Town of Pines holiday rentals

We found 652 holiday rentals — enter your dates for availability
Discover a selection of 8 homes and other holiday rentals in Town of Pines that are perfect for your trip. Holiday rentals offer the amenities that you expect for your stay with friends, family or just your pet, such as Wi-Fi and a washer and dryer. You'll be able to choose a property to rent for everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Town of Pines

Showing deals for:13 Nov - 20 Nov

Stairs going down to the cottage from the road, parking and unloading area.
View of cottage from the beach.
Dining
Living area
Exceptional
(43 reviews)

Charming Beach Front Cottages at Duneland Rentals.

Chesterton

8% off
AU$3,652
for 7 nights, 1 cottage
AU$522 per night
includes taxes & fees
Charming Beach Front Cottages at Duneland Rentals.
Living Room
Visit the Blue Chip Casino in Michigan City, just a 6 minute drive away.
Leeds Public House located in Downtown Michigan City
Kitchen
Exceptional
(135 reviews)

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

Michigan City

8% off
AU$4,660
for 7 nights, 1 home
AU$666 per night
includes taxes & fees
Big Family House 5 Minutes from Lake Michigan/Blue Chip Casino/Brewery/Wineries!
Living area
Exterior
Room
Private kitchen
Wonderful
(12 reviews)

ND games, lakes, casino, shopping, highways and interstates. Central location

Michigan City

8% off
AU$4,218
for 7 nights, 1 home
AU$603 per night
includes taxes & fees
ND games, lakes, casino, shopping, highways and interstates. Central location
Dining room open to kitchen and seating areas.
2nd floor screened in deck. Glimpses of the lake from here.
Lake view from queen rm.  You can see the beach path at the end of the street
Comfy living room area w TV.  Hallway to 1st fl. master bedroom in background
Exceptional
(59 reviews)

Just Steps to the Sands of Lake Michigan! Sleeps 18

Michigan City

12% off
AU$9,012
for 7 nights, 1 home
AU$1,287 per night
includes taxes & fees
Just Steps to the Sands of Lake Michigan! Sleeps 18
The home has tons of real stone on the outside and inside.
Wood burning fireplace, vaulted ceilings and an open concept floorplan.
Eat-in kitchen
Huge wraparound porch
Exceptional
(34 reviews)

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

Michigan City

15% off
AU$2,717
for 7 nights, 1 home
AU$388 per night
includes taxes & fees
Private Home w/ Fireplace & Golf Cart on Wooded Lot Near Lake Michigan Beaches
Room
Dining
Living area
Exterior
Exceptional
(12 reviews)

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

New Buffalo

8% off
AU$5,918
for 7 nights, 1 home
AU$845 per night
includes taxes & fees
Endless Summer Escape, Charming Cottage: 1 blk from beach!
Interior
Lake Kai beach with Yellow Submarine on the right.
Yellow Submarine from new Clubhouse.
Loft with 2 twin beds.
Exceptional
(33 reviews)

The Yellow Submarine in the heart of Beachwalk

Michigan City

8% off
AU$6,296
for 7 nights, 1 home
AU$899 per night
includes taxes & fees
The Yellow Submarine in the heart of Beachwalk
Living room and dining room are both spacious and comfortable.
The kitchen has a peninsula with counter seating. Great for visiting the chef!
Beautiful garden and side yard. Great for traveling with pets.
Dining
Exceptional
(36 reviews)

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

Michigan City

7% off
AU$2,766
for 7 nights, 1 home
AU$395 per night
includes taxes & fees
The 8th Street ART House. Relax and be inspired!
Enjoy endless bike trails starting at the Camper driveway
The Pool Barn Camper sits in the drive of our Pool Barn
The kitchen has sink, stovetop, microwave, toaster, and Keurig coffee maker
Share time with family and friends around the fire
Excellent
(20 reviews)

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

Chesterton

8% off
AU$2,092
for 7 nights, 1 home
AU$299 per night
includes taxes & fees
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
Property grounds
Terrace/patio
Private kitchen
Room
Exceptional
(29 reviews)

Beautiful Private Cottage, Sleeps 6, Walk to Beach

New Buffalo

9% off
AU$3,879
for 7 nights, 1 cottage
AU$554 per night
includes taxes & fees
Beautiful Private Cottage, Sleeps 6, Walk to Beach
Beach
Bedroom #1...Queen size bed
Fully equipped kitchen
3 unit building steps from the beach path
Exceptional
(52 reviews)

We Have the Beach... Without the Walk!

Michigan City

9% off
AU$4,132
for 7 nights, 1 apartment
AU$590 per night
includes taxes & fees
We Have the Beach... Without the Walk!
Dining Room with seating for 8.
Spacious wrap around deck w/ new dining table and furniture in 2022
Living room with fireplace and television (cable and amazon fire stick)
Kitchen with doorway to deck with gas Weber grill
Exceptional
(68 reviews)

Charming Beachfront Home w/huge backyard, walk over dune to the beach!

Michigan City

8% off
AU$6,424
for 7 nights, 1 home
AU$918 per night
includes taxes & fees
Charming Beachfront Home w/huge backyard, walk over dune to the beach!
Private kitchen
Interior
Room
Living area
Exceptional
(28 reviews)

Walk to the Beach from Beachy Farmhouse - Lake Michigan & Hot Tub. Pet-Friendly!

Michigan City

8% off
AU$3,199
for 7 nights, 1 home
AU$457 per night
includes taxes & fees
Walk to the Beach from Beachy Farmhouse - Lake Michigan & Hot Tub. Pet-Friendly!
Children’s area
Property grounds
Private kitchen
Room
Exceptional
(7 reviews)

Villa Vesta-Newly renovated and furnished, Pet friendly, hot tub Lake Retreat

Michigan City

12% off
AU$3,417
for 7 nights, 1 home
AU$488 per night
includes taxes & fees
Villa Vesta-Newly renovated and furnished, Pet friendly, hot tub Lake Retreat
Entryway
Balcony
Open Concept Living Area
Outside of Home in Winter
Wonderful
(22 reviews)

Beach Condo I Steps From Lake Mich

Michigan City

6% off
AU$1,040
for 7 nights, 1 apartment
AU$149 per night
includes taxes & fees
Beach Condo I Steps From Lake Mich
Private kitchen
Living area
Room
Interior
Exceptional
(41 reviews)

Elm Street Retreat - A cozy home all your own!

Michigan City

7% off
AU$1,317
for 7 nights, 1 home
AU$188 per night
includes taxes & fees
Elm Street Retreat - A cozy home all your own!
Interior
Living area
Private kitchen
Property grounds
Exceptional
(14 reviews)

South Wind, walk to the beach, zoo, & more!

Michigan City

8% off
AU$2,753
for 7 nights, 1 apartment
AU$393 per night
includes taxes & fees
South Wind, walk to the beach, zoo, & more!
Terrace/patio
Pool
Exterior
Private kitchen
Exceptional
(54 reviews)

Sweet Inn Coach House near beautiful beach on Lake Michigan in Beachwalk

Michigan City

8% off
AU$3,511
for 7 nights, 1 cottage
AU$502 per night
includes taxes & fees
Sweet Inn Coach House near beautiful beach on Lake Michigan in Beachwalk
Property grounds
Private kitchen
Living area
Dining
Excellent
(58 reviews)

Treehouse Bungalow- Quaint and Cozy Getaway!

Michigan City

7% off
AU$1,969
for 7 nights, 1 cottage
AU$281 per night
includes taxes & fees
Treehouse Bungalow- Quaint and Cozy Getaway!
Exterior
Screened-in Porch
Dining Area
Resort Clubhouse
Exceptional
(232 reviews)

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

Michigan City

8% off
AU$2,643
for 7 nights, 1 home
AU$378 per night
includes taxes & fees
Family Retreat-Beachwalk-Grill-AC-Free WiFi-Pool Table-Bikes-Grill-Golf Cart
Dining
Interior
Living area
Exterior
Excellent
(19 reviews)

2 BD Condo I Steps From Lake Mich

Michigan City

6% off
AU$1,084
for 7 nights, 1 apartment
AU$155 per night
includes taxes & fees
2 BD Condo I Steps From Lake Mich
Private kitchen
Exterior
Interior
Living area
Excellent
(5 reviews)

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

Chesterton

8% off
AU$1,600
for 7 nights, 1 home
AU$229 per night
includes taxes & fees
The Porter Nook! 5 minutes to Indiana Dunes, Pet Friendly
Private kitchen
Exterior
Interior
Dining
Exceptional
(43 reviews)

Uptown Penthouse on Pine: By Lake Michigan, Shopping & Casino!

Michigan City

7% off
AU$2,114
for 7 nights, 1 apartment
AU$302 per night
includes taxes & fees
Uptown Penthouse on Pine: By Lake Michigan, Shopping & Casino!
Dining
Outdoor dining
Exterior
Private kitchen
Wonderful
(20 reviews)

Collect Moments Not Things

Michigan City

12% off
AU$2,419
for 7 nights, 1 home
AU$346 per night
includes taxes & fees
Collect Moments Not Things
  • 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

The natural setting of Town of Pines is ready to explore

The wildlife and beaches create a pretty picture of Town of Pines. One of the city's many top draws is its bird watching. Indiana Dunes State Park and Indiana Dunes National Park are just a couple of the must-see attractions in the area. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Activities and attractions in Town of Pines

Are you searching for attractions to see in the area? Venture out of your cosy holiday rental and experience everything that makes Town of Pines a one-of-a-kind holiday spot. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Washington Park Zoo (4.3 mi / 6.9 km)
  • Shady Creek Winery (7.4 mi / 12 km)
  • Whittaker Woods Golf Course (12 mi / 19.3 km)
  • Local (13.9 mi / 22.3 km)
  • Oasis Splash Pad (4.4 mi / 7 km)
  • Lyon Oaks Golf Course (9.1 mi / 14.6 km)

Exploring the natural landscape of Town of Pines

Whether you're an active traveller or just want to take in the scenery, Town of Pines is a great place to get out in nature. Here are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Indiana Dunes National Park (5.8 mi / 9.3 km)
  • Beverly Shores Beach (1.2 mi / 2 km)
  • Lake View Beach (1.8 mi / 2.9 km)
  • Dunbar Beach (2.2 mi / 3.5 km)
  • Kemil Beach (2.5 mi / 4.1 km)
  • Mount Baldy Beach (2.6 mi / 4.2 km)

How to get to and around Town of Pines

Fly into Chicago Midway Airport (MDW), the closest airport, located 40.9 mi (65.8 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could book a flight to Chicago O'Hare International Airport (ORD), which is 52.7 mi (84.8 km) away.

Frequently asked questions

What is the most popular type of holiday home accommodation in Town of Pines?
Based on our research, houses are considered the most popular property type in Town of Pines. But naturally, everyone's idea of an epic stay can differ. Stayz has holiday homes of all shapes, sizes and budgets, and we'll help you find the perfect fit.
How much does it cost to rent a holiday home in Town of Pines?
The average price for a holiday home in Town of Pines depends on several factors, like property type, length of stay and season. Whether you'd like a villa with space for extended family or a quaint cabin just enough for two, just add your travel dates to see stays with unbeatable value.
How much does it cost to rent a beach house in Town of Pines?
Prices for beach houses in Town of Pines can differ depending on the size and style of the property and when you plan to travel. All you need to do is enter your travel dates into Stayz and the number of guests to view your options and prices. From there you can use our filters to narrow your search results by nearby activities, ratings, amenities and more.
What are popular home amenities in Town of Pines?
The most popular home amenities people are searching for in Town of Pines include a barbecue grill, a firepit and a garden. Whether you're travelling with friends, family or even pets, Stayz holiday homes provide the best amenities for beginning new traditions with the people that matter most.
What are the top attractions for families in Town of Pines?
There are plenty of fun things to see and do with the family in Town of Pines, such as:
  • Lake View Beach
  • Washington Park Beach
  • Washington Park Zoo
How old do you have to be to rent a holiday home in Town of Pines?
The minimum age is generally 16, 18 or 21. It can change from one property to another on Stayz, so look at the rules of your chosen Town of Pines holiday home before booking.
How long can I rent a holiday home in Town of Pines for?
The length of time you can rent a holiday home in Town of Pines varies according to the property. Just enter your chosen travel dates to see a list of options offering extended stays. With loads of amenities like laundries and air conditioning, as well as some offering weekly or monthly discounted prices, you're sure to discover someplace just right to call your home away from home in Town of Pines.