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

Lakeside Vacation Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Lakeside vacation rentals

Terrace/patio

1. Cherry Street Guesthouse with private wooded yard & firepit, 3 blocks to town!

Cherry Street Guesthouse with private wooded yard & firepit, 3 blocks to town!
Three Oaks
9.4 out of 10, Exceptional, (73 reviews)
"Very cute place close to the acorn. We will book again! Thanks for hosting us!"
United States
Cassie R.
The price is AED 716
AED 1,028 total
includes taxes & fees
16 Aug - 17 Aug
Cherry Street Guesthouse with private wooded yard & firepit, 3 blocks to town!
TV, fireplace, books, computer monitors

2. 5 min to Warren Dunes! Private Wooded Retreat w/ Sunroom, Firepit & Fireplace

5 min to Warren Dunes! Private Wooded Retreat w/ Sunroom, Firepit & Fireplace
Shorewood-Tower Hills-Harbert
10.0 out of 10, Exceptional, (3 reviews)
"Cute woods getaway very close to the dunes and easy to get around. Very clean and well managed property."
United States
Cameron V.
5 min to Warren Dunes! Private Wooded Retreat w/ Sunroom, Firepit & Fireplace
Interior

3. Peach by the Beach! 1 Bdrm Apt close to downtown

Peach by the Beach! 1 Bdrm Apt close to downtown
Downtown New Buffalo
9.6 out of 10, Exceptional, (31 reviews)
"Close to downtown, convenient location."
United States
Jim B.
The price is AED 918
AED 1,050 total
includes taxes & fees
31 Aug - 1 Sep
Peach by the Beach! 1 Bdrm Apt close to downtown
1 bedroom, WiFi (free), bed sheets

4. Country Barn Studio Getaway

Country Barn Studio Getaway
Berrien Springs
9.2 out of 10, Wonderful, (20 reviews)
"Enjoyed all aspects of the stay especially the chickens walking with us around the property. Good location and very nice people!!"
United States
Eric R.
The price is AED 441
AED 672 total
includes taxes & fees
16 Aug - 17 Aug
Country Barn Studio Getaway
TV, fireplace, offices

5. Spacious 5-Bedroom Sawyer Farmhouse Retreat

Spacious 5-Bedroom Sawyer Farmhouse Retreat
Sawyer
9.8 out of 10, Exceptional, (29 reviews)
"Property was very spacious and extremely clean!"
United States
Kelly P.
The price is AED 951
AED 1,565 total
includes taxes & fees
13 Sep - 14 Sep
Spacious 5-Bedroom Sawyer Farmhouse Retreat
2 bedrooms, desk, iron/ironing board, travel crib

6. Cozy 2 bed - Steps to Journeyman - Pets OK - Fast Wi-Fi

Cozy 2 bed - Steps to Journeyman - Pets OK - Fast Wi-Fi
Three Oaks
10.0 out of 10, Exceptional, (1 review)
"This was my first VRBO experience and was honestly the best decision I ever made on a whim. The property was clean, the host answered my questions, and the photos were accurate. Though small, the property was great and included comfortable beds, one king sized. I was pleasantly surprised at the size of the larger bedroom. The photos were accurate. We were permitted to bring both of our dogs, though we ended up leaving one home. I was glad because the space was rather small.The property was...
United States
Kaysey B.
The price is AED 790
AED 1,504 total
includes taxes & fees
25 Aug - 26 Aug
Cozy 2 bed - Steps to Journeyman - Pets OK - Fast Wi-Fi
Coffee/tea maker, fridge, microwave, oven

7. 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, (3 reviews)
"Came for 50th birthday with family! Everything was perfect and great location "
United States
Jennifer W.
The price is AED 687
AED 824 total
includes taxes & fees
18 Aug - 19 Aug
Archer's Retreat-Sleeps 10-1/2 mile to Lake Michigan! Pet/Kid Friendly
Exterior

8. Pied-à-terre Allium - Bunk House at Petite Acres

Pied-à-terre Allium - Bunk House at Petite Acres
New Buffalo
10.0 out of 10, Exceptional, (1 review)
"Very cute, great for a girls trip"
United States
Lauren A.
The price is AED 1,165
AED 2,671 total
includes taxes & fees
17 Aug - 18 Aug
Pied-à-terre Allium - Bunk House at Petite Acres
Sun loungers, beach towels

9. 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
9.0 out of 10, Wonderful, (9 reviews)
"This is a great choice for anyone looking to stay near Warren Dunes. The beds are comfy, the property is well maintained, and it’s centrally located to just about everything. We had a lovely stay. "
United States
Nicole M.
The price is AED 1,080
AED 2,140 total
includes taxes & fees
2 Sep - 3 Sep
Book Your Spring Escape! Relax & Recharge in Hot Tub - Minutes to Dining & Shops
TV, books

10. 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)
"Great stay, loved the place!"
United States
Ryan J.
The price is AED 692
AED 1,776 total
includes taxes & fees
31 Aug - 1 Sep
Eagle`s Beach Nest: Pet-Friendly*Fenced*Walk2Beach
Coffee/tea maker, fridge, microwave, oven

11. 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 AED 842
AED 1,957 total
includes taxes & fees
26 Aug - 27 Aug
Eagles Beach Nest 2:Pet-Friendly*Fenced*Walk2Beach
Coffee/tea maker, fridge, microwave, oven

12. 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 AED 836
AED 2,577 total
includes taxes & fees
1 Sep - 2 Sep
Sq Toe`s Last Resort:Pet-Friendly*Fenced* GameRoom
3 bedrooms, iron/ironing board, WiFi (free), bed sheets

13. Featherbone Farmhouse- Comfy Gem 1 Block to Town. Perfect for families & groups!

Featherbone Farmhouse- Comfy Gem 1 Block to Town. Perfect for families & groups!
Three Oaks
9.0 out of 10, Wonderful, (15 reviews)
"Property was perfect for our stay. Great house with all the comfortable and necessary amenities. Easy walk to the main street of town with access to restaurants and shops. Quaint and quiet and just what we wanted for our family of four. "
United States
Anonymous traveler
The price is AED 1,289
AED 2,369 total
includes taxes & fees
16 Aug - 17 Aug
Featherbone Farmhouse- Comfy Gem 1 Block to Town. Perfect for families & groups!
Outdoor dining

14. 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, (30 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 AED 1,535
AED 2,582 total
includes taxes & fees
26 Aug - 27 Aug
Breezy Chic: Fresh Spring Vibes at The Modern Oak walkable to town!
Sun loungers, beach towels

15. Charming Cottage w/ HOT TUB - 5 Min from LAKE MICHIGAN!

Charming Cottage w/ HOT TUB - 5 Min from LAKE MICHIGAN!
Bridgman
9.6 out of 10, Exceptional, (9 reviews)
"Charming, clean and well appointed spot, great for our getaway! "
United States
Jenelle O.
The price is AED 992
AED 1,344 total
includes taxes & fees
23 Aug - 24 Aug
Charming Cottage w/ HOT TUB - 5 Min from LAKE MICHIGAN!
Smart TV, fireplace, books, stereo

16. 3BR 2b New Buff cottage dogs ok, steps to dwntn restaurants&shops, walk to beach

3BR 2b New Buff cottage dogs ok, steps to dwntn restaurants&shops, walk to beach
Downtown New Buffalo
10.0 out of 10, Exceptional, (14 reviews)
"Loved staying in this cottage. Super close to everything, clean and overall in a great location. Hosts were very helpful and easy to communicate with. Highly recommend! Will look to stay here again for sure. "
United States
Miranda S.
The price is AED 1,157
AED 2,167 total
includes taxes & fees
2 Sep - 3 Sep
3BR 2b New Buff cottage dogs ok, steps to dwntn restaurants&shops, walk to beach
Outdoor dining

17. 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 AED 735
AED 942 total
includes taxes & fees
8 Sep - 9 Sep
Be Our -Country- Guest
TV

18. EC Taylor Coach House. Cozy 1-bedroom coach house in lovely New Carlisle,Indiana

EC Taylor Coach House. Cozy 1-bedroom coach house in lovely New Carlisle,Indiana
New Carlisle
10.0 out of 10, Exceptional, (3 reviews)
"Amazing place to book, it felt like home, I was completely satisfied, thank u again"
United States
Danane K.
The price is AED 469
AED 789 total
includes taxes & fees
25 Aug - 26 Aug
EC Taylor Coach House. Cozy 1-bedroom coach house in lovely New Carlisle,Indiana
Interior

19. 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)
"Location was perfect for the events we were attending. Beds were comfortable and we felt at home."
United States
Connie B.
The price is AED 808
AED 1,600 total
includes taxes & fees
20 Aug - 21 Aug
Cozy Country Escape - Convenient to New Buffalo, Notre Dame & Amazon data center
Indoor pool, outdoor pool

20. 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, (37 reviews)
"Beautiful location. Although we were there for one night there was so much to enjoy."
United States
Cassandra T.
The price is AED 1,833
AED 2,876 total
includes taxes & fees
8 Sep - 9 Sep
Creekside House on 30 Acres with Kayaks/Pool/Farm/River/Trails/Pets, near Beach
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

Blue Chip Casino Hotel and Spa

Blue Chip Casino Hotel and Spa

8/10 Good
"The room was amazing, staff at the cafe and restaurant by the counter not very friendly and responsive, except room cleaner lady she was super nice and also waitress in the Lakeside kitchen was very nice, helpful and overall saved our mood after the staff by the counter. Casino is great, dealers were friendly. When was a tornado we felt safe with staff, they took care of us in the best professional manner. Thank you."
Marina 3-night trip
Posted 8 hours ago
Blue Chip Casino Hotel and Spa

Frequently asked questions

Are there vacation rentals in Lakeside?

Yes, you can find vacation rentals near popular attractions in Lakeside, or you can choose a secluded option if you're looking for relaxation. Lakeside is known for its lake views and architecture. Make sure you have time to check out the forests and shopping during your trip.

What are some of the best vacation home rentals that Lakeside has to offer?

Carrie's Cottage - Charming Duplex Style 3 Bedroom Cottage with Beach Access!: This Lakeside vacation home rental is located on a lake and has a patio, a private yard, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family.

How many vacation rentals will I find in Lakeside?

With 44 Expedia vacation rentals, you're sure to find just the right place for your Lakeside stay.

What can I see and do in Lakeside?

Cultural attractions include Burnison Galleries, whereas Lake Michigan is a spot to enjoy nature. Eleanor O'Connor Wilson Woods Preserve and Edward and Elizabeth Leonard Wildlife Preserve are other places to visit while you're in town.

What are vacation rentals like in Lakeside?

Vacation rentals are privately owned accommodations you can stay in for several days or longer in Lakeside. Vacation rentals offer extras like WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of security away from public hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for a family trip or a small group gathering.