Holiday rentals near Glassman Park

We found 937 holiday rentals — enter your dates for availability

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November 2025

December 2025

Select the perfect holiday home within close proximity to Glassman Park. Holiday rentals offer the amenities that you expect for your stay with friends, family or just your pet, such as air conditioning and a pool. You'll be sure to find a property to rent that has what everyone needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts - Glassman Park

Showing deals for:6 Feb - 13 Feb

Open concept living/dining/kitchen for the family to gather.

Exceptional

(15 reviews)

Gorgeous new house - minutes from the beach!

Harbert, MI

8% off

for 7 nights, 1 home

NZ$1,917 per night

includes taxes & fees

15x32 saltwater, heated pool with tanning shelf!

Exceptional

(62 reviews)

Vintage, restored home w/ pool, hot tub & courtyard-just blocks to town & beach

New Buffalo, MI

8% off

for 7 nights, 1 home

NZ$1,015 per night

includes taxes & fees

Exceptional

(26 reviews)

Blue Heron Private Retreat in heart of New Buffalo- pool now open!

New Buffalo, MI

9% off

for 7 nights, 1 home

NZ$859 per night

includes taxes & fees

Large heated pool with sun shelf! Plenty of room for relaxing in the sun.

Exceptional

(10 reviews)

NEW! Warren Woods Pool Retreat on private 5 acres, new large heated pool & hotub

Lakeside, MI

8% off

for 7 nights, 1 home

NZ$1,279 per night

includes taxes & fees

Exceptional

(35 reviews)

Private Cherry Beach Pool House with large heated pool & hot tub!

Three Oaks, MI

8% off

for 7 nights, 1 home

NZ$1,261 per night

includes taxes & fees

Living room with leather sectional sofa, wood-burning fireplace and streaming tv

Exceptional

(34 reviews)

Creekside House on 30 Acres with Kayaks/Pool/Farm/River/Trails/Pets, near Beach

Union Pier, MI

8% off

for 7 nights, 1 home

NZ$729 per night

includes taxes & fees

Exceptional

(42 reviews)

Three Oaks Creek House -- Perfect -- NEW HOT TUB! 3BR +king bed in screenhouse

Three Oaks, MI

20% off

for 7 nights, 1 home

NZ$434 per night

includes taxes & fees

Exceptional

(30 reviews)

Spacious 5 bedroom home with private pool, hot tub & 10 minute walk to the beach

New Buffalo, MI

8% off

for 7 nights, 1 home

NZ$1,199 per night

includes taxes & fees

Exceptional

(128 reviews)

Beautifully Decorated Home W / Hot Tub, Very Close to Beach, Large Wooded Lot

Union Pier, MI

9% off

for 7 nights, 1 home

NZ$1,382 per night

includes taxes & fees

Exceptional

(79 reviews)

Red Oak-5 bedroom with in ground pool, fireplace-walk to restaurants

New Buffalo, MI

8% off

for 7 nights, 1 home

NZ$861 per night

includes taxes & fees

Exceptional

(9 reviews)

Charming Sawyer Retreat Near Lake Michigan – Explore Local Beaches, & Wineries!

Sawyer, MI

8% off

for 7 nights, 1 home

NZ$606 per night

includes taxes & fees

Exceptional

(98 reviews)

The White House - spacious 5 bedroom, with hot tub - blocks from everything!!!!

New Buffalo, MI

8% off

for 7 nights, 1 home

NZ$948 per night

includes taxes & fees

Front of One of our 2 Cottages on the Property. This is Cottage A

Wonderful

(66 reviews)

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

Lakeside, MI

8% off

for 7 nights, 1 cottage

NZ$395 per night

includes taxes & fees

Exceptional

(37 reviews)

Harbert Cottage , Fall Bike trails! Notre Dame Football ,Hot Tub &Pet Friendly

Sawyer, MI

9% off

for 7 nights, 1 cottage

NZ$661 per night

includes taxes & fees

Street View of the
Amorini House. @nd driveway has large found about.

Exceptional

(105 reviews)

Amorini House! Absolutely Beautiful With Pool And Olympic Size Volleyball Court

Union Pier, MI

8% off

for 7 nights, 1 home

NZ$671 per night

includes taxes & fees

Semi private beach short walk down the block

Wonderful

(50 reviews)

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

Lakeside, MI

8% off

for 7 nights, 1 home

NZ$491 per night

includes taxes & fees

Overhead view of main house and guest apartment on the right

Exceptional

(214 reviews)

Amazing Lake Views, Beach Access, Hot Tub, Fire Pit, Screened Porch & Game Room

New Buffalo, MI

13% off

for 7 nights, 1 home

NZ$1,544 per night

includes taxes & fees

Exceptional

(69 reviews)

The Getaway - Three Oaks Cottage 3 BR 1.5 Bath - Week Stay Discount

Three Oaks, MI

17% off

for 7 nights, 1 home

NZ$415 per night

includes taxes & fees

Exceptional

(46 reviews)

Romantic Modern Casita Nestled In The Woods. PET FRIENDLY!! Close to Beach 🏖️

Union Pier, MI

8% off

for 7 nights, 1 home

NZ$280 per night

includes taxes & fees

Exceptional

(97 reviews)

Recently renovated with new oversized private pool in downtown New Buffalo!

New Buffalo, MI

9% off

for 7 nights, 1 home

NZ$840 per night

includes taxes & fees

Exceptional

(69 reviews)

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

Lakeside, MI

8% off

for 7 nights, 1 home

NZ$423 per night

includes taxes & fees

Front of the cottage with amazing porch!

Exceptional

(195 reviews)

Luxury 5 Star Cottage with Pool; summer filling up fast - walk to beach/downtown

New Buffalo, MI

8% off

for 7 nights, 1 home

NZ$818 per night

includes taxes & fees

Exceptional

(51 reviews)

Luxury Townhome In The Heart Of Downtown New Buffalo

New Buffalo, MI

5% off

for 7 nights, 1 home

NZ$1,040 per night

includes taxes & fees

Find spaces that suit your style

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Find the best place to stay - Glassman Park

Premier Host

Lakeside Grove Cottage - Perfect Lakeside Village/Beach Location

Sleeps 6 · 3 bedrooms · 1 bathroom

Premier Host

Perfect for Two! A little hideaway in the woods. Tiny House / Romantic Getaway

Sleeps 3 · 1 bedroom · 1 bathroom

Magnificent Home, Saltwater Pool. Walk to beach! Hot Tub Open year round!

Sleeps 16 · 4 bedrooms · 4 bathrooms

Private Inground Pool with Inn in Background

Premier Host

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

Sleeps 25 · 9 bedrooms · 6+ bathrooms

Premier Host

LUXURY Lakefront Property on Private Beach with Stunning Lake Views and Sunsets

Sleeps 20 · 5 bedrooms · 5+ bathrooms

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