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 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Lakeside vacation rentals

Terrace/patio

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, (77 reviews)
"Great to walk to town. Nice area to road bike etc."
United States
jeffrey
$280 nightly
The price is $280
Aug 30 - Aug 31
Total with taxes and fees
Cherry Street Guesthouse with private wooded yard & firepit, 3 blocks to town!
Living area

2. 5 min to Warren Dunes! Private Wooded Retreat w/ Sunroom, Firepit & Fireplace

5 min to Warren Dunes! Private Wooded Retreat w/ Sunroom, Firepit & Fireplace
Shorewood-Tower Hills-Harbert
10.0 out of 10, Exceptional, (5 reviews)
$429 nightly
The price is $452
Sep 1 - Sep 2
Total with taxes and fees
5 min to Warren Dunes! Private Wooded Retreat w/ Sunroom, Firepit & Fireplace
Living area

3. 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, (15 reviews)
"Loved staying in this cottage. Super close to everything, clean and overall in a great location. Hosts were very helpful and easy to communicate with. Highly recommend! Will look to stay here again for sure. "
United States
Miranda S.
$439 nightly
The price is $451
Sep 2 - Sep 3
Total with taxes and fees
3BR 2b New Buff cottage dogs ok, steps to dwntn restaurants&shops, walk to beach
Living area

4. 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)
"Great stay, loved the place!"
United States
Ryan J.
$439 nightly
The price is $449
Aug 31 - Sep 1
Total with taxes and fees
Eagle`s Beach Nest: Pet-Friendly*Fenced*Walk2Beach
Living area

5. 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.
$364 nightly
The price is $378
Sep 13 - Sep 14
Total with taxes and fees
Spacious 5-Bedroom Sawyer Farmhouse Retreat
Private kitchen

6. 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.
$657 nightly
The price is $668
Sep 23 - Sep 24
Total with taxes and fees
Sq Toe`s Last Resort:Pet-Friendly*Fenced* GameRoom
Living area

7. 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.
$508 nightly
The price is $516
Sep 3 - Sep 4
Total with taxes and fees
Walk to Town, Beach, Game Room, Firepit Stay
Private kitchen

8. 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
$496 nightly
The price is $508
Sep 23 - Sep 24
Total with taxes and fees
Eagles Beach Nest 2:Pet-Friendly*Fenced*Walk2Beach
Interior

9. 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)
"Close to downtown, convenient location."
United States
Jim B.
$257 nightly
The price is $257
Aug 31 - Sep 1
Total with taxes and fees
Peach by the Beach! 1 Bdrm Apt close to downtown
Beach

10. Book Your Spring Escape! Relax & Recharge in Hot Tub - Minutes to Dining & Shops

Book Your Spring Escape! Relax & Recharge in Hot Tub - Minutes to Dining & Shops
Sawyer
9.2 out of 10, Wonderful, (11 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
$524 nightly
The price is $540
Sep 22 - Sep 23
Total with taxes and fees
Book Your Spring Escape! Relax & Recharge in Hot Tub - Minutes to Dining & Shops
Living area

11. Steps to Journeyman - Cozy Stay - Fast Wi-Fi - Pets OK - Near Lake Michigan

Steps to Journeyman - Cozy Stay - Fast Wi-Fi - Pets OK - Near Lake Michigan
Three Oaks
10.0 out of 10, Exceptional, (3 reviews)
"Great Three Oaks location, clean stylish home, easy to communicate with owner. Really enjoyed our stay!"
United States
MAURA T.
$439 nightly
The price is $462
Sep 3 - Sep 4
Total with taxes and fees
Steps to Journeyman - Cozy Stay - Fast Wi-Fi - Pets OK - Near Lake Michigan
Private kitchen

12. 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.
$136 nightly
The price is $152
Sep 14 - Sep 15
Total with taxes and fees
Newely Remodeled Studio!
Marina

13. 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)
"Great place and great communication with host"
United States
Anonymous traveler
$505 nightly
The price is $522
Aug 31 - Sep 1
Total with taxes and fees
Luxury Downtown Getaway: 2BR Condo Near New Buffalo’s Top Attractions!
Interior

14. 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, (86 reviews)
"We lived our stay. Close to local wineries and breweries and such a nice hot tub. Home was clean and all necessities provided. "
United States
Carrie A.
$284 nightly
The price is $298
Aug 30 - Aug 31
Total with taxes and fees
Warren Dunes - Large 2 Br-2 Bath, Hot Tub, Wbfpl , Next To Wineries
Outdoor dining

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.
$526 nightly
The price is $543
Sep 2 - Sep 3
Total with taxes and fees
Breezy Chic: Fresh Spring Vibes at The Modern Oak walkable to town!
Exterior

16. Pied-à-terre Allium - The Bunk House at Petite Acres

Pied-à-terre Allium - The Bunk House at Petite Acres
New Buffalo
10.0 out of 10, Exceptional, (1 review)
"Very cute, great for a girls trip"
United States
Lauren A.
$679 nightly
The price is $715
Sep 1 - Sep 2
Total with taxes and fees
Pied-à-terre Allium - The Bunk House at Petite Acres
Interior

17. Cozy Country Escape - Convenient to New Buffalo, Notre Dame & Amazon data center

Cozy Country Escape - Convenient to New Buffalo, Notre Dame & Amazon data center
New Carlisle
9.6 out of 10, Exceptional, (29 reviews)
"Cozy Country Escape is a perfect name for this location! It was so quiet & relaxing.The unit was very clean, Jackie, the property manager, was very prompt & thorough in her response to questions & entry instructions. The view of Lake Hudson was beautiful, especially at sunset."
United States
Dianne K.
$389 nightly
The price is $436
Sep 3 - Sep 4
Total with taxes and fees
Cozy Country Escape - Convenient to New Buffalo, Notre Dame & Amazon data center
Pool

18. 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, (37 reviews)
"Beautiful location. Although we were there for one night there was so much to enjoy."
United States
Cassandra T.
$744 nightly
The price is $783
Sep 8 - Sep 9
Total with taxes and fees
Creekside House on 30 Acres with Kayaks/Pool/Farm/River/Trails/Pets, near Beach
Private kitchen

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, (4 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.
$420 nightly
The price is $442
Sep 17 - Sep 18
Total with taxes and fees
Archer's Retreat-Sleeps 10-1/2 mile to Lake Michigan! Pet/Kid Friendly
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
"One of nicest casino hotels we’ve been to."
Stuart 1-night trip
Posted 2 hours ago
Four Winds Casino Resort – New Buffalo

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 $376 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?

Home Away From Home... But With A Beach!: This vacation home rental near Lakeside is located in the city center and has a garden, a selection of games, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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.