Red bridge over the Housatonic River

Canaan house rentals

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March 2026

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Explore Canaan house rentals

Image of Villa Mariana Blackberry River. Luxury, pool, comfort, peaceful nature, updated

Premier Host

Villa Mariana Blackberry River. Luxury, pool, comfort, peaceful nature, updated

Sleeps 11 · 4 bedrooms · 3 bathrooms

Image of Fickle Fox Farm. It’s snow season! Lifts are open. Fireplace is crackling!

Premier Host

Fickle Fox Farm. It’s snow season! Lifts are open. Fireplace is crackling!

Sleeps 11 · 3 bedrooms · 2+ bathrooms

Image of A Design-Lover's Retreat in Litchfield County, CT - Escape to Pennybrook Cottage

Premier Host

A Design-Lover's Retreat in Litchfield County, CT - Escape to Pennybrook Cottage

Sleeps 4 · 2 bedrooms · 2+ bathrooms

Image of Charming Lakefront Cottage; Boat, Swim, Fish, Hike, Bike, Golf, majestic Views

Charming Lakefront Cottage; Boat, Swim, Fish, Hike, Bike, Golf, majestic Views

Sleeps 6 · 2 bedrooms · 1 bathroom

Top rated house rentals - Canaan

Image of Quiet woodland retreat near Great Barrington

Starflower House

First time in the Berkshires! Loved it, House was clean and worked well for our ski weekend

Maria V.

Stayed Feb 2021

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Enjoy full kitchens, laundry, pools, gardens and more
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