Vacation rentals in Simsbury, CT

Best vacation rentals and Airbnb offers in Simsbury, CT

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

Apartment, Simsbury

Cozy studio in adorable Hartford with refreshing AC for your stay.Great location is a apartment in Simsbury. 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 Simsbury. 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!

Apartment, Simsbury

Convenient Hartford Condo < 2 Mi to Dtwn! is a apartment in Simsbury, 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 Simsbury, 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

Apartment, Simsbury

Pratt St Brand New Studio Loft Elevator Building is a apartment in Simsbury. 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 Simsbury. 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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The Bushnell Suite C2 CURRENT Upgrades are Underway Daily!

Apartment, Simsbury

The Bushnell Suite C2 CURRENT Upgrades are Underway Daily! is a apartment in Simsbury, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring…

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About The Bushnell Suite C2 CURRENT Upgrades are Underway Daily!

The Bushnell Suite C2 CURRENT Upgrades are Underway Daily! is a apartment in Simsbury, 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 $902.

From$129/night

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Vacation rentals with a pool in Simsbury, 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

Apartment, Simsbury

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

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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 Simsbury, 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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Elegant 3 Bedroom Modern Peaceful Home with Pool in CT

Holiday Home, Simsbury

Elegant 3 Bedroom Modern Peaceful Home with Pool in CT is a holiday home in Simsbury, with pool access, parking, and room for a group. This stay gives travelers a comfortable base for…

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About Elegant 3 Bedroom Modern Peaceful Home with Pool in CT

Elegant 3 Bedroom Modern Peaceful Home with Pool in CT is a holiday home in Simsbury, 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 fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,257.

From$751/night

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

Holiday Home, Simsbury

Quiet Mid-Century Getaway. 4 bedrooms. Perfect for your next family gathering. is a holiday home in Simsbury, 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 Simsbury, 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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Peaceful Modern B&B with Comfort & Charm

B & B, Simsbury

Peaceful Modern B&B with Comfort & Charm is a b & b in Simsbury, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Peaceful Modern B&B with Comfort & Charm

Peaceful Modern B&B with Comfort & Charm is a b & b in Simsbury, with pool access 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, pool, parking, free parking, and fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,118.

From$160/night

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Vacation rentals with parking in Simsbury, CT

Find vacation rentals that make arriving by car easier.

Vintage Windsor Home: Private Yard & Covered Deck

Holiday Home, Simsbury

Vintage Windsor Home: Private Yard & Covered Deck is a holiday home in Simsbury, with outdoor space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Vintage Windsor Home: Private Yard & Covered Deck

Vintage Windsor Home: Private Yard & Covered Deck is a holiday home in Simsbury, with outdoor 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,272.

From$182/night

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Spacious 3-Bedroom Home Awaits 2nd Floor - Designed for Comfort & Relaxation!!!

Apartment, Simsbury

Spacious 3-Bedroom Home Awaits 2nd Floor - Designed for Comfort & Relaxation!!! is a apartment in Simsbury, with parking, room for a group, and a quieter setting. This stay gives travelers…

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About Spacious 3-Bedroom Home Awaits 2nd Floor - Designed for Comfort & Relaxation!!!

Spacious 3-Bedroom Home Awaits 2nd Floor - Designed for Comfort & Relaxation!!! is a apartment in Simsbury, with parking, 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, parking, free parking, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,310.

From$187/night

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Charming 3-bedroom house with wishing well,WiFi and AC in Bloomfield

Holiday Home, Simsbury

Charming 3-bedroom house with wishing well,WiFi and AC in Bloomfield is a holiday home in Simsbury, with pet-friendly space, parking, and kitchen access. This stay gives travelers a…

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About Charming 3-bedroom house with wishing well,WiFi and AC in Bloomfield

Charming 3-bedroom house with wishing well,WiFi and AC in Bloomfield is a holiday home in Simsbury, 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 $1,928.

From$275/night

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Inviting 3 Bedroom Mid-Century Modern in Canton, CT

Holiday Home, Simsbury

Inviting 3 Bedroom Mid-Century Modern in Canton, CT is a holiday home in Simsbury, 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 Simsbury, 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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Pet-friendly vacation rentals in Simsbury, CT

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

The Traveler Suite C1 CURRENT Upgrades are Underway Daily!

Apartment, Simsbury

The Traveler Suite C1 CURRENT Upgrades are Underway Daily! is a apartment in Simsbury, 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 Simsbury, 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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Charming 2-bedroom house centrally located in Bristol

Holiday Home, Simsbury

Charming 2-bedroom house centrally located in Bristol is a holiday home in Simsbury, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Charming 2-bedroom house centrally located in Bristol

Charming 2-bedroom house centrally located in Bristol is a holiday home in Simsbury, 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 $1,154.

From$165/night

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comfortable home away from home

Holiday Home, Simsbury

comfortable home away from home is a holiday home in Simsbury, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About comfortable home away from home

comfortable home away from home is a holiday home in Simsbury, 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 $1,285.

From$184/night

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The Blue Back Bungalow

Apartment, Simsbury

The Blue Back Bungalow is a apartment in Simsbury, 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 The Blue Back Bungalow

The Blue Back Bungalow is a apartment in Simsbury, 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 $1,508.

From$215/night

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Vacation rentals with a kitchen in Simsbury, CT

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

Fall in Love with New England Charm this Fall!!!

Apartment, Simsbury

Fall in Love with New England Charm this Fall!!! is a apartment in Simsbury, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Fall in Love with New England Charm this Fall!!!

Fall in Love with New England Charm this Fall!!! is a apartment in Simsbury, 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 $1,320.

From$189/night

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Beautifully Lit Spacious 3-Bedroom House!!

Holiday Home, Simsbury

Beautifully Lit Spacious 3-Bedroom House!! is a holiday home in Simsbury, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the…

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About Beautifully Lit Spacious 3-Bedroom House!!

Beautifully Lit Spacious 3-Bedroom House!! is a holiday home in Simsbury, 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 $1,373.

From$196/night

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3-bedroom apartment steps to Downtown Hartford

Apartment, Simsbury

3-bedroom apartment steps to Downtown Hartford is a apartment in Simsbury, 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 Simsbury, 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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Location, is the key for this 3 bedroom!

Apartment, Simsbury

Location, is the key for this 3 bedroom! is a apartment in Simsbury, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About Location, is the key for this 3 bedroom!

Location, is the key for this 3 bedroom! is a apartment in Simsbury, 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 wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,633.

From$233/night

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Family-friendly vacation rentals in Simsbury, CT

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

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

Cottage, Simsbury

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

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

Hike, Bike & Relax: Huckleberry Hill Home w/ Yard! is a cottage in Simsbury, 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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Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.

Holiday Home, Simsbury

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

Holiday Home, Simsbury

Lake Congamond Cozy Stylish Comfortable House is a holiday home in Simsbury, 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 Simsbury, 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

Holiday Home, Simsbury

Charming East Granby house with AC and WiFi 3 minutes to Bradley Airport is a holiday home in Simsbury, 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 Simsbury, 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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