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Check prices for these dates

Next weekend
31 Jan - 2 Feb
In two weeks
7 Feb - 9 Feb
In one month
21 Feb - 23 Feb
In two months
21 Mar - 23 Mar

Compare 900 Vacation Homes in Lakeside with updated reviews, rates, and availability.

Beautiful Family Cottage in Beachwalk-Grill-AC-Free Wifi-Kids Haven.
The Troll's Den

Beautiful Family Cottage in Beachwalk-Grill-AC-Free Wifi-Kids Haven.

9.6 out of 10, Exceptional, (208)
"We needed a second house for an expanding family. This was down the street from the larger house and worked very well. One thought- the headspace between the bunk beds is not large enough for adults to sleep there. "
Beautiful Family Cottage in Beachwalk-Grill-AC-Free Wifi-Kids Haven.
Farmesque with a splash of modern
Exterior

Farmesque with a splash of modern

10.0 out of 10, Exceptional, (27)
"Perfect for our girls night- everything was beautiful and we had a blast. Some from the party may be coming back for a family weekend. "
The price is AED 731
AED 1,671 total
includes taxes & fees
26 Jan - 27 Jan
Farmesque with a splash of modern
BEACHFRONT LAKE MICHIGAN w/Lookout Tower & Lake Views - Sleeps 13
Main Level | Living Room

BEACHFRONT LAKE MICHIGAN w/Lookout Tower & Lake Views - Sleeps 13

9.4 out of 10, Exceptional, (51)
"Christmas whit the family, nice view "
BEACHFRONT LAKE MICHIGAN w/Lookout Tower & Lake Views - Sleeps 13
Brand New House, Sleeps 8, Private Beach Rights, Hot Tub!
Exterior

Brand New House, Sleeps 8, Private Beach Rights, Hot Tub!

10.0 out of 10, Exceptional, (47)
"We were very impressed with this home! It was clean, beautifully decorated, and very comfortable! We had an amazing weekend! The hot tub was such a bonus! "
Brand New House, Sleeps 8, Private Beach Rights, Hot Tub!
Modern Farmhouse Retreat-10 Min Walk to Lake Michigan-Hot Tub-Sauna
Exterior

Modern Farmhouse Retreat-10 Min Walk to Lake Michigan-Hot Tub-Sauna

10.0 out of 10, Exceptional, (78)
"Family enjoyed the stay. Great location "
Modern Farmhouse Retreat-10 Min Walk to Lake Michigan-Hot Tub-Sauna
Perfect Family Retreat-Beachwalk-AC-Free WiFi-GolfCart-Grill--Music Lovers-Bikes
East of the Sun - front view

Perfect Family Retreat-Beachwalk-AC-Free WiFi-GolfCart-Grill--Music Lovers-Bikes

10.0 out of 10, Exceptional, (96)
"Property was clean and comfortable, plenty of room, everyone enjoyed the karaoke "
Perfect Family Retreat-Beachwalk-AC-Free WiFi-GolfCart-Grill--Music Lovers-Bikes
Perfect Family Friendly Getaway!
Your own private, heated pool!

Perfect Family Friendly Getaway!

10.0 out of 10, Exceptional, (40)
"Enjoyed our stay! The home is family-friendly, well-stocked and has a spacious living space."
Perfect Family Friendly Getaway!
Roomy and Cozy 3bd 2ba just mins from Indiana Dunes
Outdoor dining

Roomy and Cozy 3bd 2ba just mins from Indiana Dunes

9.6 out of 10, Exceptional, (17)
"Had a great time at this cottage. Convenient location in between Michigan City and Chesterton. Plenty of space and large fenced in back yard. Right on W. Dunes Highway, so super easy to get anywhere. Kitchen was fully stocked to cook our own meals and 3 different areas for people to watch tv. Never felt like we were on top of each other, Had a great holiday weekend stay!"
Roomy and Cozy 3bd 2ba just mins from Indiana Dunes
View of the lake from 2 decks in this 6BR Lake Shore Dr home, steps to the beach
View of the lake from the huge front deck

View of the lake from 2 decks in this 6BR Lake Shore Dr home, steps to the beach

9.0 out of 10, Wonderful, (73)
"The house was clean and quite adequate for our 3 day stay. We met Mr. Marshall when we arrived (he was there with a crew working on furniture and some repairs). He was very pleasant, as was the crew. We like to cook for ourselves. The stove was not completely functional -- shelves do not fit, and the interior needs a good cleaning. The towel rack above the second floor bathroom toilet is pulling of the wall and could use some attention. Rick Ginther (for the Ginther Siblings)"
The price is AED 1,466
AED 2,954 total
includes taxes & fees
26 Jan - 27 Jan
View of the lake from 2 decks in this 6BR Lake Shore Dr home, steps to the beach
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, (92)
"If you are travelling with a big group, this is good house to stay at. We had 5 families with kids and we fit comfortably. The house was clean and has all you need. Host is responsive and very helpful. "
Big Family House 5 Minutes from Lake Michigan/Blue Chip Casino/Brewery/Wineries!
Family Retreat-Beachwalk-Grill-AC-Free WiFi-Pool Table-Bikes-Grill-Golf Cart
Exterior

Family Retreat-Beachwalk-Grill-AC-Free WiFi-Pool Table-Bikes-Grill-Golf Cart

10.0 out of 10, Exceptional, (179)
"We recently stayed at the Valhalla! The home was exactly has described and was even decorated for Christmas! Any questions we had were promptly answered by Anders. Cozy fireplace and plenty of games for us to use along with a pool table in the basement. We are hoping to visit another time! "
Family Retreat-Beachwalk-Grill-AC-Free WiFi-Pool Table-Bikes-Grill-Golf Cart
Beachwalk vacation home . 6 bedrooms plus a den.
Royal Retreat with the golf cart ! Golf cart for use spring through December 1st

Beachwalk vacation home . 6 bedrooms plus a den.

10.0 out of 10, Exceptional, (227)
"We have stayed at this house multiple times. and we love it!! It’s super well equipped and such a great house for gatherings. We will be back next year!!! "
Beachwalk vacation home . 6 bedrooms plus a den.
Waterfront Home on Lake W/ Private Hot Tub, Amazing View, Private Beach, & WiFi

Waterfront Home on Lake W/ Private Hot Tub, Amazing View, Private Beach, & WiFi

9.2 out of 10, Wonderful, (32)
"Nice house "
Waterfront Home on Lake W/ Private Hot Tub, Amazing View, Private Beach, & WiFi
Kid-friendly Michiana cottage! Summer dates open - including 4th of July!
Front Porch

Kid-friendly Michiana cottage! Summer dates open - including 4th of July!

10.0 out of 10, Exceptional, (51)
"Loved this place and so clean and perfect for our girls weekend!"
Kid-friendly Michiana cottage! Summer dates open - including 4th of July!
2025 Open! Three Night Min! New Buffalo Home Walking Distance To Downtown and Be
Lots Of Light!

2025 Open! Three Night Min! New Buffalo Home Walking Distance To Downtown and Be

9.4 out of 10, Exceptional, (19)
"Great location and perfect size for a large group "
2025 Open! Three Night Min! New Buffalo Home Walking Distance To Downtown and Be
5BR on 5 Acres Hot Tub Pickleball Huge Game Rm

5BR on 5 Acres Hot Tub Pickleball Huge Game Rm

9.4 out of 10, Exceptional, (8)
"We had a great holiday stay. We enjoyed almost all of available outdoor and indoor activities. "
5BR on 5 Acres Hot Tub Pickleball Huge Game Rm
Newly renovated, 7700 Sq. Ft, 8BR, 7BTH, Heated Pool, Hot Tub, Extra Game Bldg
The Sawyer Rear View

Newly renovated, 7700 Sq. Ft, 8BR, 7BTH, Heated Pool, Hot Tub, Extra Game Bldg

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...
Newly renovated, 7700 Sq. Ft, 8BR, 7BTH, Heated Pool, Hot Tub, Extra Game Bldg
Beautiful 4 Bed House in New Buffalo with Pool & Hot Tub Close to Lake & Main St
Pool

Beautiful 4 Bed House in New Buffalo with Pool & Hot Tub Close to Lake & Main St

9.2 out of 10, Wonderful, (19)
"Great location, quiet neighborhood. One hiccup but Rishi was quick to resolve. The kitchen/dining was smaller than what the pictures led us to believe otherwise, all was good. "
Beautiful 4 Bed House in New Buffalo with Pool & Hot Tub Close to Lake & Main St
Breezy Pad, Close to the Lake, with Hot Tub
Great outdoor space!

Breezy Pad, Close to the Lake, with Hot Tub

9.2 out of 10, Wonderful, (71)
"Was a great place to hang and relax for the night! Got to visit wineries in the day and cozy up in the hot tub in the evening, great location! "
The price is AED 400
AED 685 total
includes taxes & fees
26 Jan - 27 Jan
Breezy Pad, Close to the Lake, with Hot Tub
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, (57)
"We rented the unit for a family gathering, multiple family units gathering in a central location. House worked great for our needs. Listing accurate to description. Open floor plan was very accommodating for family socializing together."
Hot tub open all year! Private heated pool, sleeps 10 near downtown 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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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, (59)
"Cottages were very clean & nicely decorated. The enclosed adjoining porch was great that made it easy for us to go back & forth between the cottages. Kitchen/dining areas were great. Love the oversized stoves as it made cooking for 15 easy. Overall a very nice place. "
1 or 2 Fun Cottages Sleep 2-10-20 People. Pool & Hot Tub. Steps to Beach + More
Lakeside Summer Cottage: Family-Friendly Beach Escape with Private Lake Michigan Access

Lakeside Summer Cottage: Family-Friendly Beach Escape with Private Lake Michigan Access

9.0 out of 10, Wonderful, (22)
"Perfect place to stay if youre looking to relax at a beautiful beach nearby."
Lakeside Summer Cottage: Family-Friendly Beach Escape with Private Lake Michigan Access
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.