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
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Lakeside holiday rentals

Pool

Heated year-round pool, hot tub, close to Lake Michigan beaches!

Heated year-round pool, hot tub, close to Lake Michigan beaches!
Lakeside
The price is HK$16,469
HK$28,939 total
includes taxes & fees
27 Jul - 28 Jul
Heated year-round pool, hot tub, close to Lake Michigan beaches!
Smart TV, video games, books, computer monitors

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)
"We enjoyed our stay. It’s a fun property being an old school building and they’ve added lots of for the kids and adults. "
United States
Tim D.
The price is HK$8,525
HK$15,154 total
includes taxes & fees
19 Aug - 20 Aug
Schoolhouse now 5K Sq ft Lux BNB: Gym, Sauna, HotTub, GameRoom, Billiards, pets
Dining

Charming 8 Bedroom Home And Coach House ~ Great for Summer Getaways!

Charming 8 Bedroom Home And Coach House ~ Great for Summer Getaways!
Union Pier
9.8 out of 10, Exceptional, (88 reviews)
"Weather was great really enjoyed our time here"
United States
Jamie S.
The price is HK$5,882
HK$9,725 total
includes taxes & fees
16 Aug - 17 Aug
Charming 8 Bedroom Home And Coach House ~ Great for Summer Getaways!
Terrace/patio

Private Beach Steps to the Lake.

Private Beach Steps to the Lake.
Union Pier
10.0 out of 10, Exceptional, (93 reviews)
"Great stay for a week by the beach with family! Perfect location to walk right down to the beach each day. Excited to come back one day!"
United States
Jalen W.
The price is HK$6,666
HK$11,199 total
includes taxes & fees
10 Aug - 11 Aug
Private Beach Steps to the Lake.
Terrace/patio

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, (71 reviews)
"A charming little place, perfect for two people for a get away. "
United States
Kaleigh A.
The price is HK$1,529
HK$2,188 total
includes taxes & fees
2 Aug - 3 Aug
Cherry Street Guesthouse with private wooded yard & firepit, 3 blocks to town!
Indoor pool, outdoor pool

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, (36 reviews)
"Beautiful location. Although we were there for one night there was so much to enjoy."
United States
Cassandra T.
The price is HK$5,090
HK$7,553 total
includes taxes & fees
26 Aug - 27 Aug
Creekside House on 30 Acres with Kayaks/Pool/Farm/River/Trails/Pets, near Beach
3 bedrooms, iron/ironing board, free WiFi, bed sheets

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$2,753
HK$5,059 total
includes taxes & fees
2 Aug - 3 Aug
Featherbone Farmhouse- Comfy Gem 1 Block to Town. Perfect for families & groups!
Coffee/tea maker, fridge, microwave, oven

Secluded Retreat, Hot Tub, Fire Pit, Wildlife Views, Near New Buffalo Beach!

Secluded Retreat, Hot Tub, Fire Pit, Wildlife Views, Near New Buffalo Beach!
New Buffalo
10.0 out of 10, Exceptional, (25 reviews)
"Perfect stay! The house was spotless, stylish, and located perfectly. Tori was incredibly responsive. Highly recommended"
United States
kimberly b.
The price is HK$5,898
HK$6,737 total
includes taxes & fees
25 Aug - 26 Aug
Secluded Retreat, Hot Tub, Fire Pit, Wildlife Views, Near New Buffalo Beach!
Coffee/tea maker, fridge, microwave, oven

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$3,519
HK$7,584 total
includes taxes & fees
13 Aug - 14 Aug
Sq Toe`s Last Resort:Pet-Friendly*Fenced* GameRoom
Outdoor dining

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$2,902
HK$5,060 total
includes taxes & fees
25 Aug - 26 Aug
Breezy Chic: Fresh Spring Vibes at The Modern Oak walkable to town!
Interior

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, (29 reviews)
"Close to downtown, convenient location."
United States
Jim B.
The price is HK$1,961
HK$2,243 total
includes taxes & fees
10 Aug - 11 Aug
Peach by the Beach! 1 Bdrm Apt close to downtown
TV, fireplace, books, computer monitors

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, (2 reviews)
"Allison was an outstanding host from start to finish. Before we arrived during a heat wave, she proactively reached out to get our arrival time and adjusted the A/C to ensure we were comfortable. We were welcomed with a bottle of local wine, and the house was exactly as described—clean, well-organized, and stocked with helpful instructions throughout.When a severe storm caused a temporary power outage, Allison kept us informed and checked in on us. Checkout was easy, and she even helped us...
United States
Colleen T.
The price is HK$2,534
HK$4,458 total
includes taxes & fees
9 Aug - 10 Aug
5 min to Warren Dunes! Private Wooded Retreat w/ Sunroom, Firepit & Fireplace
Marina

Luxury Downtown Getaway: 2BR Condo Near New Buffalo’s Top Attractions!

Luxury Downtown Getaway: 2BR Condo Near New Buffalo’s Top Attractions!
Downtown New Buffalo
10.0 out of 10, Exceptional, (33 reviews)
"Great location right between shopping, eatery area and the beach. Will definitely be coming back!!"
United States
Sheila W.
The price is HK$3,840
HK$5,960 total
includes taxes & fees
28 Jul - 29 Jul
Luxury Downtown Getaway: 2BR Condo Near New Buffalo’s Top Attractions!
TV, books

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$1,899
HK$4,303 total
includes taxes & fees
19 Aug - 20 Aug
Eagle`s Beach Nest: Pet-Friendly*Fenced*Walk2Beach
Pool

Seen on TV - Epic Indoor Pool with hot tub close to beach

Seen on TV - Epic Indoor Pool with hot tub close to beach
Bridgman
10.0 out of 10, Exceptional, (16 reviews)
"The pool area is amazing."
United States
Angela K.
Seen on TV - Epic Indoor Pool with hot tub close to beach
Coffee/tea maker, fridge, microwave, oven

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$2,080
HK$4,487 total
includes taxes & fees
26 Aug - 27 Aug
Eagles Beach Nest 2:Pet-Friendly*Fenced*Walk2Beach
Exterior

Windflower - Upscale 2 Bedroom Villa at Petite Acres

Windflower - Upscale 2 Bedroom Villa at Petite Acres
New Buffalo
The price is HK$2,619
HK$4,741 total
includes taxes & fees
27 Jul - 28 Jul
Windflower - Upscale 2 Bedroom Villa at Petite Acres
Interior

Designer 5BR Retreat, 4 Min Drive to Beach, Hot Tub, Family Friendly

Designer 5BR Retreat, 4 Min Drive to Beach, Hot Tub, Family Friendly
New Buffalo
10.0 out of 10, Exceptional, (2 reviews)
"Wonderful property with lots of options to have a good time for a family friendly getaway"
United States
Amany M.
The price is HK$6,039
HK$9,584 total
includes taxes & fees
24 Aug - 25 Aug
Designer 5BR Retreat, 4 Min Drive to Beach, Hot Tub, Family Friendly
TV, fireplace, video games, stereo

Huge Family Home w/ Pool - 13 Mi to Lake Michigan!

Huge Family Home w/ Pool - 13 Mi to Lake Michigan!
La Porte
9.4 out of 10, Exceptional, (50 reviews)
"Owner very willing to make sure your stay was pleasant."
United States
David M.
Huge Family Home w/ Pool - 13 Mi to Lake Michigan!
Interior

Weko Beach Retreat - Hot Tub, Fire Pit, Near Lake Michigan

Weko Beach Retreat - Hot Tub, Fire Pit, Near Lake Michigan
Bridgman
10.0 out of 10, Exceptional, (18 reviews)
"We had a wonderful stay, would stay here again. Denise was kind and available throughout the trip. We enjoyed the hot tub which was clean, the fire pit, and the cozy beds. "
United States
Jenna J.
The price is HK$2,525
HK$3,882 total
includes taxes & fees
26 Aug - 27 Aug
Weko Beach Retreat - Hot Tub, Fire Pit, Near Lake Michigan
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

Microtel Inn & Suites by Wyndham Michigan City

Microtel Inn & Suites by Wyndham Michigan City

10/10 Excellent
"Was a very pleasant stay."
Leila 1-night trip
Posted 5 hours ago
Microtel Inn & Suites by Wyndham Michigan City

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?

Carrie's Cottage - Charming Duplex Style 3 Bedroom Cottage with Beach Access!: This highly rated holiday home rental in Lakeside is located on a lake, and has a patio, a private garden and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

How many holiday rentals will I find in Lakeside?

With 43 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.