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Rolling Prairie Vacation 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!, vacation 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, vacation 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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Luxury Cottage with Pool; 2021 summer weekly rentals only - filling up fast, vacation 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, vacation 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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Apple Blossom Resort. 3 Homes. 11 Bedrooms/12 Bathroom. Pool. Hot Tub. Fire-Pit, vacation 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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Cottage In The Heart Of Harbor Country - Steps From Town, vacation rental in Rolling Prairie

Cottage In The Heart Of Harbor Country - Steps From Town

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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SoulShine Inn - Pets welcome-Fully fenced backyard-Relaxed cancelation, vacation 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!, vacation 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 luxury modern farmhouse cottage: walk to beach/downtown New Buffalo & pool!, vacation 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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3BR Condo Close To The Beach!, vacation rental in Rolling Prairie

3BR Condo Close To The Beach!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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The White House - Brand New 5 bedroom, with hot tub - blocks from everything!!!!, vacation 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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Stay in downtown Three Oaks overlooking the main street!, vacation 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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Summer is FANTASTIC in New Buffalo - Winter is AMAZING as well!  Check It Out!, vacation 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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~~~~~Cottage Moe~~~~~, vacation rental in Rolling Prairie

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

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Country Setting, Nearby Historic New Carlisle, Restaurants, Beaches And Wineries, vacation 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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New cottage with pool and walkable to downtown/beach, vacation 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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This is it.... You Won't Be Disappointed!, vacation rental in Rolling Prairie

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

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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$275/NT Marina Views Pools Walk to all Beach 1.5 blk Roof top Deck, vacation rental in Rolling Prairie

$275/NT Marina Views Pools Walk to all Beach 1.5 blk Roof top Deck

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Luxury Townhome In The Heart Of Downtown New Buffalo, vacation 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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FALL RATES $300/nt Hot tub Firepit Bikes Large deck/yard Bar Walk to Brewery, vacation 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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The Hickory House -Three Oaks, MI Retreat for 14 - 6 BR, 2.5 Bath, vacation 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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Sleeps 12, Private Pool, Secluded, Yet 6 Min. From 3 Oaks And 15 To New Buffalo, vacation 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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Red Oak -New Home with in-ground pool-walking distance to restaurants/town, vacation 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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Check out our mid week specials!!, vacation rental in Rolling Prairie

Check out our mid week specials!!

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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3 Bedroom Cottage- walking distance to beach & downtown New Buffalo- Come Enjoy!, vacation 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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Downtown New Buffalo Retreat with Sprawling Indoor Space and Great Backyard, vacation rental in Rolling Prairie

Downtown New Buffalo Retreat with Sprawling Indoor Space and Great Backyard

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Stay at the Historic Acorn Theater in Downtown Three Oaks!, vacation 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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5 Blocks To The Beach ~ 2 Blocks To Downtown ~ Walk To Everything!, vacation 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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The Sycamore Cottage - 2 Bedroom & 1.5 Bathroom - Steps to Downtown, vacation 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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Immaculately clean, relaxing retreat convenient to the best of Harbor Country!, vacation 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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Prime Beach Time,  7 blocks from beach, vacation rental in Rolling Prairie

Prime Beach Time, 7 blocks from beach

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Stunning Renovated Designer Victorian House with Beautiful Vintage Details, vacation 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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Lakefront cottage on scenic Hudson Lake, vacation rental in Rolling Prairie

Lakefront cottage on scenic Hudson Lake

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Vacation in paradise 3 BR, 2.5 bath, decks, patio, private pool access, vacation rental in Rolling Prairie

Vacation in paradise 3 BR, 2.5 bath, decks, patio, private pool access

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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$275/NT Blocks to town/beach Fenced yard Playground across street, vacation rental in Rolling Prairie

$275/NT Blocks to town/beach Fenced yard Playground across street

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Ideal Location - Spacious Open Concept Refurbished Boat House - Sleeps 9!, vacation rental in Rolling Prairie

Ideal Location - Spacious Open Concept Refurbished Boat House - Sleeps 9!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Amani Na Cheza!  - Your Peaceful and Fun Getaway Home, vacation rental in Rolling Prairie

Amani Na Cheza! - Your Peaceful and Fun Getaway Home

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Stunning Inn On 30 Acres With Pool, Woods, River, Trails, Farm, Near Beach!, vacation rental in Rolling Prairie

Stunning Inn On 30 Acres With Pool, Woods, River, Trails, Farm, Near Beach!

8 bedrooms
9 bathrooms
Sleeps 24
Match: Sleeps
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New Buffalo - Downtown, Close to Beach, Private Pool, vacation 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!, vacation 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, vacation 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!, vacation 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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Downtown New Buffalo!, vacation rental in Rolling Prairie

Downtown New Buffalo!

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Home right on the water, private dock, and large land!, vacation 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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Deb Michigan Hot Tub House                                                     ., vacation rental in Rolling Prairie

Deb Michigan Hot Tub House .

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Three Oaks Inn at Ashmoor Estate, vacation 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, vacation rental in Rolling Prairie

Lakefront 4 Bedroom Home on Pine Lake

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

Sycamore Guesthouse, Three Oaks, Michigan

5 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps
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CaLLinG all LaKe LoVers, YeAr RouNd CHaRm, vacation rental in Rolling Prairie

CaLLinG all LaKe LoVers, YeAr RouNd CHaRm

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Villa Vino, vacation rental in Rolling Prairie

Villa Vino

5 bedrooms
2 bathrooms
Sleeps 16
Match: Sleeps
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