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

Lakeside Vacation Rentals

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.
$1,096 nightly
The price is $1,096
Nov 8 - Nov 9
Total with taxes and fees
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.
$961 nightly
The price is $981
Dec 1 - Dec 2
Total with taxes and fees
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.
$283 nightly
The price is $299
Nov 8 - Nov 9
Total with taxes and fees
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
$451 nightly
The price is $485
Nov 15 - Nov 16
Total with taxes and fees
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
$216 nightly
The price is $216
Nov 5 - Nov 6
Total with taxes and fees
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, (191 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
$261 nightly
The price is $270
Nov 9 - Nov 10
Total with taxes and fees
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.
$744 nightly
The price is $783
Nov 30 - Dec 1
Total with taxes and fees
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.
$548 nightly
The price is $577
Dec 1 - Dec 2
Total with taxes and fees
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.
$649 nightly
The price is $649
Nov 8 - Nov 9
Total with taxes and fees
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.
$467 nightly
The price is $494
Dec 1 - Dec 2
Total with taxes and fees
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.
$424 nightly
The price is $437
Nov 16 - Nov 17
Total with taxes and fees
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.
$397 nightly
The price is $397
Nov 10 - Nov 11
Total with taxes and fees
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.
$469 nightly
The price is $483
Nov 8 - Nov 9
Total with taxes and fees
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
$451 nightly
The price is $485
Nov 18 - Nov 19
Total with taxes and fees
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
$356 nightly
The price is $362
Nov 9 - Nov 10
Total with taxes and fees
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.
$256 nightly
The price is $262
Nov 5 - Nov 6
Total with taxes and fees
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.
$512 nightly
The price is $517
Nov 9 - Nov 10
Total with taxes and fees
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
$489 nightly
The price is $502
Nov 5 - Nov 6
Total with taxes and fees
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)
"Came for 50th birthday with family! Everything was perfect and great location "
United States
Jennifer W.
$383 nightly
The price is $404
Nov 9 - Nov 10
Total with taxes and fees
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
$1,046 nightly
The price is $1,104
Nov 8 - Nov 9
Total with taxes and fees
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

Spark by Hilton Stevensville

Spark by Hilton Stevensville

8/10 Good
"There was a few hiccups along the way, but by the time we left, we were in good standing and we enjoyed our trip. Everything that was wrong. The first night was fixed so they do help you and they do work with you. They are understanding."
Kimberly 3-night trip
Posted 14 hours ago
Spark by Hilton Stevensville

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Lakeside in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $187 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

Explore a world of travel with Expedia

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.