Vacation rentals in Rolling Prairie, IN

55 available vacation rental offers

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Best vacation rentals and Airbnb offers in Rolling Prairie, IN

The Neighborhood Hotel - New Buffalo 102 - King Porch - Rolling Prairie, IN

The Neighborhood Hotel - New Buffalo 102 - King Porch

Apartment, Rolling Prairie

The Neighborhood Hotel - New Buffalo 102 - King Porch is a apartment in Rolling Prairie, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About The Neighborhood Hotel - New Buffalo 102 - King Porch

The Neighborhood Hotel - New Buffalo 102 - King Porch is a apartment in Rolling Prairie, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, parking, paid parking, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,676.

From$361/night
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The Cozy Canopy - Rolling Prairie, IN

The Cozy Canopy

Cabin, Rolling Prairie

The Cozy Canopy is a cabin in Rolling Prairie. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

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About The Cozy Canopy

The Cozy Canopy is a cabin in Rolling Prairie. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, ac, air conditioning, heating, and internet.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,064.

From$152/night
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Vintage Apartment in Historic Downtown La Porte! - Rolling Prairie, IN

Vintage Apartment in Historic Downtown La Porte!

Apartment, Rolling Prairie

Vintage Apartment in Historic Downtown La Porte! is a apartment in Rolling Prairie, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Vintage Apartment in Historic Downtown La Porte!

Vintage Apartment in Historic Downtown La Porte! is a apartment in Rolling Prairie, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, parking, paid parking, and heating.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,704.

From$165/night
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Cozy 1-bedroom house in peaceful La Porte with AC and hot tub - Rolling Prairie, IN

Cozy 1-bedroom house in peaceful La Porte with AC and hot tub

Holiday Home, Rolling Prairie

Cozy 1-bedroom house in peaceful La Porte with AC and hot tub is a holiday home in Rolling Prairie, with kitchen access and room for a group. This stay gives travelers a comfortable base…

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About Cozy 1-bedroom house in peaceful La Porte with AC and hot tub

Cozy 1-bedroom house in peaceful La Porte with AC and hot tub is a holiday home in Rolling Prairie, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,294.

From$185/night
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Vacation rentals with a pool in Rolling Prairie, IN

Add a pool to the search when you want an easy place to cool off between outings.

Merchant Street Retreat - Rolling Prairie, IN

Merchant Street Retreat

Holiday Home, Rolling Prairie

Merchant Street Retreat is a holiday home in Rolling Prairie, with pool access and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Merchant Street Retreat

Merchant Street Retreat is a holiday home in Rolling Prairie, with pool access and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, hot tub, and ourdoor pool.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $8,093.

From$828/night
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Harbor Dunes Cottage Retreat - Community Pool - Rolling Prairie, IN

Harbor Dunes Cottage Retreat - Community Pool

Holiday Home, Rolling Prairie

Harbor Dunes Cottage Retreat - Community Pool is a holiday home in Rolling Prairie, with pool access, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for…

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About Harbor Dunes Cottage Retreat - Community Pool

Harbor Dunes Cottage Retreat - Community Pool is a holiday home in Rolling Prairie, with pool access, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,378.

From$483/night
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Luxury Downtown Getaway: 2BR Condo Near New Buffalo’s Top Attractions! - Rolling Prairie, IN

Luxury Downtown Getaway: 2BR Condo Near New Buffalo’s Top Attractions!

Apartment, Rolling Prairie

Luxury Downtown Getaway: 2BR Condo Near New Buffalo’s Top Attractions! is a apartment in Rolling Prairie, with pool access, kitchen access, and room for a group. This stay gives travelers a…

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About Luxury Downtown Getaway: 2BR Condo Near New Buffalo’s Top Attractions!

Luxury Downtown Getaway: 2BR Condo Near New Buffalo’s Top Attractions! is a apartment in Rolling Prairie, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,435.

From$491/night
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Cozy 2-bedroom condo in New Buffalo with indoor/outdoor pools - Rolling Prairie, IN

Cozy 2-bedroom condo in New Buffalo with indoor/outdoor pools

Condo, Rolling Prairie

Cozy 2-bedroom condo in New Buffalo with indoor/outdoor pools is a condo in Rolling Prairie, with pool access, parking, and room for a group. This stay gives travelers a comfortable base…

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About Cozy 2-bedroom condo in New Buffalo with indoor/outdoor pools

Cozy 2-bedroom condo in New Buffalo with indoor/outdoor pools is a condo in Rolling Prairie, with pool access, parking, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, gym, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,754.

From$536/night
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Vacation rentals with parking in Rolling Prairie, IN

Find vacation rentals that make arriving by car easier.

Backyard Oasis w Downtown Walkability, Fire Pit - Rolling Prairie, IN

Backyard Oasis w Downtown Walkability, Fire Pit

Holiday Home, Rolling Prairie

Backyard Oasis w Downtown Walkability, Fire Pit is a holiday home in Rolling Prairie, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Backyard Oasis w Downtown Walkability, Fire Pit

Backyard Oasis w Downtown Walkability, Fire Pit is a holiday home in Rolling Prairie, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,245.

From$321/night
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Serene Log Cabin Forest Retreat - 25 min from Indiana Dunes & Lake MI Beach! - Rolling Prairie, IN

Serene Log Cabin Forest Retreat - 25 min from Indiana Dunes & Lake MI Beach!

Cabin, Rolling Prairie

Serene Log Cabin Forest Retreat - 25 min from Indiana Dunes & Lake MI Beach! is a cabin in Rolling Prairie, with pet-friendly space, easy beach access, and parking. This stay gives…

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About Serene Log Cabin Forest Retreat - 25 min from Indiana Dunes & Lake MI Beach!

Serene Log Cabin Forest Retreat - 25 min from Indiana Dunes & Lake MI Beach! is a cabin in Rolling Prairie, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,276.

From$325/night
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Happy Acres: Modern Luxury Country Farmhouse - Rolling Prairie, IN

Happy Acres: Modern Luxury Country Farmhouse

Holiday Home, Rolling Prairie

Happy Acres: Modern Luxury Country Farmhouse is a holiday home in Rolling Prairie, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Happy Acres: Modern Luxury Country Farmhouse

Happy Acres: Modern Luxury Country Farmhouse is a holiday home in Rolling Prairie, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,575.

From$368/night
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In the Heart of Three Oaks - Steps to Downtown - Rolling Prairie, IN

In the Heart of Three Oaks - Steps to Downtown

Holiday Home, Rolling Prairie

In the Heart of Three Oaks - Steps to Downtown is a holiday home in Rolling Prairie, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About In the Heart of Three Oaks - Steps to Downtown

In the Heart of Three Oaks - Steps to Downtown is a holiday home in Rolling Prairie, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,640.

From$377/night
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Pet-friendly vacation rentals in Rolling Prairie, IN

Bring your pet along with stays that welcome four-legged travelers.

Come relax in the country! - Rolling Prairie, IN

Come relax in the country!

Holiday Home, Rolling Prairie

Come relax in the country! is a holiday home in Rolling Prairie, with pet-friendly space, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring…

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About Come relax in the country!

Come relax in the country! is a holiday home in Rolling Prairie, with pet-friendly space, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,355.

From$194/night
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Boutique Two Bedroom Apartment - Rolling Prairie, IN

Boutique Two Bedroom Apartment

Apartment, Rolling Prairie

Boutique Two Bedroom Apartment is a apartment in Rolling Prairie, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Boutique Two Bedroom Apartment

Boutique Two Bedroom Apartment is a apartment in Rolling Prairie, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,158.

From$308/night
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Willow on the Pond - Waterfront, seasonal pool, 4 Bedrooms - MTM Premier - Rolling Prairie, IN

Willow on the Pond - Waterfront, seasonal pool, 4 Bedrooms - MTM Premier

Holiday Home, Rolling Prairie

Willow on the Pond - Waterfront, seasonal pool, 4 Bedrooms - MTM Premier is a holiday home in Rolling Prairie, with pet-friendly space, pool access, and easy beach access. This stay gives…

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About Willow on the Pond - Waterfront, seasonal pool, 4 Bedrooms - MTM Premier

Willow on the Pond - Waterfront, seasonal pool, 4 Bedrooms - MTM Premier is a holiday home in Rolling Prairie, with pet-friendly space, pool access, and easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,225.

From$318/night
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Renovated Victorian Home with Private Garden & Fire Pit! - Rolling Prairie, IN

Renovated Victorian Home with Private Garden & Fire Pit!

Holiday Home, Rolling Prairie

Renovated Victorian Home with Private Garden & Fire Pit! is a holiday home in Rolling Prairie, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for…

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About Renovated Victorian Home with Private Garden & Fire Pit!

Renovated Victorian Home with Private Garden & Fire Pit! is a holiday home in Rolling Prairie, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,346.

From$335/night
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Vacation rentals with a kitchen in Rolling Prairie, IN

Compare stays with kitchen access for longer trips and easier meals.

Welcome to The Cabin on Pine Lake! Lakefront home on Pine Lake with a private boat dock, direct lake access, firepit and beautiful water views. Family-friendly amenities make this an easy, relaxing getaway for anyone looking to enjoy lake life. - Rolling Prairie, IN

Welcome to The Cabin on Pine Lake! Lakefront home on Pine Lake with a private boat dock, direct lake access, firepit and beautiful water views. Family-friendly amenities make this an easy, relaxing getaway for anyone looking to enjoy lake life.

Holiday Home, Rolling Prairie

Welcome to The Cabin on Pine Lake! Lakefront home on Pine Lake with a private boat dock, direct lake access, firepit and beautiful water views. Family-friendly amenities make this an easy,…

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About Welcome to The Cabin on Pine Lake! Lakefront home on Pine Lake with a private boat dock, direct lake access, firepit and beautiful water views. Family-friendly amenities make this an easy, relaxing getaway for anyone looking to enjoy lake life.

Welcome to The Cabin on Pine Lake! Lakefront home on Pine Lake with a private boat dock, direct lake access, firepit and beautiful water views. Family-friendly amenities make this an easy, relaxing getaway for anyone looking to enjoy lake life. is a holiday home in Rolling Prairie, with kitchen access, room for a group, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,526.

From$361/night
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Charming, cozy and 5 star home STEPS to Journeyman & Acorn Theatre! Large yard! - Rolling Prairie, IN

Charming, cozy and 5 star home STEPS to Journeyman & Acorn Theatre! Large yard!

Holiday Home, Rolling Prairie

Charming, cozy and 5 star home STEPS to Journeyman & Acorn Theatre! Large yard! is a holiday home in Rolling Prairie, with kitchen access. This stay gives travelers a comfortable base for…

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About Charming, cozy and 5 star home STEPS to Journeyman & Acorn Theatre! Large yard!

Charming, cozy and 5 star home STEPS to Journeyman & Acorn Theatre! Large yard! is a holiday home in Rolling Prairie, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,657.

From$380/night
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Three Oaks Home Close To Everything! Two Night Summer Min! - Rolling Prairie, IN

Three Oaks Home Close To Everything! Two Night Summer Min!

Holiday Home, Rolling Prairie

Three Oaks Home Close To Everything! Two Night Summer Min! is a holiday home in Rolling Prairie, with pet-friendly space, parking, and kitchen access. This stay gives travelers a…

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About Three Oaks Home Close To Everything! Two Night Summer Min!

Three Oaks Home Close To Everything! Two Night Summer Min! is a holiday home in Rolling Prairie, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,717.

From$388/night
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Cottage In The Heart Of Harbor Country - Steps From Town - Rolling Prairie, IN

Cottage In The Heart Of Harbor Country - Steps From Town

Holiday Home, Rolling Prairie

Cottage In The Heart Of Harbor Country - Steps From Town is a holiday home in Rolling Prairie, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable…

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About Cottage In The Heart Of Harbor Country - Steps From Town

Cottage In The Heart Of Harbor Country - Steps From Town is a holiday home in Rolling Prairie, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,719.

From$388/night
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Family-friendly vacation rentals in Rolling Prairie, IN

Plan a trip with stays that give families more room to spread out.

Cozy Cottage With Lake View/Hosted by MTM Premier Property Management - Rolling Prairie, IN

Cozy Cottage With Lake View/Hosted by MTM Premier Property Management

Holiday Home, Rolling Prairie

Cozy Cottage With Lake View/Hosted by MTM Premier Property Management is a holiday home in Rolling Prairie, with pet-friendly space and kitchen access. This stay gives travelers a…

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About Cozy Cottage With Lake View/Hosted by MTM Premier Property Management

Cozy Cottage With Lake View/Hosted by MTM Premier Property Management is a holiday home in Rolling Prairie, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,483.

From$212/night
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CHARMING & ECLECTIC LAKEFRONT COTTAGE- Kayak.Grill.Fish.Bonfire.Bike #Lakelife - Rolling Prairie, IN

CHARMING & ECLECTIC LAKEFRONT COTTAGE- Kayak.Grill.Fish.Bonfire.Bike #Lakelife

Cottage, Rolling Prairie

CHARMING & ECLECTIC LAKEFRONT COTTAGE- Kayak.Grill.Fish.Bonfire.Bike #Lakelife is a cottage in Rolling Prairie, with parking and kitchen access. This stay gives travelers a comfortable base…

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About CHARMING & ECLECTIC LAKEFRONT COTTAGE- Kayak.Grill.Fish.Bonfire.Bike #Lakelife

CHARMING & ECLECTIC LAKEFRONT COTTAGE- Kayak.Grill.Fish.Bonfire.Bike #Lakelife is a cottage in Rolling Prairie, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,816.

From$259/night
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Rent out Papas Cottage to make memories of a lifetime - Rolling Prairie, IN

Rent out Papas Cottage to make memories of a lifetime

Holiday Home, Rolling Prairie

Rent out Papas Cottage to make memories of a lifetime is a holiday home in Rolling Prairie, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable…

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About Rent out Papas Cottage to make memories of a lifetime

Rent out Papas Cottage to make memories of a lifetime is a holiday home in Rolling Prairie, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,822.

From$260/night
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Beautifully Remodeled Lake Cottage with Stunning view of Stone Lake - Rolling Prairie, IN

Beautifully Remodeled Lake Cottage with Stunning view of Stone Lake

Cottage, Rolling Prairie

Beautifully Remodeled Lake Cottage with Stunning view of Stone Lake is a cottage in Rolling Prairie, with kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Beautifully Remodeled Lake Cottage with Stunning view of Stone Lake

Beautifully Remodeled Lake Cottage with Stunning view of Stone Lake is a cottage in Rolling Prairie, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,314.

From$331/night
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