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Lakeside, MI Holiday Rentals
Holiday Rentals
USA
Michigan (MI)
Berrien County
Lakeside, MI Holiday Rentals
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Air Conditioning (64)
Internet or Wifi (63)
Grill (62)
Other outdoor space (57)
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Suitability
Kid friendly (61)
Pet friendly (26)
Smoking allowed (3)
Wheelchair access (0)
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Property type
Holiday Rental House (64)
Condominium/Apartment (0)
Cabin Holiday Rental (0)
Private Room (0)
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Distinctive Features
Waterfront (9)
Boat Available (8)
Private Chef (0)
Private Beach (0)
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Distance from
5 km
Lakeside Antiques
Chikaming Country Club
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64 rentals
in Lakeside.
Dog-friendly cottage with private beach, screened porch, wood fireplace & AC
13
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps
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Beautiful 1920's Cottage Steps away from private Lake Michigan beach, Sleeps 8
11
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
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Carrie's Cottage - Charming Duplex Style 3 Bedroom Cottage with Beach Access!
20
Holiday Rental House
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5 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
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Your search has ended!!!
26
Holiday Rental House
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4 bedrooms
5 bathrooms
Sleeps 13
Match:
Sleeps
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New, modern 6 bd home with private pool, hot tub and close to beach
25
Holiday Rental House
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7 bedrooms
7 bathrooms
Sleeps 20
Match:
Sleeps
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Short walk to the beach & backs up to the woods!
92
Holiday Rental House
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3 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps
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Lake Front Cottage in Michigan's Harbor Country "Sandy Shores 2"
11
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
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**SPRING DISCOUNT!** (See description) One Bedroom Cottage with Private Beach!
10
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
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Sep Open! - UNION PIER HOME WITH PRIVATE HEATED POOL and BEACH ACCESS!
10
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
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**SPRING DISCOUNT!** (See description) Two Bedroom Cottage with Private Beach!
10
Holiday Rental House
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3 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps
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Updated, bright, and peaceful cottage in Lakeside
9
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 4
Match:
Sleeps
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Newly Remodeled 2bd cottage
14
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
Match:
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**SPRING DISCOUNT!** (See description) Two Bedroom Cottage with Private Beach!
15
Holiday Rental House
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3 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps
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Lakeside Grove Cottage - Perfect Lakeside Village/Beach Location
8
Holiday Rental House
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3 bedrooms
1 bathroom
Sleeps 6
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Sleeps
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Garden-style cottage with easy beach access, screened porch & small yard
5
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
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Sleeps
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(2025 Open!) LAKEFRONT HOME WITH PRIVATE HEATED POOL!
9
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 5
Match:
Sleeps
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Experience Tranquility at Dunedin Cottage:The Perfect Retreat in Harbor Country!
39
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 8
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Beach Lovers home w/Private Assoc Beach 1 blk fire pit screened porch
10
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 5
Match:
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Walk to Assn beach from Stylish Coastal Cottage
2
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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**SPRING DISCOUNT!** (See description) Updated Lake House with Private Beach!
9
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
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Dog-Friendly Home with WiFi, Central AC, Wood Fireplace, & Private Beach Access
10
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 8
Match:
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Beautiful Lakeside MI vacation home with association beach access SPRING Summer
10
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
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Cozy Lakeside Cottage.... with access to a private beach!
19
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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Inviting home with high-speed WiFi, fireplace, washer/dryer & wet bar
5
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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Brand New House, Sleeps 8, Private Beach Rights, Hot Tub!
33
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
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Fully-renovated lakefront home with beach cabana, association beach, & firepit
10
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 8
Match:
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(2025 Open!) Lakeside Home Walking Distance To Association Beach!
3
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
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Winter Getaways Available - SAVINGS for Winter Bookings
10
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
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(3 Nt Min!) LAKESIDE HOME CLOSE TO ASSOCIATION BEACH & PRIVATE HOT TUB!
3
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
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Newly Renovated Cottage in Lakeside Heated Private Pool Sleeps 10
3
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 10
Match:
Sleeps
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(2025 Open!) LAKESIDE HOME WITH PRIVATE POOL and ASSOCIATION BEACH ACCESS!
21
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
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(2025 Open/ 3 Nt Min) Harbert Home With Private Hot Tub Steps To Beach!
14
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
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ON LAKE MICHIGAN & PRIVATE BEACH.
10
Holiday Rental House
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6 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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Lakeside Escape Steps to Lake Michigan Beach!
2
Holiday Rental House
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7 bedrooms
3 bathrooms
Sleeps 12
Match:
Sleeps
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5 BR Cottage a Short Walk to Pier Street Beach Access.
10
Holiday Rental House
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6 bedrooms
2 bathrooms
Sleeps 10
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Sleeps
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Fantastic family home near the lake with WiFi and large deck
10
Holiday Rental House
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3 bedrooms
4 bathrooms
Sleeps 6
Match:
Sleeps
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2025 Open! PRIVATE HOT TUB AND ASSOCIATION BEACH ACCESS!
37
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 10
Match:
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(2025 Open!) ASSOCIATION BEACH ACCESS and PRIVATE TENNIS COURT!
26
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 10
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Sleeps
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Juniper Presents: Landmark Home 1 Block from Lake MI w/ Game Room + EV Charger
10
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 10
Match:
Sleeps
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NEW! Warren Woods Pool Retreat on private 5 acres, new large heated pool & hotub
5
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 10
Match:
Sleeps
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As seen on
(2025 Open!) LAKESIDE HOME CLOSE TO PRIVATE ASSOCIATION BEACH!
10
Holiday Rental House
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5 bedrooms
3 bathrooms
Sleeps 15
Match:
Sleeps
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Stylish & Well-Equipped Home with Private Outdoor Pool, WiFi, Deck, Gas Grill
6
Holiday Rental House
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5 bedrooms
4 bathrooms
Sleeps 8
Match:
Sleeps
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Private Beach Access! Harbor Country Perfection!
7
Holiday Rental House
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5 bedrooms
4 bathrooms
Sleeps 15
Match:
Sleeps
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(2025 Open!) Lakefront Home With Private Beach!!
4
Holiday Rental House
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6 bedrooms
4 bathrooms
Sleeps 14
Match:
Sleeps
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Contemporary Farmhouse, 4200 sq ft on 9 acres with private neighborhood beach.
21
Holiday Rental House
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7 bedrooms
5 bathrooms
Sleeps 14
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Sleeps
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Stunning home w/Private Association Beach 2 Screened Porches
12
Holiday Rental House
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6 bedrooms
4 bathrooms
Sleeps 12
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Sleeps
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*SPRING DISCOUNT!* Right on Lake Michigan! Large 2 acre yard and private beach
10
Holiday Rental House
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7 bedrooms
5 bathrooms
Sleeps 24
Match:
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Luxury pool, hot tub, guest house, walkable to Lake Michigan. What else do you
2
Holiday Rental House
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7 bedrooms
6 bathrooms
Sleeps 14
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1 or 2 Fun Cottages Sleep 2-10-20 People. Pool & Hot Tub. Steps to Beach + More
51
Holiday Rental House
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9 bedrooms
4 bathrooms
Sleeps 20
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Sleeps
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Lakefront Home w 5 Decks -Cozy Winter Getaway with Wood Burning Fireplace
1
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
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Sleeps
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1
2
Showing results 1-50 of 64
Frequently Asked Questions about Lakeside
Do any holiday rentals in Lakeside have a pool?
Yes, here are some popular holiday rentals in Lakeside that have a pool:
Dog-friendly cottage with private beach, screened porch, wood fireplace & AC
Beautiful 1920's Cottage Steps away from private Lake Michigan beach, Sleeps 8
Carrie's Cottage - Charming Duplex Style 3 Bedroom Cottage with Beach Access!
See all holiday rentals with a pool in Lakeside on Tripadvisor
Do any holiday rentals in Lakeside have internet access?
Yes, here are some popular holiday rentals in Lakeside that have internet access:
Dog-friendly cottage with private beach, screened porch, wood fireplace & AC
Beautiful 1920's Cottage Steps away from private Lake Michigan beach, Sleeps 8
Carrie's Cottage - Charming Duplex Style 3 Bedroom Cottage with Beach Access!
See all holiday rentals in Lakeside on Tripadvisor
What are the best pet friendly rentals in Lakeside?
The best pet friendly rentals in Lakeside are:
Dog-friendly cottage with private beach, screened porch, wood fireplace & AC
Carrie's Cottage - Charming Duplex Style 3 Bedroom Cottage with Beach Access!
Short walk to the beach & backs up to the woods!
See all pet friendly holiday rentals in Lakeside on Tripadvisor
What are some great rentals in Lakeside that are kid friendly?
Some of the most popular kid friendly rentals in Lakeside are:
Dog-friendly cottage with private beach, screened porch, wood fireplace & AC
Beautiful 1920's Cottage Steps away from private Lake Michigan beach, Sleeps 8
Carrie's Cottage - Charming Duplex Style 3 Bedroom Cottage with Beach Access!
See all kid friendly holiday rentals in Lakeside on Tripadvisor
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