Lakeside Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Lakeside vacation rentals

A wooden deck with a bench and two chairs, overlooking a body of water and trees.

1. Private Beach Steps to the Lake.

Private Beach Steps to the Lake.
Union Pier
10.0 out of 10, Exceptional, (97 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 CA $771
CA $1,538 total
includes taxes & fees
Nov 9 - Nov 10
Private Beach Steps to the Lake.
A wicker sofa with white cushions, a wooden table with a bowl of green plants, and a glass of water.

2. 7BR 5K SqFt Schoolhouse • Sauna, Hot Tub, Gym & 2 Game Rooms

7BR 5K SqFt Schoolhouse • Sauna, Hot Tub, Gym & 2 Game Rooms
Union Pier
8.6 out of 10, Excellent, (14 reviews)
"Place was as expected, great for the purpose of our stay with multiple young adults. Host was great at communicating. "
United States
Jennifer O.
The price is CA $500
CA $1,467 total
includes taxes & fees
Dec 8 - Dec 9
7BR 5K SqFt Schoolhouse • Sauna, Hot Tub, Gym & 2 Game Rooms
A modern kitchen with a large island, bar stools, and a seating area with a bench.

3. Home in Union Pier, MI

Home in Union Pier, MI
Union Pier
10.0 out of 10, Exceptional, (1 review)
"We had a great stay in this beautiful home! It's open and airy and was very clean. The beds were all comfortable. We loved having a full kitchen and lots of space to relax as well. Plenty of towels, dish soap, paper towels, etc. Our boys loved the game room/rec area. The owner was very polite and responsive with any questions we had. Would stay again! Thanks!"
United States
Stacy S.
The price is CA $168
CA $422 total
includes taxes & fees
Nov 9 - Nov 10
Home in Union Pier, MI
A residential area with multiple houses, a covered outdoor seating area, and a well-maintained lawn.

4. Dogwood - Upscale 2 Bedroom Villa at Petite Acres

Dogwood - Upscale 2 Bedroom Villa at Petite Acres
3.0 star property
New Buffalo
The price is CA $458
CA $739 total
includes taxes & fees
Nov 15 - Nov 16
Dogwood - Upscale 2 Bedroom Villa at Petite Acres
A small, single-story cabin with a porch, surrounded by a garden and trees.

5. 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, (83 reviews)
"Great to walk to town. Nice area to road bike etc."
United States
jeffrey
The price is CA $210
CA $304 total
includes taxes & fees
Nov 9 - Nov 10
Cherry Street Guesthouse with private wooded yard & firepit, 3 blocks to town!
A kitchen with a granite countertop, stainless steel sink, and white cabinetry.

6. 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, (193 reviews)
"Great space for an overnight stay, clean and spacious. We went for a Notre Dame game and was about 35 minutes away."
United States
Jaime
The price is CA $188
CA $375 total
includes taxes & fees
Nov 9 - Nov 10
Stay in downtown Three Oaks overlooking the main street!
A covered outdoor dining area with a table and chairs, surrounded by large windows offering a view of a forested area.

7. River's Edge on 30 Acres with Kayaks/Pool/Farm/River/Trails/Pets, near Beach

River's Edge on 30 Acres with Kayaks/Pool/Farm/River/Trails/Pets, near Beach
Union Pier
9.8 out of 10, Exceptional, (20 reviews)
"The property was lovely and the Inn keepers were super sweet and happy to help us with anything we needed. Thank you . "
United States
LIndsay M.
The price is CA $559
CA $1,098 total
includes taxes & fees
Dec 7 - Dec 8
River's Edge on 30 Acres with Kayaks/Pool/Farm/River/Trails/Pets, near Beach
A covered pool area with seating and a sign indicating 'Pool Rules'.

8. 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, (38 reviews)
"Beautiful location. Although we were there for one night there was so much to enjoy."
United States
Cassandra T.
The price is CA $461
CA $810 total
includes taxes & fees
Dec 7 - Dec 8
Creekside House on 30 Acres with Kayaks/Pool/Farm/River/Trails/Pets, near Beach
A modern kitchen with a large island, stainless steel appliances, and a unique ceiling design.

9. 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, (26 reviews)
"Super nice place.!!!"
United States
Citlaly D.
The price is CA $879
CA $955 total
includes taxes & fees
Nov 9 - Nov 10
Secluded Retreat, Hot Tub, Fire Pit, Wildlife Views, Near New Buffalo Beach!
A covered pool area with seating and a sign indicating 'Pool Rules'.

10. 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 CA $419
CA $725 total
includes taxes & fees
Dec 2 - Dec 3
Deerpath Cottage-30 Acres with Indoor Pool, Farm, Kayaking, Trails, by Beach!
A wooden cabin with a porch, outdoor seating, and a garden area.

11. 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, (33 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 CA $273
CA $580 total
includes taxes & fees
Dec 8 - Dec 9
Breezy Chic: Fresh Spring Vibes at The Modern Oak walkable to town!
A waterfront property with a dock, a large tree, and a house with a balcony overlooking the water.

12. 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, (41 reviews)
"Home was clean and location was perfect for walking everywhere; beach, restaurants, marina, etc."
United States
Matthew S.
The price is CA $328
CA $585 total
includes taxes & fees
Nov 10 - Nov 11
Luxury Downtown Getaway: 2BR Condo Near New Buffalo’s Top Attractions!
Cozy living room with gas fireplace and mini fridge bar cart for entertaining.

13. 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, (18 reviews)
"Great property with excellent location to all downtown activities as well as the beach."
United States
christian s.
The price is CA $311
CA $661 total
includes taxes & fees
Nov 9 - Nov 10
3BR 2b New Buff cottage dogs ok, steps to dwntn restaurants&shops, walk to beach
A residential area with multiple houses, a covered outdoor seating area, and a well-maintained lawn.

14. Goldenrod -upscale 2 Bedroom at Petite Acres

Goldenrod -upscale 2 Bedroom at Petite Acres
3.0 star property
New Buffalo
The price is CA $425
CA $703 total
includes taxes & fees
Nov 18 - Nov 19
Goldenrod -upscale 2 Bedroom at Petite Acres
A modern kitchen with stainless steel appliances, a wooden island, and a dining area with white chairs.

15. 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 CA $138
CA $501 total
includes taxes & fees
Nov 9 - Nov 10
Eagles Beach Nest 2:Pet-Friendly*Fenced*Walk2Beach
A compact kitchen with white cabinets, a granite countertop, and a visible stove.

16. Sawyer Getaway | Walk to Downtown

Sawyer Getaway | Walk to Downtown
Shorewood-Tower Hills-Harbert
10.0 out of 10, Exceptional, (2 reviews)
"Great place right in the heart of town. It was clean, quiet and the perfect spot for a quick little get away. My son and I had a great trip! Awesome kids music park right next door!"
United States
Jason C.
The price is CA $122
CA $354 total
includes taxes & fees
Nov 10 - Nov 11
Sawyer Getaway | Walk to Downtown
A modern kitchen with white cabinetry, stainless steel appliances, and a dining area with a wooden table and chairs.

17. 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 CA $139
CA $729 total
includes taxes & fees
Nov 16 - Nov 17
Sq Toe`s Last Resort:Pet-Friendly*Fenced* GameRoom
An outdoor hot tub with a control panel, surrounded by a concrete deck, under string lights.

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

Relax & Recharge in Hot Tub - Minutes to Warren Dunes - 3BR 2BA
Sawyer
9.4 out of 10, Exceptional, (13 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 CA $316
CA $709 total
includes taxes & fees
Nov 9 - Nov 10
Relax & Recharge in Hot Tub - Minutes to Warren Dunes - 3BR 2BA
A modern kitchen with white cabinets, a central island, stainless steel appliances, and a blue rug.

19. 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, (7 reviews)
"A hidden gem! This was one of the best VRBO experiences that we have had! So many personal touches that make you feel at home and that you don’t want to ever leave. Host was amazing and readily available for any questions and willing to help with any suggestions. We already are thinking about when we can book again and stay for longer. You will not be disappointed with your booking here. So close to Warren Dunes and so many cute places to eat."
United States
Heather A.
The price is CA $230
CA $553 total
includes taxes & fees
Nov 9 - Nov 10
Archer's Retreat-Sleeps 10-1/2 mile to Lake Michigan! Pet/Kid Friendly
A modern house with a large glass front, surrounded by trees.

20. Maison Foxglove - 4 BR Luxe Home at Petite Acres in New Buffalo

Maison Foxglove - 4 BR Luxe Home at Petite Acres in New Buffalo
New Buffalo
The price is CA $722
CA $1,547 total
includes taxes & fees
Nov 9 - Nov 10
Maison Foxglove - 4 BR Luxe Home at Petite Acres in New Buffalo
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

A dining area with high ceilings, wooden beams, and large windows with a view of the outdoors.
The Brewery Lodge Hotel

The Brewery Lodge Hotel

The Brewery Lodge Hotel
Michigan City

10/10 Excellent

Huge room, great restaurant. Nice walking trails
Canada
Christopher
Reviewed August 19, 2024
The Brewery Lodge Hotel

Find out more about Lakeside

Everything you need to know about Lakeside vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Lakeside vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Lakeside vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Lakeside vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Lakeside. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Lakeside vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Lakeside vacation rentals we have selected for you start as low as CA $121 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Lakeside rentals

At Expedia, we put the best Lakeside vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Lakeside rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Lakeside vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Lakeside. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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 45 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.