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Winesburg Vacation Rentals

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50 rentals in Winesburg.
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Christi's Hideaway Cabin in Winesburg, Ohio, vacation rental in Winesburg
Christi's Hideaway Cabin in Winesburg, Ohio, vacation rental in Winesburg
Christi's Hideaway Cabin in Winesburg, Ohio, vacation rental in Winesburg

Christi's Hideaway Cabin in Winesburg, Ohio

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Wrap Around Decks w/Beautiful View & Hot Tub, vacation rental in Winesburg
Wrap Around Decks w/Beautiful View & Hot Tub, vacation rental in Winesburg
Wrap Around Decks w/Beautiful View & Hot Tub, vacation rental in Winesburg

Wrap Around Decks w/Beautiful View & Hot Tub

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Luxe Amish Country Apartment with Rooftop Terrace!, vacation rental in Winesburg
Luxe Amish Country Apartment with Rooftop Terrace!, vacation rental in Winesburg
Luxe Amish Country Apartment with Rooftop Terrace!, vacation rental in Winesburg

Luxe Amish Country Apartment with Rooftop Terrace!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Chestnut Barn built in 1830 is nestled in the quaint Amish town of Winesburg, vacation rental in Winesburg
The Chestnut Barn built in 1830 is nestled in the quaint Amish town of Winesburg, vacation rental in Winesburg
The Chestnut Barn built in 1830 is nestled in the quaint Amish town of Winesburg, vacation rental in Winesburg

The Chestnut Barn built in 1830 is nestled in the quaint Amish town of Winesburg

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Modern Apartment w/ Rooftop Patio & Sweeping Views, vacation rental in Winesburg
Modern Apartment w/ Rooftop Patio & Sweeping Views, vacation rental in Winesburg
Modern Apartment w/ Rooftop Patio & Sweeping Views, vacation rental in Winesburg

Modern Apartment w/ Rooftop Patio & Sweeping Views

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Chestnut Barn, Quaint, 1830s in Amish Country , vacation rental in Winesburg
The Chestnut Barn, Quaint, 1830s in Amish Country , vacation rental in Winesburg
The Chestnut Barn, Quaint, 1830s in Amish Country , vacation rental in Winesburg

The Chestnut Barn, Quaint, 1830s in Amish Country

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Cowgirl Quarters, vacation rental in Winesburg
Cowgirl Quarters, vacation rental in Winesburg
Cowgirl Quarters, vacation rental in Winesburg

Cowgirl Quarters

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Copper Creek Lodge * Lux-Crete Ranch, vacation rental in Winesburg
Copper Creek Lodge * Lux-Crete Ranch, vacation rental in Winesburg
Copper Creek Lodge * Lux-Crete Ranch, vacation rental in Winesburg

Copper Creek Lodge * Lux-Crete Ranch

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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3 Bed, 1 bath home with private inground pool in the heart of Amish country, vacation rental in Winesburg
3 Bed, 1 bath home with private inground pool in the heart of Amish country, vacation rental in Winesburg
3 Bed, 1 bath home with private inground pool in the heart of Amish country, vacation rental in Winesburg

3 Bed, 1 bath home with private inground pool in the heart of Amish country

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Jemma’s Hideaway in Amish Country, vacation rental in Winesburg
Jemma’s Hideaway in Amish Country, vacation rental in Winesburg
Jemma’s Hideaway in Amish Country, vacation rental in Winesburg

Jemma’s Hideaway in Amish Country

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Kingsway Guesthouse. Come, relax, and enjoy your time in Amish country!, vacation rental in Winesburg
Kingsway Guesthouse. Come, relax, and enjoy your time in Amish country!, vacation rental in Winesburg
Kingsway Guesthouse. Come, relax, and enjoy your time in Amish country!, vacation rental in Winesburg

Kingsway Guesthouse. Come, relax, and enjoy your time in Amish country!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful guest house in Berlin, the ❤️ of Ohio’s Amish country

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Escape to our romantic stone cottage by a pond overlooking Amish country, vacation rental in Winesburg
Escape to our romantic stone cottage by a pond overlooking Amish country, vacation rental in Winesburg
Escape to our romantic stone cottage by a pond overlooking Amish country, vacation rental in Winesburg

Escape to our romantic stone cottage by a pond overlooking Amish country

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Peaceful, Spacious, Historic Stone Cottage Getaway, vacation rental in Winesburg
Peaceful, Spacious, Historic Stone Cottage Getaway, vacation rental in Winesburg
Peaceful, Spacious, Historic Stone Cottage Getaway, vacation rental in Winesburg

Peaceful, Spacious, Historic Stone Cottage Getaway

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Luxurious, Spacious, Peaceful, Spectacular Sunrises/Sunsets, Ideal for Families, vacation rental in Winesburg
Luxurious, Spacious, Peaceful, Spectacular Sunrises/Sunsets, Ideal for Families, vacation rental in Winesburg
Luxurious, Spacious, Peaceful, Spectacular Sunrises/Sunsets, Ideal for Families, vacation rental in Winesburg

Luxurious, Spacious, Peaceful, Spectacular Sunrises/Sunsets, Ideal for Families

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 20
Match: Sleeps
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Escape To Our Clean Quiet Fully Furnished Cabins Nestled In Amish Country, vacation rental in Winesburg
Escape To Our Clean Quiet Fully Furnished Cabins Nestled In Amish Country, vacation rental in Winesburg
Escape To Our Clean Quiet Fully Furnished Cabins Nestled In Amish Country, vacation rental in Winesburg

Escape To Our Clean Quiet Fully Furnished Cabins Nestled In Amish Country

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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The Cabin at Saltcreek Pond ~ 20 minutes from Berlin~ Enjoy the outdoor hotub!, vacation rental in Winesburg
The Cabin at Saltcreek Pond ~ 20 minutes from Berlin~ Enjoy the outdoor hotub!, vacation rental in Winesburg
The Cabin at Saltcreek Pond ~ 20 minutes from Berlin~ Enjoy the outdoor hotub!, vacation rental in Winesburg

The Cabin at Saltcreek Pond ~ 20 minutes from Berlin~ Enjoy the outdoor hotub!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Romantic Vista Cottage - Walnut Creek,  walking distance to restaurants, shops., vacation rental in Winesburg
Romantic Vista Cottage - Walnut Creek,  walking distance to restaurants, shops., vacation rental in Winesburg
Romantic Vista Cottage - Walnut Creek,  walking distance to restaurants, shops., vacation rental in Winesburg

Romantic Vista Cottage - Walnut Creek, walking distance to restaurants, shops.

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Romantic Cottage in Amish Country, vacation rental in Winesburg
Romantic Cottage in Amish Country, vacation rental in Winesburg
Romantic Cottage in Amish Country, vacation rental in Winesburg

Romantic Cottage in Amish Country

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Pine Valley Guesthouse newly -updated home, vacation rental in Winesburg
Pine Valley Guesthouse newly -updated home, vacation rental in Winesburg
Pine Valley Guesthouse newly -updated home, vacation rental in Winesburg

Pine Valley Guesthouse newly -updated home

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Unit in Amish Country, vacation rental in Winesburg
Beautiful Unit in Amish Country, vacation rental in Winesburg
Beautiful Unit in Amish Country, vacation rental in Winesburg

Beautiful Unit in Amish Country

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Family Friendly Barndominium in Amish Country (Sleeps 8), vacation rental in Winesburg
Family Friendly Barndominium in Amish Country (Sleeps 8), vacation rental in Winesburg
Family Friendly Barndominium in Amish Country (Sleeps 8), vacation rental in Winesburg

Family Friendly Barndominium in Amish Country (Sleeps 8)

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Rustic Dundee Log Cabin w/ Hot Tub & Forest Views!, vacation rental in Winesburg
Rustic Dundee Log Cabin w/ Hot Tub & Forest Views!, vacation rental in Winesburg
Rustic Dundee Log Cabin w/ Hot Tub & Forest Views!, vacation rental in Winesburg

Rustic Dundee Log Cabin w/ Hot Tub & Forest Views!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Remodeled Amish home in Wilmot

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Log cabin in Amish country, vacation rental in Winesburg
Log cabin in Amish country, vacation rental in Winesburg
Log cabin in Amish country, vacation rental in Winesburg

Log cabin in Amish country

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Your Home Away From Home, vacation rental in Winesburg
Your Home Away From Home, vacation rental in Winesburg
Your Home Away From Home, vacation rental in Winesburg

Your Home Away From Home

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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NEW! Millersburg Home w/ Covered Porch & Fire Pit!, vacation rental in Winesburg
NEW! Millersburg Home w/ Covered Porch & Fire Pit!, vacation rental in Winesburg
NEW! Millersburg Home w/ Covered Porch & Fire Pit!, vacation rental in Winesburg

NEW! Millersburg Home w/ Covered Porch & Fire Pit!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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NEW! Charming Amish Country Getaway w/ Fire Pit!, vacation rental in Winesburg
NEW! Charming Amish Country Getaway w/ Fire Pit!, vacation rental in Winesburg
NEW! Charming Amish Country Getaway w/ Fire Pit!, vacation rental in Winesburg

NEW! Charming Amish Country Getaway w/ Fire Pit!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Entire House, vacation rental in Winesburg
Entire House, vacation rental in Winesburg
Entire House, vacation rental in Winesburg

Entire House

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Newly Renovated Home w/ Farm Views in Amish Area!, vacation rental in Winesburg
Newly Renovated Home w/ Farm Views in Amish Area!, vacation rental in Winesburg
Newly Renovated Home w/ Farm Views in Amish Area!, vacation rental in Winesburg

Newly Renovated Home w/ Farm Views in Amish Area!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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fresh modern 3/Bd wk end getaway in Amish country, vacation rental in Winesburg
fresh modern 3/Bd wk end getaway in Amish country, vacation rental in Winesburg
fresh modern 3/Bd wk end getaway in Amish country, vacation rental in Winesburg

fresh modern 3/Bd wk end getaway in Amish country

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Log Cabin  Suite  A, vacation rental in Winesburg
Log Cabin  Suite  A, vacation rental in Winesburg
Log Cabin  Suite  A, vacation rental in Winesburg

Log Cabin Suite A

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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NEW! Timeless Winesburg House with Private Balcony, vacation rental in Winesburg
NEW! Timeless Winesburg House with Private Balcony, vacation rental in Winesburg
NEW! Timeless Winesburg House with Private Balcony, vacation rental in Winesburg

NEW! Timeless Winesburg House with Private Balcony

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Rustic Suite - Main Street Lodge in Berlin, vacation rental in Winesburg
Rustic Suite - Main Street Lodge in Berlin, vacation rental in Winesburg
Rustic Suite - Main Street Lodge in Berlin, vacation rental in Winesburg

Rustic Suite - Main Street Lodge in Berlin

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Sanctum Inn: 6 bedrooms, 7 1/2 bath vacation house in heart of Amish country, vacation rental in Winesburg
Sanctum Inn: 6 bedrooms, 7 1/2 bath vacation house in heart of Amish country, vacation rental in Winesburg
Sanctum Inn: 6 bedrooms, 7 1/2 bath vacation house in heart of Amish country, vacation rental in Winesburg

Sanctum Inn: 6 bedrooms, 7 1/2 bath vacation house in heart of Amish country

Holiday Rental House
6 bedrooms
8 bathrooms
Sleeps 14
Match: Sleeps
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Log Cabin  Suite  B, vacation rental in Winesburg
Log Cabin  Suite  B, vacation rental in Winesburg
Log Cabin  Suite  B, vacation rental in Winesburg

Log Cabin Suite B

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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NEW! Quaint Winesburg Cottage w/ Porch & Pond!, vacation rental in Winesburg
NEW! Quaint Winesburg Cottage w/ Porch & Pond!, vacation rental in Winesburg
NEW! Quaint Winesburg Cottage w/ Porch & Pond!, vacation rental in Winesburg

NEW! Quaint Winesburg Cottage w/ Porch & Pond!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Farmhouse of Blessing, vacation rental in Winesburg
Farmhouse of Blessing, vacation rental in Winesburg
Farmhouse of Blessing, vacation rental in Winesburg

Farmhouse of Blessing

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Deluxe Lodge Suite 102, vacation rental in Winesburg
Deluxe Lodge Suite 102, vacation rental in Winesburg
Deluxe Lodge Suite 102, vacation rental in Winesburg

Deluxe Lodge Suite 102

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Deluxe Lodge Suite 204, vacation rental in Winesburg
Deluxe Lodge Suite 204, vacation rental in Winesburg
Deluxe Lodge Suite 204, vacation rental in Winesburg

Deluxe Lodge Suite 204

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Deluxe Lodge Suite 203, vacation rental in Winesburg
Deluxe Lodge Suite 203, vacation rental in Winesburg
Deluxe Lodge Suite 203, vacation rental in Winesburg

Deluxe Lodge Suite 203

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Historic Raber House, on Berlin’s Main Street, vacation rental in Winesburg
Historic Raber House, on Berlin’s Main Street, vacation rental in Winesburg
Historic Raber House, on Berlin’s Main Street, vacation rental in Winesburg

Historic Raber House, on Berlin’s Main Street

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Deluxe Lodge Suite 101, vacation rental in Winesburg
Deluxe Lodge Suite 101, vacation rental in Winesburg
Deluxe Lodge Suite 101, vacation rental in Winesburg

Deluxe Lodge Suite 101

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Wildwood Hill Cabin. Secluded in Woods. Hot Tub, vacation rental in Winesburg
Wildwood Hill Cabin. Secluded in Woods. Hot Tub, vacation rental in Winesburg
Wildwood Hill Cabin. Secluded in Woods. Hot Tub, vacation rental in Winesburg

Wildwood Hill Cabin. Secluded in Woods. Hot Tub

Condo/Apartment
0 bedrooms
0 bathrooms
Sleeps 2
Match: Sleeps
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Dreamy Vintage Cottage near Amish Country, Ohio, vacation rental in Winesburg
Dreamy Vintage Cottage near Amish Country, Ohio, vacation rental in Winesburg
Dreamy Vintage Cottage near Amish Country, Ohio, vacation rental in Winesburg

Dreamy Vintage Cottage near Amish Country, Ohio

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Beyond Cute Cottage, vacation rental in Winesburg
Beyond Cute Cottage, vacation rental in Winesburg
Beyond Cute Cottage, vacation rental in Winesburg

Beyond Cute Cottage

Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Spacious, Newly renovated home in Winesburg OH., vacation rental in Winesburg
Spacious, Newly renovated home in Winesburg OH., vacation rental in Winesburg
Spacious, Newly renovated home in Winesburg OH., vacation rental in Winesburg

Spacious, Newly renovated home in Winesburg OH.

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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3Bedroom 2bath Amish farmhouse, vacation rental in Winesburg
3Bedroom 2bath Amish farmhouse, vacation rental in Winesburg
3Bedroom 2bath Amish farmhouse, vacation rental in Winesburg

3Bedroom 2bath Amish farmhouse

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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The Magnolia House in Wilmot Ohio, vacation rental in Winesburg
The Magnolia House in Wilmot Ohio, vacation rental in Winesburg
The Magnolia House in Wilmot Ohio, vacation rental in Winesburg

The Magnolia House in Wilmot Ohio

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Country Home in With Fireplace Near Berlin Ohio, vacation rental in Winesburg
Country Home in With Fireplace Near Berlin Ohio, vacation rental in Winesburg
Country Home in With Fireplace Near Berlin Ohio, vacation rental in Winesburg

Country Home in With Fireplace Near Berlin Ohio

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 12
Match: Sleeps
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