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

Lakeside Holiday 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 holiday 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 HK$1,530
HK$2,197 total
includes taxes & fees
18 Aug - 19 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.
The price is HK$1,942
HK$3,754 total
includes taxes & fees
17 Aug - 18 Aug
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 HK$1,766
HK$2,017 total
includes taxes & fees
23 Aug - 24 Aug
Peach by the Beach! 1 Bdrm Apt close to downtown
1 bedroom, free WiFi, 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 HK$942
HK$1,436 total
includes taxes & fees
25 Aug - 26 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 HK$1,749
HK$3,004 total
includes taxes & fees
13 Sept - 14 Sept
Spacious 5-Bedroom Sawyer Farmhouse Retreat
2 bedrooms, desk, iron/ironing board, travel cot

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 HK$1,687
HK$3,213 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 HK$1,397
HK$1,677 total
includes taxes & fees
14 Sept - 15 Sept
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 HK$2,456
HK$5,670 total
includes taxes & fees
1 Sept - 2 Sept
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 HK$2,200
HK$4,443 total
includes taxes & fees
2 Sept - 3 Sept
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 HK$1,478
HK$3,795 total
includes taxes & fees
31 Aug - 1 Sept
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 HK$1,808
HK$4,192 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 HK$1,814
HK$5,543 total
includes taxes & fees
2 Sept - 3 Sept
Sq Toe`s Last Resort:Pet-Friendly*Fenced* GameRoom
3 bedrooms, iron/ironing board, free WiFi, 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 traveller
The price is HK$2,754
HK$5,062 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 HK$2,519
HK$4,600 total
includes taxes & fees
31 Aug - 1 Sept
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
9.8 out of 10, Exceptional, (11 reviews)
"Charming, clean and well appointed spot, great for our getaway! "
United States
Jenelle O.
The price is HK$2,119
HK$2,872 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 HK$2,393
HK$4,538 total
includes taxes & fees
2 Sept - 3 Sept
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 HK$1,569
HK$2,013 total
includes taxes & fees
8 Sept - 9 Sept
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 HK$1,003
HK$1,686 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 HK$1,726
HK$3,419 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 HK$3,916
HK$6,145 total
includes taxes & fees
8 Sept - 9 Sept
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

10/10 Excellent
"Shout to Lisa at the front desk. Lisa was awesome and should be promoted!"
Shane 4-night trip
Posted 10 hours ago
Blue Chip Casino Hotel and Spa

Find out more about Lakeside

Search for holiday rentals in Lakeside on Expedia! You can easily find your home rentals, villas, holiday apartments in Lakeside using one of the methods below:

  • View our selection of featured holiday rentals in Lakeside
  • Use the map to find apartments and other holiday homes in the Lakeside neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Lakeside while they last

Look no further and take a look at our great range of rental properties in Lakeside!

Frequently asked questions

Are there holiday rentals in Lakeside?

Yes, there are holiday rentals close to the most popular sights in Lakeside, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Lakeside has to offer?

Family Retreat-Beachwalk-Grill-AC-Free WiFi-Pool Table-Bikes-Grill-Golf Cart: This holiday home rental outside of Lakeside is located near the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals will I find in Lakeside?

With 44 Expedia holiday rentals, you're guaranteed 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 holiday rentals like in Lakeside?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Lakeside. Holiday rentals feature extras such as WiFi and washers and dryers so you'll have everything you need. If you're concerned about a clean environment, holiday rentals can provide a sense of seclusion away from public hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive option for a small group gathering.