Town of Pines Holiday Rentals

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Holiday Rentals in Town of Pines

The Neighborhood Hotel - Grand Beach

4.0 star property
New Buffalo
9.6 out of 10, Exceptional, (64)
"Great stay for a large family, stayed in the 3 bedroom suite. "
United States
Mario-Julie
The Neighborhood Hotel - Grand Beach

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

Michigan City
9.6 out of 10, Exceptional, (121)
"the house was very spacious and clean. "
United States
Haley G.
Big Family House 5 Minutes from Lake Michigan/Blue Chip Casino/Brewery/Wineries!

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

Michigan City
9.6 out of 10, Exceptional, (243)
"We enjoyed our stay. Everything was picturesque and would definitely recommend staying here."
United States
Carrie H.
Beautiful Family Cottage in Beachwalk-Grill-AC-Free Wifi-Kids Haven.

Red Oak-5 bedroom with in ground pool, fireplace-walk to restaurants

New Buffalo
10.0 out of 10, Exceptional, (79)
"Our stay at Red Oak was wonderful! The house was beautiful! Mary was an excellent host!"
United States
Kelly D.
Red Oak-5 bedroom with in ground pool, fireplace-walk to restaurants

Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly

Porter Beach
10.0 out of 10, Exceptional, (129)
"Awesome location and view. lots of beach amenities and everything you need to have fun. The only thing I would like are better bigger beds. "
United States
Chris W.
Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly

BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.

Michigan City
9.4 out of 10, Exceptional, (125)
"The location was PERFECT. Just a 5 minute walk down a sandy path to a beautiful beach and Lake Michigan! The tiny cottage was perfect for two people. The bed however is very very hard. If you’re young you’d be okay, but us older folks don’t do well on firm beds lolOther than that our weekend stay was perfect!"
United States
Natasha W.
The price is NZ$316
includes taxes & fees
13 Nov - 14 Nov
BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.

Lifetime Memories*Big Beach Front House*Fire Place/Pit*Free WiFi*Paddle Boards

Michigan City
9.8 out of 10, Exceptional, (149)
"My family has rented this property for a number of years now and always enjoy our time. Plenty of space and amenities for all. We were blessed with great weather, which always adds to vacation time. We will do it again!"
United States
Mari S.
Lifetime Memories*Big Beach Front House*Fire Place/Pit*Free WiFi*Paddle Boards

Lakefront! Secluded, HotTub, Fire Pit, Private Dock&boats 90 Min from Chicago

Union Pier
10.0 out of 10, Exceptional, (133)
"Very comfortable, steps to a dock, use of canoe, fishing, hot tub, Firepit for roasting marsh mellows. Very pleasant stay."
United States
Kenneth
Lakefront! Secluded, HotTub, Fire Pit, Private Dock&boats 90 Min from Chicago

Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes

Chesterton
8.8 out of 10, Excellent, (89)
"I stayed one night in this apartment and had a great experience. The town is cute, the location is perfect, just a short drive from the Indiana Dunes, and the place was clean and convenient for a quick trip. The host communicated clearly and promptly, which made everything easy. Highly recommend!"
United States
Megan M.
The price is NZ$198
includes taxes & fees
13 Nov - 14 Nov
Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes

Hot tub open all year! Private heated pool, sleeps 10 near downtown New Buffalo!

New Buffalo
9.2 out of 10, Wonderful, (70)
"Great backyard space to hang out. Awesome location to walk and explore the area and an easy drive to other spots along the lake. The few minor issues we had were quickly communicated and addressed with the owner, so the trip went on without a hitch."
United States
Laura P.
Hot tub open all year! Private heated pool, sleeps 10 near downtown New Buffalo!

Charming & cozy in-town retreat in the heart of New Buffalo

Downtown New Buffalo
10.0 out of 10, Exceptional, (167)
"What a perfect getaway! The house was spotless, super comfy, and in the best location. Our two dogs were in heaven with the fenced yard, and we all loved the dog beach at Warren Dunes just 20 minutes away. So many little touches made our stay extra special. We can’t wait to come back!"
United States
Enid H.
Charming & cozy in-town retreat in the heart of New Buffalo

VIP! LUXURY 4BD 5min to Lake Michigan beach Big Pool with heater!!

Michigan City
8.8 out of 10, Excellent, (23)
"Good location great pool host was nice to deal with. Had a good time"
United States
T H.
The price is NZ$919
includes taxes & fees
13 Nov - 14 Nov
VIP! LUXURY 4BD 5min to Lake Michigan beach Big Pool with heater!!

Warm late summer dates still open in Sept 2025: 1-4, 7-11, 15-19, 21-26. Enjoy!

Downtown New Buffalo
10.0 out of 10, Exceptional, (182)
"Great house for our family! It was clean and spacious and very convenient to everything fun in New Buffalo!"
United States
Amelia F.
Warm late summer dates still open in Sept 2025: 1-4, 7-11, 15-19, 21-26. Enjoy!

2 miles from Dunes National Park. A Unique Boutique Hotel.

Chesterton
9.0 out of 10, Wonderful, (4)
"Great Vrbo! Very nice, very clean, enough room for everyone! We loved it!"
United States
Val S.
The price is NZ$2,770
includes taxes & fees
16 Nov - 17 Nov
2 miles from Dunes National Park. A Unique Boutique Hotel.

Sand & Sun Getaway | 4BR w/ Game Room + 2 Living Areas |Game Room | Minutes to Beach

Michigan City
9.4 out of 10, Exceptional, (30)
"Nice"
United States
Maryellen W.
The price is NZ$624
includes taxes & fees
17 Nov - 18 Nov
Sand & Sun Getaway | 4BR w/ Game Room + 2 Living Areas |Game Room | Minutes to Beach

View of the lake from 2 decks in this 6BR Lake Shore Dr home, steps to the beach

Michigan City
8.6 out of 10, Excellent, (87)
"The house is 1930,s. Plenty of room for a large family. Six bedrooms were adequate! Negative- 30 steps to climb to access the house. Some repair and updating is needed."
United States
Lois W.
The price is NZ$1,422
includes taxes & fees
4 Dec - 5 Dec
View of the lake from 2 decks in this 6BR Lake Shore Dr home, steps to the beach

7 Bedroom Lake Shore Dr. Beach Home - NEWLY BUILT HOME! Steps to the beach!

Michigan City
9.0 out of 10, Wonderful, (64)
"We were a large group- 5 families. We all fit in the house with plenty of room. Kitchen and eating area work well for big meals. Beach access was perfect. House is a little run down, but all just cosmetic and what I expect from a vacation rental. I would rent again."
United States
Eliza B.
7 Bedroom Lake Shore Dr. Beach Home - NEWLY BUILT HOME! Steps to the beach!

Beach house with Private Heated Pool, Jacuzzi, Firepit. Steps to beach and park.

New Buffalo
9.4 out of 10, Exceptional, (12)
"We were pleased with all amenities at the house. Wish beach on Lake Michigan had been easier to access."
United States
Glenda F.
Beach house with Private Heated Pool, Jacuzzi, Firepit. Steps to beach and park.

On Lake Shore Drive, Across St From Beach & Beach Stop, Lake MI Views

Michigan City
9.6 out of 10, Exceptional, (75)
"Fabulous, private, quiet. Two minute walk to beach (literally). Well outfitted kitchen. Favorite spot was the porch! Everything needed for a beach vacation was provided. Throughly and absolutely enjoyed our stay. "
United States
Katie M.
The price is NZ$901
includes taxes & fees
20 Nov - 21 Nov
On Lake Shore Drive, Across St From Beach & Beach Stop, Lake MI Views

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

Michigan City
10.0 out of 10, Exceptional, (204)
"Super host, great amenities and really nice home for 6 adults and 4 children. "
United States
Judith M.
Family Retreat-Beachwalk-Grill-AC-Free WiFi-Pool Table-Bikes-Grill-Golf Cart
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Town of Pines Hotel Reviews

Find out more about Town of Pines

Everything you need to know about Town of Pines holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Town of Pines holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Town of Pines holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Town of Pines holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Town of Pines. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Town of Pines holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Town of Pines holiday rentals we have selected for you start as low as NZ$198 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Town of Pines rentals

At Expedia, we put the best Town of Pines holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Town of Pines rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Town of Pines holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Town of Pines. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Town of Pines?

Yes, there are holiday rentals close to the most popular sights in Town of Pines, or you can select a more secluded option if you're looking for a relaxing stay. Town of Pines is known for its beaches.

What are some of the best holiday rentals that Town of Pines has to offer?

Big Family House 5 Minutes from Lake Michigan/Blue Chip Casino/Brewery/Wineries!: This holiday home rental outside of Town of Pines is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Town of Pines?

With 6 Expedia holiday rentals, you're guaranteed to find just the right place for your Town of Pines stay.

What can I see and do in Town of Pines?

Explore the area and family-friendly sights such as Washington Park Zoo, or get out into nature at a spot like Indiana Dunes National Park. Beverly Shores Beach and Central Beach are a couple of places you'll find in the wider area.

What are holiday rentals like in Town of Pines?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Town of Pines. Holiday rentals offer amenities such as WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of seclusion away from shared hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive choice for family trips or small group gatherings.