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

Holiday Rentals in Lakeside

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Our top choices for Lakeside holiday rentals

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 €990
includes taxes & fees
4 Nov - 5 Nov
Private Beach Steps to the Lake.

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

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.
Home in Union Pier, MI

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 €478
includes taxes & fees
4 Nov - 5 Nov
Dogwood - Upscale 2 Bedroom Villa at Petite Acres

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 €196
includes taxes & fees
4 Nov - 5 Nov
Cherry Street Guesthouse with private wooded yard & firepit, 3 blocks to town!

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
The price is €235
includes taxes & fees
4 Nov - 5 Nov
Stay in downtown Three Oaks overlooking the main street!

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

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.
Creekside House on 30 Acres with Kayaks/Pool/Farm/River/Trails/Pets, near Beach

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 €585
includes taxes & fees
4 Nov - 5 Nov
Secluded Retreat, Hot Tub, Fire Pit, Wildlife Views, Near New Buffalo Beach!

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 €445
includes taxes & fees
1 Dec - 2 Dec
Deerpath Cottage-30 Acres with Indoor Pool, Farm, Kayaking, Trails, by Beach!

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 €386
includes taxes & fees
3 Dec - 4 Dec
Breezy Chic: Fresh Spring Vibes at The Modern Oak walkable to town!

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

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 €429
includes taxes & fees
8 Nov - 9 Nov
3BR 2b New Buff cottage dogs ok, steps to dwntn restaurants&shops, walk to beach

14. Goldenrod -upscale 2 Bedroom at Petite Acres

Goldenrod -upscale 2 Bedroom at Petite Acres
3.0 star property
New Buffalo
The price is €478
includes taxes & fees
4 Nov - 5 Nov
Goldenrod -upscale 2 Bedroom at Petite Acres

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
Eagles Beach Nest 2:Pet-Friendly*Fenced*Walk2Beach

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.
Sawyer Getaway | Walk to Downtown

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 €477
includes taxes & fees
3 Dec - 4 Dec
Sq Toe`s Last Resort:Pet-Friendly*Fenced* GameRoom

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 €485
includes taxes & fees
3 Dec - 4 Dec
Relax & Recharge in Hot Tub - Minutes to Warren Dunes - 3BR 2BA

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.
Archer's Retreat-Sleeps 10-1/2 mile to Lake Michigan! Pet/Kid Friendly

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 €968
includes taxes & fees
4 Nov - 5 Nov
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

Find out more about Lakeside

Everything you need to know about Lakeside holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Lakeside holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Lakeside holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Lakeside holiday rentals we have selected for you start as low as €170 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 holiday 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 holiday.

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 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?

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

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.