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Compare 897 Vacation Homes in Lakeside with updated reviews, rates, and availability.

Cozy Holiday Getaway for the Family
We decorate for the holidays and would love to host you and your family!

Cozy Holiday Getaway for the Family

10.0 out of 10, Exceptional, (40)
"Enjoyed our stay! The home is family-friendly, well-stocked and has a spacious living space."
Cozy Holiday Getaway for the Family
Carrie's Cottage - Charming Duplex Style 3 Bedroom Cottage with Beach Access!
Semi private beach short walk down the block

Carrie's Cottage - Charming Duplex Style 3 Bedroom Cottage with Beach Access!

9.0 out of 10, Wonderful, (40)
"This was a 4 day getaway to relax. While there is no water view from the property, a short walk and some steps led us to the perfect semiprivate beach. There were umbrellas, chairs and 2 kayaks available to use. Despite it being mid September, the water was swimmable and the temps were high 80s. We brought our dogs with us and they loved swimming in the water. I can't speak to how busy it is during the peak summertime, but we had the entire stretch to ourselves. Loved that! We got to meet the...
Carrie's Cottage - Charming Duplex Style 3 Bedroom Cottage with Beach Access!
Hot tub open all year! Private heated pool, sleeps 10 near downtown New Buffalo!
Heated pool open late April to mid October!

Hot tub open all year! Private heated pool, sleeps 10 near downtown New Buffalo!

9.2 out of 10, Wonderful, (56)
"Overall we had a great weekend! The open layout of the house was perfect for hanging out and relaxing. The backyard is truly amazing and we loved having the option of using the hot tub. We did wish the house would have had some blankets for us to use since it was pretty chilly and it seemed like the heat had a hard time keeping up. "
Hot tub open all year! Private heated pool, sleeps 10 near downtown New Buffalo!
Big Family House 5 Minutes from Lake Michigan/Blue Chip Casino/Brewery/Wineries!
Dining Table

Big Family House 5 Minutes from Lake Michigan/Blue Chip Casino/Brewery/Wineries!

9.8 out of 10, Exceptional, (91)
"Thanksgiving family get away for 4 days was great in this property. Plenty of bed rooms big table. Great stove. We cooked there all 4 days. Has a grill. Very close to outlets. Very happy with your stay!"
Big Family House 5 Minutes from Lake Michigan/Blue Chip Casino/Brewery/Wineries!
Spacious home with game room, hot tub, fireplace, fast WiFi & home theater

Spacious home with game room, hot tub, fireplace, fast WiFi & home theater

9.6 out of 10, Exceptional, (21)
"Had relatives from 5 states converge for a wedding celebration late September. Property was great arrangement presenting multiple sleeping arrangements and diverse recreational activities. Could spend time with family for cards, games or hot tubbing. Quite time on the patio or multiple balconies was also a treat."
Spacious home with game room, hot tub, fireplace, fast WiFi & home theater
Cozy and Private Home with Fireplace on Wooded Lot Near Lake Michigan Beaches
Vaulted ceilings, open floorplan, and loft with additional queen bed.

Cozy and Private Home with Fireplace on Wooded Lot Near Lake Michigan Beaches

10.0 out of 10, Exceptional, (25)
"From start to finish we had a wonderful time at the Michiana Rose! Alex was quick to answer our questions, immaculate cottage, comfy beds, well-equipped kitchen, enjoyed having the golf cart for beach trips & sunset watching! We look forward to our next stay right there!tbeach"
Cozy and Private Home with Fireplace on Wooded Lot Near Lake Michigan Beaches
NEW LISTING—-UNION PIER PERFECTION—HOT TUB, FIRE PIT, WALK TO LAKE!!
Exterior detail

NEW LISTING—-UNION PIER PERFECTION—HOT TUB, FIRE PIT, WALK TO LAKE!!

9.8 out of 10, Exceptional, (32)
"Overall great stay. Came with 3 college girls friends for a quick weekend. Property was clean, cute and cozy. A few items that the property does not have that would have been nice are an iron/ironing board and a blow dryer. Hot tub appeared new and a great addition : nice to relax in the evenings. Overall house was clean, well equipped and well maintained. Would recommend to anyone looking for a place to stay in the Union Pier area. "
NEW LISTING—-UNION PIER PERFECTION—HOT TUB, FIRE PIT, WALK TO LAKE!!
7700 Sq. Ft, 8 BR, 7 BTH Compound. Heated Pool, Hot Tub, 2 miles From Beach.
The Sawyer Rear View

7700 Sq. Ft, 8 BR, 7 BTH Compound. Heated Pool, Hot Tub, 2 miles From Beach.

2.0 star property
10.0 out of 10, Exceptional, (4)
"WOW! Cannot say enough about this property besides our group will be returning. I came for a weekend away with 12 women and from the moment we arrived, we were welcomed and found everything we could have hoped for and more. The owner met us to show us around the HUGE property and made sure we had what we needed (wifi, thermostats, working the TVs, etc.). He even left a gift of local goodies and gave us great recs on nearby restaurants and hiking trails. After that personal touch, we all...
7700 Sq. Ft, 8 BR, 7 BTH Compound. Heated Pool, Hot Tub, 2 miles From Beach.
Michigan City Mansion / Hot Tub / Fire Pit / Pet Friendly
Unwind in Your Private Backyard Oasis

Michigan City Mansion / Hot Tub / Fire Pit / Pet Friendly

10.0 out of 10, Exceptional, (3)
"It was incredible experience! The location was ideal, providing easy access to all stores.The property was clean, well-maintained, and equipped with everything we needed for a comfortable stay. The host was very responsive. Check-in and check-out were seamless, which made our trip even more enjoyable."
Michigan City Mansion / Hot Tub / Fire Pit / Pet Friendly
Walk to the Beach from Beachy Farmhouse - Lake Michigan & Hot Tub. Pet-Friendly!
Terrace/patio

Walk to the Beach from Beachy Farmhouse - Lake Michigan & Hot Tub. Pet-Friendly!

Walk to the Beach from Beachy Farmhouse - Lake Michigan & Hot Tub. Pet-Friendly!
Lifetime Memories*Big Beach Front House*Fire Place/Pit*Free WiFi*Paddle Boards
View of lake from third floor deck

Lifetime Memories*Big Beach Front House*Fire Place/Pit*Free WiFi*Paddle Boards

9.8 out of 10, Exceptional, (131)
"The house is amazing! So much space for people to sleep. Everything was clean. The only suggestion that I would have is to have more bar stools to be in the kitchen for people to sit around. I know the island is small but people still always congregate in the kitchen and it would be nice to have more bar stools! "
Lifetime Memories*Big Beach Front House*Fire Place/Pit*Free WiFi*Paddle Boards
Spacious home near nightlife, beaches, dunes, zoo, and Lake Michigan charters.
Exterior

Spacious home near nightlife, beaches, dunes, zoo, and Lake Michigan charters.

7.6 out of 10, Good, (18)
"This quaint old house was in a great location. It had tons of room and plenty of beds. Everything was clean and well taken care of. "
The price is SAR 499
SAR 971 total
includes taxes & fees
31 Dec - 1 January 2025
Spacious home near nightlife, beaches, dunes, zoo, and Lake Michigan charters.
Large 4 Bedroom 3 Bath home with a short walk To Sheridan Beach!
Exterior

Large 4 Bedroom 3 Bath home with a short walk To Sheridan Beach!

8.8 out of 10, Excellent, (78)
"The beds were comfortable, gas stove was nice, back deck was nice. The kids enjoyed their stay. The neighborhood was nice. It was newly painted a beautiful blue. The CO2 detector was alarming, but the fire dept said it just needed to be replaced. Good assortment of games, beach toys, wagon and outdoor toys. We did not mind the older furniture because we did not need to be yelling at the kids all the time lol. I had read other reviews, so we brought a few our own pots and pans. We would stay here...
The price is SAR 1,123
SAR 2,279 total
includes taxes & fees
26 Dec - 27 Dec
Large 4 Bedroom 3 Bath home with a short walk To Sheridan Beach!
Farmesque with a splash of modern
Exterior

Farmesque with a splash of modern

10.0 out of 10, Exceptional, (22)
"Very clean property, host was quick to reply with questions. Will stay here again "
The price is SAR 747
SAR 1,712 total
includes taxes & fees
5 Jan - 6 January 2025
Farmesque with a splash of modern
Beautiful 2-Story Home Near Beach with Firepit, WiFi, Central AC - Dogs OK

Beautiful 2-Story Home Near Beach with Firepit, WiFi, Central AC - Dogs OK

9.6 out of 10, Exceptional, (19)
"Very Nice place to stay and close to everything.."
Beautiful 2-Story Home Near Beach with Firepit, WiFi, Central AC - Dogs OK
Classic European style meets Lake Michigan
Exterior

Classic European style meets Lake Michigan

9.6 out of 10, Exceptional, (17)
"Loved the house, super clean and comfortable. Hot tub was hot, clean and ready for us! Our unexpected fav hangout spot was the heated garage with so much ping pong and foosball played, and giant tv on! So much fun, plenty of room for our group and kitchen came fully stocked with all types of pans and anything we needed to cook Thanksgiving dinner. We had a great time! Only thing we didn’t love was that it wasn’t the BEST walking in the area for kids cause no sidewalks but that was a pretty minor...
The price is SAR 507
SAR 1,547 total
includes taxes & fees
5 Jan - 6 January 2025
Classic European style meets Lake Michigan
Lake Michigan Beachfront Home for Large Groups, Private Beach Access
Dreams of Duneland

Lake Michigan Beachfront Home for Large Groups, Private Beach Access

10.0 out of 10, Exceptional, (64)
"We enjoyed everything about this house. It was well stocked with the essentials and was very clean. Easily fit grandparents and two families of 4. Loved the location on the dune and the incredible short walk to the beach access. Would definitely stay here again. "
Lake Michigan Beachfront Home for Large Groups, Private Beach Access
Secluded Pool Playhouse: Hot Tub, Games, Fire Pit
Unwind in our hot tub, the perfect spot to relax after a day of adventures.

Secluded Pool Playhouse: Hot Tub, Games, Fire Pit

9.8 out of 10, Exceptional, (13)
"We enjoyed I'll stay. Only thing is, the floors are very cold, & its cold in the living room always eventho the heat be on. My mom said it was cold. Other than that my family loved the getaway we had togther."
Secluded Pool Playhouse: Hot Tub, Games, Fire Pit
1 bed/1 bath, 1.5 blocks to beach/town, dog friendly
front doors of Cottage 1 (left) and Cottage 2 (right)

1 bed/1 bath, 1.5 blocks to beach/town, dog friendly

10.0 out of 10, Exceptional, (18)
"Came for a weekend wedding to beautiful Michigan and had the absolute best time at this spot! The space was clean and safe, the bed was SO comfy! Cannot wait to come back!"
1 bed/1 bath, 1.5 blocks to beach/town, dog friendly
Sq Toe's Last Resort: Pet-Friendly / Fenced / Game Room / Walk to Beach
Open Concept Kitchen and Living Room

Sq Toe's Last Resort: Pet-Friendly / Fenced / Game Room / Walk to Beach

10.0 out of 10, Exceptional, (6)
"Nice cozy place within walking distance to lots of restaurants. "
The price is SAR 443
SAR 1,351 total
includes taxes & fees
5 Jan - 6 January 2025
Sq Toe's Last Resort: Pet-Friendly / Fenced / Game Room / Walk to 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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Other property types in Lakeside

Carrie's Cottage - Charming Duplex Style 3 Bedroom Cottage with Beach Access!
Semi private beach short walk down the block

Carrie's Cottage - Charming Duplex Style 3 Bedroom Cottage with Beach Access!

9.0 out of 10, Wonderful, (40)
"This was a 4 day getaway to relax. While there is no water view from the property, a short walk and some steps led us to the perfect semiprivate beach. There were umbrellas, chairs and 2 kayaks available to use. Despite it being mid September, the water was swimmable and the temps were high 80s. We brought our dogs with us and they loved swimming in the water. I can't speak to how busy it is during the peak summertime, but we had the entire stretch to ourselves. Loved that! We got to meet the...
Carrie's Cottage - Charming Duplex Style 3 Bedroom Cottage with Beach Access!
1 or 2 Fun Cottages Sleep 2-10-20 People. Pool & Hot Tub. Steps to Beach + More
Front of One of our 2 Cottages on the Property. This is Cottage A

1 or 2 Fun Cottages Sleep 2-10-20 People. Pool & Hot Tub. Steps to Beach + More

9.2 out of 10, Wonderful, (57)
"Great set up with both cottages. Everyone loved their bedrooms and the common areas were great for having everyone together. Our host was very accommodating and easy to communicate with. I would recommend this property to anyone."
1 or 2 Fun Cottages Sleep 2-10-20 People. Pool & Hot Tub. Steps to Beach + More
Lakeside Summer Cottage(Union Pier, Mi)- access to private Lake MI beach

Lakeside Summer Cottage(Union Pier, Mi)- access to private Lake MI beach

9.0 out of 10, Wonderful, (22)
"Perfect place to stay if youre looking to relax at a beautiful beach nearby."
Lakeside Summer Cottage(Union Pier, Mi)- access to private Lake MI 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.