A calm river with a bridge, surrounded by autumn-colored trees and a dock with boats.

Holiday Homes in Lakeside

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Lakeside holiday homes

A modern kitchen with white cabinetry, stainless steel appliances, and a dining area with a wooden table and chairs.

1. Sq Toe`s Last Resort:Pet-Friendly*Fenced* GameRoom

Sq Toe`s Last Resort:Pet-Friendly*Fenced* GameRoom
New Buffalo
9.8 out of 10, Exceptional, (19 reviews)
"Host was responsive and communicative. Place was exactly as pictured and described. Great location. Amazing garage. "
United States
Scott W.
The price is NZ$1,066
includes taxes & fees
15 Sept - 16 Sept
Sq Toe`s Last Resort:Pet-Friendly*Fenced* GameRoom
A modern kitchen with stainless steel appliances, a wooden island, and a dining area with white chairs.

2. Eagles Beach Nest 2:Pet-Friendly*Fenced*Walk2Beach

Eagles Beach Nest 2:Pet-Friendly*Fenced*Walk2Beach
Downtown New Buffalo
10.0 out of 10, Exceptional, (33 reviews)
"Very close to everything the town had to offer."
United States
Craig S.
The price is NZ$780
includes taxes & fees
22 Sept - 23 Sept
Eagles Beach Nest 2:Pet-Friendly*Fenced*Walk2Beach
A modern kitchen with white cabinets, a central island, stainless steel appliances, and a blue rug.

3. Archer's Retreat-Sleeps 10-1/2 mile to Lake Michigan! Pet/Kid Friendly

Archer's Retreat-Sleeps 10-1/2 mile to Lake Michigan! Pet/Kid Friendly
Sawyer
10.0 out of 10, Exceptional, (5 reviews)
"Came for 50th birthday with family! Everything was perfect and great location "
United States
Jennifer W.
The price is NZ$708
includes taxes & fees
14 Sept - 15 Sept
Archer's Retreat-Sleeps 10-1/2 mile to Lake Michigan! Pet/Kid Friendly
A modern living room with a grey sofa, a small ottoman, and a patterned rug. There is a kitchen area with a dark countertop and hanging pots.

4. Eagle`s Beach Nest: Pet-Friendly*Fenced*Walk2Beach

Eagle`s Beach Nest: Pet-Friendly*Fenced*Walk2Beach
Downtown New Buffalo
10.0 out of 10, Exceptional, (24 reviews)
"The home was exactly what we needed for the family trip."
United States
Allison A.
The price is NZ$683
includes taxes & fees
15 Sept - 16 Sept
Eagle`s Beach Nest: Pet-Friendly*Fenced*Walk2Beach
A modern living room with a stone fireplace, wooden ceiling, and a dining area with a wooden table and chairs.

5. Walk to Town, Beach, Game Room, Firepit Stay

Walk to Town, Beach, Game Room, Firepit Stay
New Buffalo
9.6 out of 10, Exceptional, (5 reviews)
"Fun spot, close to many activities to enjoy."
United States
Jody W.
The price is NZ$828
includes taxes & fees
23 Sept - 24 Sept
Walk to Town, Beach, Game Room, Firepit Stay
A living room with a stone fireplace, a grey sofa, a coffee table, and large windows with curtains.

6. Spacious 5-Bedroom Sawyer Farmhouse Retreat

Spacious 5-Bedroom Sawyer Farmhouse Retreat
Sawyer
9.8 out of 10, Exceptional, (31 reviews)
"Property was very spacious and extremely clean!"
United States
Kelly P.
The price is NZ$573
includes taxes & fees
16 Sept - 17 Sept
Spacious 5-Bedroom Sawyer Farmhouse Retreat
A beach with footprints leading to a wooden post, and the sun setting over the ocean.

7. Relax & Recharge in Hot Tub - Minutes to Warren Dunes - 3BR 2BA

Relax & Recharge in Hot Tub - Minutes to Warren Dunes - 3BR 2BA
Sawyer
9.2 out of 10, Wonderful, (12 reviews)
"Amazing location! So close to the dunes and fun restaurants, shops, and bars. There’s a great backyard for at-home hangs, too!"
United States
Emily
The price is NZ$788
includes taxes & fees
5 Oct - 6 Oct
Relax & Recharge in Hot Tub - Minutes to Warren Dunes - 3BR 2BA
A modern living room with a large wooden dining table, white chairs, a grey sofa, and a fireplace.

8. Warren Dunes - Large 2 Br-2 Bath, Hot Tub, Wbfpl , Next To Wineries

Warren Dunes - Large 2 Br-2 Bath, Hot Tub, Wbfpl , Next To Wineries
Bridgman
9.0 out of 10, Wonderful, (88 reviews)
"Perfect space for 2-5! The hot tub was fantastic, beds were comfortable, and shower was nice."
United States
Ryan G.
Warren Dunes - Large 2 Br-2 Bath, Hot Tub, Wbfpl , Next To Wineries
A wooden cabin with a porch, outdoor seating, and a garden area.

9. Breezy Chic: Fresh Spring Vibes at The Modern Oak walkable to town!

Breezy Chic: Fresh Spring Vibes at The Modern Oak walkable to town!
Three Oaks
10.0 out of 10, Exceptional, (31 reviews)
"The house was well stocked, very comfortable, and in great condition. Everything inside was of high quality. We really enjoyed being within close walking distance of Journeyman Distillery along with the local shops and restaurants. We would stay here again if in the area."
United States
Jack P.
The price is NZ$836
includes taxes & fees
6 Oct - 7 Oct
Breezy Chic: Fresh Spring Vibes at The Modern Oak walkable to town!
A wicker sofa with white cushions, a wooden table with a bowl of green plants, and a glass of water.

10. Schoolhouse now 5K Sq ft Lux BNB: Gym, Sauna, HotTub, GameRoom, Billiards, pets

Schoolhouse now 5K Sq ft Lux BNB: Gym, Sauna, HotTub, GameRoom, Billiards, pets
Union Pier
8.6 out of 10, Excellent, (13 reviews)
"Place was as expected, great for the purpose of our stay with multiple young adults. Host was great at communicating. "
United States
Jennifer O.
The price is NZ$1,682
includes taxes & fees
14 Sept - 15 Sept
Schoolhouse now 5K Sq ft Lux BNB: Gym, Sauna, HotTub, GameRoom, Billiards, pets
A large indoor swimming pool with a glass ceiling, surrounded by lounge chairs and a hot tub.

11. Deerpath Cottage-30 Acres with Indoor Pool, Farm, Kayaking, Trails, by Beach!

Deerpath Cottage-30 Acres with Indoor Pool, Farm, Kayaking, Trails, by Beach!
Union Pier
10.0 out of 10, Exceptional, (2 reviews)
"Lovely stay!"
United States
Kristin D.
The price is NZ$1,138
includes taxes & fees
14 Sept - 15 Sept
Deerpath Cottage-30 Acres with Indoor Pool, Farm, Kayaking, Trails, by Beach!
A covered pool area with seating and a sign indicating 'Pool Rules'.

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

Creekside House on 30 Acres with Kayaks/Pool/Farm/River/Trails/Pets, near Beach
New Buffalo
9.8 out of 10, Exceptional, (38 reviews)
"Beautiful location. Although we were there for one night there was so much to enjoy."
United States
Cassandra T.
The price is NZ$1,304
includes taxes & fees
23 Sept - 24 Sept
Creekside House on 30 Acres with Kayaks/Pool/Farm/River/Trails/Pets, near Beach
A gazebo with a rusted metal roof and a circular floor, surrounded by gravel and trees.

13. Be Our -Country- Guest

Be Our -Country- Guest
New Carlisle
10.0 out of 10, Exceptional, (7 reviews)
"Great location!! "
United States
Kathy P.
The price is NZ$416
includes taxes & fees
14 Sept - 15 Sept
Be Our -Country- Guest
A spacious living area with a wooden staircase, a sofa, a patterned armchair, and a wall with a 'celebrate family memories' sign.

14. Cozy Country Escape - Convenient to New Buffalo, Notre Dame & Amazon data center

Cozy Country Escape - Convenient to New Buffalo, Notre Dame & Amazon data center
New Carlisle
9.6 out of 10, Exceptional, (29 reviews)
"Cozy Country Escape is a perfect name for this location! It was so quiet & relaxing.The unit was very clean, Jackie, the property manager, was very prompt & thorough in her response to questions & entry instructions. The view of Lake Hudson was beautiful, especially at sunset."
United States
Dianne K.
The price is NZ$740
includes taxes & fees
20 Sept - 21 Sept
Cozy Country Escape - Convenient to New Buffalo, Notre Dame & Amazon data center
A covered outdoor dining area with a table and chairs, surrounded by large windows offering a view of a forested area.

15. River's Edge on 30 Acres with Kayaks/Pool/Farm/River/Trails/Pets, near Beach

River's Edge on 30 Acres with Kayaks/Pool/Farm/River/Trails/Pets, near Beach
Union Pier
9.8 out of 10, Exceptional, (20 reviews)
"We had a wonderful moms/dayghters weekend away. The house was perfect for us as 3 moms and daughters - each having our own space and the college girls getting the bunk room to share stories and giggle as much as they desired. It’s a great location for visiting wineries and relaxing after a long semester/fall. "
United States
Anne S.
The price is NZ$1,968
includes taxes & fees
21 Sept - 22 Sept
River's Edge on 30 Acres with Kayaks/Pool/Farm/River/Trails/Pets, near Beach
A beach with a pier extending into the water, a lighthouse in the distance, and the sun setting over the horizon.

16. The Boutique at Midtown Central / Hot Tub / Pet Friendly

The Boutique at Midtown Central / Hot Tub / Pet Friendly
Michigan City
9.6 out of 10, Exceptional, (19 reviews)
"Cute and cozy"
United States
angel R.
The price is NZ$517
includes taxes & fees
14 Sept - 15 Sept
The Boutique at Midtown Central / Hot Tub / Pet Friendly
A modern living room with a sofa, coffee table, and TV. There is a dining area with a table and chairs. The room has wooden flooring and a large window with blinds.

17. Sand & Sun Getaway | Drive to Beach Game Room + 2 Living Areas |Game Room | Minutes to Beach

Sand & Sun Getaway | Drive to Beach Game Room + 2 Living Areas |Game Room | Minutes to Beach
Michigan City
9.4 out of 10, Exceptional, (40 reviews)
"Enjoyed our stay. Lots of room, easy to find, close to Lake Michigan, and received clear and helpful communication from the property manager/owner before and during our stay. "
United States
Daniel A.
Sand & Sun Getaway | Drive to Beach Game Room + 2 Living Areas |Game Room | Minutes to Beach
A wicker chair on a wooden porch with a lantern and greenery in the background.

18. Romantic Cozy Home in "America’s Nicest Town"

Romantic Cozy Home in "America’s Nicest Town"
Buchanan
9.8 out of 10, Exceptional, (17 reviews)
"Very comfortable home in excellent location. Very well furnished and maintained."
United States
Jan P.
The price is NZ$385
includes taxes & fees
28 Sept - 29 Sept
Romantic Cozy Home in "America’s Nicest Town"
A wooden boardwalk leading to a sandy beach with the ocean in the background.

19. Singing Sands Trl | Hot Tub Retreat | Dogs OK

Singing Sands Trl | Hot Tub Retreat | Dogs OK
Michigan City
9.6 out of 10, Exceptional, (33 reviews)
"Serene atmosphere perfect for relaxation away from the loud busy city"
United States
Ally P.
Singing Sands Trl | Hot Tub Retreat | Dogs OK
A modern kitchen with white cabinetry, a stainless steel dishwasher, and pendant lighting.

20. Michigan City Gem! Huge Backyard-Grill- Sleeps 10

Michigan City Gem! Huge Backyard-Grill- Sleeps 10
Michigan City
The price is NZ$688
includes taxes & fees
16 Sept - 17 Sept
Michigan City Gem! Huge Backyard-Grill- Sleeps 10
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 Lakeside Hotel Reviews

Pine Lake Resort and Banquets

Pine Lake Resort and Banquets

10/10 Excellent
"Good"
David 1-night trip
Posted 1 hour ago
Pine Lake Resort and Banquets

Find out more about Lakeside

Lakeside Holiday Homes information

Number of reviews
447
Accommodation
1077 Holiday Homes
Lowest Price
NZ$385
Highest Price
NZ$1,968