Vacation rentals in Winchester, CT

34 available vacation rental offers

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Best vacation rentals and Airbnb offers in Winchester, CT

Cozy Attic 10 min to Llitchfield - Winchester, CT

Cozy Attic 10 min to Llitchfield

Apartment, Winchester

Cozy Attic 10 min to Llitchfield is a apartment 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 Cozy Attic 10 min to Llitchfield

Cozy Attic 10 min to Llitchfield 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 $1,080.

From$154/night
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Relax And Enjoy A Fun Getaway At The Bacchus Cottage! - Winchester, CT

Relax And Enjoy A Fun Getaway At The Bacchus Cottage!

Cottage, Winchester

Relax And Enjoy A Fun Getaway At The Bacchus Cottage! is a cottage in Winchester, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for…

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About Relax And Enjoy A Fun Getaway At The Bacchus Cottage!

Relax And Enjoy A Fun Getaway At The Bacchus Cottage! is a cottage 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, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,145.

From$164/night
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Cozy Cabin Style Apt Private 1st Flr 1 Bdrm - Winchester, CT

Cozy Cabin Style Apt Private 1st Flr 1 Bdrm

Apartment, Winchester

Cozy Cabin Style Apt Private 1st Flr 1 Bdrm 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 Cozy Cabin Style Apt Private 1st Flr 1 Bdrm

Cozy Cabin Style Apt Private 1st Flr 1 Bdrm 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 $1,339.

From$191/night
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Cozy Modern Farmhouse Private Apt - 3 Beds - Winchester, CT

Cozy Modern Farmhouse Private Apt - 3 Beds

Apartment, Winchester

Cozy Modern Farmhouse Private Apt - 3 Beds 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 Cozy Modern Farmhouse Private Apt - 3 Beds

Cozy Modern Farmhouse Private Apt - 3 Beds 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 $1,401.

From$200/night
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Vacation rentals with parking in Winchester, CT

Find vacation rentals that make arriving by car easier.

Inviting 3 Bedroom Mid-Century Modern in Canton, CT - Winchester, CT

Inviting 3 Bedroom Mid-Century Modern in Canton, CT

Holiday Home, Winchester

Inviting 3 Bedroom Mid-Century Modern in Canton, CT is a holiday home in Winchester, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Inviting 3 Bedroom Mid-Century Modern in Canton, CT

Inviting 3 Bedroom Mid-Century Modern in Canton, CT 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 $2,027.

From$290/night
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Classy Private Apt - 3 Beds 2nd Flr - Near Downtown - Winchester, CT

Classy Private Apt - 3 Beds 2nd Flr - Near Downtown

Apartment, Winchester

Classy Private Apt - 3 Beds 2nd Flr - Near Downtown is a apartment in Winchester, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Classy Private Apt - 3 Beds 2nd Flr - Near Downtown

Classy Private Apt - 3 Beds 2nd Flr - Near Downtown 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 $2,245.

From$321/night
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Hike, Bike & Relax: Huckleberry Hill Home w/ Yard! - Winchester, CT

Hike, Bike & Relax: Huckleberry Hill Home w/ Yard!

Holiday Home, Winchester

Hike, Bike & Relax: Huckleberry Hill Home w/ Yard! is a holiday home in Winchester, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for…

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About Hike, Bike & Relax: Huckleberry Hill Home w/ Yard!

Hike, Bike & Relax: Huckleberry Hill Home w/ Yard! is a holiday home 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: kitchen, with kitchen, parking, free parking, and fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,361.

From$337/night
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Private Historic Retreat • Waterfall • Gardens - Winchester, CT

Private Historic Retreat • Waterfall • Gardens

Holiday Home, Winchester

Private Historic Retreat · Waterfall · Gardens is a holiday home in Winchester, with parking and a quieter setting. This stay gives travelers a comfortable base for exploring the area,…

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About Private Historic Retreat • Waterfall • Gardens

Private Historic Retreat · Waterfall · Gardens is a holiday home in Winchester, with parking 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: parking, free parking, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,440.

From$491/night
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Pet-friendly vacation rentals in Winchester, CT

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

Tranquil Home 10 mins from Mohawk Mountain: Skiing, hiking, nature! - Winchester, CT

Tranquil Home 10 mins from Mohawk Mountain: Skiing, hiking, nature!

Holiday Home, Winchester

Tranquil Home 10 mins from Mohawk Mountain: Skiing, hiking, nature! is a holiday home in Winchester, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base…

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About Tranquil Home 10 mins from Mohawk Mountain: Skiing, hiking, nature!

Tranquil Home 10 mins from Mohawk Mountain: Skiing, hiking, nature! 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 $3,122.

From$446/night
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Woodridge Lake Great Escape-special April 5+ days promotion! - Winchester, CT

Woodridge Lake Great Escape-special April 5+ days promotion!

Holiday Home, Winchester

Woodridge Lake Great Escape-special April 5+ days promotion! is a holiday home in Winchester, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a…

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About Woodridge Lake Great Escape-special April 5+ days promotion!

Woodridge Lake Great Escape-special April 5+ days promotion! is a holiday home in Winchester, with pet-friendly space, 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: pool, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,679.

From$526/night
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Romantic and Secluded Berkshire's Gem - Winchester, CT

Romantic and Secluded Berkshire's Gem

Cabin, Winchester

Romantic and Secluded Berkshire's Gem is a cabin in Winchester, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Romantic and Secluded Berkshire's Gem

Romantic and Secluded Berkshire's Gem 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 wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,669.

From$667/night
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Lovely vacation home on secluded hillside with views and heated pool - Winchester, CT

Lovely vacation home on secluded hillside with views and heated pool

Holiday Home, Winchester

Lovely vacation home on secluded hillside with views and heated pool is a holiday home in Winchester, with pool access. This stay gives travelers a comfortable base for exploring the area,…

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About Lovely vacation home on secluded hillside with views and heated pool

Lovely vacation home on secluded hillside with views and heated pool is a holiday home in Winchester, with pool 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.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,779.

From$683/night
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Vacation rentals with a kitchen in Winchester, CT

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

Riverside Farm - Winchester, CT

Riverside Farm

Holiday Home, Winchester

Riverside Farm is a holiday home in Winchester, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with…

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About Riverside Farm

Riverside Farm is a holiday home 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, hot tub, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,908.

From$415/night
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Bellhaven- Charming 4-bedroom house in Canaan, CT - Winchester, CT

Bellhaven- Charming 4-bedroom house in Canaan, CT

Holiday Home, Winchester

Bellhaven- Charming 4-bedroom house in Canaan, CT is a holiday home in Winchester, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Bellhaven- Charming 4-bedroom house in Canaan, CT

Bellhaven- Charming 4-bedroom house in Canaan, CT 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 $3,203.

From$458/night
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Historic Litchfield Hills Saltbox on Large Estate! - Winchester, CT

Historic Litchfield Hills Saltbox on Large Estate!

Holiday Home, Winchester

Historic Litchfield Hills Saltbox on Large Estate! is a holiday home in Winchester, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Historic Litchfield Hills Saltbox on Large Estate!

Historic Litchfield Hills Saltbox on Large Estate! is a holiday home 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, free wifi, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,697.

From$528/night
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Litchfield County Farmhouse Retreat in Vineyard Area - Winchester, CT

Litchfield County Farmhouse Retreat in Vineyard Area

Holiday Home, Winchester

Litchfield County Farmhouse Retreat in Vineyard Area is a holiday home in Winchester, with kitchen access and a quieter setting. This stay gives travelers a comfortable base for exploring…

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About Litchfield County Farmhouse Retreat in Vineyard Area

Litchfield County Farmhouse Retreat in Vineyard Area 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: free wifi, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,707.

From$672/night
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Family-friendly vacation rentals in Winchester, CT

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

Hike, Bike & Relax: Huckleberry Hill Home w/ Yard! - Winchester, CT

Hike, Bike & Relax: Huckleberry Hill Home w/ Yard!

Cottage, Winchester

Hike, Bike & Relax: Huckleberry Hill Home w/ Yard! is a cottage in Winchester, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for…

Read more

About Hike, Bike & Relax: Huckleberry Hill Home w/ Yard!

Hike, Bike & Relax: Huckleberry Hill Home w/ Yard! is a cottage 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 $2,725.

From$273/night
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Log Cabin w/ fire pit, close to Ski Catamount, Butternut Ski, Great Barrington - Winchester, CT

Log Cabin w/ fire pit, close to Ski Catamount, Butternut Ski, Great Barrington

Holiday Home, Winchester

Log Cabin w/ fire pit, close to Ski Catamount, Butternut Ski, Great Barrington is a holiday home in Winchester, with parking and kitchen access. This stay gives travelers a comfortable base…

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About Log Cabin w/ fire pit, close to Ski Catamount, Butternut Ski, Great Barrington

Log Cabin w/ fire pit, close to Ski Catamount, Butternut Ski, Great Barrington 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, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,782.

From$397/night
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Cozy Berkshires Lakefront Cottage! NEW - Winchester, CT

Cozy Berkshires Lakefront Cottage! NEW

Holiday Home, Winchester

Cozy Berkshires Lakefront Cottage! NEW is a holiday home in Winchester, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Cozy Berkshires Lakefront Cottage! NEW

Cozy Berkshires Lakefront Cottage! NEW is a holiday home 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, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,023.

From$432/night
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Spacious family home with open floor plan...close to lake and clubhouse! - Winchester, CT

Spacious family home with open floor plan...close to lake and clubhouse!

Holiday Home, Winchester

Spacious family home with open floor plan...close to lake and clubhouse! is a holiday home in Winchester, with pool access and room for a group. This stay gives travelers a comfortable base…

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About Spacious family home with open floor plan...close to lake and clubhouse!

Spacious family home with open floor plan...close to lake and clubhouse! is a holiday home in Winchester, with pool 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: pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,337.

From$477/night
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