few of the area's noteworthy sights, all within 30 miles (48.2 km) of the city centre:

  • Indiana Dunes Visitor Center (1.7 mi / 2.7 km)
  • Indiana Dunes National Park (2.7 mi / 4.3 km)
  • Dune Acres Beach (3.5 mi / 5.6 km)
  • Kemil Beach (5.7 mi / 9.1 km)
  • Portage Lakefront Beach (6.2 mi / 9.9 km)
  • Lake View Beach (6.4 mi / 10.3 km)

Seasonal weather in Chesterton

If warm-weather activities are high on your list, July, August, June and September are the hottest months to visit, when temperatures average 21°C.

Transport to and around Chesterton

The nearest airport is in Chicago Midway Airport (MDW), located 37 mi (59.6 km) from the city centre. If you're unable to find a flight that fits your schedule, you can also fly into Chicago O'Hare International Airport (ORD), which is 50.2 mi (80.7 km) away.

Frequently asked questions

What is the best area to stay in Chesterton when booking a holiday rental?
When considering a holiday rental in Chesterton, Indiana, the area around the downtown district is an excellent choice. This charming neighbourhood offers a variety of properties, ranging from cosy cottages to spacious family homes, making it suitable for different group sizes and preferences. Staying here allows easy access to local amenities and eateries, giving you a taste of the community's welcoming atmosphere.One of the top attractions nearby is the Indiana Dunes National Park, renowned for its stunning sandy beaches and scenic trails, superb for outdoor enthusiasts and nature lovers alike. Additionally, the Chesterton European Market, held weekly during the warmer months, showcases local produce, crafts, and food, providing a delightful experience for visitors looking to immerse themselves in the local culture.
Where are the best areas for renting a beach house in Chesterton?
For renting a beach house in Chesterton, Indiana, the best areas to consider are those near the Indiana Dunes National Park, particularly the sections along Lake Michigan. The beaches in this region, such as those at West Beach and Kemil Beach, offer picturesque views and sandy shores, making them popular spots for families and beachgoers alike.In terms of amenities, many beach houses in this area come equipped with features like spacious decks, outdoor grills, and fire pits, great for evening gatherings after a day in the sun. Additionally, properties often include fully equipped kitchens, allowing guests to prepare meals with local ingredients, and comfortable living spaces to relax in after a day of exploration.The nearby town of Chesterton itself offers a quaint atmosphere with local shops and eateries, enhancing the overall experience. Visitors can also take advantage of the scenic hiking trails and wildlife viewing opportunities within the national park.
What is the most popular type of holiday rental accomodation in Chesterton?
In Chesterton, holiday houses are the most popular type of holiday rental, with about 108 available across the area. These spacious homes often feature multiple bedrooms, fully equipped kitchens, and outdoor spaces, making them ideal for families or groups. Many are situated near local attractions such as the Indiana Dunes National Park and the scenic Lake Michigan shoreline.In addition to holiday houses, there are around 32 cottages and 32 apartments that offer a more compact yet comfortable stay. Cottages typically come with rustic charm and may include amenities like fireplaces and gardens, while apartments provide a convenient base with essential amenities for shorter stays. Several mobile homes and cabins are also available, suiting those seeking a great experience in a more natural setting.
Are there any family house rentals in Chesterton?
In Chesterton, Indiana, there are numerous family-friendly house rentals available—specifically, around 37 properties to choose from. The town is known for its charming atmosphere and is conveniently located near attractions like the Indiana Dunes National Park, where families can enjoy outdoor activities such as hiking and beach outings.Many of the homes in Chesterton offer spacious living areas, fully equipped kitchens ideal for preparing family meals, and outdoor spaces superb for children to play. Additional conveniences like Wi-Fi and air conditioning are typically included, ensuring a comfortable stay for all guests.Exploring the local area, visitors can find inviting parks, quaint shops, and delightful dining options.
Can I rent a holiday home with a pool or hot tub in Chesterton?
In Chesterton, Indiana, there are several holiday homes available for rent that feature pools or hot tubs. This charming town, located near the beautiful Indiana Dunes National Park, offers a variety of options for travellers looking to relax and enjoy the outdoors. Many of these properties come with spacious backyards, private pools, and hot tubs, providing ideal settings for families or groups to unwind after a day of exploring.Amenities such as fully equipped kitchens, comfortable living areas, and outdoor dining spaces are commonly found, making these rentals great for both relaxation and entertaining.
Are there pet-friendly house rentals in Chesterton?
In Chesterton, Indiana, there are several pet-friendly house rentals available, providing a welcoming environment for travellers with pets. Many of these homes come equipped with desirable amenities such as spacious backyards, fully equipped kitchens, and comfortable living areas, making them ideal for families or groups.The area is conveniently located near the Indiana Dunes National Park, where you can explore beautiful landscapes and enjoy outdoor activities with your furry companions. The park features walking trails, sandy beaches along Lake Michigan, and picnic areas, allowing for memorable day trips. Additionally, Chesterton has various local parks and pet-friendly cafes, ideal for those travelling with pets.
Are there any remote work holiday rentals in Chesterton?
In Chesterton, Indiana, there are numerous remote work holiday rentals available, with around 176 options to choose from. This charming town offers a variety of properties well-suited for those looking to balance work and leisure. Many rentals feature dedicated workspaces, including desks and comfortable chairs, allowing for a productive environment. High-speed Wi-Fi is often provided, both in the rooms and public areas, ensuring seamless connectivity for remote work.Chesterton is conveniently located near attractions such as the Indiana Dunes National Park, where you can take a break from work to enjoy beautiful sandy beaches and scenic trails. The town itself has a quaint atmosphere, with local shops, restaurants, and parks that provide a pleasant backdrop for your stay. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Chesterton?
In Chesterton, popular rental amenities include well-equipped kitchens, which allow guests to prepare their own meals during their stay. Many properties also feature decks or patios, providing outdoor spaces for relaxation and dining al fresco. Onsite parking is commonly available, making it convenient for those travelling by car. Additionally, rentals often include coffee and tea makers, great for starting the day with a warm beverage.
When is the best time to visit Chesterton for a holiday rental?
The best time to visit Chesterton for a holiday rental is during the peak season from June to August, with July being the most popular month. This vibrant period draws families and outdoor enthusiasts eager to explore the picturesque Indiana Dunes National Park, where sandy beaches and scenic trails offer a wealth of activities.During these summer months, visitors can enjoy warm temperatures averaging between 20 to 30 degrees Celsius, superb for sunbathing, hiking, and taking part in local events like the Chesterton European Market, which showcases regional crafts and cuisine. The lively option during this time enhances the overall holiday experience, making it an ideal choice for those seeking adventure and community engagement.For travellers looking for a more budget-friendly option, consider visiting in December. While this month sees fewer tourists, it provides a unique opportunity to experience Chesterton's charming winter landscape and festive holiday lights. The quieter streets are superb for a peaceful getaway, allowing for cosy evenings in your holiday rental.Ultimately, the choice of when to visit Chesterton will depend on whether you prefer the bustling energy of summer activities or the serene beauty of winter's embrace.
What are the top attractions in Chesterton?
In Chesterton, Indiana, visitors can explore a variety of attractions that highlight the area's natural beauty and local culture. One of the main draws is the Indiana Dunes National Park, where guests can enjoy scenic hiking trails, picturesque beaches along Lake Michigan, and opportunities for birdwatching. This park is superb for those who appreciate outdoor activities and stunning landscapes.The Chesterton European Market, held on Saturdays during the warmer months, offers a vibrant setting with local artisans, fresh produce, and handmade goods, making it a great spot for experiencing local flavours and community spirit.Additionally, the nearby Coffee Creek Watershed Preserve provides serene walking paths and educational opportunities about the local ecosystem, ideal for nature enthusiasts.
Are all fees included in the Chesterton holiday homes prices shown on Bookabach?
Bookabach provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Chesterton holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Chesterton with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Chesterton holiday homes?
You can find great discounts on holiday homes in Chesterton on Bookabach, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Chesterton holiday home booking on Bookabach?
To find Chesterton holiday rentals with free cancellation, just use Bookabach's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Chesterton?
A long-stay holiday home in Chesterton is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Chesterton holiday home?
Book your Chesterton holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Chesterton?
Prices for holiday homes in Chesterton vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Chesterton to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Bookabach as a host?
Joining Bookabach as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.