Vacation rentals in Winchester, TX

Best vacation rentals and Airbnb offers in Winchester, TX

Terrys Water Front Bungalow on The RiversEdge AC Heat in a private campground!

Holiday Home, Winchester

Terrys Water Front Bungalow on The RiversEdge AC Heat in a private campground! is a holiday home in Winchester, with pet-friendly space and parking. This stay gives travelers a comfortable…

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About Terrys Water Front Bungalow on The RiversEdge AC Heat in a private campground!

Terrys Water Front Bungalow on The RiversEdge AC Heat in a private campground! is a holiday home 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 $547.

From$78/night

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Cozy Cabin on 22 Private Acres in Smithville, TX Peaceful Hill Country Retreat

Apartment, Winchester

Cozy Cabin on 22 Private Acres in Smithville, TX Peaceful Hill Country Retreat is a apartment in Winchester, with parking, kitchen access, and a quieter setting. This stay gives travelers a…

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About Cozy Cabin on 22 Private Acres in Smithville, TX Peaceful Hill Country Retreat

Cozy Cabin on 22 Private Acres in Smithville, TX Peaceful Hill Country Retreat is a apartment in Winchester, with parking, 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $661.

From$94/night

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Fishing Pond: ‘Minerva’s Cottage’ in West Point!

Holiday Home, Winchester

Fishing Pond: ‘Minerva’s Cottage’ in West Point! is a holiday home in Winchester, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Fishing Pond: ‘Minerva’s Cottage’ in West Point!

Fishing Pond: ‘Minerva’s Cottage’ in West Point! is a holiday home 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, parking, paid parking, heating, and non smoking::room.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $988.

From$96/night

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Adorable Guest Cabin In The Woods

Cabin, Winchester

Adorable Guest Cabin In The Woods is a cabin in Winchester. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or…

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About Adorable Guest Cabin In The Woods

Adorable Guest Cabin In The Woods is a cabin in Winchester. 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 $715.

From$102/night

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Vacation rentals with a pool in Winchester, TX

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

Victorian 1920s 5 bdrm w/ Pool, antiquer’s dream

Holiday Home, Winchester

Victorian 1920s 5 bdrm w/ Pool, antiquer’s dream is a holiday home in Winchester, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Victorian 1920s 5 bdrm w/ Pool, antiquer’s dream

Victorian 1920s 5 bdrm w/ Pool, antiquer’s dream is a holiday home in Winchester, with pool 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, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,184.

From$312/night

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NEW Pool House, on A Ranch, 15 miles from Round Top

Guest House, Winchester

NEW Pool House, on A Ranch, 15 miles from Round Top is a guest house in Winchester, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About NEW Pool House, on A Ranch, 15 miles from Round Top

NEW Pool House, on A Ranch, 15 miles from Round Top is a guest house in Winchester, with pool 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, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,412.

From$345/night

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Windy Hill Retreat | Modern Farmhouse with Views, Cowboy Pool & Firepit

Holiday Home, Winchester

Windy Hill Retreat · Modern Farmhouse with Views, Cowboy Pool & Firepit is a holiday home in Winchester, with pool access, kitchen access, and a quieter setting. This stay gives travelers a…

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About Windy Hill Retreat | Modern Farmhouse with Views, Cowboy Pool & Firepit

Windy Hill Retreat · Modern Farmhouse with Views, Cowboy Pool & Firepit is a holiday home in Winchester, 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, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,269.

From$467/night

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Private home with pool minutes from downtown La Grange and Antique Shopping

Holiday Home, Winchester

Private home with pool minutes from downtown La Grange and Antique Shopping is a holiday home in Winchester, with pool access and kitchen access. This stay gives travelers a comfortable…

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About Private home with pool minutes from downtown La Grange and Antique Shopping

Private home with pool minutes from downtown La Grange and Antique Shopping is a holiday home in Winchester, with pool 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, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,508.

From$501/night

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Vacation rentals with parking in Winchester, TX

Find vacation rentals that make arriving by car easier.

Waterfront Smithville River House

Holiday Home, Winchester

Waterfront Smithville River House is a holiday home in Winchester, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Waterfront Smithville River House

Waterfront Smithville River House is a holiday home in Winchester, with easy beach access, 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 $970.

From$139/night

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Dodo's Place on 22 acres outside of Smithville, TX

Cabin, Winchester

Dodo's Place on 22 acres outside of Smithville, TX is a cabin in Winchester, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Dodo's Place on 22 acres outside of Smithville, TX

Dodo's Place on 22 acres outside of Smithville, TX 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 $1,071.

From$153/night

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Warda Bluff Creek Ranch - Longhorns and Trails

Apartment, Winchester

Warda Bluff Creek Ranch - Longhorns and Trails 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 Warda Bluff Creek Ranch - Longhorns and Trails

Warda Bluff Creek Ranch - Longhorns and Trails 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, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,191.

From$170/night

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22 miles to Round Top, 3/2 w/ trailer parking, relaxing cozy cabin w/ lake, wifi

Cabin, Winchester

22 miles to Round Top, 3/2 w/ trailer parking, relaxing cozy cabin w/ lake, wifi is a cabin in Winchester, with parking, kitchen access, and a quieter setting. This stay gives travelers a…

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About 22 miles to Round Top, 3/2 w/ trailer parking, relaxing cozy cabin w/ lake, wifi

22 miles to Round Top, 3/2 w/ trailer parking, relaxing cozy cabin w/ lake, wifi is a cabin in Winchester, with parking, 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 parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,783.

From$255/night

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Pet-friendly vacation rentals in Winchester, TX

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

2 Queen Beds|Nsmk,Kitchen

Apartment, Winchester

2 Queen Beds · Nsmk,Kitchen is a apartment in Winchester, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About 2 Queen Beds|Nsmk,Kitchen

2 Queen Beds · Nsmk,Kitchen is a apartment 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: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $946.

From$135/night

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Steps to Downtown, Parks, and it's Dog-friendly!

Holiday Home, Winchester

Steps to Downtown, Parks, and it's Dog-friendly! is a holiday home in Winchester, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Steps to Downtown, Parks, and it's Dog-friendly!

Steps to Downtown, Parks, and it's Dog-friendly! is a holiday home 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 $977.

From$140/night

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Seclusion in the Lost Pines hosted by Jan

Cabin, Winchester

Seclusion in the Lost Pines hosted by Jan 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 Seclusion in the Lost Pines hosted by Jan

Seclusion in the Lost Pines hosted by Jan 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 $995.

From$142/night

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River Shack w/ private enclosed spa.

Holiday Home, Winchester

River Shack w/ private enclosed spa. is a holiday home 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 River Shack w/ private enclosed spa.

River Shack w/ private enclosed spa. is a holiday home 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 $1,376.

From$197/night

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Vacation rentals with a kitchen in Winchester, TX

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

Secluded Tiny Home, firepit stargaze hike pond

Cabin, Winchester

Secluded Tiny Home, firepit stargaze hike pond 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 Secluded Tiny Home, firepit stargaze hike pond

Secluded Tiny Home, firepit stargaze hike pond 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 $1,072.

From$153/night

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Secluded Tiny Cabin with firepit, stargaze and hike

Cabin, Winchester

Secluded Tiny Cabin with firepit, stargaze and hike 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 Secluded Tiny Cabin with firepit, stargaze and hike

Secluded Tiny Cabin with firepit, stargaze and hike 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 $1,087.

From$155/night

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Fenced Yard! Peaceful Retreat in Smithville

Holiday Home, Winchester

Fenced Yard! Peaceful Retreat in Smithville is a holiday home in Winchester, with pet-friendly space, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for…

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About Fenced Yard! Peaceful Retreat in Smithville

Fenced Yard! Peaceful Retreat in Smithville is a holiday home in Winchester, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,130.

From$161/night

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Relaxing 2-bedroom cabin on Lake Jean

Cabin, Winchester

Relaxing 2-bedroom cabin on Lake Jean is a cabin in Winchester, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the…

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About Relaxing 2-bedroom cabin on Lake Jean

Relaxing 2-bedroom cabin on Lake Jean is a cabin in Winchester, with pet-friendly space, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,621.

From$232/night

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Family-friendly vacation rentals in Winchester, TX

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

The Country Cottage w/ Beautiful Views-5 mi. from historic downtown

Holiday Home, Winchester

The Country Cottage w/ Beautiful Views-5 mi. from historic downtown is a holiday home in Winchester, with parking and kitchen access. This stay gives travelers a comfortable base for…

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About The Country Cottage w/ Beautiful Views-5 mi. from historic downtown

The Country Cottage w/ Beautiful Views-5 mi. from historic downtown is a holiday home 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 $1,237.

From$177/night

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Restful cottage close to antique shopping and mountain biking

Cottage, Winchester

Restful cottage close to antique shopping and mountain biking is a cottage in Winchester, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Restful cottage close to antique shopping and mountain biking

Restful cottage close to antique shopping and mountain biking is a cottage in Winchester, with pool 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, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,812.

From$259/night

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Charming 1-bedroom cottage 8 minutes from Round Top-WiFi, AC -zHEN House Silo #1

Cottage, Winchester

Charming 1-bedroom cottage 8 minutes from Round Top-WiFi, AC -zHEN House Silo #1 is a cottage in Winchester, with parking and room for a group. This stay gives travelers a comfortable base…

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About Charming 1-bedroom cottage 8 minutes from Round Top-WiFi, AC -zHEN House Silo #1

Charming 1-bedroom cottage 8 minutes from Round Top-WiFi, AC -zHEN House Silo #1 is a cottage in Winchester, with 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, free wifi, parking, free parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,054.

From$293/night

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Family Home w/ Covered Patio & Grill in La Grange

Cottage, Winchester

Family Home w/ Covered Patio & Grill in La Grange is a cottage in Winchester, with pet-friendly space, outdoor space, and kitchen access. This stay gives travelers a comfortable base for…

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About Family Home w/ Covered Patio & Grill in La Grange

Family Home w/ Covered Patio & Grill in La Grange is a cottage in Winchester, with pet-friendly space, outdoor 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 $3,255.

From$395/night

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