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

Holiday Homes in Lakeside

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

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

Private kitchen

1. 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 nice place and all as advertised. Would stay here again"
United States
Murray
The price is AU$624
includes taxes & fees
10 Sept - 11 Sept
Eagles Beach Nest 2:Pet-Friendly*Fenced*Walk2Beach
Living area

2. 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 AU$675
includes taxes & fees
10 Sept - 11 Sept
Walk to Town, Beach, Game Room, Firepit Stay
Private kitchen

3. 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 AU$884
includes taxes & fees
15 Sept - 16 Sept
Sq Toe`s Last Resort:Pet-Friendly*Fenced* GameRoom
Living area

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 AU$554
includes taxes & fees
5 Oct - 6 Oct
Eagle`s Beach Nest: Pet-Friendly*Fenced*Walk2Beach
Living area

5. Spacious 5-Bedroom Sawyer Farmhouse Retreat

Spacious 5-Bedroom Sawyer Farmhouse Retreat
Sawyer
9.8 out of 10, Exceptional, (30 reviews)
"Property was very spacious and extremely clean!"
United States
Kelly P.
The price is AU$468
includes taxes & fees
13 Sept - 14 Sept
Spacious 5-Bedroom Sawyer Farmhouse Retreat
Beach

6. Book Your Spring Escape! Relax & Recharge in Hot Tub - Minutes to Dining & Shops

Book Your Spring Escape! Relax & Recharge in Hot Tub - Minutes to Dining & Shops
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 AU$728
includes taxes & fees
29 Sept - 30 Sept
Book Your Spring Escape! Relax & Recharge in Hot Tub - Minutes to Dining & Shops
Living area

7. 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 AU$1,559
includes taxes & fees
15 Sept - 16 Sept
Schoolhouse now 5K Sq ft Lux BNB: Gym, Sauna, HotTub, GameRoom, Billiards, pets
Interior

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.
The price is AU$375
includes taxes & fees
13 Sept - 14 Sept
Warren Dunes - Large 2 Br-2 Bath, Hot Tub, Wbfpl , Next To Wineries
Pool

9. 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 AU$913
includes taxes & fees
15 Sept - 16 Sept
Deerpath Cottage-30 Acres with Indoor Pool, Farm, Kayaking, Trails, by Beach!
Outdoor dining

10. 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 AU$758
includes taxes & fees
29 Sept - 30 Sept
Breezy Chic: Fresh Spring Vibes at The Modern Oak walkable to town!
Interior

11. 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 AU$595
includes taxes & fees
16 Sept - 17 Sept
Cozy Country Escape - Convenient to New Buffalo, Notre Dame & Amazon data center
Beach

12. Cozy House Retreat: Exclusive Full Yard & Porch-2 Miles to Beach and Mt Baldy

Cozy House Retreat: Exclusive Full Yard & Porch-2 Miles to Beach and Mt Baldy
Michigan City
9.8 out of 10, Exceptional, (30 reviews)
"It was a cute little place to stay"
United States
Janielle K.
The price is AU$303
includes taxes & fees
15 Sept - 16 Sept
Cozy House Retreat: Exclusive Full Yard & Porch-2 Miles to Beach and Mt Baldy
Outdoor dining

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 AU$340
includes taxes & fees
14 Sept - 15 Sept
Be Our -Country- Guest
Pool

14. 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 AU$1,061
includes taxes & fees
23 Sept - 24 Sept
Creekside House on 30 Acres with Kayaks/Pool/Farm/River/Trails/Pets, near Beach
Beach

15. 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 Boutique at Midtown Central / Hot Tub / Pet Friendly
Outdoor dining

16. 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 AU$1,544
includes taxes & fees
28 Sept - 29 Sept
River's Edge on 30 Acres with Kayaks/Pool/Farm/River/Trails/Pets, near Beach
Terrace/patio

17. 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 AU$346
includes taxes & fees
28 Sept - 29 Sept
Romantic Cozy Home in "America’s Nicest Town"
Living area

18. 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, (39 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.
The price is AU$609
includes taxes & fees
13 Sept - 14 Sept
Sand & Sun Getaway | Drive to Beach Game Room + 2 Living Areas |Game Room | Minutes to Beach
Beach

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.
The price is AU$461
includes taxes & fees
10 Sept - 11 Sept
Singing Sands Trl | Hot Tub Retreat | Dogs OK
Beach

20. Duplex | Firepit | Game Room | Hot Tub-all year

Duplex | Firepit | Game Room | Hot Tub-all year
Michigan City
8.4 out of 10, Very good, (19 reviews)
"It’s was very clean , comfortable beds too "
United States
Donna
The price is AU$341
includes taxes & fees
10 Sept - 11 Sept
Duplex | Firepit | Game Room | Hot Tub-all year
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Lakeside Hotel Reviews

Fairfield Inn & Suites by Marriott New Buffalo

Fairfield Inn & Suites by Marriott New Buffalo

8/10 Good
"Clean and up-to-date. The only problem was they had one person working on the breakfast and you can tell she was frustrated and irritated."
Hope 1-night trip
Posted 3 hours ago
Fairfield Inn & Suites by Marriott New Buffalo

Find out more about Lakeside

Lakeside Holiday Homes information

Number of reviews
489
Accommodation
1066 Holiday Homes
Lowest Price
AU$303
Highest Price
AU$1,559