Vacation rentals in Winchester, OH

54 available vacation rental offers

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Best vacation rentals and Airbnb offers in Winchester, OH

Beautiful studio in historic downtown Maysville - Winchester, OH

Beautiful studio in historic downtown Maysville

Apartment, Winchester

Beautiful studio in historic downtown Maysville is a apartment in Winchester, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Beautiful studio in historic downtown Maysville

Beautiful studio in historic downtown Maysville is a apartment in Winchester, 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 $702.

From$100/night
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The Huntsmen - Winchester, OH

The Huntsmen

Cabin, Winchester

The Huntsmen is a cabin in Winchester, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About The Huntsmen

The Huntsmen is a cabin in Winchester, with pet-friendly space 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, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $705.

From$101/night
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Country Cabin in Amish Country - Winchester, OH

Country Cabin in Amish Country

Cabin, Winchester

Country Cabin in Amish Country is a cabin in Winchester, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About Country Cabin in Amish Country

Country Cabin in Amish Country is a cabin in Winchester, 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, kitchen, with kitchen, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $882.

From$126/night
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Secluded in Amish Country and peaceful - Winchester, OH

Secluded in Amish Country and peaceful

Cabin, Winchester

Secluded in Amish Country and peaceful is a cabin in Winchester, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Secluded in Amish Country and peaceful

Secluded in Amish Country and peaceful is a cabin in Winchester, 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 $882.

From$126/night
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Vacation rentals with parking in Winchester, OH

Find vacation rentals that make arriving by car easier.

Glamping Cabin | Huge Window | Tree House Feel - Winchester, OH

Glamping Cabin | Huge Window | Tree House Feel

Cabin, Winchester

Glamping Cabin · Huge Window · Tree House Feel is a cabin in Winchester, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Glamping Cabin | Huge Window | Tree House Feel

Glamping Cabin · Huge Window · Tree House Feel is a cabin in Winchester, with pet-friendly space 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, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $596.

From$85/night
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Stout Cabin w/ Fire Pit: 1 Mi to Ohio River! - Winchester, OH

Stout Cabin w/ Fire Pit: 1 Mi to Ohio River!

Cabin, Winchester

Stout Cabin w/ Fire Pit: 1 Mi to Ohio River! is a cabin in Winchester, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Stout Cabin w/ Fire Pit: 1 Mi to Ohio River!

Stout Cabin w/ Fire Pit: 1 Mi to Ohio River! is a cabin in Winchester, 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 $855.

From$122/night
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Extended Stays by Lee House Inn - Winchester, OH

Extended Stays by Lee House Inn

Apartment, Winchester

Extended Stays by Lee House Inn is a apartment in Winchester, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About Extended Stays by Lee House Inn

Extended Stays by Lee House Inn is a apartment in Winchester, 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 ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,202.

From$150/night
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Country Charm Cabin - Winchester, OH

Country Charm Cabin

Cabin, Winchester

Country Charm Cabin is a cabin in Winchester, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About Country Charm Cabin

Country Charm Cabin is a cabin in Winchester, 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, hot tub, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,152.

From$165/night
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Pet-friendly vacation rentals in Winchester, OH

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

Glamping Cabin | Huge Window | Cliff and Animal Views - Winchester, OH

Glamping Cabin | Huge Window | Cliff and Animal Views

Cabin, Winchester

Glamping Cabin · Huge Window · Cliff and Animal Views is a cabin in Winchester, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing…

Read more

About Glamping Cabin | Huge Window | Cliff and Animal Views

Glamping Cabin · Huge Window · Cliff and Animal Views is a cabin in Winchester, with pet-friendly space. 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, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $596.

From$85/night
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Hopewell Croft - Southern Ohio Cabin Rental - Winchester, OH

Hopewell Croft - Southern Ohio Cabin Rental

Cabin, Winchester

Hopewell Croft - Southern Ohio Cabin Rental is a cabin in Winchester, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Hopewell Croft - Southern Ohio Cabin Rental

Hopewell Croft - Southern Ohio Cabin Rental is a cabin in Winchester, 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 $1,450.

From$207/night
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Secluded cabin located in Amish country - Winchester, OH

Secluded cabin located in Amish country

Cabin, Winchester

Secluded cabin located in Amish country is a cabin in Winchester, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

Read more

About Secluded cabin located in Amish country

Secluded cabin located in Amish country is a cabin in Winchester, 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, hot tub, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,534.

From$219/night
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Cozy private getaway built for couples to reconnect !! - Winchester, OH

Cozy private getaway built for couples to reconnect !!

Cabin, Winchester

Cozy private getaway built for couples to reconnect !! is a cabin in Winchester, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Cozy private getaway built for couples to reconnect !!

Cozy private getaway built for couples to reconnect !! is a cabin in Winchester, 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, hot tub, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,619.

From$231/night
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Vacation rentals with a kitchen in Winchester, OH

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

The Outdoorsman - Winchester, OH

The Outdoorsman

Cabin, Winchester

The Outdoorsman is a cabin in Winchester, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About The Outdoorsman

The Outdoorsman is a cabin in Winchester, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $996.

From$142/night
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Luxury and Character in Maysville, Kentucky - Winchester, OH

Luxury and Character in Maysville, Kentucky

Apartment, Winchester

Luxury and Character in Maysville, Kentucky is a apartment in Winchester, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

Read more

About Luxury and Character in Maysville, Kentucky

Luxury and Character in Maysville, Kentucky is a apartment in Winchester, 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 $1,120.

From$160/night
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Southern Ohio Retreat w/ Private Hot Tub - Winchester, OH

Southern Ohio Retreat w/ Private Hot Tub

Holiday Home, Winchester

Southern Ohio Retreat w/ Private Hot Tub is a holiday home in Winchester, with kitchen access and a quieter setting. This stay gives travelers a comfortable base for exploring the area,…

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About Southern Ohio Retreat w/ Private Hot Tub

Southern Ohio Retreat w/ Private Hot Tub is a holiday home in Winchester, with 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: hot tub, kitchen, with kitchen, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,151.

From$164/night
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Spacious 3-bedroom apartment with WiFi, AC in charming Ripley - Winchester, OH

Spacious 3-bedroom apartment with WiFi, AC in charming Ripley

Apartment, Winchester

Spacious 3-bedroom apartment with WiFi, AC in charming Ripley is a apartment in Winchester, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base…

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About Spacious 3-bedroom apartment with WiFi, AC in charming Ripley

Spacious 3-bedroom apartment with WiFi, AC in charming Ripley is a apartment in Winchester, with parking, 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,260.

From$180/night
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Family-friendly vacation rentals in Winchester, OH

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

Stout Cabin w/ Fire Pit: 1 Mi to Ohio River! - Winchester, OH

Stout Cabin w/ Fire Pit: 1 Mi to Ohio River!

Cottage, Winchester

Stout Cabin w/ Fire Pit: 1 Mi to Ohio River! is a cottage in Winchester, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Stout Cabin w/ Fire Pit: 1 Mi to Ohio River!

Stout Cabin w/ Fire Pit: 1 Mi to Ohio River! is a cottage in Winchester, 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 $975.

From$126/night
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The Beach House - Winchester, OH

The Beach House

Cottage, Winchester

The Beach House is a cottage in Winchester, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

Read more

About The Beach House

The Beach House is a cottage in Winchester, with pet-friendly space, easy beach access, 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 $895.

From$128/night
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Escape to The Red Barn! Private Retreat on 8 acres w/Firepit & Stocked Pond! - Winchester, OH

Escape to The Red Barn! Private Retreat on 8 acres w/Firepit & Stocked Pond!

Cabin, Winchester

Escape to The Red Barn! Private Retreat on 8 acres w/Firepit & Stocked Pond! is a cabin in Winchester, with kitchen access and a quieter setting. This stay gives travelers a comfortable…

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About Escape to The Red Barn! Private Retreat on 8 acres w/Firepit & Stocked Pond!

Escape to The Red Barn! Private Retreat on 8 acres w/Firepit & Stocked Pond! is a cabin in Winchester, with 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, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,537.

From$220/night
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Amish Country Farm Stay: Family-Friendly Getaway by Rocky Fork Lake - Winchester, OH

Amish Country Farm Stay: Family-Friendly Getaway by Rocky Fork Lake

Holiday Home, Winchester

Amish Country Farm Stay: Family-Friendly Getaway by Rocky Fork Lake is a holiday home in Winchester, with parking, kitchen access, and room for a group. This stay gives travelers a…

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About Amish Country Farm Stay: Family-Friendly Getaway by Rocky Fork Lake

Amish Country Farm Stay: Family-Friendly Getaway by Rocky Fork Lake is a holiday home in Winchester, with parking, 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,708.

From$244/night
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