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
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Lakeside vacation rentals

A small, single-story cabin with a porch, surrounded by a garden and trees.

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, (80 reviews)
"Great to walk to town. Nice area to road bike etc."
United States
jeffrey
The price is ￥29,954
￥42,704 total
includes taxes & fees
Oct 5 - Oct 6
Cherry Street Guesthouse with private wooded yard & firepit, 3 blocks to town!
A beach with a building on the left, a clear sky, and calm sea.

2. Sawyer Getaway | Walk to Downtown

Sawyer Getaway | Walk to Downtown
Shorewood-Tower Hills-Harbert
10.0 out of 10, Exceptional, (1 review)
"Was a great experience. The apartment was super clean everything worked well. Easy checkin and checkout process. Grocery store right below was so convenient. Real close to dunes . We loved the whole experience oh and pet friendly also our pup loved it."
United States
Chad F.
The price is ￥12,725
￥39,909 total
includes taxes & fees
Sep 16 - Sep 17
Sawyer Getaway | Walk to Downtown
A kitchen with a granite countertop, stainless steel sink, and white cabinetry.

3. Stay in downtown Three Oaks overlooking the main street!

Stay in downtown Three Oaks overlooking the main street!
Three Oaks
9.8 out of 10, Exceptional, (188 reviews)
"Place was amazing!! "
United States
Betsy T.
The price is ￥30,722
￥55,453 total
includes taxes & fees
Oct 12 - Oct 13
Stay in downtown Three Oaks overlooking the main street!
A modern kitchen with stainless steel appliances, a wooden island, and a dining area with white chairs.

4. 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 close to everything the town had to offer."
United States
Craig S.
The price is ￥27,420
￥69,516 total
includes taxes & fees
Oct 5 - Oct 6
Eagles Beach Nest 2:Pet-Friendly*Fenced*Walk2Beach
A modern kitchen with white cabinetry, stainless steel appliances, and a dining area with a wooden table and chairs.

5. 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 ￥25,439
￥96,305 total
includes taxes & fees
Sep 15 - Sep 16
Sq Toe`s Last Resort:Pet-Friendly*Fenced* GameRoom
A modern living room with a grey sofa, a small ottoman, and a patterned rug. There is a kitchen area with a dark countertop and hanging pots.

6. 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 ￥17,793
￥60,335 total
includes taxes & fees
Sep 13 - Sep 14
Eagle`s Beach Nest: Pet-Friendly*Fenced*Walk2Beach
A hot tub with a control panel, a wooden wall, and a stone-like exterior.

7. BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.

BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.
Michigan City
9.2 out of 10, Wonderful, (140 reviews)
"Such a beautiful location, easy access to the the beach, and the view was gorgeous. Also, the entertainment options in the Miami were incredible. Will absolutely visit again."
United States
Katie K.
The price is ￥19,201
￥40,430 total
includes taxes & fees
Sep 14 - Sep 15
BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.
A living room with a stone fireplace, a grey sofa, a coffee table, and large windows with curtains.

8. 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 ￥28,943
￥52,092 total
includes taxes & fees
Sep 13 - Sep 14
Spacious 5-Bedroom Sawyer Farmhouse Retreat
A modern living room with a stone fireplace, wooden ceiling, and a dining area with a wooden table and chairs.

9. 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 ￥16,697
￥75,456 total
includes taxes & fees
Sep 17 - Sep 18
Walk to Town, Beach, Game Room, Firepit Stay
A kitchen with wooden cabinets, a microwave, a stove, and a dishwasher.

10. Beach Town Retreat | 2BR Near Dunes and Downtown

Beach Town Retreat | 2BR Near Dunes and Downtown
Shorewood-Tower Hills-Harbert
The price is ￥29,301
￥59,785 total
includes taxes & fees
Oct 12 - Oct 13
Beach Town Retreat | 2BR Near Dunes and Downtown
A beach with footprints leading to a wooden post, and the sun setting over the ocean.

11. Relax & Recharge in Hot Tub - Minutes to Warren Dunes - 3BR 2BA

Relax & Recharge in Hot Tub - Minutes to Warren Dunes - 3BR 2BA
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 ￥31,290
￥72,030 total
includes taxes & fees
Oct 5 - Oct 6
Relax & Recharge in Hot Tub - Minutes to Warren Dunes - 3BR 2BA

12. 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, (16 reviews)
"We loved this property!"
United States
Robin L.
The price is ￥33,194
￥71,930 total
includes taxes & fees
Sep 13 - Sep 14
3BR 2b New Buff cottage dogs ok, steps to dwntn restaurants&shops, walk to beach
A living room with a TV on a wooden stand, a white gumball machine, a wicker basket, and a round wooden table with a magazine and remote control.

13. 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, (32 reviews)
"Conveniently located to everything"
United States
Cheryl G.
The price is ￥34,562
￥39,170 total
includes taxes & fees
Sep 21 - Sep 22
Peach by the Beach! 1 Bdrm Apt close to downtown
A modern kitchen with stainless steel appliances, wooden cabinets, and built-in shelves.

14. Newely Remodeled Studio!

Newely Remodeled Studio!
Michigan City
9.2 out of 10, Wonderful, (24 reviews)
"It was amazing and close by the dunes for our National Park and hiking day. Nice area with lots of restaurants around, and the place was super clean and cozy!"
United States
JoC S.
The price is ￥12,442
￥23,397 total
includes taxes & fees
Sep 14 - Sep 15
Newely Remodeled Studio!
A wooden cabin with a porch, outdoor seating, and a garden area.

15. 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 ￥40,141
￥78,368 total
includes taxes & fees
Oct 6 - Oct 7
Breezy Chic: Fresh Spring Vibes at The Modern Oak walkable to town!
A sunset over a beach with people standing on the shore.

16. 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, (31 reviews)
"It was a cute little place to stay"
United States
Janielle K.
Cozy House Retreat: Exclusive Full Yard & Porch-2 Miles to Beach and Mt Baldy
A waterfront property with a dock, a large tree, and a house with a balcony overlooking the water.

17. 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, (34 reviews)
"We had a great trip! The condo was very spacious and located right next to everything we wanted to do."
United States
Gabrielle J.
The price is ￥44,101
￥78,084 total
includes taxes & fees
Sep 15 - Sep 16
Luxury Downtown Getaway: 2BR Condo Near New Buffalo’s Top Attractions!
A modern living room with a large wooden dining table, white chairs, a grey sofa, and a fireplace.

18. 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 ￥34,738
￥41,454 total
includes taxes & fees
Sep 13 - Sep 14
Warren Dunes - Large 2 Br-2 Bath, Hot Tub, Wbfpl , Next To Wineries
A gazebo with a rusted metal roof and a circular floor, surrounded by gravel and trees.

19. 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 ￥29,334
￥37,523 total
includes taxes & fees
Sep 14 - Sep 15
Be Our -Country- Guest
A large indoor swimming pool with a glass ceiling, surrounded by lounge chairs and a hot tub.

20. 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 ￥62,074
￥102,684 total
includes taxes & fees
Sep 14 - Sep 15
Deerpath Cottage-30 Acres with Indoor Pool, Farm, Kayaking, Trails, by 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
"What ud expect from a casino hot"
Charles 1-night trip
Posted 4 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 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?

Family Retreat-Beachwalk-Grill-AC-Free WiFi-Pool Table-Bikes-Grill-Golf Cart: This vacation home rental near Lakeside is located near the beach and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

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.