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Top Holiday Rentals in Town of Pines

The Neighborhood Hotel - Grand Beach

4.0 star property
9.6 out of 10, Exceptional, (55)
"Had a wonderful stay at cottage 13, all necessary amenities were available and nice quaint location. Very nice stay overall. "
The Neighborhood Hotel - Grand Beach

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

10.0 out of 10, Exceptional, (72)
"This house is a great setup and well taken care of. The owners are very responsive and location is close to everything."
Red Oak-5 bedroom with in ground pool, fireplace-walk to restaurants

Walkable cozy cottage, Outlet Mall across street!

9.6 out of 10, Exceptional, (17)
"Loved the cottage it had everything we needed very nice!"
The price is £234
includes taxes & fees
7 Sept - 8 Sept
Walkable cozy cottage, Outlet Mall across street!

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

10.0 out of 10, Exceptional, (108)
"Great location near the beach. Comfortable house and clean with nice amenities. Check in was super easy. "
Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly

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

10.0 out of 10, Exceptional, (193)
"We loved our stay here. I can’t wait to come back in the summer months"
Family Retreat-Beachwalk-Grill-AC-Free WiFi-Pool Table-Bikes-Grill-Golf Cart

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

9.4 out of 10, Exceptional, (116)
"Very nice relaxing stay. "
The price is £183
includes taxes & fees
2 Sept - 3 Sept
BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.

Treehouse Bungalow- Quaint and Cozy Getaway!

8.8 out of 10, Excellent, (49)
"Unsafe parking, uncomfortable couch and beds. We didn’t stay the night due to the poor conditions."
The price is £333
includes taxes & fees
12 Aug - 13 Aug
Treehouse Bungalow- Quaint and Cozy Getaway!

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

10.0 out of 10, Exceptional, (168)
"This property is beautiful with a lot of space, bedrooms, and bathrooms. The location was perfect for walking to the beach, restaurants, and shopping. Can't wait to visit again!"
Warm late summer dates still open in Sept 2025: 1-4, 7-11, 15-19, 21-26. Enjoy!

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

9.0 out of 10, Wonderful, (61)
"We had a fantastic time together."
7 Bedroom Lake Shore Dr. Beach Home - NEWLY BUILT HOME! Steps to the beach!

Kid-friendly Michiana cottage! Summer dates open - including 4th of July!

10.0 out of 10, Exceptional, (56)
"Loved this place and so clean and perfect for our girls weekend!"
Kid-friendly Michiana cottage! Summer dates open - including 4th of July!

Spacious home near nightlife, beaches, dunes, zoo, and Lake Michigan charters.

7.6 out of 10, Good, (22)
"Had a great time and enjoyed our stay "
Spacious home near nightlife, beaches, dunes, zoo, and Lake Michigan charters.

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

8.8 out of 10, Excellent, (10)
"Great pool hostess was very helpful"
The price is £154
includes taxes & fees
21 Aug - 22 Aug
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes

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

9.2 out of 10, Wonderful, (65)
"Had the best weekend at this house. The house was clean, updated, and had everything we could need. Will be staying again. "
Hot tub open all year! Private heated pool, sleeps 10 near downtown New Buffalo!

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

8.6 out of 10, Excellent, (82)
"Great house, beautiful view, very clean"
The price is £474
includes taxes & fees
25 Aug - 26 Aug
View of the lake from 2 decks in this 6BR Lake Shore Dr home, steps to the beach

Juniper Presents: Lakefront Getaway and Outdoor Living Redefined

9.4 out of 10, Exceptional, (100)
"Our family spent the holiday at this incredible house and everything was perfect. We would definitely stay here again and highly recommend it. "
Juniper Presents: Lakefront Getaway and Outdoor Living Redefined

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

9.8 out of 10, Exceptional, (140)
"Just perfect!! 4 levels. Plenty of back yard room and the beach was fantastic!!Everything was as stated in information!!Recommend to anybody. !!!"
Lifetime Memories*Big Beach Front House*Fire Place/Pit*Free WiFi*Paddle Boards

3BR Condo Close To The Beach! In/OutDoor Pools

10.0 out of 10, Exceptional, (96)
"Lovely condo in great location"
3BR Condo Close To The Beach! In/OutDoor Pools

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

10.0 out of 10, Exceptional, (209)
"We had a great stay; the layout was great for our family vacation."
Amazing Lake Views, Beach Access, Hot Tub, Fire Pit, Screened Porch & Game Room

Newely Remodeled Studio!

9.0 out of 10, Wonderful, (15)
"This was a perfect spot for an easy no frills stay"
The price is £131
includes taxes & fees
7 Sept - 8 Sept
Newely Remodeled Studio!

Charming 1-bedroom apt in house by creek with AC, in delightful Portage

10.0 out of 10, Exceptional, (4)
"Easy check in and wonderful host. Great place to stay near Indiana Dunes and train station to Chicago. "
Charming 1-bedroom apt in house by creek with AC, in delightful Portage
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

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?

Red Oak-5 bedroom with in ground pool, fireplace-walk to restaurants : This holiday home rental outside of Town of Pines is located on a lake, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 5 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 patio, a terrace and a garden so that you can immerse yourself in your holiday.

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

With 5 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.