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Lakeside Holiday Rentals

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50 rentals in Lakeside.
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Beautiful 1920's Cottage Steps away from private Lake Michigan beach, Sleeps 8, holiday rental in Lakeside

Beautiful 1920's Cottage Steps away from private Lake Michigan beach, Sleeps 8

4 bedrooms
2 bathrooms
Sleeps 8
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Cottage close to private beach - Summer dates available, holiday rental in Lakeside

Cottage close to private beach - Summer dates available

3 bedrooms
2 bathrooms
Sleeps 8
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Spring Time is coming soon....., holiday rental in Lakeside

Spring Time is coming soon.....

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Lakeside, MI - year round lake house! Booking for fall, winter and summer 2021, holiday rental in Lakeside

Lakeside, MI - year round lake house! Booking for fall, winter and summer 2021

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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**SPRING DISCOUNT!** (See description) One Bedroom Cottage with Private Beach!, holiday rental in Lakeside

**SPRING DISCOUNT!** (See description) One Bedroom Cottage with Private Beach!

1 bedroom
1 bathroom
Sleeps 4
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2 FUN 4 Bedroom 2 Bath COTTAGES each Sleep 10 people Beach-Pool-Hot Tub and More, holiday rental in Lakeside

2 FUN 4 Bedroom 2 Bath COTTAGES each Sleep 10 people Beach-Pool-Hot Tub and More

8 bedrooms
4 bathrooms
Sleeps 20
Match: Sleeps
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Your Pool Party is Calling, holiday rental in Lakeside

Your Pool Party is Calling

3 bedrooms
2 bathrooms
Sleeps 10
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LAKEFRONT PRIVATE BEACH SCRND PORCH PETS AMAZING VIEWS, holiday rental in Lakeside

LAKEFRONT PRIVATE BEACH SCRND PORCH PETS AMAZING VIEWS

5 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Fun Spacious 4 Bedrm 2 Bath Cottage Sleeps 10 Pool, Hot tub, Steps to Beach More, holiday rental in Lakeside

Fun Spacious 4 Bedrm 2 Bath Cottage Sleeps 10 Pool, Hot tub, Steps to Beach More

4 bedrooms
2 bathrooms
Sleeps 10
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Your Pool Party is Calling, holiday rental in Lakeside

Your Pool Party is Calling

3 bedrooms
2 bathrooms
Sleeps 10
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NEW! Lakeside Escape Steps to Lake Michigan Beach!, holiday rental in Lakeside

NEW! Lakeside Escape Steps to Lake Michigan Beach!

1 bedroom
3 bathrooms
Sleeps 12
Match: Sleeps
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1/2 Block To Lake Michigan Beach!   Fire-pit!   Week of 4th of July Available!, holiday rental in Lakeside

1/2 Block To Lake Michigan Beach! Fire-pit! Week of 4th of July Available!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Retreat to a Stylish Cottage in Union Pier, holiday rental in Lakeside

Retreat to a Stylish Cottage in Union Pier

3 bedrooms
2 bathrooms
Sleeps 7
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Woodsy Cottage In The Heart Of Union Pier, holiday rental in Lakeside

Woodsy Cottage In The Heart Of Union Pier

3 bedrooms
2 bathrooms
Sleeps 6
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75 Paces to Beach Stairs and  to LUNA GOWDY BEACH, holiday rental in Lakeside

75 Paces to Beach Stairs and to LUNA GOWDY BEACH

2 bedrooms
1 bathroom
Sleeps 4
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Cedar Hollow Cottage: 4 Bed/2 Bath with HOT TUB and steps to beach!, holiday rental in Lakeside

Cedar Hollow Cottage: 4 Bed/2 Bath with HOT TUB and steps to beach!

4 bedrooms
2 bathrooms
Sleeps 10
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Great Studio 1 1/2 blocks to the beach at Lake Michigan ! Large yard to relax in, holiday rental in Lakeside

Great Studio 1 1/2 blocks to the beach at Lake Michigan ! Large yard to relax in

0 bedrooms
1 bathroom
Sleeps 4
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Sun's Up - Bar Down! 5Bed, 3 Bath + Hot Tub, Walk to 2 Beaches, holiday rental in Lakeside

Sun's Up - Bar Down! 5Bed, 3 Bath + Hot Tub, Walk to 2 Beaches

5 bedrooms
3 bathrooms
Sleeps 11
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Now Booking for 2021!  Great guest reviews!, holiday rental in Lakeside

Now Booking for 2021! Great guest reviews!

4 bedrooms
3 bathrooms
Sleeps 10
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BREEZY LANE-FAMILY BEACH COTTAGE, SHORT WALK TO PRIVATE LAKE MICHIGAN BEACH, holiday rental in Lakeside

BREEZY LANE-FAMILY BEACH COTTAGE, SHORT WALK TO PRIVATE LAKE MICHIGAN BEACH

6 bedrooms
2 bathrooms
Sleeps 15
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Close To Beach, Family Friendly, holiday rental in Lakeside

Close To Beach, Family Friendly

3 bedrooms
2 bathrooms
Sleeps 9
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Harbor Country Retreat with Private Pool.  Perfect family getaway!, holiday rental in Lakeside

Harbor Country Retreat with Private Pool. Perfect family getaway!

3 bedrooms
2 bathrooms
Sleeps 8
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Cozy Beach Cottage BIG YARD 1 Blk to Private Beach. 3 NIGHT MINIMUM Stay for 2BR, holiday rental in Lakeside

Cozy Beach Cottage BIG YARD 1 Blk to Private Beach. 3 NIGHT MINIMUM Stay for 2BR

2 bedrooms
1 bathroom
Sleeps 6
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Eco-Secluded Lakefront House-Hot Tub-90 min from Chicago-Featured in NY Times!, holiday rental in Lakeside

Eco-Secluded Lakefront House-Hot Tub-90 min from Chicago-Featured in NY Times!

2 bedrooms
2 bathrooms
Sleeps 8
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HARBOR HAVEN (Union Pier, MI): Cozy home with indoor fireplace!, holiday rental in Lakeside

HARBOR HAVEN (Union Pier, MI): Cozy home with indoor fireplace!

2 bedrooms
2 bathrooms
Sleeps 5
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$325/NT Walk to Town Large Yard Fire Pit Gas Grill Beach .2.5 blocks, holiday rental in Lakeside

$325/NT Walk to Town Large Yard Fire Pit Gas Grill Beach .2.5 blocks

4 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
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1 bed/1 bath, 1.5 blocks to beach/town, dog friendly, screened porch, holiday rental in Lakeside

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

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Steps to town Blks to beach Scrnd Porch Fire pit Large Yard BBall hoop, holiday rental in Lakeside

Steps to town Blks to beach Scrnd Porch Fire pit Large Yard BBall hoop

3 bedrooms
3 bathrooms
Sleeps 10
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Charming 3 bedroom 2 bath home, screen porch, fire pit, big yard/sleeps 8, holiday rental in Lakeside

Charming 3 bedroom 2 bath home, screen porch, fire pit, big yard/sleeps 8

3 bedrooms
2 bathrooms
Sleeps 8
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Blue Sky Cottage@ Union Pier, Michigan, holiday rental in Lakeside

Blue Sky Cottage@ Union Pier, Michigan

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Union Pier MI  - 6BR Private Pool, Many Amenities, Summer or Winter Hideaway!, holiday rental in Lakeside

Union Pier MI - 6BR Private Pool, Many Amenities, Summer or Winter Hideaway!

6 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
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Large private beach in Union Pier with availability for July and August 2020!, holiday rental in Lakeside

Large private beach in Union Pier with availability for July and August 2020!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Cozy Michigan cottage open all winter! Fireplace, cable tv & wifi-sleeps 6, holiday rental in Lakeside

Cozy Michigan cottage open all winter! Fireplace, cable tv & wifi-sleeps 6

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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NEW LISTING! 4BR/3.5BA home with private beach now booking for August 2020!, holiday rental in Lakeside

NEW LISTING! 4BR/3.5BA home with private beach now booking for August 2020!

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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2 bed/1 bath, 1.5 blocks to beach/town, dog friendly, holiday rental in Lakeside

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

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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1 bed/1 bath, 1.5 blocks to beach/town, dog friendly, holiday rental in Lakeside

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

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Modern Architectural Beach Home Steps From The Beach, holiday rental in Lakeside

Modern Architectural Beach Home Steps From The Beach

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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2 bed/1 bath, 1.5 blocks to beach/town, dog friendly, holiday rental in Lakeside

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

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Fully Renovated House in Union Pier - 10 Person Home, holiday rental in Lakeside

Fully Renovated House in Union Pier - 10 Person Home

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful, large 3 br. townhome with pool, and 5 minute walk to the beach!, holiday rental in Lakeside

Beautiful, large 3 br. townhome with pool, and 5 minute walk to the beach!

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Shorewinds Beach House on LakeShore, holiday rental in Lakeside

Shorewinds Beach House on LakeShore

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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1 bed/1 bath, 1.5 blocks to beach/town, dog friendly, holiday rental in Lakeside

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

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Beautifully renovated 2 bedroom duplex, holiday rental in Lakeside

Beautifully renovated 2 bedroom duplex

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Private and Serene on 23 Acres 2 Minutes to Lake Michigan, holiday rental in Lakeside

Private and Serene on 23 Acres 2 Minutes to Lake Michigan

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Cozy Union Pier House w/ Hot Tub, Deck, & Backyard, holiday rental in Lakeside

Cozy Union Pier House w/ Hot Tub, Deck, & Backyard

4 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps
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A Quaint Country Cottage in Scenic Harbor Country!, holiday rental in Lakeside

A Quaint Country Cottage in Scenic Harbor Country!

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Union Pier Craftsman Cottage - Walk to Lake/Beach!, holiday rental in Lakeside

Union Pier Craftsman Cottage - Walk to Lake/Beach!

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Charming Vintage Union Pier Home - Walk to Beach!, holiday rental in Lakeside

Charming Vintage Union Pier Home - Walk to Beach!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Cozy cottage tucked away in the heart of Union Pier!, holiday rental in Lakeside

Cozy cottage tucked away in the heart of Union Pier!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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NEW! Renovated, Spacious Retreat in Union Pier!, holiday rental in Lakeside

NEW! Renovated, Spacious Retreat in Union Pier!

1 bedroom
2 bathrooms
Sleeps 10
Match: Sleeps
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