Vacation rentals in Canaan, NY

30 available vacation rental offers

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Best vacation rentals and Airbnb offers in Canaan, NY

Vacation Village in the Berkshires - Canaan, NY

8.8 ★ 2,389 reviews

Vacation Village in the Berkshires

Condo, Canaan

Vacation Village in the Berkshires is a condo in Canaan, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About Vacation Village in the Berkshires

Vacation Village in the Berkshires is a condo in Canaan, 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: pool, free wifi, gym, and condominium.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $964.

From$114/night

The Central Downtown Inn & Suites - Canaan, NY

8.6 ★ 368 reviews

The Central Downtown Inn & Suites

Guest House, Canaan

The Central Downtown Inn & Suites is a guest house in Canaan, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About The Central Downtown Inn & Suites

The Central Downtown Inn & Suites is a guest house in Canaan, 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, free parking, and ac.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $973.

From$124/night

Hideaway Inn Lenox - Canaan, NY

8 ★ 3 reviews

Hideaway Inn Lenox

Guest House, Canaan

Hideaway Inn Lenox is a guest house in Canaan, with parking. 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 Hideaway Inn Lenox

Hideaway Inn Lenox is a guest house in Canaan, 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, kids friendly, kids friendly videos or books, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,099.

From$268/night

Unique Yeti-Theme Ski On Off Suite Jiminy-Sleeps 4 - Canaan, NY

Unique Yeti-Theme Ski On Off Suite Jiminy-Sleeps 4

Apartment, Canaan

Unique Yeti-Theme Ski On Off Suite Jiminy-Sleeps 4 is a apartment in Canaan, with pool access and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About Unique Yeti-Theme Ski On Off Suite Jiminy-Sleeps 4

Unique Yeti-Theme Ski On Off Suite Jiminy-Sleeps 4 is a apartment in Canaan, 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: free cancellation, pool, free wifi, and gym.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $950.

From$117/night

Family-friendly vacation rentals in Canaan, NY

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

The Cottage - Canaan, NY

The Cottage

B & B, Canaan

The Cottage is a b & b in Canaan, with pet-friendly space and easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About The Cottage

The Cottage is a b & b in Canaan, with pet-friendly space and easy beach 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, free wifi, pet friendly, and pets friendly.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,396.

From$312/night

Family-Friendly Hancock Home: Walk to Slopes! - Canaan, NY

Family-Friendly Hancock Home: Walk to Slopes!

Holiday Home, Canaan

Family-Friendly Hancock Home: Walk to Slopes! is a holiday home in Canaan, with pool access and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About Family-Friendly Hancock Home: Walk to Slopes!

Family-Friendly Hancock Home: Walk to Slopes! is a holiday home in Canaan, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,184.

From$345/night

Family-friendly Hancock Home: Walk to Slopes! - Canaan, NY

Family-friendly Hancock Home: Walk to Slopes!

Apartment, Canaan

Family-friendly Hancock Home: Walk to Slopes! is a apartment in Canaan, with pet-friendly space, pool access, and room for a group. This stay gives travelers a comfortable base for…

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About Family-friendly Hancock Home: Walk to Slopes!

Family-friendly Hancock Home: Walk to Slopes! is a apartment in Canaan, with pet-friendly space, 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: free cancellation, pool, free wifi, pet friendly, and pets friendly.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,679.

From$427/night

Historic New Lebanon Hideaway on 33 Private Acres! - Canaan, NY

Historic New Lebanon Hideaway on 33 Private Acres!

Cottage, Canaan

Historic New Lebanon Hideaway on 33 Private Acres! is a cottage in Canaan, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Historic New Lebanon Hideaway on 33 Private Acres!

Historic New Lebanon Hideaway on 33 Private Acres! is a cottage in Canaan, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,849.

From$456/night

Vacation rentals with a pool in Canaan, NY

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

Deluxe Ski On Off 1BR Suite Sleeps 4 on Jiminy Mtn - Canaan, NY

Deluxe Ski On Off 1BR Suite Sleeps 4 on Jiminy Mtn

Apartment, Canaan

Deluxe Ski On Off 1BR Suite Sleeps 4 on Jiminy Mtn is a apartment in Canaan, with pool access and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About Deluxe Ski On Off 1BR Suite Sleeps 4 on Jiminy Mtn

Deluxe Ski On Off 1BR Suite Sleeps 4 on Jiminy Mtn is a apartment in Canaan, 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: free cancellation, pool, free wifi, and gym.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,032.

From$117/night

Gorgeous New Zen Suite Sleeps 4-Ski On Off Jiminy - Canaan, NY

Gorgeous New Zen Suite Sleeps 4-Ski On Off Jiminy

Apartment, Canaan

Gorgeous New Zen Suite Sleeps 4-Ski On Off Jiminy is a apartment in Canaan, with pool access and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About Gorgeous New Zen Suite Sleeps 4-Ski On Off Jiminy

Gorgeous New Zen Suite Sleeps 4-Ski On Off Jiminy is a apartment in Canaan, 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: free cancellation, pool, free wifi, and gym.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,032.

From$117/night

Must See Pirate Suite Ski On Off Jiminy - Mtn View Fully Redone Decor - Canaan, NY

Must See Pirate Suite Ski On Off Jiminy - Mtn View Fully Redone Decor

Apartment, Canaan

Must See Pirate Suite Ski On Off Jiminy - Mtn View Fully Redone Decor is a apartment in Canaan, with pool access. This stay gives travelers a comfortable base for exploring the area,…

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About Must See Pirate Suite Ski On Off Jiminy - Mtn View Fully Redone Decor

Must See Pirate Suite Ski On Off Jiminy - Mtn View Fully Redone Decor is a apartment in Canaan, 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, pool, free wifi, and gym.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,001.

From$124/night

The Inn at Stockbridge - Canaan, NY

9.8 ★ 99 reviews

The Inn at Stockbridge

B & B, Canaan

The Inn at Stockbridge is a b & b in Canaan, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family…

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About The Inn at Stockbridge

The Inn at Stockbridge is a b & b in Canaan, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,782.

From$461/night

Vacation rentals with parking in Canaan, NY

Find vacation rentals that make arriving by car easier.

Historic New Lebanon Hideaway on 33 Private Acres! - Canaan, NY

Historic New Lebanon Hideaway on 33 Private Acres!

Holiday Home, Canaan

Historic New Lebanon Hideaway on 33 Private Acres! is a holiday home in Canaan, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Historic New Lebanon Hideaway on 33 Private Acres!

Historic New Lebanon Hideaway on 33 Private Acres! is a holiday home in Canaan, 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 wifi, parking, paid parking, non smoking::room, and non smoking rooms.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,838.

From$412/night

The Cornell Inn, Lenox & The Berkshires - Canaan, NY

The Cornell Inn, Lenox & The Berkshires

B & B, Canaan

The Cornell Inn, Lenox & The Berkshires is a b & b in Canaan, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires is a b & b in Canaan, 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 breakfast, free wifi, for couples, wine or champagne, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,497.

From$310/night

Eastgate Inn B&B - Canaan, NY

Eastgate Inn B&B

B & B, Canaan

Eastgate Inn B&B is a b & b in Canaan, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

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About Eastgate Inn B&B

Eastgate Inn B&B is a b & b in Canaan, 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 breakfast, free wifi, parking, paid parking, and fireplace.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,723.

From$215/night

Gateways Inn - Canaan, NY

Gateways Inn

B & B, Canaan

Gateways Inn is a b & b in Canaan, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

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About Gateways Inn

Gateways Inn is a b & b in Canaan, 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 breakfast, free wifi, parking, and paid parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,621.

From$441/night