Lakeside Holiday Rentals

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Check prices for these dates

In two weeks
12 Dec - 14 Dec
In two months
23 Jan - 25 Jan
In three months
20 Feb - 22 Feb
In four months
20 Mar - 22 Mar

Holiday Rentals in Lakeside

Beach nearby, sun-loungers, beach towels
Carrie's Cottage - Charming Duplex Style 3 Bedroom Cottage with Beach Access!

Holiday Home in Lakeside

9.0 out of 10, Wonderful, (50)
"This is our second time renting Carrie's Cottage and we absolutely love it. Perfect location to visit all the cute towns in this part of Michigan, walking distance to a beautiful beach, and plenty of space for adults and young children. We hope to be back again!"
United States
Marthe G.
Carrie's Cottage - Charming Duplex Style 3 Bedroom Cottage with Beach Access!
Beach nearby, sun-loungers
1 or 2 Fun Cottages Sleep 2-10-20 People. Pool & Hot Tub. Steps to Beach + More

Cottage in Lakeside

9.2 out of 10, Wonderful, (66)
"Great rental for multiple families. It was terrific having a pool and the beach was wonderful and close by."
United States
Renay S.
1 or 2 Fun Cottages Sleep 2-10-20 People. Pool & Hot Tub. Steps to Beach + More
Premium bedding, memory-foam beds, blackout curtains, free WiFi
The Neighborhood Hotel - Grand Beach

Apartment in New Buffalo

4.0 star property
9.6 out of 10, Exceptional, (65)
"Absolutely perfect, we loved every bit of our stay!"
United States
Rebecca
The Neighborhood Hotel - Grand Beach
Pool
Beautiful Family Cottage in Beachwalk-Grill-AC-Free Wifi-Kids Haven.

Holiday Home in Michigan City

9.6 out of 10, Exceptional, (245)
"House had everything we needed, great resort neighborhood for kids "
United States
Kathryne I.
Beautiful Family Cottage in Beachwalk-Grill-AC-Free Wifi-Kids Haven.
Outdoor dining
Red Oak-5 bedroom with in ground pool, fireplace-walk to restaurants

Holiday Home in New Buffalo

10.0 out of 10, Exceptional, (79)
"The house was perfect for our family vacation with the pool and location!! Better than advertised. "
United States
Michael D.
Red Oak-5 bedroom with in ground pool, fireplace-walk to restaurants
Property grounds
BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.

Apartment in Michigan City

9.4 out of 10, Exceptional, (126)
"Was as described great stay"
United States
Amber C.
The price is HK$770
HK$1,664 total
includes taxes & fees
29 Nov - 30 Nov
BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.
Exterior
Big Family House 5 Minutes from Lake Michigan/Blue Chip Casino/Brewery/Wineries!

Holiday Home in Michigan City

9.6 out of 10, Exceptional, (121)
"We enjoyed everything about the house it could have used a little weed eating but other than that it was perfect my family enjoyed their stay Thank you again"
United States
Barb W.
Big Family House 5 Minutes from Lake Michigan/Blue Chip Casino/Brewery/Wineries!
Smart TV, DVD player, books
Breezy Pad, Close to the Lake, with Hot Tub

Holiday Home in St Joseph

9.2 out of 10, Wonderful, (106)
"We stayed at the Breezy pad for a family vacation and it was wonderful. We were able to bring our dog with and the house was very dog and family friendly. We loved that it was close to plenty of beaches and the neighborhood was very family friendly and quiet. We will definitely be making this a yearly family vacation. "
United States
Anna E.
The price is HK$949
HK$1,395 total
includes taxes & fees
1 Dec - 2 Dec
Breezy Pad, Close to the Lake, with Hot Tub
Outdoor spa tub
Newly renovated, 7700 Sq. Ft, 8BR, 7BTH, Heated Pool, Hot Tub, Arcade Game Barn

Holiday Home in Sawyer

2.0 star property
10.0 out of 10, Exceptional, (28)
"House was perfect for our multi family family vacation! Amenities were wonderful and its clear that Tim is passionate about hosting a wonderful saty for all his guests! "
United States
Kristy D.
Newly renovated, 7700 Sq. Ft, 8BR, 7BTH, Heated Pool, Hot Tub, Arcade Game Barn
Outdoor pool, a heated pool
New luxury home steps to downtown w/yr round heated pool

Holiday Home in Downtown New Buffalo

10.0 out of 10, Exceptional, (32)
"Heather's home is amazing - beautifully appointed, amazing location, and perfect for a large group. Her hospitality is the best in a vacation home we've ever experienced, and we will return! "
United States
Monica B.
New luxury home steps to downtown w/yr round heated pool
Interior
Lifetime Memories*Big Beach Front House*Fire Place/Pit*Free WiFi*Paddle Boards

Holiday Home in Michigan City

9.8 out of 10, Exceptional, (149)
"The house was a great location. Close to the beach. We had a wonderful time!"
United States
Jim W.
Lifetime Memories*Big Beach Front House*Fire Place/Pit*Free WiFi*Paddle Boards
Fridge, microwave, oven, stovetop
Beachwalk - 7 bedrooms near the beach. Hot tub & golf cart. Great family house

Holiday Home in Michigan City

10.0 out of 10, Exceptional, (244)
"Great place to stay with a big family "
United States
Larry Y.
Beachwalk - 7 bedrooms near the beach. Hot tub & golf cart. Great family house
Smart TV, fireplace, table football, books
Sand & Sun Getaway | 4BR w/ Game Room + 2 Living Areas |Game Room | Minutes to Beach

Holiday Home in Michigan City

9.4 out of 10, Exceptional, (31)
"Nice"
United States
Maryellen W.
The price is HK$568
HK$2,718 total
includes taxes & fees
30 Nov - 1 Dec
Sand & Sun Getaway | 4BR w/ Game Room + 2 Living Areas |Game Room | Minutes to Beach
Fridge, microwave, oven, stovetop
Cozy Cottage with view of Lake Michigan

Holiday Home in St. Joseph

10.0 out of 10, Exceptional, (51)
"Wonderful place to stay! ...especially with kids! The cookies waiting for us was a nice touch! "
United States
Nedra S.
Cozy Cottage with view of Lake Michigan
Outdoor pool, a heated pool
VIP! LUXURY 4BD 5min to Lake Michigan beach Big Pool with heater!!

Villa in Michigan City

8.8 out of 10, Excellent, (23)
"Good location great pool host was nice to deal with. Had a good time"
United States
T H.
The price is HK$1,122
HK$4,271 total
includes taxes & fees
29 Nov - 30 Nov
VIP! LUXURY 4BD 5min to Lake Michigan beach Big Pool with heater!!
Smart TV, fireplace, video games, DVD player
Lakefront! Secluded, HotTub, Fire Pit, Private Dock&boats 90 Min from Chicago

Holiday Home in Union Pier

10.0 out of 10, Exceptional, (133)
"Very comfortable, steps to a dock, use of canoe, fishing, hot tub, Firepit for roasting marsh mellows. Very pleasant stay."
United States
Kenneth
Lakefront! Secluded, HotTub, Fire Pit, Private Dock&boats 90 Min from Chicago
Smart TV
The Sycamore Cottage - 2 BR & 1.5 Bath - Hot Tub - Steps to Downtown

Holiday Home in Three Oaks

10.0 out of 10, Exceptional, (77)
"Nice little house in great location. Clean and comfortable!"
United States
susan s.
The price is HK$1,429
HK$2,340 total
includes taxes & fees
30 Nov - 1 Dec
The Sycamore Cottage - 2 BR & 1.5 Bath - Hot Tub - Steps to Downtown
Property grounds
Modern Farmhouse Retreat-10 Min Walk to Lake Michigan-Hot Tub-Sauna

Holiday Home in Michigan City

10.0 out of 10, Exceptional, (118)
"The place was even better than the photos. It was a great place to stay."
United States
Alex B.
Modern Farmhouse Retreat-10 Min Walk to Lake Michigan-Hot Tub-Sauna
Outdoor spa tub
Blue Chill | WalktoBeach | HotTub-all yr | Dogs OK

Holiday Home in Michigan City

9.6 out of 10, Exceptional, (49)
"Great stay. Easy beach access. Enjoyed the hot tub and Pac-Man gaming. Beds were comfortable. Had all we needed."
United States
Tori M.
The price is HK$770
HK$2,563 total
includes taxes & fees
30 Nov - 1 Dec
Blue Chill | WalktoBeach | HotTub-all yr | Dogs OK
Private kitchenette
Sunset Dunes Vacation Villas

Villa in Bridgman

3.0 star property
9.6 out of 10, Exceptional, (12)
"The apartment was wonderful, close to the Red Bud Race track, restaurants, and of course, the beach! We would definitely stay here again. "
United States
NANCY
Sunset Dunes Vacation Villas
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

Four Winds Casino Resort – New Buffalo

Four Winds Casino Resort – New Buffalo

10/10 Excellent
"Our room was clean and well appointed. The staff was very nice. "
Christine 1-night trip
Posted 1 day ago
Four Winds Casino Resort – New Buffalo

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?

Beautiful Family Cottage in Beachwalk-Grill-AC-Free Wifi-Kids Haven.: This holiday home rental outside of Lakeside offers a balcony, a selection of games and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals will I find in Lakeside?

With 45 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.