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Rolling Prairie Holiday Rentals

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50 rentals in Rolling Prairie.
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10 acres of privacy Pup/ Bike/ walking Nirvana! 7 minutes to hip 3 Oaks!, holiday rental in Rolling Prairie

10 acres of privacy Pup/ Bike/ walking Nirvana! 7 minutes to hip 3 Oaks!

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Beautiful Lake Home -> Near New Buffalo - 3 BD / 2 BA, holiday rental in Rolling Prairie

Beautiful Lake Home -> Near New Buffalo - 3 BD / 2 BA

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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NEW! Family Home w/ Pool - 13 Mi to Lake Michigan!, holiday rental in Rolling Prairie

NEW! Family Home w/ Pool - 13 Mi to Lake Michigan!

8 bedrooms
4 bathrooms
Sleeps 18
Match: Sleeps
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Luxury Cottage with Pool; 2021 summer weekly rentals only - filling up fast, holiday rental in Rolling Prairie

Luxury Cottage with Pool; 2021 summer weekly rentals only - filling up fast

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Easy Walk to Town and the Beach, But Feel Like You're Away From It All, holiday rental in Rolling Prairie

Easy Walk to Town and the Beach, But Feel Like You're Away From It All

3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Cottage In The Heart Of Harbor Country - Steps From Town, holiday rental in Rolling Prairie

Cottage In The Heart Of Harbor Country - Steps From Town

3 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
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Apple Blossom Resort. 3 Homes. 11 Bedrooms/12 Bathroom. Pool. Hot Tub. Fire-Pit, holiday rental in Rolling Prairie

Apple Blossom Resort. 3 Homes. 11 Bedrooms/12 Bathroom. Pool. Hot Tub. Fire-Pit

12 bedrooms
14 bathrooms
Sleeps 48
Match: Sleeps
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Newer luxury cottage with heated pool near town & beach.  Outstanding reviews!, holiday rental in Rolling Prairie

Newer luxury cottage with heated pool near town & beach. Outstanding reviews!

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Charming & cozy in-town retreat in the heart of New Buffalo, holiday rental in Rolling Prairie

Charming & cozy in-town retreat in the heart of New Buffalo

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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SoulShine Inn - Pets welcome-Fully fenced backyard-Relaxed cancelation, holiday rental in Rolling Prairie

SoulShine Inn - Pets welcome-Fully fenced backyard-Relaxed cancelation

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Stunning brand new 3 bed/2 bath designer cottage in downtown Three Oaks!, holiday rental in Rolling Prairie

Stunning brand new 3 bed/2 bath designer cottage in downtown Three Oaks!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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New Designer Luxury Cottage ~ Jan & Feb discounts for extended stays, holiday rental in Rolling Prairie

New Designer Luxury Cottage ~ Jan & Feb discounts for extended stays

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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New luxury modern farmhouse cottage: walk to beach/downtown New Buffalo & pool!, holiday rental in Rolling Prairie

New luxury modern farmhouse cottage: walk to beach/downtown New Buffalo & pool!

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Summer is FANTASTIC in New Buffalo - Winter is AMAZING as well!  Check It Out!, holiday rental in Rolling Prairie

Summer is FANTASTIC in New Buffalo - Winter is AMAZING as well! Check It Out!

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Stay in downtown Three Oaks overlooking the main street!, holiday rental in Rolling Prairie

Stay in downtown Three Oaks overlooking the main street!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The White House - Brand New 5 bedroom, with hot tub - blocks from everything!!!!, holiday rental in Rolling Prairie

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

5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Country Setting, Nearby Historic New Carlisle, Restaurants, Beaches And Wineries, holiday rental in Rolling Prairie

Country Setting, Nearby Historic New Carlisle, Restaurants, Beaches And Wineries

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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~~~~~Cottage Moe~~~~~, holiday rental in Rolling Prairie

~~~~~Cottage Moe~~~~~

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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This is it.... You Won't Be Disappointed!, holiday rental in Rolling Prairie

This is it.... You Won't Be Disappointed!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Luxury Townhome In The Heart Of Downtown New Buffalo, holiday rental in Rolling Prairie

Luxury Townhome In The Heart Of Downtown New Buffalo

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Sleeps 12, Private Pool, Secluded, Yet 6 Min. From 3 Oaks And 15 To New Buffalo, holiday rental in Rolling Prairie

Sleeps 12, Private Pool, Secluded, Yet 6 Min. From 3 Oaks And 15 To New Buffalo

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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New cottage with pool and walkable to downtown/beach, holiday rental in Rolling Prairie

New cottage with pool and walkable to downtown/beach

4 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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FALL RATES $300/nt Hot tub Firepit Bikes Large deck/yard Bar Walk to Brewery, holiday rental in Rolling Prairie

FALL RATES $300/nt Hot tub Firepit Bikes Large deck/yard Bar Walk to Brewery

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Check out our mid week specials!!, holiday rental in Rolling Prairie

Check out our mid week specials!!

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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The Hickory House -Three Oaks, MI Retreat for 14 - 6 BR, 2.5 Bath, holiday rental in Rolling Prairie

The Hickory House -Three Oaks, MI Retreat for 14 - 6 BR, 2.5 Bath

6 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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3 Bedroom Cottage- walking distance to beach & downtown New Buffalo- Come Enjoy!, holiday rental in Rolling Prairie

3 Bedroom Cottage- walking distance to beach & downtown New Buffalo- Come Enjoy!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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5 Blocks To The Beach ~ 2 Blocks To Downtown ~ Walk To Everything!, holiday rental in Rolling Prairie

5 Blocks To The Beach ~ 2 Blocks To Downtown ~ Walk To Everything!

5 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Stay at the Historic Acorn Theater in Downtown Three Oaks!, holiday rental in Rolling Prairie

Stay at the Historic Acorn Theater in Downtown Three Oaks!

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Immaculately clean, relaxing retreat convenient to the best of Harbor Country!, holiday rental in Rolling Prairie

Immaculately clean, relaxing retreat convenient to the best of Harbor Country!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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New Buffalo 2 Bdrm Condo with Pool Near Beach-Midweek Special Rate!!!, holiday rental in Rolling Prairie

New Buffalo 2 Bdrm Condo with Pool Near Beach-Midweek Special Rate!!!

2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Prime Beach Time,  7 blocks from beach, holiday rental in Rolling Prairie

Prime Beach Time, 7 blocks from beach

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Lakefront cottage on scenic Hudson Lake, holiday rental in Rolling Prairie

Lakefront cottage on scenic Hudson Lake

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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The Sycamore Cottage - 2 Bedroom & 1.5 Bathroom - Steps to Downtown, holiday rental in Rolling Prairie

The Sycamore Cottage - 2 Bedroom & 1.5 Bathroom - Steps to Downtown

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Stunning Renovated Designer Victorian House with Beautiful Vintage Details, holiday rental in Rolling Prairie

Stunning Renovated Designer Victorian House with Beautiful Vintage Details

3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Red Oak -New Home with in-ground pool-walking distance to restaurants/town, holiday rental in Rolling Prairie

Red Oak -New Home with in-ground pool-walking distance to restaurants/town

4 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Nice Relaxing  Family-Friendly Property Reduced winter prices now 199 per night, holiday rental in Rolling Prairie

Nice Relaxing Family-Friendly Property Reduced winter prices now 199 per night

3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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New Buffalo - Downtown, Close to Beach, Private Pool, holiday rental in Rolling Prairie

New Buffalo - Downtown, Close to Beach, Private Pool

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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The super comfy Buck!, holiday rental in Rolling Prairie

The super comfy Buck!

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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2 bedroom house UNWIND & ENJOY, holiday rental in Rolling Prairie

2 bedroom house UNWIND & ENJOY

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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New Buffalo home away from home. 3 BR Condo w/  Pool.  Close to the Beach!, holiday rental in Rolling Prairie

New Buffalo home away from home. 3 BR Condo w/ Pool. Close to the Beach!

3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Home right on the water, private dock, and large land!, holiday rental in Rolling Prairie

Home right on the water, private dock, and large land!

3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Brand New Custom Built One Block To Downtown New Buffalo & Three Blocks To Beach, holiday rental in Rolling Prairie

Brand New Custom Built One Block To Downtown New Buffalo & Three Blocks To Beach

5 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
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Brand new home - 4 bedrooms, 3.5 baths.  Walk to EVERYTHING in NB!!  Sleeps 12!, holiday rental in Rolling Prairie

Brand new home - 4 bedrooms, 3.5 baths. Walk to EVERYTHING in NB!! Sleeps 12!

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Three Oaks Inn at Ashmoor Estate, holiday rental in Rolling Prairie

Three Oaks Inn at Ashmoor Estate

5 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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Lakefront 4 Bedroom Home on Pine Lake, holiday rental in Rolling Prairie

Lakefront 4 Bedroom Home on Pine Lake

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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'The Peachtree Cottage' w/ Hot Tub in New Buffalo!, holiday rental in Rolling Prairie

'The Peachtree Cottage' w/ Hot Tub in New Buffalo!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Sycamore Guesthouse, Three Oaks, Michigan, holiday rental in Rolling Prairie

Sycamore Guesthouse, Three Oaks, Michigan

5 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps
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Villa Vino, holiday rental in Rolling Prairie

Villa Vino

5 bedrooms
2 bathrooms
Sleeps 16
Match: Sleeps
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NEW! Quiet Cabin w/ Grill, Pond + Walking Trails!, holiday rental in Rolling Prairie

NEW! Quiet Cabin w/ Grill, Pond + Walking Trails!

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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NEW! Home, < 2 Mi to New Buffalo Beach & Boat Ramp, holiday rental in Rolling Prairie

NEW! Home, < 2 Mi to New Buffalo Beach & Boat Ramp

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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