Canaan Vacation Rentals
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5 mi
46 rentals in Canaan.
Fickle Fox Farm. Leaf Peepers and Skiers! This is your season.
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1700s Farmhouse with Modern Amenities and Comfort. Pool, Hot Tub, Views.
Rental Home
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Canaan Valley Home, A Berkshires Getaway
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Beautiful farmhouse for perfect country escape - close to skiing, 5 fireplaces.
Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Bellhaven- Charming 4-bedroom house in Canaan, CT
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Villa Mariana Blackberry River. Luxury, pool, comfort, peaceful nature, updated
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Music Mtn Farmhouse - Mystical Country Retreat
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Cozy Log Cabin Retreat with Pool on 4 Acres
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Close to Lime Rock, Prep Schools, 3 Ski Areas
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Captivating Artisan Built Home With Spectacular Water Views
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The following properties within 20 miles of Canaan match all your filters:
Charming Lakefront Cottage; Boat, Swim, Fish, Hike, Bike, Golf, majestic Views
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Serene Salisbury Rental Home on 26 Acres w/ Deck!
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Romantic and Secluded Berkshire's Gem
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Salisbury Cottage Retreat
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Adirondack-Style/Cottage-Beautiful Lake & Mountain Views-Peaceful!
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Little House in the Woods by Evergreen Home
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Meadow Top Cottage: beautiful mountain views
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Berkshire Getaway Walk to Winery, Brewery or Distillery with Peloton!
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Converted Berkshire schoolhouse on a quiet river
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Konkapot Cottage, Pastoral Bliss With Wide Views
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Spacious Home nestled along the Blackberry River in Northwest CT
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Beautiful Berkshires Farmhouse with game room and plenty of room
Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Serene Berkshire Artist's House
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Modern Farmhouse in the Southern Berkshires
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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6 BR 'CAMP' House on Twin Lakes - Epic Historic Property
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The Race Mountain House
Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Serenity Summit: Hot Tub, Mountain Views, Book Now
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Spectacular 88-acre Berkshires Retreat w/ Tennis Court - Family Friendly
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Gorgeous Sheffield Home in Heart of Berkshires
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Charming Ashley Falls Getaway
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Rest Relax Enjoy the Berkshires! Sparkling, New, Open and Spacious!
Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Curated Contemporary for lakes, forest & ski hills
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Luxurious Mountain Retreat - Private 40-Acre Family Haven
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Rustic House w/ Heating + Pool
Condo/Apartment
0 bedrooms
0 bathrooms
Sleeps 10
Match: Sleeps
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Antique Farmhouse Totally Restored
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COME STAY AT THE SHEFFIELD CHALET!
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The Blue Elm - A Historic Berkshire Cottage
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Luxurious, modernist barn in peaceful northwestern Connecticut - private swim!
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Ashley Falls Home w/ Fire Pit: Hike & Ski!
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BEAUTIFUL 4-SEASON RENTAL DIRECTLY ON TWIN LAKES
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Guesthouse Cabin vacation rentals in Berkshire County
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BEAUTIFUL TWIN LAKES RENTAL - Weekly or Seasonal Term Available
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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BERKSHIRE MOUNTAIN LAKEFRONT LOG HOUSE FAMILY RETREAT
Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Cheerful 3-bedroom cottage with woodstove
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Beautiful Berkshire Home - Enjoy summer, fall & winter attractions
Rental Home
4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Meadow Top Cottage: Countryside Cottage on 72 Acres
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Showing results 1-46 of 46
Frequently Asked Questions about Canaan
- Yes, here are some popular vacation rentals in Canaan that have a pool:
- Fickle Fox Farm. Leaf Peepers and Skiers! This is your season.
- 1700s Farmhouse with Modern Amenities and Comfort. Pool, Hot Tub, Views.
- Canaan Valley Home, A Berkshires Getaway
- Yes, here are some popular vacation rentals in Canaan that have internet access:
- Fickle Fox Farm. Leaf Peepers and Skiers! This is your season.
- 1700s Farmhouse with Modern Amenities and Comfort. Pool, Hot Tub, Views.
- Canaan Valley Home, A Berkshires Getaway
- Some of the most popular kid friendly rentals in Canaan are:
- Fickle Fox Farm. Leaf Peepers and Skiers! This is your season.
- 1700s Farmhouse with Modern Amenities and Comfort. Pool, Hot Tub, Views.
- Canaan Valley Home, A Berkshires Getaway