Town of Pines holiday homes

We found 677 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:11 Dec - 18 Dec

Beach
Living room with oversized sectional and amazing lake views
Outdoor dining
Private kitchen
Exceptional
(226 reviews)

Amazing Lake Views, Beach Access, Hot Tub, Fire Pit, Screened Porch & Game Room

New Buffalo

13% off
NZ$10,363
for 7 nights, 1 home
NZ$1,480 per night
includes taxes & fees
Amazing Lake Views, Beach Access, Hot Tub, Fire Pit, Screened Porch & Game Room
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$4,548
for 7 nights, 1 cottage
NZ$650 per night
includes taxes & fees
Charming Beach Front Cottages at Duneland Rentals.
Living area
Exterior
Private kitchen
Room
Wonderful
(13 reviews)

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

Michigan City

8% off
NZ$5,252
for 7 nights, 1 home
NZ$750 per night
includes taxes & fees
ND games, lakes, casino, shopping, highways and interstates. Central location
Great living room space with plenty of space to relax.
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
(38 reviews)

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

Michigan City

7% off
NZ$3,350
for 7 nights, 1 home
NZ$479 per night
includes taxes & fees
The 8th Street ART House. Relax and be inspired!
Outdoor dining
Dining
Living area
Room
Exceptional
(13 reviews)

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

New Buffalo

7% off
NZ$7,288
for 7 nights, 1 home
NZ$1,041 per night
includes taxes & fees
Endless Summer Escape, Charming Cottage: 1 blk from beach!
Enjoy endless bike trails starting at the Camper driveway
The Pool Barn Camper sits in the drive of our Pool Barn
Check out the hammock, swings, and tree house
Share time with family and friends around the fire
Very good
(22 reviews)

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

Chesterton

8% off
NZ$1,821
for 7 nights, 1 home
NZ$260 per night
includes taxes & fees
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
The home has tons of real stone on the outside and inside.
Wood burning fireplace, vaulted ceilings and an open concept floorplan.
Huge wraparound porch
Eat-in kitchen
Exceptional
(34 reviews)

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

Michigan City

15% off
NZ$2,907
for 7 nights, 1 home
NZ$415 per night
includes taxes & fees
Private Home w/ Fireplace & Golf Cart on Wooded Lot Near Lake Michigan Beaches
Living area
Lake Kai beach with Yellow Submarine on the right.
Interior
Yellow Submarine from new Clubhouse.
Exceptional
(35 reviews)

The Yellow Submarine in the heart of Beachwalk

Michigan City

8% off
NZ$7,828
for 7 nights, 1 home
NZ$1,118 per night
includes taxes & fees
The Yellow Submarine in the heart of Beachwalk
Room
Terrace/patio
Living area
Property grounds
Exceptional
(29 reviews)

Beautiful Private Cottage, Sleeps 6, Walk to Beach

New Buffalo

9% off
NZ$4,834
for 7 nights, 1 cottage
NZ$691 per night
includes taxes & fees
Beautiful Private Cottage, Sleeps 6, Walk to Beach
Check out the tree house
The "Pool Barn" offers plenty to do inside, outside, and in the area.
Rock on the tree swing and enjoy the view
ONE LARGE ROOM includes 4 beds and all interior amenities
Wonderful
(21 reviews)

The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes

Chesterton

8% off
NZ$3,113
for 7 nights, 1 apartment
NZ$445 per night
includes taxes & fees
The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes
Enjoy your morning coffee/tea/mimosa on the sun porch! 
Great game table!
Beach
Love seat and chair great for your morning beverage!
King bed, two reading lamps, desk, closet with hangers.
Exceptional
(109 reviews)

Just Steps Away from The Beach on Lake Michigan - Sheridan Beach

Michigan City

7% off
NZ$3,902
for 7 nights, 1 home
NZ$557 per night
includes taxes & fees
Just Steps Away from The Beach on Lake Michigan - Sheridan Beach
Comfy living area
Bedroom #1...Queen size bed
Beach
3 unit building steps from the beach path
Exceptional
(53 reviews)

We Have the Beach... Without the Walk!

Michigan City

9% off
NZ$4,099
for 7 nights, 1 apartment
NZ$586 per night
includes taxes & fees
We Have the Beach... Without the Walk!
Room
Interior
Private kitchen
Living area
Exceptional
(29 reviews)

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

Michigan City

8% off
NZ$3,907
for 7 nights, 1 home
NZ$558 per night
includes taxes & fees
Walk to the Beach from Beachy Farmhouse - Lake Michigan & Hot Tub. Pet-Friendly!
Open Concept Living Area
Balcony
Kitchen
Entryway
Wonderful
(24 reviews)

Beach Condo I Steps From Lake Mich

Michigan City

6% off
NZ$1,221
for 7 nights, 1 apartment
NZ$174 per night
includes taxes & fees
Beach Condo I Steps From Lake Mich
Dining Room / Living Room area
Cottages along Lake Kai
Resort Clubhouse
Kitchen
Exceptional
(119 reviews)

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

Michigan City

8% off
NZ$7,146
for 7 nights, 1 home
NZ$1,021 per night
includes taxes & fees
Perfect Family Retreat-Beachwalk-AC-Free WiFi-GolfCart-Grill--Music Lovers-Bikes
Interior
Living area
Exterior
Room
Exceptional
(42 reviews)

Elm Street Retreat - A cozy home all your own!

Michigan City

7% off
NZ$1,496
for 7 nights, 1 home
NZ$214 per night
includes taxes & fees
Elm Street Retreat - A cozy home all your own!
Interior
Living area
Property grounds
Dining
Exceptional
(14 reviews)

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

Michigan City

8% off
NZ$3,337
for 7 nights, 1 apartment
NZ$477 per night
includes taxes & fees
South Wind, walk to the beach, zoo, & more!
Kitchen
Screened-in Porch
Dining Area
Resort Clubhouse
Exceptional
(238 reviews)

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

Michigan City

8% off
NZ$3,510
for 7 nights, 1 home
NZ$501 per night
includes taxes & fees
Family Retreat-Beachwalk-Grill-AC-Free WiFi-Pool Table-Bikes-Grill-Golf Cart
Property grounds
Pool
Private kitchen
Exterior
Exceptional
(57 reviews)

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

Michigan City

8% off
NZ$4,288
for 7 nights, 1 cottage
NZ$613 per night
includes taxes & fees
Sweet Inn Coach House near beautiful beach on Lake Michigan in Beachwalk
Dining
Private kitchen
Living area
Property grounds
Excellent
(60 reviews)

Treehouse Bungalow- Quaint and Cozy Getaway!

Michigan City

7% off
NZ$2,194
for 7 nights, 1 cottage
NZ$313 per night
includes taxes & fees
Treehouse Bungalow- Quaint and Cozy Getaway!
Beach Walk
Private Deck
Kitchen
Queen Size Bedroom
Exceptional
(15 reviews)

Lake Breeze Stylish Beach Boho 1BD w/ Private Deck

Michigan City

6% off
NZ$1,227
for 7 nights, 1 apartment
NZ$175 per night
includes taxes & fees
Lake Breeze Stylish Beach Boho 1BD w/ Private Deck
Resort Pool
Exterior
Resort Clubhouse with Tower
Second upstairs bedroom
Exceptional
(266 reviews)

Beautiful Family Cottage in Beachwalk-Grill-AC-Free Wifi-Kids Haven.

Michigan City

8% off
NZ$2,007
for 7 nights, 1 home
NZ$287 per night
includes taxes & fees
Beautiful Family Cottage in Beachwalk-Grill-AC-Free Wifi-Kids Haven.
Living area
Exterior
Private kitchen
Room
Exceptional
(8 reviews)

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

Chesterton

7% off
NZ$1,729
for 7 nights, 1 home
NZ$247 per night
includes taxes & fees
The Porter Nook! 5 minutes to Indiana Dunes, Pet Friendly
Living area
Property grounds
Exterior detail
Casino
Exceptional
(13 reviews)

NEW Coastal Cottage - 10 Minute WALK to Lake Michigan Beach - Pet Friendly

Michigan City

8% off
NZ$3,144
for 7 nights, 1 home
NZ$449 per night
includes taxes & fees
NEW Coastal Cottage - 10 Minute WALK to Lake Michigan Beach - Pet Friendly
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    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. 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)
  • Oasis Splash Pad (4.4 mi / 7 km)
  • Lyon Oaks Golf Course (9.1 mi / 14.6 km)
  • Legacy Hills Golf Club (11 mi / 17.7 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:

  • Beverly Shores Beach (1.2 mi / 2 km)
  • Central Beach (1.7 mi / 2.7 km)
  • Lake View Beach (1.8 mi / 2.9 km)
  • Kemil Beach (2.5 mi / 4.1 km)
  • Mount Baldy Beach (2.6 mi / 4.2 km)
  • Washington Park Beach (4.4 mi / 7.1 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 best area to stay in Town Of Pines when booking a holiday rental?
When considering a holiday rental in the Town of Pines, Indiana, one of the most appealing areas to stay is the vicinity near Lake Michigan. This charming neighbourhood offers a serene atmosphere, great for those looking to escape the hustle and bustle. The proximity to the lake not only provides stunning views but also access to beautiful beaches, ideal for relaxing or enjoying a variety of water activities.In this area, visitors can explore the nearby Indiana Dunes National Park, which is a top attraction known for its breathtaking natural landscapes and extensive hiking trails. The park features picturesque sand dunes, diverse wildlife, and opportunities for bird watching, making it a fantastic spot for nature enthusiasts. Additionally, the charming local parks provide recreational options for families and solo travellers alike.The Town of Pines boasts a modest number of properties available for holiday rentals, suiting different preferences and budgets. Whether you seek a quaint cottage or a more spacious home, you're likely to find something that suits your needs.
When is the best time to visit Town Of Pines for a holiday rental?
The best time to visit the Town of Pines for a holiday rental is during the vibrant summer months of June to August. This peak season draws holidayers eager to enjoy the warm weather and the area's charming beachside atmosphere. With temperatures typically ranging from 20 to 30 degrees Celsius, it's an ideal time for outdoor activities such as picnicking, hiking, and relaxing by the lake.August stands out as the most popular month, offering a lively ambiance filled with family gatherings and local events. Visitors can take part in the community spirit and take advantage of the numerous outdoor amenities, from scenic nature trails to nearby beaches, superb for a day of sunbathing or swimming.If you're looking for a more budget-friendly option, consider planning your visit in January. While it may be the low season, this month provides a unique opportunity to explore the serene winter landscape and enjoy the quiet charm of the Town of Pines without the crowds.
What are the top attractions in Town Of Pines?
In Town of Pines, Indiana, visitors can appreciate the serene natural beauty and outdoor activities that the area has to offer. The nearby Indiana Dunes National Park is a significant draw, featuring miles of sandy beaches along Lake Michigan, stunning dunes, and various trails for hiking and birdwatching. This national park is ideal for nature enthusiasts and those looking to relax by the lake.Another popular attraction is the picturesque Lake Shore Drive, which provides scenic views of the surrounding landscape and is great for leisurely drives or walks. The community itself is small and charming, making it an excellent spot for a peaceful getaway.
Are all fees included in the Town of Pines 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 Town of Pines holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Town of Pines 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 Town of Pines holiday homes?
You can find great discounts on holiday homes in Town of Pines 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 Town of Pines holiday home booking on Bookabach?
To find Town of Pines 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 Town of Pines?
A long-stay holiday home in Town of Pines 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 Town of Pines holiday home?
Book your Town of Pines 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 Town of Pines?
Prices for holiday homes in Town of Pines 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 Town of Pines 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.