Vacation rentals in Windsor, CT

71 available vacation rental offers

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Best vacation rentals and Airbnb offers in Windsor, CT

Cozy studio in adorable Hartford with refreshing AC for your stay.Great location - Windsor, CT

Cozy studio in adorable Hartford with refreshing AC for your stay.Great location

Apartment, Windsor

Cozy studio in adorable Hartford with refreshing AC for your stay.Great location is a apartment in Windsor. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Cozy studio in adorable Hartford with refreshing AC for your stay.Great location

Cozy studio in adorable Hartford with refreshing AC for your stay.Great location is a apartment in Windsor. 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 $665.

From$95/night
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Convenient Hartford Condo < 2 Mi to Dtwn! - Windsor, CT

Convenient Hartford Condo < 2 Mi to Dtwn!

Apartment, Windsor

Convenient Hartford Condo < 2 Mi to Dtwn! is a apartment in Windsor, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Convenient Hartford Condo < 2 Mi to Dtwn!

Convenient Hartford Condo < 2 Mi to Dtwn! is a apartment in Windsor, 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 $1,247.

From$120/night
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Pratt St Brand New Studio Loft Elevator Building - Windsor, CT

Pratt St Brand New Studio Loft Elevator Building

Apartment, Windsor

Pratt St Brand New Studio Loft Elevator Building is a apartment in Windsor. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About Pratt St Brand New Studio Loft Elevator Building

Pratt St Brand New Studio Loft Elevator Building is a apartment in Windsor. 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, ac, air conditioning, tv, and cctv inside.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,092.

From$126/night
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Central Chic Pad - with Free Parking, Heat & AC - Windsor, CT

Central Chic Pad - with Free Parking, Heat & AC

Apartment, Windsor

Central Chic Pad - with Free Parking, Heat & AC is a apartment in Windsor, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Central Chic Pad - with Free Parking, Heat & AC

Central Chic Pad - with Free Parking, Heat & AC is a apartment in Windsor, 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 washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $886.

From$127/night
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Vacation rentals with a pool in Windsor, CT

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

Charming 1-bedroom apartment with WiFi, AC in brilliant East Windsor - Windsor, CT

Charming 1-bedroom apartment with WiFi, AC in brilliant East Windsor

Apartment, Windsor

Charming 1-bedroom apartment with WiFi, AC in brilliant East Windsor is a apartment in Windsor, with pool access, parking, and room for a group. This stay gives travelers a comfortable base…

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About Charming 1-bedroom apartment with WiFi, AC in brilliant East Windsor

Charming 1-bedroom apartment with WiFi, AC in brilliant East Windsor is a apartment in Windsor, 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: pool, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,334.

From$191/night
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Simsbury 1820 House - Windsor, CT

Simsbury 1820 House

B & B, Windsor

Simsbury 1820 House is a b & b in Windsor, with pool access. 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 Simsbury 1820 House

Simsbury 1820 House is a b & b in Windsor, 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, free breakfast, pool, free wifi, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,160.

From$253/night
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Quiet Mid-Century Getaway. 4 bedrooms. Perfect for your next family gathering. - Windsor, CT

Quiet Mid-Century Getaway. 4 bedrooms. Perfect for your next family gathering.

Holiday Home, Windsor

Quiet Mid-Century Getaway. 4 bedrooms. Perfect for your next family gathering. is a holiday home in Windsor, with pool access, kitchen access, and room for a group. This stay gives…

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About Quiet Mid-Century Getaway. 4 bedrooms. Perfect for your next family gathering.

Quiet Mid-Century Getaway. 4 bedrooms. Perfect for your next family gathering. is a holiday home in Windsor, 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: pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $9,715.

From$1,388/night
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Vacation rentals with parking in Windsor, CT

Find vacation rentals that make arriving by car easier.

Cozy 1-bedroom apartment in beautiful Manchester with AC,Free Parking - Windsor, CT

Cozy 1-bedroom apartment in beautiful Manchester with AC,Free Parking

Apartment, Windsor

Cozy 1-bedroom apartment in beautiful Manchester with AC,Free Parking is a apartment in Windsor, with parking and room for a group. This stay gives travelers a comfortable base for…

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About Cozy 1-bedroom apartment in beautiful Manchester with AC,Free Parking

Cozy 1-bedroom apartment in beautiful Manchester with AC,Free Parking is a apartment in Windsor, 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, washer, dryer, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,079.

From$154/night
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Charming 2-bedroom townhome in wonderful West Hartford near Blue Back Square! - Windsor, CT

Charming 2-bedroom townhome in wonderful West Hartford near Blue Back Square!

Holiday Home, Windsor

Charming 2-bedroom townhome in wonderful West Hartford near Blue Back Square! is a holiday home in Windsor, with parking, kitchen access, and room for a group. This stay gives travelers a…

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About Charming 2-bedroom townhome in wonderful West Hartford near Blue Back Square!

Charming 2-bedroom townhome in wonderful West Hartford near Blue Back Square! is a holiday home in Windsor, 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 $1,298.

From$185/night
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Comfortable home away from home - Windsor, CT

Comfortable home away from home

Holiday Home, Windsor

Comfortable home away from home is a holiday home in Windsor, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Comfortable home away from home

Comfortable home away from home is a holiday home in Windsor, 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, free wifi, pet friendly, pets friendly, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,043.

From$223/night
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2-bedroom apartment in welcoming Windsor with AC and comfort. - Windsor, CT

2-bedroom apartment in welcoming Windsor with AC and comfort.

Apartment, Windsor

2-bedroom apartment in welcoming Windsor with AC and comfort. is a apartment in Windsor, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About 2-bedroom apartment in welcoming Windsor with AC and comfort.

2-bedroom apartment in welcoming Windsor with AC and comfort. is a apartment in Windsor, 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, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,745.

From$249/night
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Pet-friendly vacation rentals in Windsor, CT

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

Cozy 1-bedroom house in adorable East Granby - Windsor, CT

Cozy 1-bedroom house in adorable East Granby

Holiday Home, Windsor

Cozy 1-bedroom house in adorable East Granby is a holiday home in Windsor, with pet-friendly space, parking, and room for a group. This stay gives travelers a comfortable base for exploring…

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About Cozy 1-bedroom house in adorable East Granby

Cozy 1-bedroom house in adorable East Granby is a holiday home in Windsor, with pet-friendly space, 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, pet friendly, pets friendly, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,023.

From$146/night
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Cozy 1-bedroom with WiFi, central air, in unit laundry in enjoyable Manchester - Windsor, CT

Cozy 1-bedroom with WiFi, central air, in unit laundry in enjoyable Manchester

Apartment, Windsor

Cozy 1-bedroom with WiFi, central air, in unit laundry in enjoyable Manchester is a apartment in Windsor, with pet-friendly space, parking, and kitchen access. This stay gives travelers a…

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About Cozy 1-bedroom with WiFi, central air, in unit laundry in enjoyable Manchester

Cozy 1-bedroom with WiFi, central air, in unit laundry in enjoyable Manchester is a apartment in Windsor, 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 $1,060.

From$151/night
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The Traveler Suite C1 CURRENT Upgrades are Underway Daily! - Windsor, CT

The Traveler Suite C1 CURRENT Upgrades are Underway Daily!

Apartment, Windsor

The Traveler Suite C1 CURRENT Upgrades are Underway Daily! is a apartment in Windsor, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring…

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About The Traveler Suite C1 CURRENT Upgrades are Underway Daily!

The Traveler Suite C1 CURRENT Upgrades are Underway Daily! is a apartment in Windsor, 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 $1,138.

From$163/night
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3-bedroom apartment in nice East Hartford with WiFi, AC - Windsor, CT

3-bedroom apartment in nice East Hartford with WiFi, AC

Apartment, Windsor

3-bedroom apartment in nice East Hartford with WiFi, AC is a apartment in Windsor, with pet-friendly space and room for a group. This stay gives travelers a comfortable base for exploring…

Read more

About 3-bedroom apartment in nice East Hartford with WiFi, AC

3-bedroom apartment in nice East Hartford with WiFi, AC is a apartment in Windsor, with pet-friendly space 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, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,326.

From$189/night
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Vacation rentals with a kitchen in Windsor, CT

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

Bright & Peaceful Studio Hideaway - Cozy, Quiet & Central - Windsor, CT

Bright & Peaceful Studio Hideaway - Cozy, Quiet & Central

Apartment, Windsor

Bright & Peaceful Studio Hideaway - Cozy, Quiet & Central is a apartment in Windsor, with kitchen access and a quieter setting. This stay gives travelers a comfortable base for exploring…

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About Bright & Peaceful Studio Hideaway - Cozy, Quiet & Central

Bright & Peaceful Studio Hideaway - Cozy, Quiet & Central is a apartment in Windsor, 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, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,256.

From$179/night
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Downtown and secluded - Windsor, CT

Downtown and secluded

Holiday Home, Windsor

Downtown and secluded is a holiday home in Windsor, 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 Downtown and secluded

Downtown and secluded is a holiday home in Windsor, 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 $1,407.

From$201/night
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3-bedroom apartment steps to Downtown Hartford - Windsor, CT

3-bedroom apartment steps to Downtown Hartford

Apartment, Windsor

3-bedroom apartment steps to Downtown Hartford is a apartment in Windsor, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About 3-bedroom apartment steps to Downtown Hartford

3-bedroom apartment steps to Downtown Hartford is a apartment in Windsor, 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 $1,474.

From$211/night
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Beautiful 2-bedroom apartment with AC in cool Windsor - Windsor, CT

Beautiful 2-bedroom apartment with AC in cool Windsor

Apartment, Windsor

Beautiful 2-bedroom apartment with AC in cool Windsor is a apartment in Windsor, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Beautiful 2-bedroom apartment with AC in cool Windsor

Beautiful 2-bedroom apartment with AC in cool Windsor is a apartment in Windsor, 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, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,022.

From$289/night
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Family-friendly vacation rentals in Windsor, CT

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

Luxe Lady Executive & Family Retreat 1 Bedroom Townhouse - Windsor, CT

Luxe Lady Executive & Family Retreat 1 Bedroom Townhouse

Holiday Home, Windsor

Luxe Lady Executive & Family Retreat 1 Bedroom Townhouse is a holiday home in Windsor, with room for a group and a quieter setting. This stay gives travelers a comfortable base for…

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About Luxe Lady Executive & Family Retreat 1 Bedroom Townhouse

Luxe Lady Executive & Family Retreat 1 Bedroom Townhouse is a holiday home in Windsor, with 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 cancellation, ac, air conditioning, heating, and non smoking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,254.

From$179/night
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Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL. - Windsor, CT

Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.

Holiday Home, Windsor

Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL. is a holiday home in Windsor, with pet-friendly space and kitchen access. This stay gives travelers a…

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About Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.

Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL. is a holiday home in Windsor, 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 $1,956.

From$279/night
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Lake Congamond Cozy Stylish Comfortable House - Windsor, CT

Lake Congamond Cozy Stylish Comfortable House

Holiday Home, Windsor

Lake Congamond Cozy Stylish Comfortable House is a holiday home in Windsor, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Lake Congamond Cozy Stylish Comfortable House

Lake Congamond Cozy Stylish Comfortable House is a holiday home in Windsor, 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 $2,017.

From$288/night
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Charming East Granby house with AC and WiFi 3 minutes to Bradley Airport - Windsor, CT

Charming East Granby house with AC and WiFi 3 minutes to Bradley Airport

Holiday Home, Windsor

Charming East Granby house with AC and WiFi 3 minutes to Bradley Airport is a holiday home in Windsor, with parking and kitchen access. This stay gives travelers a comfortable base for…

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About Charming East Granby house with AC and WiFi 3 minutes to Bradley Airport

Charming East Granby house with AC and WiFi 3 minutes to Bradley Airport is a holiday home in Windsor, 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 $2,923.

From$418/night
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