Chesterton holiday rentals

We found 1,320 holiday rentals — enter your dates for availability
Discover a selection of 33 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:6 Nov - 13 Nov

Private kitchen
Pool
Dining
Living area
Exceptional
(128 reviews)

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

New Buffalo

9% off
AU$9,604
for 7 nights, 1 home
AU$1,372 per night
includes taxes & fees
Salt water Pool.Remodeled 5 bed.4 bath home! Private! Saltwater heated pool open
Private kitchen
Point of interest
Living room
Living area
Exceptional
(85 reviews)

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

New Buffalo

8% off
AU$4,566
for 7 nights, 1 cottage
AU$652 per night
includes taxes & fees
~~~~~Cottage Moe~~~~~
Dining
View of cottage from the beach.
Living area
Dining
Exceptional
(43 reviews)

Charming Beach Front Cottages at Duneland Rentals.

Chesterton

8% off
AU$3,657
for 7 nights, 1 cottage
AU$522 per night
includes taxes & fees
Charming Beach Front Cottages at Duneland Rentals.
View of the private beach from the backyard deck
Back deck
Front of main house
Back of main house
Exceptional
(126 reviews)

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

Union Pier

9% off
AU$16,645
for 7 nights, 1 home
AU$2,378 per night
includes taxes & fees
LUXURY Lakefront Property on Private Beach with Stunning Lake Views and Sunsets
Interior
Gazebo area overlooking pool
Private commercial size pool
Newly renovated kitchen
Exceptional
(103 reviews)

HEATED POOL OPEN oversized private pool downtown New Buffalo!

New Buffalo

9% off
AU$4,728
for 7 nights, 1 home
AU$675 per night
includes taxes & fees
HEATED POOL OPEN oversized private pool downtown New Buffalo!
Living area
Exterior detail
Living area
Living area
Exceptional
(103 reviews)

Charming Three Oaks Cottage - dog friendly with a fenced yard and hot tub!

Three Oaks

12% off
AU$2,496
for 7 nights, 1 cottage
AU$357 per night
includes taxes & fees
Charming Three Oaks Cottage - dog friendly with a fenced yard and hot tub!
Private pool and hot tub
Private pool and hot tub
Pool
Private pool and hot tub
Exceptional
(31 reviews)

Spacious 5 bedroom home with private pool, hot tub & 10 minute walk to the beach

New Buffalo

8% off
AU$6,806
for 7 nights, 1 home
AU$972 per night
includes taxes & fees
Spacious 5 bedroom home with private pool, hot tub & 10 minute walk to the beach
The beach is a 15 minute walk away
Vaulted ceilings, open floorplan, and loft with additional queen bed.
Very private with no neighbors on either side of the house.
Huge wraparound porch
Exceptional
(34 reviews)

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

Michigan City

15% off
AU$2,720
for 7 nights, 1 home
AU$389 per night
includes taxes & fees
Private Home w/ Fireplace & Golf Cart on Wooded Lot Near Lake Michigan Beaches
1st Fl. Great room
'Serendipity' Front of House
Rear View - Outdoor deck, hot tub, outdoor shower and gas barbecue grill.
Entryway Foyer
Exceptional
(133 reviews)

Beautifully Decorated Home W / Hot Tub, Very Close to Beach, Large Wooded Lot

Union Pier

9% off
AU$7,662
for 7 nights, 1 home
AU$1,095 per night
includes taxes & fees
Beautifully Decorated Home W / Hot Tub, Very Close to Beach, Large Wooded Lot
Open living/dining area where everyone can gather! Large windows face the beach
Front entry. Walkway around to back deck. View of 2nd floor screened porch.
Front of house. Bistro table out front for morning coffee.
Back deck with grill and a small backyard space.
Exceptional
(57 reviews)

Just Steps to the Sands of Lake Michigan! Sleeps 18

Michigan City

12% off
AU$9,025
for 7 nights, 1 home
AU$1,289 per night
includes taxes & fees
Just Steps to the Sands of Lake Michigan! Sleeps 18
Living room and dining room are both spacious and comfortable.
Great living room space with plenty of space to relax.
Living room has a bar cabinet with wine and cocktail glasses.
Living room details.
Exceptional
(35 reviews)

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

Michigan City

7% off
AU$2,769
for 7 nights, 1 home
AU$396 per night
includes taxes & fees
The 8th Street ART House. Relax and be inspired!
Kitchen
Quintessential Cottage - Memories Are Made Here
Welcome
Dining room
Exceptional
(103 reviews)

2 blocks to the beach and pet friendly.. Memories are Made Here

Union Pier

12% off
AU$4,400
for 7 nights, 1 cottage
AU$629 per night
includes taxes & fees
2 blocks to the beach and pet friendly.. Memories are Made Here
This is the second master bedroom in the house. It has a large en-suite bathroom with a waterfall shower, dual sinks, and a bidet!
Experience the Lighthouse with all of its amenties including a hot tub, boat dock, large patio, game room, kayaks & SUP, bikes, EV charger, rent a boat & more!
The Lighthouse is walkable to the private or public beach. You can also arrive in style to Lake Michigan by boating down the Galien River.
1 of 2 Master bedrooms! This Master has a king size Tempur-Pedic bed with the ability for each person to adjust their side of the bed. There is a small, private ensuite bathroom plus access to the back patio!
Exceptional
(7 reviews)

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

New Buffalo

8% off
AU$15,281
for 7 nights, 1 home
AU$2,183 per night
includes taxes & fees
Riverfront Retreat, Hot Tub, Walk to Beach + Downtown, Kayaks & Bikes!
Private kitchen
Property grounds
Beach
Private kitchen
Exceptional
(10 reviews)

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

Gary

8% off
AU$4,437
for 7 nights, 1 apartment
AU$634 per night
includes taxes & fees
Cozy 3-bedroom 3 bathroom condo with AC, WiFi in charming Miller Beach
There is also a full bed next to the bathroom/shower
The Pool Barn Camper sits in the drive of our Pool Barn
The tip out provides extra room inside for the kitchen and couch/sleeper
The master bedroom has a queen bed
Wonderful
(18 reviews)

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

Chesterton

8% off
AU$2,095
for 7 nights, 1 home
AU$299 per night
includes taxes & fees
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
Living area
Exterior
Terrace/patio
Interior detail
Exceptional
(12 reviews)

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

New Buffalo

7% off
AU$6,011
for 7 nights, 1 home
AU$859 per night
includes taxes & fees
Endless Summer Escape, Charming Cottage: 1 blk from beach!
Living area
House is located on a double lot, lots of yard space.
Exterior
Great room, gas fireplace.
Wonderful
(89 reviews)

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

Union Pier

8% off
AU$5,151
for 7 nights, 1 home
AU$736 per night
includes taxes & fees
Located in beautiful Union Pier Michigan. Private beach less than 2 blocks away
Lake Kai beach with Yellow Submarine on the right.
Screened porch view of Lake Kai
Exterior
Front entrance. Street parking for 2 cars.
Exceptional
(33 reviews)

The Yellow Submarine in the heart of Beachwalk

Michigan City

8% off
AU$6,305
for 7 nights, 1 home
AU$901 per night
includes taxes & fees
The Yellow Submarine in the heart of Beachwalk
Indoor Porch 1
Pool
Entrance
Living area
Exceptional
(53 reviews)

Close To Beach ~ Private Lovely Pool ~ Family-Friendly Vacation Getaway!

Union Pier

8% off
AU$5,606
for 7 nights, 1 home
AU$801 per night
includes taxes & fees
Close To Beach ~ Private Lovely Pool ~ Family-Friendly Vacation Getaway!
Private kitchen
Gazebo overlooking pool
Private oversized heated commercial size pool
Living room with smart tv, Queen sofa bed
Exceptional
(34 reviews)

HEATED POOL OPEN. Blue Heron Private Retreat in heart of New Buffalo

New Buffalo

9% off
AU$5,766
for 7 nights, 1 home
AU$824 per night
includes taxes & fees
HEATED POOL OPEN. Blue Heron Private Retreat in heart of New Buffalo
Terrace/patio
Living area
Exterior
Property grounds
Exceptional
(13 reviews)

Modern Oasis • 2 blocks to Beach • Rooftop Terrace

Gary

8% off
AU$3,116
for 7 nights, 1 home
AU$445 per night
includes taxes & fees
Modern Oasis • 2 blocks to Beach • Rooftop Terrace
Exterior
☀️
Outdoor dining
Exterior
Exceptional
(7 reviews)

Blocks from the beach with giant covered deck, firepit, and grill!

Gary

8% off
AU$2,283
for 7 nights, 1 apartment
AU$326 per night
includes taxes & fees
Blocks from the beach with giant covered deck, firepit, and grill!
Exterior
Exterior
Living area
Exterior
Exceptional
(28 reviews)

Charming Victorian, Private Hot Tub

New Buffalo

8% off
AU$8,841
for 7 nights, 1 home
AU$1,263 per night
includes taxes & fees
Charming Victorian, Private Hot Tub
Large screen porch with table and fold-flat couches.
Living room with leather sectional sofa, wood-burning fireplace and streaming tv
45-ft long heated pool and hot tub for guests to use. Open all year.
Fire pit with Adirondack chairs. Weber gas grill, picnic table, free firewood.
Exceptional
(36 reviews)

Creekside House on 30 Acres with Kayaks/Pool/Farm/River/Trails/Pets, near Beach

Union Pier

8% off
AU$6,207
for 7 nights, 1 home
AU$887 per night
includes taxes & fees
Creekside House on 30 Acres with Kayaks/Pool/Farm/River/Trails/Pets, near Beach

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    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. Take in top local attractions such as Indiana Dunes National Park and Lake Michigan. 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)
  • Turkey Creek Golf Course (16.4 mi / 26.4 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 National Park (2.7 mi / 4.3 km)
  • Indiana Dunes Visitor Center (1.7 mi / 2.7 km)
  • Dune Acres Beach (3.5 mi / 5.6 km)
  • Kemil Beach (5.7 mi / 9.1 km)
  • Dunbar Beach (6 mi / 9.7 km)
  • Portage Lakefront Beach (6.2 mi / 9.9 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 most popular type of holiday home accommodation in Chesterton?
According to our research, houses are the most sought-after type of holiday property in Chesterton. But that goes without saying, everyone's idea of an epic trip isn't the same. Stayz has holiday homes of all sizes, shapes and budgets, so you're bound to find the perfect fit for you.
How much does it cost to rent a holiday home in Chesterton?
Length of stay, property type and season are some of the things that can affect the price of a holiday home. Simply click on your dates of travel to find your ideal match. From comfy cottages to expansive villas, all Stayz holiday homes provide amazing value.
How much does it cost to rent a beach house in Chesterton?
Prices for beach houses in Chesterton may vary depending on the size and type of the property and when you plan to travel. Simply enter your dates of travel into Stayz and how many guests to view your holiday home options and prices. From there you can use our filter tool to tailor your search by ratings, nearby activities, amenities and more.
Are there pet-friendly holiday homes in Chesterton?
Yes. You'll have a choice of 17 holiday homes that roll out the welcome mat in Chesterton on Stayz. Our furry companions also deserve a getaway, so simply use our search function for pet-friendly holiday homes to book a perfect pad where Spot can join in the fun.
What are popular home amenities in Chesterton?
Some of the most popular home amenities people are searching for in Chesterton include a barbecue grill, nearby museums and a garden. Whether you're hitting the road with family, buddies or even pets, Stayz holiday homes come with the best amenities for hanging out with the people you love.
Are there large group holiday homes in Chesterton?
With 11 Chesterton holiday homes that can host a group of five or more people, you can bring a few extra pals or family members along. Whether you're planning an informal get-together or a birthday party, Stayz will help you find a comfy space for the occasion.
Are there holiday homes in Chesterton that welcome kids?
Gather your whole family for a fun-packed adventure in Chesterton at one of our 17 family-friendly holiday properties. Many of these stays come with amenities that are ideally suited to getaways with children, including kitchens, living rooms and entertainment units. Simply check the "Properties good for families" filter box and pick out your favourite.
What are the top attractions for families in Chesterton?
You'll find loads of exciting things to do and see with the family in Chesterton, including:
  • Lake View Beach
  • Portage Lakefront Beach
  • Dune Acres Beach
Are there one-bedroom holiday homes in Chesterton?
Chesterton has two one-bedroom homes available. Often located in desirable areas due to their smaller size, a one-bedroom holiday home is great if you're travelling with your partner or a buddy. And with home comforts such as full kitchens and more privacy than a standard hotel, you'll be able to kick back and relax while exploring this awesome destination.
Can I find two-bedroom holiday homes in Chesterton?
You can select from five two-bedroom holiday homes in Chesterton. Settle the kids into the second room or fill it with a couple of your best friends. There's space for whoever's lucky enough to be coming along for the ride.
Are there holiday homes with WiFi in Chesterton?
There are seven holiday homes with WiFi in Chesterton. If you want to disconnect from the world on your break, but still need to be connected to the web, these getaways are just what you need. Narrow your search by applying the WiFi filter on Stayz.
How can I find holiday homes with air conditioning in Chesterton?
Chesterton has 17 holiday homes where you can chill out in air-conditioned comfort. To book a property on Stayz that comes with this amenity, enter your dates of travel and use the handy filters to select the "air conditioning" box.
How old do you have to be to rent a holiday home in Chesterton?
The minimum age is usually 16, 18 or 21. It can differ from property to property on Stayz, so look at the rules of your chosen Chesterton holiday home before booking your stay.
How long can I rent a holiday home in Chesterton for?
It's really down to the Chesterton property. To look over a list of options offering extended stays, just type your travel dates and number of people into the Stayz search page. You can enjoy having the entire place to yourself, along with home comforts like a kitchen, air conditioning and outdoor spaces where the kids can run and play. Keep an eye out for any long-term stays that offer discounted weekly or monthly prices.

More holiday ideas